If you’ve only ever dabbled in AI-writing sleuthing, you probably know two and exactly two AI writing tells: em-dashes and negative parallelism. Em-dashes were the first lambs to the slaughter, but negative parallelism is the one that really riles people up when they see it. You may not know the concept by name, but I promise, you’ve seen it and bemoaned it: it’s the “It’s not x, it’s y” construction.

Negative parallelism is a rhetorical device that defines a sentence’s subject by stating what it’s not and then quickly following with what it is. It is sometimes, although rarely, the exact right rhetorical tool for creating conceptual clarity for a reader. But that’s not why LLMs use it. Negative parallelism appears in AI writing for the same reason most of its sentence-level habits do: it gives the illusion of adding meaning and precision without actually doing so.

Sentences are precious. At least to me. Of all the units of thought, sentences are perhaps the most important ones because they are flexible and long enough to convey complex meaning while also being short enough to be memorable. I’ve had a running note in my phone for 11 years titled “sentences that changed my life,” because sentences can do that. Good sentences are sticky little chunks that follow us around and change how we think, the way great language should.

Part of what makes sentences powerful is they’re the smallest unit of language that can use form to amplify meaning. Short sentences emphasize. Long, flowing sentences with lots of dependent clauses create slowness and a sense of melody. Where you place the emphasis, where you layer in the clauses, and how long you allow a sentence to run are all the core elements of voice. Writing is, at its core, sentence-craft.

AI knows no such craft. LLM sentences are uniform, built for drama instead of meaning, and generally limited to a narrow range of structures that always adhere to the most elementary of grammatical rules. They hint at meaning with little jabs and pauses, but they do not craft it or take risks.

And of all the AI tics that make its writing “worse” than human writing, the sentence-level ones are the highest impact.

So without further ado, let’s talk about them.

AI Sentence Structure Tells

1. Uniform sentences

If you are going to look for a single sentence-level indicator of whether a piece of writing is AI-generated, this is the one I want you to pay attention to: militant uniformity.

AI sentences sound like other AI sentences, which sound like other AI sentences, which sound like other AI sentences. When humans write, we add some variation to our writing. Short sentences are followed by long ones, and sentences that start with dependent clauses are followed by ones that don’t. We follow middle school sentence rules like “put the emphasis at the end” and “use the active voice” loosely because we have the discernment to judge when they work for us and when they don’t. AI has no such judgment, and it follows these guidelines with a level of consistency that human writers just don’t.

A lot of developing your voice as a writer is about figuring out when you break rules. I, for one, love to string together dependent clauses in hard-to-defend ways because that’s how language occurs in my head, and it’s my voice so I can do what I want.

AI loves to use two to three sentence structures that are perfectly grammatical, over and over. And that, my friends, is how you identify it. Let’s work through an example.

See how every AI sentence is sort of the same? They’re all roughly the same length (15–18 words), and they all end by trailing off into some qualifying phrase. Humans can and do write that way, but AI almost always does.

The nice thing about this tell is that you can often catch it without reading closely at all. Uniform sentences look uniform. Of course, not every AI sentence is the exact same, but if everything feels super standardized, it should throw up some flags.

2. Contrasting structures: negative parallelism & correlative conjunctions

Returning quickly to negative parallelism, I find it helpful to understand why and when humans use these structures in order to understand why AI is misusing them. When humans say “not x, but y,” it’s usually to disabuse the reader of a high-probability assumption they made based on what they’d read up until that point. When I explain I’m not sleeping well, and a friend says “you must be tired,” I might respond with, “I’m not just tired, I’m getting sick” as a corrective to the (in this case, blatantly introduced) understatement in my friend’s assumption.

The problem with AI’s use of negative parallelism, and the way to differentiate its use from humans’, is that LLMs throw negative parallels around for emphasis and, in doing so, use the corrective structure to challenge a premise the reader likely never held in the first place. Negative parallelism feels obvious to us in AI writing because when we read “WWII wasn’t just a military conflict, it was a global event,” there’s something patronizing about the first clause. Because yes… we know. No one assumed it was just a military conflict, and using negative parallelism to try to explain the magnitude of WWII’s geopolitical effects is condescending but not meaning-enhancing.

The other way AI abuses negative parallelism is to exaggerate on the other side of the equation. When an LLM writes that “it’s not just another piece of software, it’s a paradigm shift,” we hate it because actually… the CRM is just another piece of software. The sentence structure adds drama at the expense of precision.

The less-recognized but equally annoying companion to negative parallelism that replicates this sin is the abuse of correlative conjunctions, word pairs that join two pieces of a sentence using a conjunction to describe their relationship like “not only… but also,” “neither… nor,” “either… or,” and “both… and.” The rule for using correlative conjunctions is that they generally connect ideas of equal grammatical weight, so the connecting word establishes their relationship. For example, when a human writes “not only did she forget my birthday, but she also sent me a happy birthday text a month late!” the conjunction is telling us that the belated text is worse than the forgetting. The point is to convey an actual relationship between ideas. The problem with how LLMs use correlative conjunctions (and the thing to look out for) is that the conjunction is used to add melodrama with no regard for whether the ideas deserve that treatment.

The problem with this construction is that, while it might be right if cutting response times is more important than reducing ticket volume, an LLM will use this phrasing regardless of whether that’s true.

Humans use these structures too, and they’re not automatically a sign of AI writing (just like all of these tells as standalones). But if you want to be able to spot LLM-generated contrasting structures, look for moments where the construction feels like it’s being used for drama instead of relational clarity.

3. Tricolons

When talking about AI writing, I’ve heard lots of people lament the way AI uses three-part lists and, you know what? Same. It also makes me sad. Because I, like many writers, love a three-part list. Some of the most memorable statements of all time were parallel three-part lists (tricolons). Life, liberty, and the pursuit of happiness. Friends, Romans, countrymen. Of the people, by the people, for the people. To name a few.

Tricolons are a specific version of the “rule of three,” a general writing principle that suggests everything is more satisfying in threes, and if you ask me, the rule of three is real, valuable, and will not be pried from our writerly hands without a fight. But tricolons — lists of three grammatically parallel items — have admittedly become a staple of AI writing, so learning how to differentiate human ones from AI-written ones can be an important skill for avoiding false-positive flags for AI writing.

The two things I look for to identify AI-written tricolons are overuse (it’s in every paragraph), and weak third parts. AI will, almost as a rule, make three-part lists where two items would have sufficed. When you see lists where it feels like the third item is there for rhythm instead of purpose, it’s more likely to be AI (although humans do this too, myself included).

Examples here are kind of tricky, but here’s what I’ve got for you.

Is “rejuvenating” adding anything? Maybe? But it’s close enough to “relaxing” that relaxing alone probably would have done the job. The pattern with AI tricolons is that the third item doesn’t introduce new information. The thing to keep an eye out for is three-part lists where the third part is all rhythm no substance.

4. Dramatic countdowns

Dramatic countdowns (a Kristen term, not a technical term) are the next sentence structure I look for in AI writing. Again, humans use these too, my favorite example being “Not me. Not Hermione. You.”

Dramatic countdowns are just negative parallelism and tricolons combined to add stakes and drama.

When humans use these types of countdowns, it’s normally because the stakes legitimately call for it. Ron’s famous “Not me” line in Harry Potter works because the characters are in a life-or-death game of chess, and Ron is actively trying to emphasize how singular Harry is.

As you’ve probably guessed by now, the problem with how AI uses dramatic countdowns is that it throws them around in all sorts of situations that simply do not warrant the drama.

1. Nobody thought it was tooling. AI is correcting a possible but irrelevant assumption no one put forward.

2. Why the drama?!?! LLMs use this construction because it adds the appearance of rigor (”we ruled out the other options”), but the effect is that it sounds like a game-show elimination for no reason.

As a general rule, if you’re not playing life-or-death wizard’s chess, you probably don’t need this construction, and it was probably written by AI.

5. Questions with immediate answers

This is another AI tell you are probably at least lightly familiar with: one-to-two-word questions followed by an immediate answer. I find that Claude in particular is deeply attached to this construction.

And the problem? It’s stupid.

The outcome? It’s bad. (Okay, I’m done, sorry.) Somewhere in writing history, someone must have been using this phrasing because it infiltrated AI training data, but I have to be honest, I have never seen a talented writer use this construction in the wild. When it comes out of an LLM, it almost always looks like a sentence fragment (article + noun, hold the verb) followed by a short, high-drama conclusion.

Question-and-answer beats can and do work in human writing, but usually only in contexts where the reader has been on the edge of their seat about something for thousands of words and the writer has successfully built enough tension to make the staccato phrasing feel relieving. Personally, I have never written something that warranted this treatment. I rarely read things that warrant it. And of all the AI tells that I’m willing to assert are stand-alone indicators of AI writing, this one is the top of my list.

You get it, but purely to create parallel structure in these sections, I’ll offer you an example.

6. False ranges

As far as AI sentence structure goes, false ranges are fairly subtle. Range constructions, “from x to y,” have a meaningful place in human writing because they express breadth and exhaustiveness. When we say “Everyone from the intern to the CEO,” instead of “every employee,” it works because it’s emphasizing that something transcends seniority and because it’s actually describing a real, literal range of job levels. Usually, when humans use a range construction, it’s to describe something that has a legitimate interior. When Woody Guthrie wrote “From California to the New York Island,” he was using a range that has actual insides. Famously, the contiguous United States.

I call AI’s use of this construction “false,” because AI will establish ranges with no intelligible inside. When AI says “from the farmhouse to the boardroom” (a real phrase it’s served me)... what exactly goes inside of that? I can hypothesize, but what the intermediate steps between farmhouse and boardroom are is not evident to me, and it is unclear to the reader what the breadth is trying to emphasize. LLM false ranges pick endpoints that feel far apart but don’t actually imply any real scope, as a fancy way of saying “this is broadly true.”

Yes, that technically conveys a breadth of adoption… but it also implies that whatever sits between teenagers and MDs (work experience? maturity? wealth? ennui?), that’s the spectrum that makes the range important. What that range is? Hard to say.

The test I use to spot AI ranges is swapping in other words. If you could put in another word like “farmers” instead of “teenagers,” to make the same point, you’re probably looking at LLM-assisted writing that is using the range structure for emphasis but, again, not meaning.

7. Participle tails

Quick refresher on your middle school English learnings: a participle is a verb that is acting as an adjective because it’s being used to modify a noun or noun phrase. Think: “highlighting,” “emphasizing,” or “underscoring.”

Participle tails, the final AI sentence-structure writing tell we’ll cover, are participle phrases that are strung onto the end of a sentence, usually to tell the reader what the rest of the sentence was trying to do.

The reason I hate them is that if you write good sentences, you shouldn’t need the participle tail. If I present a thesis statement and then pieces of evidence to support it, I shouldn’t have to write “proving the thesis” at the end of each one to make it apparent what the sentence was doing. But AI, because it cares not for great sentence craft, does try to tell you what the sentence was supposed to do because it doesn’t have any idea if it actually accomplished it or not.

AI-generated participle tails you’ve probably seen include: “signaling a broader shift…,” “highlighting the importance of…,” “reflecting a new era of…” Basically, a ton of over-explanatory add-ons that good writers simply don’t use because they trust themselves and their readers.

AI doesn’t trust you as a reader. At all. In fact, it doesn’t even know you exist or have you in mind when it’s generating tokens. So participle tails get tossed around everywhere just to be extra sure that the purpose of a sentence was clear.

What is that last phrase doing in this example? Not a whole lot other than expressing distrust for the reader’s ability to draw conclusions from otherwise plain, clear writing. Humans do use these to add meaning, but when you see them everywhere, chances are you’re looking at AI-generated writing.

None of these things in isolation—with the possible exception of the question-and-answer thing, which I stand by as weird and bad—is a guaranteed indicator of AI-generated writing. As I will continue to disclaim, these lists are intended to help you look across the many choices that go into a piece of writing and identify dense clusters of vocabulary, sentence, paragraph, and reasoning-level tells. You’re allowed to use all of these constructions and enjoy them in others’ writing.

We’ll talk about paragraph structures next week, but for now… happy sleuthing.

Talk soon. Thanks for reading. KL.

Were someone to break into my phone and search through my notes app in pursuit of passwords and identifying information, they would have to 1) navigate a sea of poems from my early twenties that would make anyone want to toss the phone from second-hand embarrassment, so good luck to them, and 2) need to wade through notes upon notes of random word lists that no one could possibly make sense of.

I have no good excuse for the poems, but the random word lists are for work. Put crudely, I imitate people for a living, and requirement no. 1 for being a good imitator is paying detailed attention to the exact words, phrases, pronunciations, grammatical mishaps, and favorite sentence structures that make up someone’s idiolect, their unique communicative fingerprint.

While most people don’t spend much time thinking about what makes their communication patterns distinct, all people have tics and quirks, invented, learned, and often borrowed from friends, educators, and family, that make their communication distinctive. For example… I love ellipses and parenthetical asides, and it was recently brought to my attention that I’m out here using the word “telos” and the verb “telegraph” more than the average person. I also love the phrase “out here.”

But when I’m writing for someone else, the very first thing I do to master their idiolect is begin a running list of words and phrases that feel unique to them. That can be words they overuse, misuse, or just choose to use in places that other people wouldn’t. There’s a lot more that goes into figuring out someone’s voice, but things like tone, grammatical preferences, and phrasing patterns take more time to spot. Repeated, misused, and uncommon words have a way of standing out, and to the average person (i.e., not a professional executive imitator), they’re also the easiest part of an idiolect to spot.

So we’re starting the practical part of this series with a list of word-choice and vocabulary tells to look for to determine whether something was written with AI. While LLMs’ idiolectic vocabulary is the result of their “writing” mechanism and not preference or experience, it shows up in the same way humans’ do, and the second you learn to read for it, it’s hard to miss.

Quick disclaimer (that I’ll include in every one of these essays): The use of any or all of these words is not surefire proof that something was written by AI. Humans both use and overuse all these words, too, and the more AI-generated writing people consume, the more they start replicating these choices… which is a whole separate diatribe for a later date. While most good writers I know are saying weepy goodbyes to words like “quietly” and “infrastructure” to avoid AI allegations, even the best writers still make these vocab choices.

The point of this series is for you to learn to look for all these tells in combination, so that you can have more power over whether you’re giving your attention to AI writing. Don’t command+f a webpage for the word “quietly” and yell WITCH. It’s not a witch hunt. You know this. I know you know this. I hope you know that I know that you know this (wouldn’t write that sentence, now would ya, Claude?). Anyhow, onward.

AI Word Choice Tells

1. Abstract, Non-Visual Nouns

The first word choice tell I look for when I suspect something might be written by AI is an abundance of abstract, non-visual nouns. Think: ecosystem, realm, infrastructure. These words do have specific meanings, but when Claude uses the word ecosystem, it’s not talking about a frog pond, and it’s not using the word infrastructure to talk about public roads. In AI writing, these ephemeral, gas-filled words mean precisely nothing. Which is the point.

Yuck, right? It sounds dramatic and stupid. But remember (told ya reading pt. 2 about how LLMs work was going to pay off), LLMs are designed to produce this type of language. When an LLM is “choosing” (computing the probability of) a word, it’s just trying to place something that is statistically compatible with the surrounding context and settling on an option that is unlikely to be wrong. Seriously, if you haven’t read pt. 2, this would be a good time to pause and do so, because it really will help. Where we pick words in hopes of being right, AI picks them in hopes of not being wrong.

So of course, it reaches for abstract nouns because they commit the writing to exactly nothing! They have broad associative meanings, fit into many contexts, and might not be good, but also aren’t… wrong?

This will be a theme across this whole essay, but when you’re specifically looking for AI noun tells, here are some of the abstract nouns to look out for: ecosystem, infrastructure, realm, framework, landscape, paradigm (or more often, paradigm shift), synergy, optimization, transformation, trajectory, dynamic (noun).

2. Intensifier Adverbs (and Adjectives)

When you learn about word choice as a writer, one of the general principles that gets drilled into you is that adverbs are signs of weakness. The English language is full of pointed, granular verbs, and if you need an adverb to convey meaning, it’s because you picked a bad verb and might want to try again.

LLMs are pretty liberal with adverbs in general, but so are humans (myself included, and I’ve made peace with that), so what you want to look for specifically is intensifier adverbs, words that are used to add emphasis or importance without adding precision. Think: actually and genuinely. In full candor, I adore these words and am in mourning over having to give them up. They’re great pacers for slowing the rhythm of a sentence, even if they don’t do much in practice.

But seeing them everywhere in AI writing has helped convince me of their hollowness. LLMs use them in adjective form too, and in both cases, they just feel so forced.

Loads of AI offenses in there, but for now, focus on the quietly. Because what do you mean you’ve been quietly building? In secret? Without telling anyone? On a silent retreat high in the Himalayas? Literally building? You were in the lab? Were the other people in the lab allowed to talk? Could people bring their AirPods?

I’m obviously being dramatic for my own amusement, but I do think it’s helpful to understand that tossing out reckless intensifier adverbs can obscure a sentence’s meaning. What the LLM is trying to do is add oomph and this illusion of importance, but it often has the opposite effect.

When you see clusters of the following adverbs/adjectives being used in abstract ways, it’s likely you’re looking at AI writing: seamlessly, quietly, importantly, crucial, pivotal, vital, vibrant, load-bearing, nuanced, significant, strategic, effective, robust, dynamic (adjective), genuinely, truly, crucially (RIP, I love this one), and fundamentally.

3. Academic Verbs

The goods news is that LLMs do sometimes use purposeful verbs. The bad news (although good for your sleuthing) is that they often use ones humans wouldn’t. There are two verb watch-outs I look for, and the first is the use of overly academic language that feels too formal for the context in which it’s being used. Think words like delve, leverage, and utilize. It’s not that people don’t also use these, but when was the last time you actually had a reason to say “utilize” instead of “use”? Maybe if you were trying to highlight your resourcefulness, you get a pass. But even then…. As Mark Twain, George Orwell, Winston Churchill, and Teddy Roosevelt all said in some fashion: never use a big word when a small one will do.

I suspect that LLMs make these choices because they’re trained on a lot of academic and formal writing, but it leaves the writing feeling airy and overcredentialed, regardless of whether the subject calls for it.

The verbs to watch for here include: utilize, leverage, facilitate, implement, demonstrate, articulate, examine, explore, underscore, navigate, foster, optimize, elevate, synthesize, deploy.

4. Metaphors as Verbs

The second verb tell you should look for is the overuse of metaphor verbs. I’m talking about words like earn, anchor, and surface that, when used literally, describe specific phenomena but that AI uses metaphorically to convey something ambiguous.

“Earn” is the one I’m most wrathful about at the moment because, like many of these metaphorical verbs, it just doesn’t make sense. Here’s an actual example pulled from one of my recent conversations with Claude.

What do you mean that an agenda item has “earned its place,” Claude?!?!? What do you possibly accomplish by expressing it that way?

Most of these types of verbs have legitimate uses, and human writing is littered with them, but, as with abstract nouns, LLMs use these words to avoid meaning rather than convey it. When you see them in clusters or in places like the example sentence above where they’re just so unnecessary, you’ve got a pretty good sign that you’re looking at LLM-assisted writing.

Metaphor verbs that I see in AI writing all the time include: earn (again, YUCK), anchor, surface, frame, position, signal, channel, drive, shape, unlock, capture, build, hold, carry, tap, and land.

None of these word choices are evil in isolation, but when you start to see the effect they have together, it’s easy to understand why AI writing can feel sort of weird. All these word choices do the same thing: create imprecise, noncommittal, overdramatic language that conveys as little as possible while trying to sound important. Words standing on other words’ shoulders wearing a trench coat, if you will.

This is by no means an exhaustive list of every word that AI uses more than the average person, but after a year of filling out my unlabeled iPhone note of AI words, I feel pretty good about this list being a representative snapshot of the types of words that today’s models use. Some of these will change, but I suspect it will be a good while before LLMs ditch the words-in-trenchcoats vibe because it’s so inherent to their basic mechanisms. And even if the precise words AI overuses change, as long as you look out for this type of vacuous, non-material language that models are designed to produce, you’ll be on your way to identifying a good chunk of AI writing.

Thanks — always — for reading. See you next week for sentence structure tells.

If you want to understand how LLMs “write,” it helps to start with a basic understanding of how LLMs work more broadly. I know you’re probably here for the listicle-style writing tips, and I swear on my life that a cornucopia of them is headed your way, but stay with me on this one. Understanding next token prediction, the foundational function of all LLMs, is really helpful for wrapping your head around why AI writes the way it does and where its writing capabilities begin and end.

I am not an expert in this subject and would never claim to be. This essay is not an authoritative, expert account of LLM mechanics. It is, however, a thoroughly researched explanation that has helped me make sense of how I engage with LLMs and can help you too.

So without further ado, let’s get into it. What makes the way LLMs write different from the way humans do.

How Humans Write

Speaking generally, when you or I write a sentence, our process quickly and subliminally goes a little like this: we form an idea (sometimes more of just a pre-verbal lump than an actual “idea”) that we want to express to someone else, and with that idea in mind, we sort through the filing cabinet of words we know to find the best combination possible for making that idea legible to someone else. A lot of the time, this process is happening autonomically in a way we don’t really detect. However, if you’ve ever had the experience of writing being “hard,” it’s probably because you’ve encountered the conscious version of this process where you are actively fishing around for the right words or the right sequence of words, and you just can’t quite land one.

In the human brain, that challenge takes on a certain urgency because being understood is consequential to us. For us, picking the right words and putting them in the right order can feel stressful and threatening because our survival-motivated brains register being misunderstood as a social threat that jeopardizes our place in the herd.

Accordingly, you can think of human writing as defined by three particular things: a starting idea, a selection process for finding the words to communicate that idea, and a sense of emotional importance that motivates us to communicate in more precise and effective ways.

Professional writing, the type you consume in magazines, books, and journals, also includes a recursive editing process where writers hack away at their original creations to try to find even better words and arrangements, but for the purpose of this piece, all you need to keep in mind is that idea + emotional stakes + word selection process = writing.

How LLMs Write

What AI does when it “writes” bears little resemblance to this process.

In layperson’s terms, LLMs like ChatGPT and Claude perform one, and arguably only one core function: next token prediction. Essentially, they “write” by taking your prompts, breaking them into tokens, converting those tokens into numbers, throwing those numbers through many layers of learned calculations, and outputting a probability distribution over possible next tokens so that they can pick the best one.

The way it “learns” (gets trained) to do that is by being repeatedly adjusted while it sorts through huge amounts of training text. These adjustments make it so that, when given different token sequences, the model becomes increasingly good at assigning a high probability to the token that actually came next in the training data. With new and improved internal parameters (numerical weights and biases), the model functionally encodes patterns in grammar, word choice, style, facts, and language structure so that when you open up your chat interface, the model behind it can use learned numerical patterns to score possible next tokens, pick the highest probability one, and then do the same thing over and over and over again until you have a response.

TL;DR—no matter how much it looks like reasoning, explaining, thinking, or writing, all LLMs really do is very advanced statistics homework, over and over and over. It’s just recursive pattern completion that involves no human-like relationship to meaning, intent, or truth.

The reason I want you to understand this is that, because all LLMs are doing is prediction, the way they write does not and cannot include our three ingredients for human writing. LLMs don’t have ideas. They don’t have truths. Even when you give them a prompt, the prompt is not an idea or a truth; it’s just a mathematical sequence of tokens that would likely be followed by the sequence of tokens it gives back. At no point in that process is there an idea, a pre-verbal lump, or a premise. There is never an idea, fledgingly and unformed but real.

There is also no word selection process. While next-token prediction seems like the same thing as finding the right word for your sentence, when you fish around in your brain for words, you implicitly have a goal for what that word must do, and you are indexing your entire lexical database to find the one that best achieves the goal. But AI has no goals or conscious lexical inventory. It has what is functionally a very large map of mathematical relationships between words, but it has no understanding of those words’ relationships to the world (because…again…it does not experience the world), so the idea of a “best” or most precise word is beyond its comprehension. It’s not even trying to predict the most probable word statistically. Just one that’s probbaly not wrong.

Perhaps most importantly, there are no emotional stakes. What drives you and me to write, and to write well, is a particular emotional discomfort that is unique to being entities cursed with consciousness. We try to say what we mean exactly as we mean it because we have entire interior universes inside of us that can only be known if we put the right words for describing them in the right order, and that is both daunting and, if you ask me, profound. The mechanics of it all aside, the stakes are what make writing interesting. And for AI… there are none. You can snark at it all you want (and I do), but it’s of no consequence to your LLM if you’re rude because it communicated poorly.

One more technical thing. It is easy to assume (and it is partially true) that if AI is writing based on probabilities, then what it’s producing must be the most common patterns in human writing. Think: standard sentence structures, familiar transitions, genre-specific norms, etc. It is true that models reflect what appears most often, but that is not the only thing determining which tokens models spit out. While they may not be searching for the most accurate way to say something, they are programmed to avoid being obviously wrong. In some sense, AI is producing the “average” of all the human inputs it is trained on, but it is more likely than humans to be generic, balanced, and low-risk in its choices. You’ll understand the significance of this as we get into the series, but just keep it in mind.

There is no amount of prompting that can make AI understand or care about what it’s “writing.” It doesn’t know what it’s doing, has no destination, no determination to express something well, and no understanding of what it’s expressing. LLMs produce text sequences that resemble human writing but are fundamentally not produced by writing. And accordingly, even the best-disguised prose will often still give off this ephemeral uncanny valley feeling like a pencil drawing that almost resembles photography, but just still… isn’t. It won’t reach for the right word because it has no motive to, and it wouldn’t dare say something risky because it can’t.

All the things about human writing — the intimacy, the frustration, the familiarity, the honesty, the embarrassment — AI cannot give them to you, not only because it’s a machine writing but because it’s not writing at all.

When I was in my early twenties, discovering via cavalier #MeToo posts on Facebook how many of my girlfriends had been assaulted and growing more aware with every new day of prefrontal lobe development that men possess inherent danger (in violence but also in their credibility vis-à-vis women’s), I developed an intense physiological revulsion toward being left alone with a man.

Boyfriends were exempted from this, but even close friends weren’t really. I would get this tight, knotted sensation just behind my belly button, and my chest would feel hot at the idea that the man sitting across from me might have an ulterior motive and was not to be trusted. To this day, I find it is hard to tell if someone’s hitting on you or trying to get something from you. I don’t mean that in a coquettish way. Young women are taught to believe both that men are dogs and also that you’re a snobbish bitch for thinking anyone would want you, and those aren’t easy messages to reconcile. They leave you (or at least left me) feeling like every man in the world just might be trying to sleep with you, but you’re also the worst for thinking so. By the time I left college, almost every one-on-one interaction I had with a man evoked both of these thoughts in me, and I found myself walking around fearful and suspicious but also viscerally mad.

I didn’t want to have to go through life conducting silent forensic analyses on all my conversations with men. I didn’t want to have to think about whether I was being naive or callous. And while I could write a whole thesis on how immediately this feeling dissipated when I graduated from the word “boyfriend” and got to start declaring that my FIANCE had planted a flag in my life, the point is only this: it is miserable to live your life harboring perpetual suspicion and anger. And now I feel like I’m doing it again.

This essay is, as the title suggests, about AI writing. And I need you to know that I do not lightly compare the feeling AI writing gives me to the feeling men give me. Writing has, for my whole life, been sacred to me in a way few things are. I wasn’t one of those kids who stumbled into writing because it was fun and creative; I turned to writing and reading as the only tools I had to expel impossibly large feelings from my childhood body before I had the skills to regulate them. Words -- mine and others -- were more important to me than most people were for the majority of my youth, and I consider myself anguished but also fortunate to understand how much it can change the course of a person’s life to encounter an idea in someone else’s words and feel in your bones, “yes, exactly.”

I take AI writing very personally. The sloppy, careless, efficiency-minded use of language to say things without expressing anything true is an affront to the most reliable and cherished lifeline in my life. And I say all this, perhaps, just so that you can understand that if this intro essay sounds angry and mean-spirited, well, it is. I am mad at every single person who has done to my relationship with writing what violence did to my relationship with men: taint and irreparably alter it so that it will never be free of distrust.

I suppose what I’m asking of you is to be angry too.

In 2025, an analysis by SEO firm Graphite found that roughly half of newly published web articles are being generated by AI. Half. As in the same amount that’s being generated by human beings. On hellscape platforms like LinkedIn, that number is even higher, and even beloved writerly corners of the internet like Substack are rife with it (looking at you, technology writers). If it feels like you can’t do anything without seeing AI writing, you’re right. You can’t.

However, the more troublesome part is that for many, many people, that’s not their experience. Numerous studies have shown that humans are largely incapable of detecting AI-generated writing, and an oft-quoted NYT piece reporting results from a blind quiz taken by more than 86,000 readers even suggested that 54% of people preferred AI-written passages. PREFERRED! Over writers like Cormac McCarthy and Carl Sagan. Ah!

If that doesn’t cause you angst, you and I are cut from different cloth. But also… I want to start this essay series by trying to convince you that it should. You should care if what you’re reading was written by a machine.

I know how it looks to be a writer screaming that writers matter, but not 18 months ago, I was at a tech company leading a team whose sole focus was automating human tasks (i.e., “AI-enabling the workforce”). I’ve been on both sides of this war, and I am not anti-AI overall, even though I know much of what I write leans that way. But I am someone who loves efficiency, crisp processes, and technology in my deepest, heart-of-hearts. In my understanding of myself, I am as much a technological optimist as I am a creative. It is because I am both of these things that I have spent the last few years thinking about AI as a writing tool every single day, and only after those years am I coming to you to say that it matters whether what you’re reading was written by a human. It really, really matters.

As a professional writer (who cares more about this free Substack than basically anything else I’ve ever written), I agonize over essays. I think about each of them for weeks, test-run the idea with Logan, write 2+ drafts, delete them, rage quit, lose sleep, murder sentences I was attached to, vengefully reject Grammarly suggestions, and generally hold myself to the standard that everything I write should contribute to the net value of the internet. I don’t tell you that in a self-congratulatory way or with confidence that I always reach that bar, but just to help you understand what it is like to be a human who writes. There is so much care, humanity, self-consciousness, concern, and effort involved. And maybe my fellow writers are more effortless and natural than I am, but this stuff comes pretty naturally to me, and it’s still brutal.

But I think that writing should be an act of love and rigor because, for god’s sake, you could be reading Steinbeck, or Baldwin, or Austen right now. You could be catching up on sleep. You could be talking to your mom! Your attention is expensive, and it’s the least we (the writing humans of the internet) can do to treat it as such. In the same way that you should be angry when someone shows up late because that’s disrespectful to your time, you should be angry when someone asks you to read something that took more time to consume than to produce because it’s disrespectful to your intellect.

Quick note that, if you’ve been here a while (i.e., if you’re one of the 50 people who read this blog who know me personally), you might clock that this is a change of heart for me. In the past, I have been really optimistic about AI writing. I’m not sure I’ve completely reneged on all that optimism, but what I have come to understand is that writing is not like building Excel models, writing code, or updating project trackers. It is not a modern performance of economic value creation meant to be done in corporate costume. We are thinking, speaking, word-ing creatures who have, for all of history, used language to bridge the gap between our interior worlds and render something knowable that we can all mutually survive in. I may still think that AI can be a valuable writing tool--it certainly is for people like non-native English speakers who have full thoughts they need assistance putting into recognizable language, or for copywriters tasked with telling you how to operate a dishwasher-- and it may even be valuable for skilled writers who use it in limited and precise ways. The line I’m trying to draw in the sand isn’t as thick or as clear as “all AI for writing bad, down with the bots!” What I care about is that there’s real thought, experience, and belief being packed into words and delivered across devices, and that’s what I think you should care about too.

The internet is already teeming with arguments for why AI writing is bad, and a lot of them are excellent. I won’t rehash them in full, but so you know where I stand: it’s built on stolen IP, it crowds out the voices of legitimate craftspeople who are going to get economically displaced, it’s wrong (confidently so) all the time, and because it is always just a performance of next-word prediction (we’ll talk about the importance of this in the next essay), it can only ever produce regurgitated averages of existing human thought.

There’s also the fact that the more AI writing we read, the less literate we get. It relies on lowest-common-denominator prose that mistrusts readers, underdevelops arguments, narrows our shared lexicon, and generally makes us dumber.

If none of that matters to you, you might be swayed by the fact that it pulls our political, social, and emotional opinions toward a vacuous middle like some hungry black hole or weak-minded centrist politician who refuses to stand for anything. AI is writing opinion pieces and offering advice online that people walk away from, either intellectually neutered or relieved that someone has officially endorsed their softest-brained beliefs.

Still, the sentiment that has motivated me to write this series is simply that publishing AI writing, especially when trying to claim authorship for it, is a cardinal violation of the implicit contract between lingual beings (i.e. just humans and maybe parrots(?!), but I try not to think about that) that we will use our words to ease the solitude of being conscious entities who can only ever experience life from behind the pane of glass that stands between our minds and other people’s. Words are our most potent salve for the loneliness of being people who cannot walk amongst each other’s minds: they give us new ways to experience and coexist in the world that we can trust because we know they were given to us by someone who also has to live with the pain of being a conscious, lonely creature.

AI’s words do not, cannot, and will never do that. They are like fraudulent art, pasta sauce made without love, and all of the corrupted, horrible, modern things that should raise in us that awful suspicion that we are not okay. And even if you like AI writing or can’t identify it, my insistence to you is that if you are going to walk around spending your one, finite, irrecoverable supply of time and neurons on something nobody loved or agonized into existence, you should at least make that choice consciously.

So, welcome to my series: A Professional Writer’s Guide to Identifying AI Writing. This is the only piece that will be ranty and emotional, and the rest will provide you with practical advice on how to identify AI word choices, sentence structures, paragraph structures, argument structures, and tones. But it is my hope that you go in mad. Mad, motivated, and determined to wander through the AI content era with the skills to distinguish human writing from AI writing, and to use your time and attention to celebrate and promote the former. You’ll catch some false negatives and some false positives along the way, and I’m okay with that risk. You also might have to continue evolving your understanding of what you’re looking for as models get sharper and more sophisticated. But this contract has two parties, and for us readers to uphold our part of the deal, we have to be willing to wade through the muck to try to find the type of writing that makes us more human and more connected.

Thanks for joining. I’ll see you next week with part 2 about how LLMs produce text and what you need to understand to get how LLMs “write".”

Thanks—always, but especially now—for reading. Talk soon.

KL

This isn’t a fun thing to know about yourself. I wish I could say I was one of those sensitive, sweet, soft-natured kids that parents dream of, but even as a girl, I was too aware of my own vulnerability not to realize that to cut through the world, you have to be sharp. Youth is so terrifying and helpless, and I was not going to tackle it unarmed. The problem was that I wasn’t cuter, or sweeter, or more athletic than the other kids; I was only quicker-witted. So small social manipulations were my weapons of choice.

In theory, being a calculative little girl could make you seem cunning and clever to others, but that wasn’t my experience. Mostly, it made me self-conscious about my ability to arouse an instinctive suspicion in others that I was secretive and cold. I always managed to have friends growing up, but there’s a thin layer of frost that coats any relationships where one person’s trying to win a game the other person doesn’t know they’re playing. Even when I wasn’t being manipulative, I couldn’t seem to thaw that feeling for the life of me, and when I get married at the end of this summer, only two friends I made before the age of twenty-five will attend.

It’s also worth noting that in my late adolescence, I experimented with being highly passive, and I have nothing good to show for that either. Whether this was a resignation from being calculating or my ultimate commitment to it is hard to say, but from the moment I entered high school debate, I seized the opportunity to become someone new and found myself inhabiting the personality of someone sweeter, less selfish, and more docile than I am by nature. I went so far as to wear bows in my hair every day to visibly signal that I was metamorphosing: I was becoming a Sweet Girl.

That multi-year stunt landed me an outrageously popular boyfriend, unintentional membership in a social echelon I had no right to be in, and the adoration of younger girls who wanted to be me (I wish I wasn’t overstating that part, but being young is weird).

But I paid a steep price for my attempt at meekness. People took advantage of me, in what I now know are horrifying ways, and I let them because I was young, lonely, and resolute that I would never be a sharp, calculating little bitch ever again. I didn’t want to be cunning and sharp, something no one seemed to like; I wanted to be so soft that someone else would feel compelled to keep me safe. “Sweet” girls don’t need to be constantly plotting their next moves, I reasoned, because when you’re beloved, someone does that for you. That was the logic, at least. But it was not my experience.

All of this is just to say, I spent many years figuring out how to be a person whose first-line defense mechanism is to treat life like a game of social chess. I’ve lived and paid rent on both sides of the very thin line that divides self-advocacy from selfishness, generosity from self-evisceration, and strategy from callousness. I’ve felt the sting of being perceived as cold, and I also still carry the bruises of being passive in the name of being likable. I know the ups and downs, nooks and crannies, and all the contours of being a calculating person.

So when I entered the workforce and found an adultscape riddled with girlbosses and an imperative to “play the corporate game,” you cannot imagine the sense of relief that flooded me. Okay, I thought hesitantly but gleefully as I geared up to be a savvy, strategic, take-no-shit, working girl who would not manipulate others for personal gain, let’s try this again.

The working world is a sharp-edged place. Sometimes that gets played up in stereotypes and media representations of fields like finance, sales, and law, but the private sector really does have a time-honed reward system in place for people who know how to “play the game.” Of course, they’d never explain it this way, but almost all companies covet “high EQ” employees who can “manage stakeholders,” “influence without authority,” and “read a room.” That makes a lot of sense: companies are giant social organisms, and for many, the easy part of being a company is figuring out what to do, and the hard part is getting people to do it. Compelling people to do what you want (even when it’s not what they want) is arguably the central skill of leadership.

But strip back the sanitizing language of Soft Skills™, and, in the crudest terms, the working world is tailor-made for calculating people who are willing to roll up their sleeves and play some human chess.

I have always felt at home in the working world, and I’ve often wondered if, in some deep part of me, this is the true reason why. I’d like to think it’s because building a career is effortful and intellectually stimulating, but it’s more than that. I am awkward in most social settings, but I am never awkward at work. “You’re so outgoing and comfortable with coworkers,” my fiancé once noted when I was curled up in a ball on our couch after a single hour of having to interact with people in a group.

But friend groups are horrifying — so many emotional dynamics to track and manage (!) — and work is simple: it’s a dog-eat-dog world where everyone’s trying to get ahead, so everyone expects you to be a little bit calculating and show your teeth. At work, being a constantly-strategizing little monster is a good thing.

Form strategic alliances, campaign for your next promotion, make sure you’re the exact right amount of visible, impress the right people, avoid the wrong people, be intentional with your messaging, nurture your personal brand—I’d spent my whole life shamefully battling the compulsion to do these things in these terms, but the workplace is still the only space I’ve ever occupied where all of it is encouraged.

It’s comforting seeing the world like this, one large game of tactics and fellow tacticians. It provides so much certainty because if life is a strategy game, it means there are good moves and bad moves; costs, benefits, and probabilities. Yes, there are real human beings on the other end of all those things, but what of it? We’re all here by contract, not goodness of heart. They’re playing the game too.

And that is the crux of it, isn’t it? The logic we use to render the working world — maybe the whole world — a strategic battlefield in the first place? We must be calculating and self-interested because others will be too, and we’re at risk of being left behind. You play for survival, not joy, because if you don’t, you’ll get left behind.

Don’t hate the player, hate the game.

Over the past two years of writing this newsletter, I’ve dedicated a lot of words to telling people “you need to be more strategic and tactical about how you… speak, socialize, work, live, breathe,” and in the process of writing that advice, I’ve also gotten a lot of the things I wanted by following it. I love the type of work I do, and I do it from wherever in the world I want to. I own my own home. I’m productive without being compulsive. And when I look back at the work that makes up my career, I can truthfully say that I’m still proud of most of it.

But it is not lost on me that, after years of personally grappling with how Machiavellian is too Machiavellian, the advice I (and other career internet-talking types) tend to give leans heavily “strategic.” Treat your influence like a renewable resource, network, self-assess, and self-brand intentionally, sacrifice in “efficient currencies.” I stand by every single one of those takes, but I also feel increasingly wary of offering up more of them. A lot of career advice demands that, to follow it, you treat life like a game to be won and a career as something to be conquered. I’m not sure that’s a bad thing to do — I do it autonomically and reap the rewards.

But as we navigate this ever-changing workforce and economy, it feels important to say, even if just once: it is a perilous and lonely thing to look at your life and only see maneuvers, objectives, and obstacles. And I’m hard-pressed to believe that if we reduce it to those things, it will turn out any better for us as a collective than it did for childhood me.

One of the less charming ideas to catch traction with the Silicon Valley oligarchy class lately is the concept of an NPC, or “non-playable character.” The phrase is lifted from the gaming world, where NPC is used quite literally and neutrally to describe characters who exist only as ambient features of their digital worlds. They speak in scripts and have no stake in the outcome of the game. They’re just… non-playable characters.

Coming from the mouths (and more often, fingertips) of today’s tech and internet types, the term’s connotation is more sinister. People who fancy themselves active players in the economy describe their less fortunate, less ambitious, less “agentic” counterparts as NPCs to suggest that there is some sort of inherent inferiority in simply following life’s scripts. Loud and proud social strategists make no effort to soften their disdain for people who naively believe in rules and follow them. What fools, they act as if the world isn’t, fundamentally, a contest with winners and losers.

These people and their worldview haunt me violently. It is at once so familiar and so divorced from the moral dilemma that has always made me feel shameful and rotten about being a calculative person at heart. The nauseating part of seeing the world as a strategy game is how it colors your view of people. A lot of the time, they look like players, other contenders with goals and dreams, and the ability to affect the world. But sometimes, when you’re scared, deep in it, and governed by scarcity instead of compassion, other human beings stop looking like players in the game and start looking an awful lot like pieces.

The moral line that separates savvy girlbosses from Sun Tzu may be thin and worn, but even in my calculating mind, the paint has always been clear here: if you’re going to approach life like it’s a game to be won, you have to treat people like players, not pieces. Maybe not players of equal skill, but always of equal worth. You have to recognize everyone as someone who can suffer and inflict suffering right back. Even people who drew terrible hands are still thinking, feeling, playing characters in the game. You never treat them like pieces.

I’m sure that the first time someone used the phrase NPC as a pejorative, they felt awfully clever. It is clever — it’s a very succinct way of describing why some people never win because they internalize the false belief that their script was already handed to them, and their character just wasn’t made for success. But I fear that the proliferation of the NPC idea, and, more importantly, the underlying logic that makes it resonate with people, illustrates how far we’ve collectively drifted from our moral center. We’ve upheld our commitment to hate the game but spare its players. But the NPCs—they’re fair game.

Recently, I found myself up late at night reading about the ruling in K.G.M. vs. Meta et al., the first-ever social media addiction court case to reach a jury in the U.S. The plaintiff was a young woman whose family sued TikTok, Google (YouTube), and Meta for “intentionally” making their daughter addicted to social media. They argued that features like infinite scroll, autoplay, and algorithm-based recommenders were designed to hook young people’s attention in a way that causes anxiety, depression, and, in this girl’s case, body dysmorphia. This March, the court found Meta and Google liable for designing their platforms to cause addiction, and the family was awarded $6 million in damages.

Landmark decision and all its implications aside, the evidence from the case tells a harrowing tale of what it means to see people as pieces. Internal Meta documents lay out years of meticulous tracking in which Meta monitored the behavior of 11-year-olds to establish that they’re uniquely likely to be repeat Instagram users (never mind that the platform’s own minimum age for use is 13). One executive memo read, “If we wanna win big with teens, we must bring them in as tweens.” A federal court also found that Meta’s lawyers had explicitly advised employees to remove internal research documenting harm to teenage girls’ mental health. Maybe those lawyers hesitated to give that advice, but maybe they just thought that if they didn’t say it, someone else would. Don’t hate the lawyer, hate the game.

In different quarters of the tech kingdom, a Human Rights Watch report came out last year documenting how Uber and DoorDash systematically misclassify workers as independent contractors to intentionally deny them basic labor protections and use opaque algorithms to assign pay that often falls below local minimum wages. While three-quarters of gig workers report being unable to afford housing, Uber posted $9.8 billion in net income last year and has nothing public to say about drivers who depend on the platform for their income being removed erratically and inexplicably, with nowhere to appeal. Tough draw on that character script.

And, of course, there is the AI of it all, because what else is there these days? Most of the major AI labs have publicly stated that they anticipate hordes of NPCs are at risk of losing their jobs in the coming years. Those same labs are pressing on, accelerating the development of technology that would cause that displacement. Fear not, OpenAI walked back their claim right before filing for a trillion-dollar IPO.

These are awfully large and extreme examples of what happens when we render the people of the world into game pieces. I know that. I also know that it is easy to be a woman with a Substack and a sense of moral superiority.

But what feels easier, as someone whose mind is wired for strategy games, is to give in to the logic that we’ve entered an era of winners and NPCs and now is the moment to finally commit to trying to win the game.

The hard, and probably imprudent, thing to do is to resist the desire to play entirely. Go analog, fight the power, never use AI. There are people who can do that, and I salute them. Worry for them… but salute. However, as someone who expends an awful lot of energy battling the instinct to just succumb to the callousness, what I am reminding myself is this: the players end up lonely and sleepless too.

When I was in high school, there was a girl I was friends with who was smart, but not smarter than me. As an adult, that sort of thing doesn’t matter, but as a kid, you’ll clutch at anything that helps you understand who you are and if you’re worth anything. This girl was bright, and she’s gone on to live a good life (which I regularly check up on via social media), but one day she said something mean and embarrassed me, and I couldn’t stop the impulse to hurt her back. I mean really hurt. It was just that I could feel the intention behind her words. Takes one to know one, I suppose, but I’ve always had a good sense for when someone’s treating you like you’re a piece in their personal game of life. Their voices get softer and more imploring. Even when — especially when — they mean you harm. They jab at you, but only in front of an audience. Everyone working an angle has tells.

This girl’s words stung, but imagining her smug satisfaction at having gotten a few social points at my expense made me see red. Fine, I thought. If she wants to play, let’s play.

I took the embarrassment in stride, smiled, and didn’t respond. Over the next week, I discreetly crawled to every single boy she’d ever wanted to impress to disclose how hurt I was from the interaction. “I guess that’s what I get for trusting her,” I sighed, verbally squeezing my wounds to make the blood run publicly. When our mutual peers started calling her a fake bitch behind her back, I reveled in the sense of victory and relief. She wasn’t fake. She was also quite nice, for the record. But she started it. I just did what all wounded, scared, calculating people do best: drag her into a game she couldn’t win because she wasn’t even clever enough to play.

There’s karmic justice in reliving these memories in a mind no longer addled with the pain of being seventeen (and unmedicated). I physically recoil from the person I was then. Causing that hurt, knowing I’d won, made me feel so secure and capable of protecting myself at that time. She’s going to think about this feeling for the rest of her life, I genuinely remember thinking. The fear that your “friends” are saying cruel things about you behind your back was one I knew painfully well. It’s going to follow her forever. That was the victory. Pain will follow her just like it follows me.

I’ll never know if she ever thought about my feat of social engineering again. It’s possible, but if I were a betting woman, I’d say it’s more likely that she hasn’t.

The only person we know for sure is still tormented by that interaction is me.

I spent the better part of my childhood longing for a place where everyone thought like me. If I’d known that what I was actually yearning for was just the middle rungs of the corporate ladder, perhaps it would have lost some of its luster, but even today, the workplace makes me feel at home in a way no one else does because it’s designed for “strategic thinkers.” There are narratives to be crafted and change to be meticulously managed, and while everyone loathes an eight-year-old who compulsively influences without authority, in a good old open-plan office, you can influence to your heart’s content.

So when I say I understand the people who look out at our volatile world and see only a game to be won, I mean that from the deepest, truest part of my heart. I also mean it just as much when I say I think you should play too. The world is sharp, and if your cunning feels like the only thing keeping you safe, you are not wrong to reach for it.

But the line between gunning for a promotion and finding yourself burying legal evidence--the line that divides the players from the pieces--is alarmingly thin, and it’s easy to miss when you’re crossing it. If anything, it’s more like grooves in the road, invisible but violent, so that for anyone who isn’t an honest-to-god sociopath, when you drift over the line, at the very least, you feel it.

I’ve spent my whole life feeling around for that line and landing dangerously far from it — in both directions. All I’ve learned in the process is that all the world’s a game, even if only because that’s what we’ve willed it to be. If you play well, you will likely find yourself drifting over the line that stands between treating people like pieces and treating them like people. It doesn’t make you a monster if you do. Doing it in the name of the game doesn’t absolve you.

Carefully, keep playing. Just keep feeling for the line.

Thanks—always—for reading. Talk soon.

I, of course, didn’t know that. I was a freshman who’d mostly debated at a small, practically backwater league in Northern Nevada, had never had a real coach, and had never succeeded at the national level in high school. I was dating one of the best freshmen in the country, and that was what I’d had going for me. That, and I was a girl. Debate teams covet those.

Walking into the Georgia State season opener, I knew a sum total of nothing about college debate. I didn’t understand the complex legal topic about applying judicial restrictions to presidential war powers, and I didn’t want to admit that because all the other Emory recruits had been top-ranked high school debaters except for me. When my assigned season debate partner had a last-minute emergency(a music festival), I was paired with a random boy who had only ever debated in a different format, and I made peace with the fact that the tournament was not going to go well for me.

And go well it did not.

“Who are these guys?” I asked one of my coaches, while looking at the pairing that said we were debating Harvard in round one.

“Just some Harvard team. Think they might be juniors,” my coach responded. He made some loose suggestions about what type of arguments they might make (a very big mystery at the first tournament of the year), and let that be that.

There was only one moment before the debate started when I considered whether I’d been misled. Coaches from almost every school in the country had crammed into the tiny, grey-toned classroom, and a few of them had set up video cameras. Debate isn’t exactly a spectator sport, so that seemed a little strange. But what did I know?

I won’t tell you about the substance of that debate, partly because it’s irrelevant and partly because I actually have no idea what happened. I remember being confused. I remember a tall, condescending boy, whom I’d later go on to coach with at Harvard, telling me he’d generously offer me the entirety of a cross-examination period to try to explain my way out of two contradictory arguments I’d allegedly made (we’ll never know if they actually contradicted each other). I remember adults in the room laughing when he said it — really, truly laughing like they were at an SNL taping.

Above all else, I remember the judge’s “reason for decision” (RFD), an explanation judges provide at the end of every debate to talk through how they evaluated the arguments and to give the loser a thorough understanding of exactly why they lost.

Our judge had signed his ballot and started giving his RFD before we’d even finished shaking the Harvard boys’ hands.

Somewhere in a document on an old hard drive, I have notes about what he said about the debate, but those parts didn’t stick with me. All I remember from the RFD is the last piece of feedback that he delivered after he’d already begun packing up his stuff. Everyone was getting up to leave the room, but he paused, turned to us, and casually added as if the thought had just occurred to him, “By the way, judges generally like to vote for teams who seem… intelligent? And you two simply did nothing to convince me that was the case.”

When I found my coach in the hallway later and explained what had happened and what the judge had said, he shrugged again. “He’s not wrong,” he replied, brushing aside my devastation. “Shake it off, kid. We’ve got to prep for round two.”

Feedback is a sticky thing. For some people, even the idea of having to give or receive constructive criticism can throw their pulse into their throat and slicken their palms. I am no delicate flower, but I understand this viscerally. In my eight years of competitive debating and eight years of debate coaching, I received and delivered more constructive feedback than the average person will likely hear in their lifetime. Every single weekend, adult after adult would look me in the eyes and tell me not only that I’d done a bad job, but also exactly how bad and in how many tiny ways. Some of those people were gentle, but lots were not. Even when I started coming up on the winning side of the ballot, they were not gentle. Policy debates are judged exclusively by former debaters, people who voluntarily dedicated their lives and identities to recreational interpersonal aggression (and it shows). Also, crucially, when I say “people,” what I mostly mean is men.

I share this story of my first debate and my tragic extracurricular choices partially for your amusement, but also to make it perfectly clear: I know about feedback.

I’ve cried over it, made students cry over it, grown from it, and helped students grow. I know what it sounds like when it’s tactful, and I’ve felt what it feels like when it’s not. I have been told literally hundreds of times that I did a bad job thinking, explaining, expressing, and doing the thing I loved most in the world. I have told the same things to children.

So when I entered the workforce after leaving college debate, I felt unreasonably prepared for the world of professional feedback I was about to give and receive. What I discovered, to what I can only understate as my absolute horror, was this: the way we talk about feedback in the modern professional world is complete and utter trash.

Open a browser window right now and look up “how to give constructive feedback at work” (don’t actually, I did this part for you). There are endless tips, tricks, methods, and programs for you, and here’s just a sample of what you’ll find to help you learn to give feedback:

Looking for a model or process for structuring feedback? Try ASBI, BOOST, COIN, CEDAR, GROW, DESC, STAR, STAR-AR, Pendleton, the sandwich method, feedforward, “I like / I wish / what if,” RADAR, AID, CUSS, or the 360-degree review methodology, to name a few.

Want to read a book about it? You’re in luck because the very concept of giving feedback has spawned a small publishing universe: Radical Candor, Nonviolent Communication, Difficult Conversations, Crucial Conversations, The Fearless Organization, and Let’s Talk are all good places to start.

If online courses are more your style, try the six-module “Giving Helpful Feedback” program on Coursera, or any of the dozens of management trainings that include at least one module on feedback.

The amount of collective brainpower we have wielded in answering the question “how do I tell another grown adult they could be doing better?” is staggering. A quick skim of the vastness of corporate resources on giving feedback would make you think that delivering constructive criticism is the hardest thing in the world.

Look, an honest flow of feedback between peers and across organizational levels is pretty high on the list of things businesses need to meet the basic criteria for “functional.” Productive dissent and debate, generous and specific critique, high-trust feedback-rich environments… there’s no shortage of corporatespeak for “people tell each other the truth.” It’s important, no matter what you call it. You already know this.

That flow is also difficult to establish for a multitude of reasons related to digital communication, power dynamics, localized team dialects, and the like. Certainly, there is also a difference between productive and unhelpful feedback. But what the thousands of corporate L&D evangelists trying to sell you their books, courses, workshops, programs, frameworks, essays, and coaching sessions would have you believe is that giving feedback is so complex and challenging that it really demands all that.

However, for most people, the challenge of giving feedback is an emotional problem, not a tactical one, and in trying to make feedback feel easier by giving it the corporate ritualizing treatment, we have unintentionally made that emotional problem so much worse.

Of all the reasons that feedback might be hard for you, the biggest one is that it’s scary. It’s scary to receive, it’s scary to give, and that’s not because we’re all trembling, sensitive cowards. Receiving feedback often registers in the brain as a “social threat,” even before our rational minds have processed it. Even just anticipating feedback that could feel like rejection or severe criticism can make our nervous system go “DANGER!” making us say “AH! ” and get all hypervigilant, defensive, or even non-responsive. Everyone is naturally anxious about receiving feedback because we are biologically wired to interpret signs of social exclusion as survival threats.

Giving feedback is hard for the exact same reason. Initiating criticism can feel like instigating social risk: you might trigger reciprocal criticism, irreparably hurt someone’s feelings, be misbranded as cruel or unfair, or just be misunderstood in a way that could threaten your social inclusion in the herd. We don’t want to cause injury because it could create social threats for us, too.

TL;DR, it’s not our fault that we’re lizard-brained critters who don’t want to be kicked out of the group because we once needed other people to survive in the forest.

The good news is that in the past three thousand centuries, we’ve made some progress in growing brains that can learn to differentiate between perceived and legitimate threats. Fear is just an emotion, and emotions can be managed—especially the misguided ones.

The bad news is that the “Situation, Behavior, Impact” model you learned in your management training course is doing absolutely nothing to help you manage it, and if anything, it’s making it worse.

As it often is, the modern workplace’s answer to our pesky little nervous systems has been the same for feedback as it has been for most other instances of our emotions overdetermining our professional behaviors: ignore the root cause, come up with a mnemonic if possible, and give people some nifty tips for doing the thing the fear has made hard.

To be clear, feedback frameworks are not without value. “Situation, Behavior, Impact” actually is a useful mental model for ensuring your feedback is specific enough to be useful, and Sir John Whitmore’s “Goal, Reality, Options, Will” model can help you make sure feedback is future-focused. Taken in isolation, almost every feedback framework has something valuable to offer you if your goal is to take your feedback from good to better.

But the reason criticism doesn’t flow freely through most organizations isn’t that the average middle manager doesn’t know feedback should be specific. It’s because they’re terrified! And instead of telling them “no need to be afraid, that’s just your lizard brain, and this stuff actually isn’t a huge deal,” we’ve done the opposite. We’ve mythologized and ritualized the very idea of feedback so that, instead of it being this valuable thing that people just, you know, do, it becomes a ten-step ceremony where you have to say the right things in the right order, with the right acronym attached. With every book, framework, and five-hour workshop, we’ve dignified the utterly ridiculous idea that makes feedback seem impossible in the first place: that it is dangerous.

At one of my past jobs, employees were encouraged to give people advance notice before giving feedback so the recipient could “mentally prepare.” In theory, this sounds humane—let some get in the right headspace to be told that they suck at making slides. Sure.

But if you’ve ever been on the receiving end of a cryptic Slack about someone having “feedback,” for you, you know that there is nothing soothing about being told you’re about to be criticized. 72 hours of advance notice just gives you exactly 72 hours to ruminate on every mistake you’ve ever made.

More importantly, since when is telling someone they suck at making slides so devastating that it requires mental preparation in the first place?

When we ceremonialize the exchange of feedback and encourage people to handle it like some sort of feral animal that will shred people to ribbons if not caged behind the bars of a five-step framework, we valorize the idea of criticism as danger, and cede ground to our brain’s primitive core that is also responsible for making tons of people mortally afraid of sponges or anything with tiny holes. While it is great to want to make feedback more useful, the idea that we must equip ourselves with corporate L&D weapons like talking scripts and checkpoints to do so only reinforces the preposterous notion that, if we go in unarmed, horrible things could happen.

And as someone who was literally called stupid by a grown man when I was an eighteen-year-old girl sitting in front of tons of adults I admired, I feel more than qualified to tell you: nothing horrible is going to happen.

Feedback is not dangerous. Not seriously, and not in the long run. Even the most mean-spirited and poorly delivered kind that’s aimed at your jugular does not constitute an existential threat. Neither does the risk of someone giving it right back or getting mad at you for telling them they’re kinda slow at Excel.

The funny thing about words is that when they get into our bloodstream, they can seem like either the most poisonous or most medicinal things in the world, all while causing not a single ounce of actual harm or healing. I’d be the first person to tell you that language is important, but let’s be so for real. At the end of the day, feedback is just a ton of words. We’re the ones allowing them to scare us half to death.

The best and only way to get better at the art of feedback is good old-fashioned exposure therapy. Because just like with every irrationally scary thing that can’t actually hurt you, you need to prove to your finicky little nervous system that it is actually a primordial evolutionary relic, and it doesn’t know anything about anything. You’re afraid of feedback because you don’t have enough evidence that your nervous system is wrong about it, and the solution is to rack up proof that you’re safe — over, and over, and over.

That goes for giving feedback, too.

I didn’t acclimatize to giving feedback (and watching it be received poorly) until many years after my debate career had ended, and I found myself spending weekends in Lexington, Kentucky, letting nineteen-year-old boys cross-examine me after giving an RFD. More than one self-important college kid has snarked at me about how I judged their debates, and you know what? I’m doing just fine, and so are they. Feedback, it turns out, no matter which side of it you’re on, is a universally survivable thing.

Instead of letting the Feedback Industrial Complex convince you that it is absolutely critical to your existence that you learn the techniques of corporate feedback, my recommendation is to take a hearty step back and consider, just for a second, that it’s just not a big deal.

Relinquish the idea of giving better feedback (for now) and enter the business of getting and giving more feedback in frequent, low-stakes, unritualized ways so that you can learn how survivable it is. Go get proof that people aren’t going to lunge at you, claws out, when you tell them that they’re not good at presenting. Sure, you could do that by scheduling a meeting to walk through the “situation, behavior, and impact” of it all, or you could just pull someone aside like a normal human being and say, “Hey, I think you lost people’s attention in that presentation by spending so much time on the technical details. Just wanted to let you know, so next time you present, you can look out for it!”

See? Not a big deal.

The more you practice feedback this way—low-stakes, low-ceremony, high-frequency—the more you’ll begin chipping away at the actual thing that’s getting in the way of your feedback-rich dreams, and the less anyone (including the people you’re most scared of exchanging feedback with) will treat it like a gladiator event. If the tools and tactics help you give feedback in clearer and more instructive ways, that’s awesome, and you should reference them. But, friends, we have to drop the rituals and all the aggrandizement. It’s making us terrified and weird.

That man judged me again, by the way. He actually judged me dozens of times throughout my four-year college debate career because I “preffed” (ordinally ranked) him so highly as a critic that he judged (and voted for me) at more tournaments than not.

He has no recollection of telling me I seemed dumb — I know because we’ve talked about it. He’s judged thousands of debates, and that one doesn’t stand out to him. I don’t think he even believes that it happened.

What we both still remember is that the final time he judged me in my senior year, he gave me the highest individual speaker score I received in any college debate.

Thanks, always, for reading. Talk soon. KL.

Which jobs are going to be AI-proof in the next 10 years?

Oof, what a question. In the past few months, I’ve found it hard to be someone who both produces and consumes career-related content without bumping into this question. It lingers in search trends, comments sections, and even my typically writerly Substack feed. But it’s understandable: the world has felt pretty dark and destabilized as of late, and most people just want to know if they’re going to be able to pay for housing in five years’ time.

But in truth, this question troubles me. Partially for the obvious reason that it’s disturbing to witness large, well-educated swaths of the population panic about basic job security, but also for the less obvious reason that the question reflects what I consider to be an unproductive fixation our society has with “jobs.”

I say “jobs” with emphatic scare quotes because, despite how we talk about them, jobs are nothing more than arbitrary, man-made task containers that organizations price for convenience. It’s the pricing part, I suspect, that makes us all weird about it. And while it would be nice to think that the bundling and pricing is driven by sound reasoning and objective market forces, the fact that there are people wandering around in broad daylight with job titles like “Wizard of Light Bulb Moments” (i.e., marketing coordinator) and six-figure salaries is all you need to know to understand how little hard-coded economic logic is at work.

Contrary to the way job listings make it seem, companies don’t price jobs; they price the people in them. And while salary ranges are often decent estimates for what the average qualified candidate will be worth, they’re loose indicators at best. Maybe that’s obvious when there are jobs on LinkedIn with $80,000-$250,000 ranges, but as someone who was privy to salary negotiations for many years, let me tell you: you’d be amazed at how a salary range can shift for the right candidate. Jobs don’t have inherent value, and they certainly don’t have predictable security guarantees. The World Economic Forum can publish as many reports as it wants, but the world’s leading labor market forecaster in 2002 could never have foreseen that their daughter would become an iOS engineer in 2026. And not for lack of imagination, but because job markets have always been tumultuous and capricious, and singular people and products (like the iPhone) can topple even the best-forecasted trends. And at the pace things are changing? To me, it feels like a fool’s errand entirely.

But wholly irrespective of tasks and how they’re bundled into jobs, the logic that has governed what makes people valuable and employable has actually stayed quite consistent over time. A standout job candidate can double their salary at the offer stage for the exact same reason that a beloved executive assistant can become one of the most job-secure people in the world, despite administrative job postings having decreased by 13% since the launch of ChatGPT: some people just think differently. About all tasks. Any tasks. Literally anything and everything they do. What those people know, and what AI is now forcing the population at large to confront, is the enduring truth that how you think, not what you think about, has always been the primary determinant of your fungibility in the workplace. The only thing that’s changed is that silicon thinkers have entered the chat.

There are many frameworks and heuristics for explaining how people think, but as a recreational (read: non-expert) neuroscience reader, I’ve found a few mental models particularly helpful for understanding the implicit hierarchy of workplace thinking. Daniel Kahneman’s popular System 1/System 2 framework and Robert Bramson’s five thinking styles model stand out, but, as far as I understand, contemporary neuroscience is rich in support for a hierarchical view of cognition. Some types of thinking are simply rarer and more sophisticated than others, and some types of people are simply more capable of them.

From my experience working across a variety of industries and functions, what I’ve come to believe is that all organizations contain three basic, industry-agnostic categories of thinkers: executors, problem solvers, and problem identifiers. Kristen’s Unscientific Taxonomy of Workplace Thinkers, if you will (or KUTWT, if you’re my fiancée who delights at random acronymizing). And long before Claude began instigating existential dread in millennials, career security was heavily determined by which of these categories you belonged to.

KUTWT Explained

Executors
The most abundant type of thinkers in the workplace is executors, people whose approach to work is to consistently do a great job at the things they’re told to. While the majority of these people hold administrative and associate-level roles, they can be found up and down the org chart. But just as late-twentieth-century knowledge-work offshoring has threatened many of these people’s careers for decades, AI has accelerated their displacement.

While great executors are necessary in every workplace, the type of thinking required to be a great executor is straightforward, procedural, and precision-focused. Executors do work such as interpreting and following plans, noticing errors, optimizing within constraints, and generally thinking about the question, “How do I do this correctly and quickly?”

If the neuroscience of it all matters to you, this type of thinking is mostly confined to the cerebellum and maps quite neatly to Kahneman’s description of System 1 automaticity and basic cerebellar loops for habit and motor control. In other words, it’s simple, highly definable thinking that’s guided by clear inputs and outputs. Most people can do it; most people can be taught how to do it; and, unfortunately, so can AI. Executors are, while valuable, as fungible (read: job insecure) as they come.

Problem Solvers
Problem solvers are a little better off. Often clustered in middle-management and high-level individual contributor roles, problem solvers are thinkers who can figure out how to fix problems and achieve goals others have set for them. Fortunately for problem solvers, they’re perfectly suited for the majority of problem-solving challenges that arise at work. When you interview them, they’re the type of people who tell you that they “work solution-backward” because, regardless of what task bundle they own, they apply analytical and creative reasoning to their work. Think (haha): convergent focus on trade-offs, root causes, and bounded options that allows them to work through complex problems to find the best solutions.

This type of thinking sits in our buddy Daniel’s System 2 category of deliberate reasoning, which engages prefrontal networks for hierarchical control and white matter pathways that converge on optimal solutions. In other words: complex stuff. Complex enough that problem solvers are often fast risers early in their careers because the complexity of their thinking allows them to self-differentiate quickly in junior, execution-heavy roles. If you’ve ever managed a team of associates, you know that these people are not hard to spot. While great executors are an asset to any team, problem solvers make the difference in keeping teams focused on the right tasks and breaking down walls.

Unfortunately for problem-solvers, they often stall out in middle management, and while they’re unbelievably valuable, they are not particularly rare. Reasoning skills—like assessing trade-offs and performing root cause analyses—are basic tenets of most people’s undergraduate education, and the rush to trim the fat in middle-management has already placed problem solvers who are not also wickedly effective executors on thin ice in the current economy.

Problem Identifiers
But that brings us to the problem identifiers, the final tier of workplace thinkers who are responsible for the indescribably challenging work of figuring out which problems need to be solved in the first place. These people, often leaders, look not just at the problems they know, but at the whole world around them, the infinite bits of context that comprise a company’s universe, and draw on a very elusive and advanced type of thinking to figure out which problems to give to the problem solvers.

Final bit of science for you: problem identification, as we understand it, draws on a very distinct neuroscience profile that can help explain both its current rarity and its resistance to both training and AI replication. Problem identification occurs through flexible prefrontal networks and parietal areas that detect subtle signals (think: feelings) before logic even kicks in. It would be reductionist to call it intuition, but that’s a part of it. Problem identification recruits numerous areas of the brain to scan multiple contexts, reframe situations, wrangle ambiguity, and eventually produce signals, so to speak, that we experience as gut feelings that something is wrong, even when it looks right. Unlike the automatic, cerebellum-driven thinking of executors or even the targeted, prefrontal path-driven analysis of problem solvers, problem intuition demands divergent thinking (yes, my neurodivergent friends, the type of thing your brains are good at), contextual intuition, and creativity. In the simplest language I can give you: it’s rare because a whole lot of your brain has to be doing a whole lot at once. But without people who can do it, organizations solve the wrong problems, make nonobvious yet devastating mistakes, and put on their own corporate productions of much ado about nothing.

Over the years, I’ve had a lot of friends, students, and employees ask how to improve at this type of thinking, and, to my dismay as a former debate educator, I don’t think I’ve ever succeeded in helping anyone do so. I’ve seen exceedingly motivated debaters passably mimic this type of thinking, but there is a palpable difference between students who “get it” and those who don’t, and I’ve never seen someone truly close the gap. Problem identification is ephemeral, philosophical, and rooted in a combination of intuiting, context-sensing, social sensing, and pattern recognizing across loosely connected domains. You can arguably teach all of these things individually, but how to combine them to see cracks where other people see smooth surfaces? I don’t know if you can.

I will also note that organizations don’t exactly incentivize this type of thinking, even though they’re reliant on it. High-nuance problem identification often looks like musing about which types of organizational knowledge are axiomatic rather than well-reasoned or hypothesizing about the theoreticals. It is particularly philosophical, as far as workplace thinking goes, and pulls you out of the world of “what” and “how” and strictly into the territory of “why” and “what if.” Unsurprisingly, most companies would actually prefer you don’t sit around philosophizing about your job, especially in this “agency” and speed-obsessed economy where the Silicon Valley Messiahs (SVMs, if you’re Logan) won’t stop talking about their pathological bias to action. The result is something of a paradox: problem identifiers are essential, but too many are a headache, making their rarity both problematic and necessary at once. I’ll leave you to ponder that on your own.

I recognize that it’s not exactly encouraging to read that only a small subset of thinkers engage in work in a way that makes them career stable, but what I hope to offer you with genuine optimism is this: if you can reckon with this reality and admit where you fall within it, it is likely the most valuable and instructive insight I can share to help you navigate the impending future.

Understanding what type of thinker you are and where the threat to your career comes from may be the most constructive thing any of us can be doing to make sense of what we need to do next.

If you’re an executor, step one is likely recognizing that AI may be a legitimate threat to your work. And while there will always be a place for exceptional executors, I suspect that workplaces of the future will demand that executors also be problem solvers and that problem-solvers be great executors. Perhaps that’s cause for solace: many problem solvers loathe execution, feel too good for it, or simply don’t have the stamina for it, and unlike problem identification, problem solving is a highly trainable critical-thinking mode. Practice using frameworks like mind maps and “why” trees. Seek out bounded puzzles (I nonfacetiously think you should pick up chess), volunteer for ambiguous tasks, fail fast, and watch your problem-solving colleagues like a hawk. Executors should certainly be learning to use AI for efficiency, but my totally unprofessional take is that if this were the type of thinking I excelled at most, I would be disproportionately putting my time into building my problem-solving skills.

I suppose for problem solvers, the imperative runs the opposite way. The more companies collapse jobs into “player-coach” roles, the more critical it will be that problem solvers dust off their execution chops and either get very good at using AI for task execution or get very comfortable rolling up their sleeves and doing precision, detail-oriented work themselves. You may not need to develop your skills, but you do need to defend your reasoning skills ruthlessly. Form and communicate opinions without AI. Do the tiring thinking without asking Claude. I know I can sound like a critical-thinking extinction doomsayer, but the downside risk of erring on the side of thinking for yourself is so low. Keep your efficiency-seeking far from your thinking, and work on ensuring you can still execute like a twenty-one-year-old Bain consultant. Play around with Claude Cowork, but also: have faith. There’s so much perceiving, sensing, and reasoning that AI still can’t touch.

My final words of warning are to the problem identifiers, even though you’re probably feeling pretty good by the end of this essay (if you made it this far, that is, in which case… thanks for reading!). But if you have the great privilege of being able to activate your whole brain at the same time to see things other people can’t see, you only have value to lose. The threat AI poses to problem identifiers is not in its capabilities but in its allure: the shiny, sexy, enticing appeal of making things just a little easier. One day I will stop writing newsletters about this, but it won’t be today: the hard parts are the point. Keep lying awake at night, haunted by the nagging feeling that something isn’t right. Continue to ponder past the point of reason. Think until your brain hurts so badly that only swimming or reality TV can soothe it. Hold the indescribable parts of being a thinking being close to your chest. Even when the calls from California are telling you to automate, shortcut, and keep up. They don’t know which jobs we’re running toward either.

Thanks—always—for reading. Talk soon.

Jogging past overgrown yards, I would jam my big toes into the fronts of my running shoes while tears streamed down my cheeks because I didn’t know what else to do: I was barely two years into my career, and it felt like it was already over.

My first job out of college was coaching competitive debate at Harvard University, followed by several years of coaching at Northwestern and Dartmouth. Coaching had not been my plan; competitive debate was the thing I’d been good at for eight years, I’d given up most of my life for it, and technically I’d already been coaching high school debate for three years, but I’d always thought that when debate was over, I’d go on to do something… else. I wasn’t sure what, since I was too busy with debate to think about it, but certainly something awaited me on the other side. Then graduation rolled around, and I felt the way anyone might have if they’d committed their whole life to one thing that disappeared in a single moment: lost, terrified, desperate to cling to whatever scraps of it I could, and horribly, debilitatingly empty.

In spite of my parents’ hesitations and my own sense that I was basically grinding a mud-crusted boot heel into the applied math degree I’d suffered for, I went into coaching for the simple reason that I was scared, and it was the least scary thing to do. I knew I could be good at it, in a moment in my life when I suddenly couldn’t remember if I’d ever been good at anything at all.

After caving to the soul-cracking amount of pressure I’d placed on myself to get a “real job,” three years later, I found myself under-employed at a marketing agency, paying my boyfriend’s rent and crying every day while running nine-minute miles past professors’ homes.

While there is nothing wrong with coaching debate (many of the smartest people I’ve ever met are debate coaches, and I will forever feel indebted to a small number of them for improving the course of my life), getting out was a relief. There is a low earnings ceiling looming over coaches’ heads and a brutal life sentence to being tired, stressed, and sick from traveling all the time to indulge in an activity that is suspiciously attractive to people with Cluster B personality disorders. I’d stayed, in part, because I was heartbroken about losing the thing that had always served as the center of gravity in my life, but also because I had no idea how to explain to people why I’d done it. How do you tell a hiring manager the type of resilience you build by constantly listening to people you admire pick apart your intellectual failings? What would it matter to a private company that I’d won a national championship, but not the important one? Unsure how to answer these questions, I jumped at the first non-debate job I could get at a marketing agency, and let out a big exhale. I had escaped having to explain myself and my career choices. For now.

I never talk about that marketing job because I didn’t learn much there, but in some ways it changed my life. People liked me at that job, and despite my continued inability to describe my past, my peers in that office respected me, which made me respect myself. I felt trusted, even though I was younger than my colleagues, and I found people coming to me with questions that neither of us knew the answer to, because I was good at figuring stuff out.

“Can figure out anything” became the first thing I could name about myself and my professional value. Within a year, I was lobbing out job applications like Tinder swipes, and when the CEO of a boutique management consultancy said in an interview, “You don’t really experience imposter syndrome, do you?” I answered honestly that no, I don’t. I’d spent many years afraid that I lacked the skill to break down the doors that stood between me and a high-growth career in business, but not once had I ever felt that if someone let me in, it was even possible that I’d fail; nothing I could do would ever be as hard as college debate was. To this day, nothing has been.

After four career pivots through marketing, consulting, strategy & operations, and eventually executive ghostwriting, where my career is currently parked, I’ve learned the hard way what it takes to build a “non-linear career,” a term that’s picking up a lot of endorsements right now from job-market prophecizers. Non-linear careers are the stuff of the future. They’re the only AI-proof path. They’re necessary since the traditional job market feels like a garbage fire inside a forest fire, inside a fire tornado (not an actual claim in the discourse yet, but consider it my personal contribution). Journalists, investors, and leaders all seem to think that the traditional career ladder with its sandpapered rungs and perpendicular angles is a thing of the past, and people need to embrace the winding way of the industry-switching, side-gig accumulating, non-linear career.

Whether these speculations are right or not, it’s not my place to say. While I’ll note that the watchers who warned of “AI layoffs” are also now whispering about “AI-layoff rebounds,” it does seem like more and more people are interested in non-traditional careers, if not simply because we’ve become petulant and impatient as a society and we think zig-zagging makes us richer faster (admittedly, it kind of does and did for me). But as someone who has dedicated many miles to jogging (and weeping) away the misery of trying to career pivot, I feel strongly that if we’re going to propagate the idea that people should be pursuing non-linear careers, we owe it to them to include a thick addendum packet that includes, at least, a bold-face, red-font warning that building a squiggly career requires dozens if not hundreds of laborious, emotionally-confronting reps telling your career story and enduring the doubt and loneliness that follows when you can’t get people to understand it.

Imagine, if you will, the following situation: you are a guest at a dinner party where you don’t know anyone, and a nice stranger who strikes up a conversation asks you about what you do. Beaming with pride, you share that you are actually one of the best underwater hockey left forwards in the world (real sport, not kidding). You’re a machine on the pool floor, and you can hold your breath for over 50 seconds during active play!

The nice stranger looks at you and smiles. “Oh!” they say politely. “Wow! That’s… good, I take it?” You nod. It’s very good. Excellent actually. Pivoting the conversation to make sure you also ask about what they do, you spend the cocktail hour learning that they run a prestigious private equity firm.

By the time the salad course comes around, you’re feeling chummy. “I’m actually hanging up my goggles soon, and hoping to go into finance,” you share with your companion between bites of frisee. “Underwater hockey takes a lot of discipline and pain tolerance--the exact same kind you need to make it in a finance career. And I think my years of captaining the team and the leadership skills I’ve built will make me a real asset in the workplace.”

“Totally,” your companion agrees with a sympathetic look before quickly turning around to talk to someone else about a deal they’re trying to close.

Maybe I should have mentioned that I manage the team budget, you think while staring at your plate, no longer feeling hungry.

This is what it feels like to try to pivot your career.

Switching careers is gnarly — both practically and emotionally. For starters, no one will tell you, but you need to develop exceptional storytelling skills in order to introspect about your experiences, create a compelling and accessible pitch for yourself, and deliver that pitch to strangers who know nothing of whatever career you’re leaving behind in a way that makes them feel like taking a chance on you.

If that sounds difficult, it’s because it is. My most exceptional and differentiating skill as a professional is breaking down complex systems and ideas, identifying what’s essential, and communicating it persuasively to others, but even for me, applying that skill to my own career story makes me sweaty and weird. There are countless reasons the act of crafting and sharing your career narrative is hard, but for most of us, the very worst part is just talking about ourselves confidently and humbly at the same time. “I promise I can do this. I don’t actually have any evidence to indicate that’s true. But I do know I am great at things that should make me great at this, too!” is not the world’s best sales pitch, which means it can’t be the one you give. To build a truly non-linear career, you need to narratively draw a bold, intelligible line through all of the turns and twists and make strangers believe that not only were all those zigs and zags sensible (as opposed to flighty or indecisive), they were actually brilliant and make you more qualified to do a job than someone who has already proven they can.

Perhaps a tactical guide to doing this awaits you in the newsletters of Christmas Future, but for now, all I mean to say is this: building the skills to succeed in a new career isn’t even close to being the hard part — building the skills to convince other people you can categorically is.

Because it takes a lot of practice and skill to pitch your way through a non-linear career, the other challenge you have to be prepared for is the emotional tenderizing process that is trying and repeatedly failing to convince people that you deserve a chance.

The internet is littered with solid wisdom on how to handle rejection and persist until you find a “yes” in an endless sea of “no,” so I will not add to it here. But there is a uniqueness to the blow rejection lands when you’re in the middle of a pivot. If our professional identities and confidence are built on successes that prove to us we are good, wandering around with no such proof can feel incredibly vulnerable and a lot like working at a used-car dealership where you are both the dealer and the car.

At the height of my frenzy applying to non-debate jobs, the thing that gnawed at me with the sharpest teeth was wondering whether I actually wasn’t cut out for the roles I wanted, and worse than just deceiving (or rather, failing to deceive) hiring managers, I was also deluding myself into thinking the things I’d done in debate qualified me to do literally anything else. I found myself asking, “If I can’t make people believe me… is it because there’s nothing real to believe in?” I had no evidence one way or another, but if no one seemed to care about any of the accomplishments I had dedicated my whole youth to, did that make me the idiot for forming my identity around the idea that they ever mattered in the first place?

Melodrama of being twenty-four aside, it is needlessly hard to hold onto the conviction that you can change your career and succeed when you have nothing to tether that belief to. Pivots require you to develop the brazen confidence and self-trust to believe in your potential in the absence of any confirmation that you should. In stepping away from a world you know, even if it’s one you’re dying to escape, and into the unknown of a new career, you render your achievements and in many ways yourself illegible to others. While that doesn’t invalidate the merit of what you’ve done up until that point, it does sit you down face-to-face with the confronting truth that, for many of us, our self-confidence rests not on our achievements but precariously on the foundation of others’ ability to understand those achievements as a sign of what we’re worth.

The problem isn’t that you’re not good, it’s that you only learned how to explain why you’re good in the words and symbols that were most legible to the people in the world you’re trying to leave, and in order to make it out, you have to get to the bottom of who you are as a professional and explain what makes you one of one in language that anyone can understand.

Learning to do this takes time and practice, but nobody in the world has better insight into what you’re capable of than you. You are the world’s leading authority on your past, your skills, and your potential, and if the story you’re telling about why you know you can succeed isn’t landing, you don’t need more spin or new language to make you legible; you need more truth. You need to look honestly, discerningly, and kindly at your career history and your achievements to identify the truest story of why you’re excellent and what that means you can do.

If I can impart any wisdom from my decade of debate, let it be that when forming an argument, bells and whistles can buy you a lot of cheap wins, but the best arguments aren’t snazzy; they’re good. They’re evidence-backed, they’re well thought-out, and they’re persuasive because they’re true.

Many professional skills and experiences are highly transferable, and the people who are advocating for non-linear careers are not lying to you when they say that being able to draw lessons and insights from different contexts does differentiate you in the working world. But this job market is grim—even for highly experienced candidates applying for roles they’ve already held. Maybe it’s true that there’s never been a better time to start a non-linear career, but there may also have never been a harder time to try to explain to people why they should let you into an industry where the current residents are already clamoring for jobs. Pivoting is hard, emotional, identity-threatening work, and the worse the job market gets, the more and more people you will be competing with who are also trying to do it.

But as a life-long career zig-zagger, what I’ll leave you with is this: it will not be just the transferable skills and a brain-numbing cover letter Claude wrote to “adapt your resume to the job description” that gets you your next job. Your non-linear career depends on the story you’re able to tell about where you’ve been and what only you can do. And load it with all the keywords you want, but in a market like this one, the most important thing you can do for yourself is take the time to figure out how to tell a story that’s true.

Best of luck,
KL

Networking, pitching, interviewing, and even just making new friends and dating all require some degree of autobiographical storytelling, and while they range in formality, they all require you to explain who you are and what you’re about in ways that are clear and, ideally, compelling. The type of storytelling we do in our professional lives rarely necessitates divulging every minute of our lives to date, but in some ways, that makes it harder. Out of our millions of experiences, we have to figure out which narrow set we can share to best help people understand how we think about ourselves and how we want them to think about us, too. No small task.

And yet, most of us have very little formal education in storytelling techniques or even meaningful experience practicing memoiristic storytelling. More than that, most everyone (save the absolute worst of us) is at least a little uncomfortable talking about ourselves because we don’t want to be perceived as self-important or boring. But especially as AI technology improves toward being able to express almost everything except for subjective experience and the creator economy continues to drive up the value of “personal brands,” which have become a foundation for millions of dollars of economic value, being able to tell your story has arguably never been more important.

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Admittedly, I’m biased. Just under a year ago, I traded in my charming little job leading operations at a software company for what had long been my dream job—ghostwriting. I know that most writers don’t want to be ghostwriters, and I get why. It’s all of the work with none of the credit, and there’s something about the opacity of it all that can make it seem more nefarious than it is.

But for me, executive ghostwriting is an actual dream. Getting to write for other people is like acting for those of us who love characters and stories but can’t seem to control what we do with our eyebrows: you meet immensely interesting people, study them in excruciating detail, try to understand them deeply, and in turn, you get to help them study, understand, and explain themselves. Equal parts writing, acting, and therapy, ghostwriting is one of the most interesting things I’ve ever done, and while I’d be grateful to never write another LinkedIn post for someone in my life, I’m never happier than when I’m interviewing someone to help them figure out how to show people who they are.

Beyond being fun, it has also been a fantastic crash course in memoiristic storytelling. In helping people sort through their lives, find the most compelling moments, and put them into words that feel true to their experiences, I’ve learned so much about what works and really doesn’t work in telling people about ourselves. So, if you find yourself struggling to communicate your personal identity, brand, and story in a way that resonates with others, here are a few of the most important lessons I’ve learned in the past year that can help you craft an honest and interesting narrative about who you are.

Stories live in scenes, not summaries.

Back when I was dating, I occasionally asked men a specific question if things started to get serious: “What story from your life feels most representative of your childhood?” Hard to answer, and usually something you need to give people a day or two to think over, but it has always been the best tool I have for understanding someone’s relationship to their family and their life so far.

For the record, I do know that this question is annoying. But we are who we are, and I’d rather be annoying and informed about the person I’m about to hand my heart over to than ignorant and charming. And besides, learning to identify the moments in your life that embody the broader stories you tell yourself is a wildly useful storytelling skill. So really, we were all winners. My interrogation victims included.

When describing our lives, we have a natural proclivity to represent them as a chronological series of major plot points: “I did X, then I did Y, then I did Z.” This impulse makes sense because, for us to cohere the multitude of experiences we have, our brains have to package them into neat little narrative arcs that help us form a stable sense of self. That’s great for our purposes — essential, even. But unfortunately, the Wikipedia summary of your life and everything that has happened in it doesn’t make for a particularly compelling tale.

To make people care about your story, you have to let them into it as it happened. And to do that, you have to tell it in the form of detailed scenes that let them experience, not just understand.

For example: The time it started pouring rain (because, of course, it did) as you stepped outside at work to get some air after receiving terrible news, and your hair dripped onto your keyboard when you tried to get back to work. The night your friend slept at the foot of your bed and woke up with bruises on her hip from the hard floor, simply because you got dumped. The way you learned you hate the taste of champagne, but drank half a bottle with your business partner at 1 pm on a Tuesday anyway, because that’s when your company sold, and nothing else felt like it mattered.

These types of vignettes might feel too granular to share when you’re talking about yourself, but, on the contrary, they are among the most potent tools you have for making your life visceral and meaningful to others. Sensory details, in particular, act like Velcro, creating a textured, hook-filled surface in our stories for people to latch onto, because our brains stick themselves to details like the fact that you spilled orange chicken on your white shirt right before the interview but got the job anyway far more easily than they attach to something like “I was tired, but I got the job anyway.”

Carefully chosen, detail-heavy vignettes can also be (and ideally are) emblematic of the broader “point” of your story — the conclusions you drew from the things that happened to you that inform who you are in the present. As my poor ex-boyfriends all know, this process of sharing representative stories is hard to get right, but it’s something you can reflect on at any time to help form a version of how you describe your life that can connect people to the thematic arcs of your personal story (think: “I healed,” “I worked harder than anyone,” “I got knocked down but got back up, etc.) This is the “show not tell” skill that editors harass writers about constantly, but it really does change the way your storytelling feels.

Think of it this way: I could tell you that my father was a big supporter of all my pursuits, or I could tell you about how he became a certified referee when I was in middle-school soccer so that he could ref other games and bring back competitor intel at tournaments. I could also tell you about the time he watched hours of YouTube videos on how to jump-serve a volleyball, then took me to a snow-covered beach at dusk in February to teach me until my fingers were so numb that the pain stopped feeling real and my serve started getting better.

Both of those stories tell you slightly different things about my father, and I might tell one over the other depending on the setting, but the point remains the same: both stories are infinitely more interesting than if all I let you know was “my dad was pretty involved.”

Sometimes, people need to get inside your head (a brief lesson on interiority).

One of the most powerful things about writing (or speaking) that sets it apart from visual storytelling media is that it’s uniquely good at letting people inside your brain. Writers do this through something called interiority: the term for all that happens within a character’s point of view. And while you need not concern yourself with the techne of internal narration vs free indirect discourse, learning to add a balanced amount of interiority to your own storytelling will make it substantially easier for people to feel like they actually know you.

The operative word here is "balanced" because, just as we are hesitant to talk about our lives, we’re especially hesitant to talk about our innermost thoughts. My experience with clients is that the lower someone’s confidence, the more likely they are to be unnecessarily guarded about their thoughts, which can make them seem closed off. The people with unreasonably high confidence… well, they’ll tell you every clever little thought they’ve ever had, making it feel like you’re being held hostage inside their brain. The trick is finding the middle ground by identifying which moments actually demand that you let people in.

The test I use when writing for people, and one I recommend you start with is asking yourself this question about your stories: “Was my reaction a natural response that anyone would have, or is there something specific about my POV that you have to understand to get why I felt/acted that way?”

Some feelings and thoughts are near-universal, which makes unpacking them seem self-indulgent. Someone died, and you felt devastated? No need to explain. But you got fired from your job, and the first thing you felt was relief? You could afford to say a little more.

When I say “more,” I don’t mean just write out “I thought I’d be upset, but I was actually relieved to never go back to that office.” What I mean is you need to let people into your inner world that explains the feeling of relief. Was that a job you took because it was someone else’s idea of a good job? Did you realize you’d been shape-shifting into a version of yourself that you didn’t like every time you went to work? These extra lines of introspection help people make sense of who you are, and like it or not, when you’re telling your story, you have to treat yourself like a character with motives, feelings, and reactions that make sense to others -- just like every great literary character.

If you want an example of memoiristic storytelling that does this well: Shoe Dog by Phil Knight. To be fair, Shoe Dog is a true showpony for every tip I have for you in this newsletter, but it is a particularly masterful display of thoughtful, balanced interiority. The way Knight describes his feelings about how he was showing up as a husband is a great template for helping others understand you—not just your story—by letting them in. Even about the stuff that makes you feel shy. Especially on the stuff you feel shy about.

The worst thing that’s happened to you is not necessarily the most interesting.

Of all the ways I find myself redirecting and challenging people’s beliefs about what makes their story compelling, this is the one that comes up most often and is hardest to convince people of. But hear me out: even if you’ve lived through some horrible shit, the worst thing that’s ever happened to you is not the only reason you’re interesting.

I understand why people assume it is. We are living through a media era that is hypersaturated with stories about trauma and hardship. Every time I get on TikTok or LinkedIn, I feel like I hear a story about someone’s struggles and how they overcame them, and while I’m not saying these stories shouldn’t get told, they’ve begun to feel compulsory, as if we implicitly agreed at some point that you don’t deserve a platform unless life’s given you a requisite amount of grief.

Even outside the media, stories of pain serve as credentials in unexpected spaces. When I was thinking about going to business school, I talked to several students at Stanford GSB who described their campus tradition of students sharing personal histories with their cohort, and they all mentioned that it has become something of a “but how have you suffered” tournament. Even in some of the world’s most academic environments, the message about how to think about your own story has succumbed to the idea that the worse it was, the more it counts. We’re being taught daily that our success matters more if we clawed our way up from something, that our agency is more impressive if we scraped it from the dirt.

The problem, beyond the emotional cost of leading with your wounds and the risk of being branded by your victimhood rather than by everything that came after, is that centering your hardships in your story declares that your suffering made you interesting. And maybe it did, but in case no one else has told you, let me be the one to inform you that you were interesting anyway.

One of my favorite projects in the past year was writing a TED Talk for a business leader who was invited to share her story. There’s not an iota of doubt in my mind that this woman has seen some hard days, but one of the joys of working with her was we never talked about them. We discussed how she was precocious, self-aware, and unusually intuitive for a kid. We talked about her adulthood and how she’s always found it easy to act in her own self-interest and enforce personal boundaries. From out of the womb to the top of her career, the moments that mattered to her, the ones we wove together into her story, were all stories of confidence and grace.

In hindsight, it’s not surprising that of all the people I’ve written for, this woman was the one who felt no need to air her trauma. To her, the whole point of her story was that she’s always known who she is and been comfortable with it. She’s the embodiment of someone whose identity has been built around narratives of innate deservedness not survivorship, and the more I sat with that, the clearer it became to me that if we let go of the fear that our story won’t matter (that we won’t matter to others), we can start to allow ourselves to get closer to the things that make us innately big, not just the things that have tried to make us small.

If you need your own examples, Yvon Chouinard, Anna Wintour, Warren Buffett, Roger Federer, and, yes, still Phil Knight are all figures who are endlessly interesting and have captivated the general public for decades with no redemption arc or suffering narrative in sight. These people’s stories interest us because of their unusual perspectives, unique strengths, sustained success, and earnest likability. And while you might not have the exceedingly good taste of Anna Wintour, there is probably something about you that is rare, intriguing, and unique to you.

Sometimes the bad things that happen to us are the inciting incidents for our journeys and need to be explained for people to understand our choices. If that’s how your story goes, tell it as such. But sometimes the bad stuff that happened is only that… bad stuff that happened along the way, not the turning point or climactic moment that you think it has to be for people to care about you. We are all capable of loving and rooting for people who haven’t experienced great harm or who don’t make that harm part of our relationship with them. So if you’re struggling to figure out what else you could have to say, go embark on the ego-fluffing journey of asking the people who love you. Ask them what they find most interesting about you and what their favorite part of your story is. My bet: it won’t be your pain.

Wishing you all the luck in the world, telling your story. Talk soon. KL.

P.S. If you’re a founder or leader who can’t figure out how to tell the world who you are… You know where to find me.

Admittedly, I probably err too far on the side of excluding AI from my daily life; I’m fearful of the unintended consequences of rapidly advancing, unregulated technologies and dubious about lining the pockets of those who disproportionately benefit from AI-ifying everything. But I am also not so naive as to believe that the Luddites are about to come out on top. I’m an AI critic, but not a skeptic: I don’t think the believers are wrong that AI has the capacity to transform how we do almost everything, and even if I did, history is all too clear on the futility of betting against men who wish to pillage new technological frontiers.

So I find myself asking the only realistic question it feels like we’ve been left with: what exactly should I be doing with my little computer helpers? It’s tempting to believe the right answer is “as much as you can,” and perhaps, if your telos is to frack every last bit of economic value from the trenches of your own behaviors, that’s your path. It’s not mine. I’m inclined to believe there is a thoughtful, balanced, bespoke way to use AI in my daily life that maximizes the value of my time and intellectual freedom while minimizing harm to myself and others. A girl with a dream, you might say.

While fumbling around for this ideal use state, one of the things I’ve been trying to do is shed the false sheen of novelty that new leagues of “narrative engineers” are shellacking AI tools with. Yes, figuring out how to work with AI is a uniquely twenty-first-century problem, but figuring out what to do when you have an army of task-absorbers at your disposal is anything but. People managers have been working through that exact same question basically for as long as organizations have had layers, and leaders of large organizations have already grappled with the question of what to do when you’ve got functionally infinite resources at your command. Human delegation is not a perfect analog for AI delegation for a number of reasons, including the differences in speed, cost, and emotional implication between giving work to a human and an LLM, but the basic manual already exists and is filed under decades of management theory.

The Age-Old Problem of Giving Work Away

Delegation is famously hard, in no small part because nothing you do before you reach a delegation-heavy role in your career really prepares you for what’s next. The path to management jobs is often paved with years of individual contributorship, during which employees are encouraged to hoard, take, do, and do more—the exact opposite of delegating. In school and associate-level jobs, we teach people to show their ambition and commitment by taking on every ounce of work they can. That behavior gets you hired and promoted, as it well should, except it then lands you in those oh-so-coveted management and leadership positions with a maladaptive tendency to grab at every task you can get your sticky little fingers on. Delegation is universally one of the hardest skills for most first-time managers to hack because they’re normally coming off of legendary runs of stuffing their cheeks full of problems instead of thinking about how to divvy them up. All to say: anyone who has ever taken on their first employee could tell you that delegation does not come naturally as an extension of any skill we teach or reward early in life.

But it also doesn’t get that much easier with time. Being good at a task neither makes you good at instructing someone else to do it nor at knowing when to give it away, and many of the managers who’ve been at it for decades are still only marginally better at discerning what work they should keep vs. release. This challenge, arguably, becomes more simple as you grow to manage more and more competent people. With highly specialized resources available, who should do what becomes obvious: of course, the lawyer should handle the contracts for you, and the engineer should write the code, even if you are capable of making a passable attempt at both.

However, as most leaders discover, the increased ease of delegation that accompanies getting more resources is often accompanied by a new and far more existential challenge: if you have a team capable of doing nearly anything as fast and as well as you can… what exactly are you good for?

AI has suddenly catapulted most of us into answering this question as we sit at our keyboards, staring at the equivalent of a team of highly specialized helpers capable of almost anything.

Learnings from the Delegation Greats

Peter Drucker, an Austrian consultant born in the early twentieth century and monickered “the man who invented management,” was perhaps the first to state the central philosophical question of delegation: what can only I do? It’s a question that lands with greater weight at the top of an organization, where, in theory, nearly everything can be given away, just like nearly everything can be given away to Claude if you really put your mind to it.

And just like we expect leaders with large teams to still do something (and something of value, we can assume, given that the market in 2026 has priced the average annual pay of an S&P 500 CEO at around $18M), the ability to give away all your work does not mean there’s wisdom in doing so. Some things (although shockingly few), leaders can only do themselves.

Alfred Sloan, the former CEO of General Motors and something of a Greek hero in management lore, was known as a profoundly good delegator. At GM’s peak, he had 500,000 employees under his control, and he was both thoughtful and generous in how he gave away work. He was not known for being overly involved in low-level decisions or territorial about high-stakes strategic ones. Most interestingly, he was famous for setting aside significant time for no tasks at all, other than wandering around his factory floors and seeing what was going on.

If you think that sounds Big Brother-ish, fair. But that’s not how his peers and employees characterized it. Accounts of Sloan describe a trusting man who was not on the floor to terrorize employees or micromanage—he walked the floor because it was where the substance of his business existed, and he didn’t want to find himself out of touch with the world he was responsible for making decisions about. He could have asked for reports, poked through summaries and readouts, or done anything else to absolve himself of that floor-walking sensemaking process and focus elsewhere. But with a near AI-level helper force at his disposal, Sloan used his precious time to do the thing that only he could: develop his own understanding of what was really happening at work.

In High Output Management, former Intel CEO Andy Grove--another famously good delegator--prescribed a similar philosophy: a manager should spend time on whatever has the highest-leverage organizational output, and often the highest-leverage thing is simply being in the room to observe. Grove saw clearly that the risk in overdelegating lies not just in giving away tasks to people who are less capable of them, but in giving away so much that you become a stranger to the very nature of the task you assigned in the first place. Grove was careful to keep himself enmeshed in customer interactions, the happenings of front-line employees, and the actual mechanics of the business he was stewarding. He seemed to understand implicitly the same thing Sloan did: time is not the only currency you’re trading in when you decide which tasks to own or give away. The value of removing yourself from an activity is almost paid out in time given back to the delegator. The price, however, is always paid in the loss of awareness--and dangerously, comprehension--of the activity itself. The question in delegating then becomes not only “can somebody else do this,” but “can I afford to lose the experience of doing it myself?”

The Human Zone of Genius

Ever since I first read it, I find myself thinking incessantly about this Hollis Robbins essay on why AI can’t write like humans. In the most reductionist terms, Robbins argues that there is a functional difference between what humans do when we write and speak and what LLMs do. When humans write and speak, we use words as signifiers: tools for reflecting languageless experiences into the minds of others as faithfully as possible to our original experience of the thing. In doing so, we create something that resembles shared reality so we can go about building relationships and making choices on common ground. That, as an aside, is so freaking cool.

Now, when AI writes, it is doing no such thing because there is no original experience to be signified. AI connects words to words, tools to tools, and abstractions to abstractions. When an LLM explains something, it is signifying a relationship between signifiers, not experiences. There is nothing true, visceral, or real in the mix. There are only interpretations of interpretations.

You can think of this like a leader getting a secondhand report from a manager who has interpreted a report from their own employee. What you’re working with is this: an employee’s experience, rendered into an imperfect interpretation of it, interpreted by another person, who then reports on their interpretation of the first interpretation so that you too can interpret it. Yikes. Because all AI can do is offer us interpretations of interpretive tools, we should expect all of its sensemaking to be about as high-fidelity as a secondhand report of a report. This type of abstraction tax is something that people like Sloan and Grove were highly wary of, and from my own experience trialing AI as a sensemaking tool, I propose that they might have been onto something that has become crucial for all of us to know.

Experiencing may not sound like a skill, but to the contrary, it really is. Discernment and decision-making--two things you’ll find on most leadership skill lists--are, after all, mostly a matter of having a really strong grasp on reality and its interrelated pieces and parts. Good judgment is mostly built on seeing the world as it is, free of the filters through which ego, insecurity, and self-interest distort most people’s sense of what is right, and being able to decipher the world in honest, undistorted ways is as much a professional skill as any of the other nebulous things like “taste” that we’re celebrating in the AI era. But, given that we may be headed down a path toward a task-free world where most of what we do is deciding instead of actual doing, it feels particularly critical that we nurse the skill of making sense of what’s real.

“Well, yeah, duh, humans are the ones who have to experience reality,” you might say, but look around, and you’ll see how tempting it is to give away this category of task and how often people are doing it.

Deciphering the world around us is the ultimate ambiguous task: no one can really tell you if you did a good job, and if you mine your history for indicators that you’re good or bad at it, you are certain to find both, meaning you’re likely to fixate on the signs that you’re bad (because we’re all just anxious little things, aren’t we?). When assessing our own judgment, most of us cherry-pick the moments when we should have seen the signs earlier, known better, realized what was happening, and stopped the disaster that, in hindsight, became obvious. Of course, there are people who do the opposite, but their situation is perhaps even more dire because AI is famously sycophantic and just reinforces their belief that they’re always right. But for the majority of people with fragile self-trust, AI is the most tempting of companions precisely because it’s so damn confident in its takes on things it’s never experienced. When we relay a tough interaction and ask if it thinks our boss is secretly disappointed in us, it promises us they aren’t. Maybe it’s right. But it wasn’t AI’s gut that twisted when our manager said, “It’s fine.”

We also ask AI to make sense of our business realities. When we ask it to review pages of customer feedback and identify themes and takeaways about how our customers feel, AI may reach the right conclusions, but it may also underestimate the exasperation conveyed by a single ellipsis…

Analyzing, synthesizing, coaching, and all sorts of names obscure the reality that when we ask AI to make sense of our own experiences and interactions, we are delegating the only type of work that can keep us close to reality. That might be incredibly practical for our calendars, but it will not serve us over time. Of the few things that only we can do, this is perhaps the most defensible one.

Humans’ understanding of the world is built on thousands of micro-signals and moments that we cannot truly share with AI. Even if we could, we’d be doing so with language, through which reality is, at best, very effectively signified. The feelings of suspicion, discomfort, intuition, momentum--the type of intelligence we feel in our limbs and our abdomen--these are artifacts of human intelligence that we, and only we, are capable of producing because at our core we are sense-making beings who are hardcoded to interpret infinite signals at all times so that in the changing world around us, we can always stay warm, fed, and dry. Our machinery is designed for interpreting and expressing what we believe is going on. AI’s is well… not.

This, by the way, is also a very good reason why you should feel guiltless about handing off a bounty of other tasks to your AI helper workforce. A non-trivial portion of the goo that fills up modern knowledge workers’ days is, if we’re being so, so honest, a cheap pantomime of computation. Formatting decks, updating budgets, tracking expenses, scheduling across time zones, filing the right thing in the right folder… The modern economy has tricked us into decades of cosplaying as robots, doing the kind of rote administrative processing that truly is suited for computer intelligence—the kind of thing that LLMs can do faster, better, and without resentment. But the opposite of those tasks, the feeling, living, perceiving, and sensemaking--I believe those are ours, and they reside in what psychologist Gay Hendricks would call our Zone of Genius--the surface area of all the things that we are not just great at but that also improve and nourish us in the act of doing them.

How to delegate has always been an identity question of sorts, a decision about not just what we can and should do but what kind of people it makes us to keep the work for ourselves. Many of business history’s best delegators knew that you could give away nearly everything and still be essential, provided you never gave away your grip on reality, the thing that entitled you to the power to delegate to tens of thousands of people in the first place.

Our LLMs will not quit if we overwork them, and our lives are not companies that will fail if we delegate poorly, but as we sit with more delegative power than most people in history have ever had, we will have to fight to deserve it. How you do that is your choice to make, but holding on to the reality of what’s happening on your own factory floor is where that fight starts.

How was I to know?

Incomprehensibly to me, I was the child of two chemical engineers who had founded a software company that sold optimization models in the nineties… a hard job to describe to a six-year-old. I’m not sure my parents ever even tried explaining their jobs to me, but my mom was a great cook, and my dad could play any song you asked him to on the piano, so it was inconsequential to me. I had all the information I needed to admire them.

Equipped with only Hollywood-induced delusions of what adults do when they grow up, I responded to Ms. Castlehill’s prompt with something resembling a ballerina. I’d considered whether I wanted to be a spy, but that seemed harder to draw, so it was the ballerina life for me.

I went on to quit ballet at the age of twelve, by which point my parents had sold their software business to a company that IBM would acquire two years later, sending my parents into retirement. My mom would come into our kitchen one morning while I was eating cereal to show the acquisition announcement in the Wall Street Journal. I was happy for them because it was clear that I was supposed to be, but I still didn’t understand what they’d done. It wouldn’t have mattered anyway; I was taken with writing poems in brightly-colored journals and reading Civil War fiction. It was too late for their careers to overdetermine my own because I had already found my calling: I was going to be a writer.

Between my parents exiting the workforce and my entering it in 2017, a lot changed in the world. I got my first iPhone, the United States got its first reality-star president (the first time around), and influencers entered the scene. Facebook acquired Instagram, the Theranos story broke, and San Francisco bloated with software engineers who had more money than friends. And at some point in that decade of dizzying technological and social change, CEOs and tech entrepreneurs Mark Zuckerberg and Elon Musk became two of the most famous people in the world.

Despite being the genetic byproduct of two tech entrepreneurs, if you’d asked me to name a single founder or CEO in my childhood, I would have barely had the wherewithal to say Steve Jobs. I knew there were people who became founders, but they held little intrigue for me. Why would they? Who were those people next to the likes of Jane Austen or C.S. Lewis? What did they matter to my peer group of aspiring astronauts and ski racers?

In hindsight, I find this ignorance odd. While I wasn’t one of those kids who tore apart laptops, I was innately curious. I’d also always been entrepreneurial; by ten, I’d sold watermelons at the beach, started teaching myself digital photography so I could sell portrait sessions, and loaned a few thousand dollars from my parents to “start a vending machine business,” with my sister where we batted our eyelashes at local landlords and installed vending machines in offices without paying any costs. As far as archetypal “founder” childhoods go, mine was definitely in the ballpark. I had upper-class entrepreneur parents, a probably hereditary knack for making my own money, and the self-confidence to ask people to pay me for things I had no qualifications to sell. It wasn’t like the business world was millions of miles away; I just didn’t know who was running it.

In some ways, the meteoric rise to fame for Silicon Valley CEO-founders that would take place in my teenage years made a lot of sense. As the CEO of Meta, Mark Zuckerberg is responsible for Facebook, Instagram, and WhatsApp, the three most-used digital apps in the world. And while Musk’s most far-reaching contribution to the average consumer’s life, PayPal, existed long before he was catapulted into Tesla-fueled mainstream fame in the mid-aughts, serial success made him an easy emblem for the 2000’s rendition of the eccentric-founder prototype established by the likes of Bill Gates and Steve Jobs in the eighties. Running companies worth as much as entire countries is an understandable reason to be famous.

And yet, if you asked the average American to identify a picture of Larry Fink--CEO of BlackRock, the world’s largest asset management firm, responsible for assets thirteen times larger than Tesla’s market cap--they likely wouldn’t even know who you were talking about. They’d also probably strike out on Jane Fraser of Citigroup and Doug McMillon of Walmart. Even though they’re all rich and powerful.

People have been creating economy-changing businesses since the inception of global trade, but their celebrity is a new phenomenon. Yes, leaders of successful businesses have always influenced policy and been people of power. But while it’s understandable why Johan van Oldenbarnevelt never became a household name, you still don’t hear kids pining for the career of Henry Ford.

However, in 2020, arguably one of the hardest years in modern history for business owners, 66% of teens ages 13 to 17 not only aspired to be entrepreneurs but actively said they were likely to become founders when they grew up. Last year, Y-Combinator reported a 110% annual increase in applicants age 18-22.

Somewhere amidst buying the film rights to founders’ lives, moving the S&P 500 with single tweets, disavowing long, traditional careers, and accumulating sickening amounts of wealth of it all, CEO-founder apparently became one of the hottest jobs in town.

Last week, while airing our AI doomsday grievances over Factime, a friend sent me Sam Kriss’s fabulous essay Child’s Play. Broadly speaking, the piece is a pointed and vivid indictment of the tech industry’s drift toward AI-fuelled outsourcing of basic human thought, a subject I soapbox about on the regular. But as part of his argument, Kriss includes a harrowing portrait of Roy Lee, the widely hated twenty-three-year-old CEO-founder of the “cheating” AI tech startup, Cluely. In the middle of the profile, Kriss and Lee discuss the founder’s early-life ambitions to start a company, and Lee shares he knew he was destined for founder-dom “since the moment [he] gained consciousness.”

“‘I could do things that other people couldn’t do,” [Lee] said… “And I feel an internal, indescribable fury when someone tells me what to do.”

Isn’t this the Lord Voldemort origin story? I texted a friend while passing along the essay. Lee’s sentiment struck me as almost comically banal: a woefully brilliant young man is shackled by normalcy, sickened by the mediocrity of his peers, and enraged by the prospect of not being in control, to the point that he has no choice but to pursue complete, corrupting power. “Overdone and uninspired,” an editor might say if you wrote a character with this backstory. “Readers wouldn’t buy it,” if you tried to turn the same person into a hero.

But here we find ourselves: deep in the storyline where, to many young people, and young men in particular, the tech CEOs are the heroes, the world they built, a dreamscape.

And make no mistake, it is their world. One where we wake up in the morning and autonomically reach for the devices they built, to open the apps they profit from, to check the headlines they dominate—all before we’ve kissed our partners good morning.

Even Lord Voldemort was too soft-ambitioned to imagine such subtle but infinite power. He just really didn’t want to die.

Not so long ago, the kids I colored and skinned my knees with wanted to be firefighters, baseball players, and singers. Sure, every first-grade class had a bad egg who swore he was going to be the president, but even he would have to get elected if he wanted to reign supreme. Yes, maybe someone’s dad ran a furniture business that their child aspired to take over, but that boy wasn’t dreaming of power. He just wanted to sell couches and make his father proud.

Then our dads stopped selling couches because Jeff Bezos figured out how to get them to people’s doors faster. The kids in older grades came back and told us not to become dancers or journalists because we wouldn’t be able to afford it in the rapidly gentrifying cities the tech elite were settling into. Right before our eyes, the grown-ups lost their houses, accumulated debt, divorced their partners, and turned up the volume on 24/7 broadcast news, filling every corner of our houses with bad news and vitriol.

Our heroes were economically leveled down to losers, but it is no coincidence who rose in their stead. Today’s economic “winners” came into power the same way all villains do: on the backs of a few “compelling ideas” that “actually make a lot of sense when you think about them,” and with offerings to our most base impulses, collective good be damned. This lot sold us widgets first and ideas second, but the message has always been the same: the world is changing, and you can either be a winner or a loser, but the choice is up to you. The path to being a winner is simple, we promise. Use our devices, believe our beliefs, and you will not get hurt.

It doesn’t take a history buff to recognize this story, and it doesn’t take an avid reader to know how it ends.

The idols of today’s youth are so different from the uninspiring corner office crowd of generations past. They’re bolder, more vocal, more uninhibited, more like them--children, that is. They speak their minds and break rules like eight-year-olds: with a gleeful, almost giddy sense of independence and nothing but hope that they won’t be caught.

Yes, we’ve challenged the reign of the silver-haired CEO, an archetype that was ripe for revision and affords only white, straight men reason to believe they can be in charge. But we have not replaced these archetypes with those men’s equally qualified female and minority counterparts.

Instead, what we’ve offered up is the hypervisible, refreshingly irreverent, uber-famous, venture-backed founder CEO. 97% of whom are--unsurprisingly--white men.

It is hard for a child to imagine the old-fashion path to power---all the good stuff sits too far on the other side of effort, struggle, and time. But the new-age tech founder’s life is just barely out of reach. Twenty-somethings can usher in millions of dollars (from investors, even if never from consumers) without any experience, a college degree, or so much as a single agreeable trait. They are, by all literary standards, villain-types. And we put them on the tallest pedestals we could find.

As the AI boom ushers in a new class of renegade “geniuses” to take up the mantle of keeping fame’s bright light on Silicon Valley, we are finally meeting the children of the celebrity-founder era. And, of course, not all of them, but crucially, many of the most visible of them, are exactly what you would expect.

Lee and his founder counterparts (Aravind Srinivas, Palmer Luckey, and Daniel Gross, to name a few) don’t aspire to be good or even well-liked, just free of the suffocating imposition of archaic systems like, you know, a liberal arts education or basic social courtesy. They just want to “build things.” What things? Anything that takes the shape of a ladder leading straight to the nouveau-American Dream, where winners like Zuckerberg, Altman, and Co. can get more than just wealth and comfort, but impunity and absolution too.

Finally, we are face-to-face with a cohort of teens, twenty-somethings, and even thirty-somethings who want to be founders because they want what all great villains want: not just simple money but “fuck you money.” The type of power that is so absolute that you never have to play nice because you can just rewrite the rules to make the nice guys lose.

To be clear, even setting the moralism of it all aside, we’ve led these people horribly astray.

Maybe I just wasn’t cut from “agentic” enough cloth, but I suspect that if half the kids who aspired to become founders were forced to run a small vending-machine empire, they wouldn’t be nearly so keen on becoming business owners. For every Mark Zuckerberg and Sam Altman running around California, there are thousands of founders floundering through down rounds and learning the hard way that a job without a manager is not the same thing as a job where you’ve escaped the tyranny of having to think about others.

Even without understanding my parents’ jobs, there was rarely a day in my childhood when the air in our house wasn’t heavy with the weight of their responsibilities. Our dinner table saw somber conversations about what to do with struggling employees, impossible decisions debated with dark circles under everyone’s eyes, and endless discussions about how to make the choice that is right, and good, and fair. I didn’t have to understand linear programming to feel the burden. Even without selling a single watermelon, I could have told you that entrepreneurship can bring you many wonderful things, but it does not make you free.

Even if it did, feeling too clever for your own good as a middle schooler is a dangerously bad reason to try to find out.

Entrepreneurs are often brave and incredible people; they carry some of the heaviest burdens and work some of the most demanding jobs on the planet. And, to be so abundantly clear, I do not think it is wrong to want to start a business any more than I believe that every bright, misunderstood child is destined for villainhood. The two people I love most in the world are founders, and I only found my third favorite person because a man I eventually worked for for many years had the audacity to build a dating app.

But what, I wonder, will our children’s children want to be when they grow up? Perhaps there will always be ballerinas among them; I suppose that’s up to us. Or perhaps we already know the ending. After all, how do you answer the question of who you want to be if all you’ve ever wanted is to answer no one at all?

Thanks—always—for reading. Talk soon.

Most of it falls into what I’d call the Totally Innocuous and Generally Obvious category. It’s true enough, hurts no one, and you could have figured it out yourself. Think: “don’t burn bridges.”

But every now and then, I encounter advice that really makes me mad. It’s normally stuff that sounds reasonable or is passing through generations on inertia alone, but that is, in practice, a reliable path to undervaluing yourself, avoiding the things that matter, or staying exactly where you are while wondering why nothing is changing

This is my running list of the worst offenders: the advice I’ve received, believed, and in some cases had to unlearn in very unfortunate ways. Here’s to hoping you can learn it the easy way.

Let your work speak for itself.

I have always wanted to know who started the rumor that your work will speak for itself. While it’s true that good work doesn’t require a PR campaign to prove that it’s good, the idea that you can just show up to work, do a great job, and everyone will notice is woefully naive.

Few people in life get what they deserve simply by the nature of deserving it. While you should certainly work hard to produce things that deserve recognition, you have to couple deserving something with going out and asking for it.

As someone who worked on a People team, let me tell you: you’d be shocked to learn how many of your coworkers are actively petitioning for promotions and raises on any given day while you are hard at work. Coworkers who you’d be horrified to find out believe they deserve a raise.

Sorry to tell you, but the people who get promotions and new opportunities are the ones who ask and fight for them. Your job has no reason to give you something you’re quietly waiting for. It costs them nothing for you to yearn in silence, especially if you believe that just doing even better work is what’s going to unlock your next raise or stretch project.

Tell your manager your goals, share the work you’re proudest of, and seek opportunities to make your best work visible. Waiting to deserve something and waiting to get it are both hard games, but only one of them ends.

Don’t be afraid to enforce your boundaries at work.

Before you get your panties in a twist, I obviously believe that people should be able to preserve their basic dignity and well-being at work. No, work should not be able to tear at every last thread of self-respect you possess. But if you find yourself in a position where your work is constantly undermining your dignity, the advice you need to hear isn’t “protect your boundaries”; it’s “get out of there now.”

But with the proliferation of therapyspeak, a new generation of employees has entered the workforce, armed with the misguided advice that aggressive self-preservation is the only way to survive the evil and exploitative nature of work.

Look, I’ve worked some gnarly jobs. I get what work can take from you. But most people’s jobs aren’t that exploitative, and when you’re hyperfixated on work-life balance, steadfast in the prioritization of your non-work activities, and inflexible with your time, you also shouldn’t be surprised that you’re having a bad time at work.

The walls you build around you to protect the conveniences and comforts of your non-work life are also standing between you and your next promotion or opportunity. But more importantly, and the thing I think we’re not talking enough about, they’re standing between you and the sense of fulfillment that comes from sacrificing to achieve something hard. Work becomes purposeful when you let it take hold in your life as an arena for building your character and self-confidence. Sure, “protecting your boundaries” will mean work can never take those things from you. But it also means it will never give them to you either.

Don’t ask for so much money; it makes you seem arrogant.

As a deeply self-conscious woman who places a lot of implicit value on self-awareness, the idea that when negotiating for money, there’s a perfect number you can say—one that’s both ambitious and self-aware—used to be the most attractive idea in the world to me. In my early career, I would spend dozens of hours benchmarking salary data, putting together pitches for my promotions, and rationalizing my way into salary asks, sign-on bonuses, and little crumbs that couldn’t possibly make people think I was better than I actually was.

Then someone gave me another piece of advice on negotiating money: say the highest number you can without laughing.

The idea that you’re going to be branded as entitled for asking for the high end of what you think you’re worth just isn’t true. It’s not. The research doesn’t support it, and even if you make the other person laugh, the reputational damage doesn’t last.

So don’t try to seem reasonable. Try to seem confident. And next time you have to ask for money, imagine that the person you’re asking is definitely going to agree with you. What number would you say if you knew they’d say yes?

Say that.

Never cause trouble.

When I was in college, I had the privilege of listening to John Lewis talk about the importance of good trouble. He attributes the idea to Rosa Parks—that in a world full of inequities and problems, there are necessary types of “trouble” we have to cause to make things change.

For me, this idea makes the shortlist of sentences that meaningfully changed my life. Like most young girls, I’d lived the majority of my life wanting to be someone “good.” I wanted to be helpful, useful, and never trouble to someone else. I was told I should want to be those things. Over and over again.

When I entered the workforce, I was told it again: “Don’t cause trouble.”

It took thinking of John Lewis, over and over, for me to remember that sometimes trouble is exactly what an organization needs, and sometimes you’re the right person to cause it.

There is, of course, a version of trouble that is always worth avoiding: drama, score-settling, personal grievances dressed up as principled dissent. Nobody needs that, and it’s not what I’m advocating for. But good trouble—the kind where you name the thing everyone is pretending not to see, push back on the decision that’s going to hurt people, or refuse to let a bad idea go uncontested because the room feels too fragile for honesty—that trouble is often the most valuable thing you can contribute.

Of the moments I’m proudest of in my career, many of them involve standing up in rooms of people who were older and more senior than me and saying “no” to ideas I thought could hurt people. These don’t always look like big, moral stances. For me, they’ve often meant saying “that half-truth will confuse people, and they deserve more information.”

Good trouble doesn’t always look like hard-lined advocacy. It can look like gently nudging people toward greater empathy or asking them to consider a problem on a longer time horizon.

But mistakes and mistreatment thrive in silence, and silence thrives in organizations where no one wants to get in trouble. You’re a grown-up with a brain, a set of values, and the ability to wield them both. So, go on. Cause some good, necessary trouble.

Don’t step on people’s toes.

Anyone I’ve ever managed would tell you that I loathe the sentence “I don’t want to step on anyone’s toes.” It is one of the phrases an employee can say to me that is most likely to make me rant (and I’m pretty easy to spin up into a rant).

But this toe-avoidant nonsense almost always comes from the mouths of the most agreeable and considerate employees I know. And most of the time, when they’re worried about stepping on toes, what they’re actually worried about is provoking people with delicate egos who have planted territorial flags all over problems that they’re not actually solving. But work is not 18th-century land; you cannot claim it by naming it after yourself and then leaving it alone.

If you’re the type of person who is worried about “stepping on toes,” I assure you that the advice you actually need is to go steamroll some toes. It sounds like politeness, but avoiding messy problems with weak ownership claims is cowardice in professional clothing, and, en masse, it produces organizations full of very polite people who are very busy not doing what needs to be done.

If you know you can help, you’re willing to put in the effort, and the only obstacle is that someone else hypothetically should be doing that job, crush as many digits as you have to in order to do what’s best for the team and the business. Yeah, you might bruise some egos. But they can take it, and so can you. I promise.

Thanks—always—for reading. Talk soon!

Namely, not a single part of it is good advice. I actually find it so disagreeable that in the process of writing an “all the worst work advice I’ve ever received” newsletter (coming soon to an inbox near you), its badness demanded more space to breathe. So I would like to adamantly insist on the opposite. You need to work harder, not smarter.

The Era of Ease

First part first: you should probably be working harder.

While there’s no shortage of laments about how Gen Z doesn’t work hard enough, the growing distrust and disinterest in hard work are hardly endemic to twenty-somethings alone. Yeah, the youngins have disavowed the corporate ladder. But millennials en masse are also itching to leave their jobs and “quiet quitting,” a term coined in 2022 to describe the anti-hustle culture choice to do the absolute minimum at a job instead of actually leaving.

Across the board, we all seem to have grown a little tired and disillusioned with hard work.

And of course we have. We live in an aesthetic hyperreality where the appearance of ease is an ever-appreciating currency. Get on Instagram, and you’re inundated with vacations, ozempic bodies, and the daily lives of hot people who seem to make gratuitous money by simply existing. Get on LinkedIn, and people are SHOUTING about how they Grew Their Side Business To Seven Figures In One Month With One Simple AI Hack! Wow!

We’re drowning in shortcuts, growth hacks, and promises that whatever it is you want, there’s a “secret” to getting it. Working “smarter” is very in vogue.

There is, of course, no shortage of hard work warriors out there spreading their gospel. Silicon Valley’s “9-9-6” hardos, for example, who work 72-hour workweeks inspired by draconian Chinese labor policy (which the Chinese Supreme Court ruled illegal in 2021, FYI), have produced no shortage of manifestos on the “grindset.” But these vignettes of Bay Area post-grads who’ve been in more war rooms than bars in the past twelve months aren’t exactly aspirational. If they’re happy sleeping on their office floors in the name of winning the AI boom, then I’m happy for them (I guess?), but when our contemporary stories about hard work tell of lives free of playtime or leisure, I, too, understand why hard work has lost its appeal.

There are also more pernicious and complex reasons we’ve become distrusting of the promise of hard work. It is challenging to hold the merit of an honest day of work in the same brain we use to witness very real systemic inequalities that render our promised meritocracy suspect at best, if not entirely defunct. Why work hard to win a race that’s rigged in favor of so few? Why enter the race at all?

I’m hard-pressed to believe that the reason we’re not working harder is as simple as laziness or entitlement. If anything, that explanation itself is lazy—as blame usually is. It can be true that people aren’t working hard enough, while also being true that our retreat from labor is a measured response to complicated times rather than a moral failure. Nuance, revolutionary. I know.

I get why people are over hard work. And still, you should be working harder anyway.

The Point of Hard Work

The crude reason you should work harder is that, realistically, neoliberalism has its claws in deep, and your refusal to participate in it will be punishing to you and only you. Phoning it in is an infinitely losing strategy for getting what you want from a system.

The more romantic reason is that there is something fundamentally vibrant about working hard that it’s worth your time to experience.

All of the best moments of my professional (and personal) life have come from needlessly, painfully hard work. Bleary-eyed nights, meals eaten at the office, relationships forged in exhaustion, and the incomparable feeling of getting time-vortexed by a task so difficult that it swallows your whole brain whole. These have been some of my most cherished memories of being a working person.

I think most people’s stories of peak professional joy involve battles hard-won or at least hard-fought. Working hard exposes us to parts of ourselves we can never meet in ease. It makes us the type of tired that lets you sleep through the night. It gives you the uniquely nourishing feeling that even if we’re on a giant spinning rock, you have done something with your time on that rock. Hard work is the only key to a door behind which some of the purest parts of our humanness remain hidden if we do not seek them out.

So, yes, you should work harder because, even though we all know the race is rigged, the person who trained harder is still more likely to cross the finish line first. But if you need a “better” reason, do it because the solution to general malaise has never been found in doing less.

The world is a frustrating place. I know. But whether your discontent is that you’re losing the rat race or that you’re just feeling like a sad little rat, hard work is the first antidote you should try.

It will possibly make you richer and more powerful. But unless you’ve tumbled down the slippery slope to nights spent in your office with a sleeping bag and soylent, it might also make you more whole.

The Cleverness Trap

Second part, second: you also shouldn’t be working smarter.

The thing about working “smarter” is that literally no one else cares. Seriously. No one’s performance review has ever said “that Jimmy… he just works so smart!” I’ll respond to your cries of “but it’s important to be resourceful!” in a second, but for now, genuinely consider the last time you admired someone because of what a “smart” worker they were.

Yes, finding easier, simpler ways to accomplish exceptional work is a good thing. Obviously? And of course you should do the best work you can while wasting as little time as possible because duh?

But it’s the pesky little “not” in “smarter, not harder” that poisons the well with its suggestion that for something to be “smart,” it must also liberate us from working hard. Working stupidly. We see these ideas juxtaposed and interpret “smart” to mean “clever”. The trouble with cleverness is that, beyond the hellscape of internet comment culture, it’s just not worth a whole lot.

If anything, it comes at a cost to any person who indulgently wields it.

Consider the fates of those who have walked the “smarter, not harder” path. The ultimate poster boy is Mark Twain’s Tom Sawyer, who tricks an unsuspecting neighborhood boy into taking over his punishment of whitewashing a fence on a Saturday while all the other boys are out playing. The thing about Tom is that, while beloved to the literary canon, he’s a little piece of shit. He deviously manipulates Ben by making it seem as if whitewashing the fence is an esteemed and elusive privilege, ultimately convincing Ben to do all the work himself.

Cunning? Sure. And the tactic does free him from hard work. But that type of cleverness has no place in the workplace where the Bens and Toms of the world have to work together again the next day. Tom’s strategy works exactly once because in real life, the Bens remember who handed them the brush.

Giving in to the alluring insinuation that the most precious resource in any work equation is your own personal time is a naive and egocentric way to build yourself a bad reputation and alienate the people you work with.

Of the people I know who are known for working “smarter,” here’s what I actually think of them: they overdelegate, undercontribute, skirt the rules, think they’re smarter than they are, put others down, make for bad teammates, and I wouldn’t hire a single one of them twice. To put it mildly.

Being more efficient can be of great benefit to an entire team, but when you follow the advice to “work smarter” without also working harder, you are often just abusing others’ generosity or naivety by offloading work onto them. In my book, that doesn’t make you smart. It just makes you mean.

Skipping the Hard Parts

Arguably, developments in AI workplace tools have created the opportunity to work “smarter” in ways that displace work onto systems instead of other people, resolving the issue of being a tricky little jerk.

This is the ultimate development for the “smarter, not harder” folks, and to their credit, tool utilization has been pretty important to this whole societal advancement stuff.

But the drive toward convenience and ease through tool adoption has also led to the slow extinction of human skills that are hard to price, so instead we pretend we’re not paying for them.

Admittedly, my beliefs about AI and its general goodness are fickle at the best of times. Some days I’m on board, and others I think that we’re slowly disintegrating the human capacity for intelligent thought. Current status: queasy but open-minded. But what I do feel certain about is that when measured on a longer time horizon, there is nothing “smart” about the erasure of the “low value” tasks that make up the beginnings of a career.

Apprenticeship is historically a cross-cultural tradition for honing and expanding our diverse human crafts. The whole concept is quite charming, really: we submit to our ineptitude, graciously study from those who have already overcome theirs, absorb the tiresome grunt work that exposes us to the basics and contours of a discipline, and then practice it until our hands bleed. We work hard at thankless tasks that our craft masters don’t want to do, and in doing so, we begin to build experience. When we’ve mastered the basics, the cycle resets. We repeat it indefinitely until we are performing at the highest echelon of our craft, perhaps even expanding its bounds, and taking on our own apprentices so that, through grueling hard work, they too can become great.

However, no more are the days of tediously learning until your hands blister. Claude will do the that part for you. No need to hunt someone down to get feedback. Claude will give that too. Novices need not concern themselves with the messy business of terrible first drafts because ChatGPT can produce perfectly average ones for them. Under the imperative to work “smarter,” an employee can siphon off any and all “low value” tasks that apprenticeships are built on and instead find themselves with an abundance of time to perform “high value” tasks for which they possess none of the experience to accomplish.

What the apprenticeship model of working harder to become smarter gets right is that information is no substitute for wisdom, and capability is only a primitive evolution of real excellence. While the new age AI-enabled pseudo-masters of the workforce may be making slide decks in half the time, they’re doing so at the expense of their own development. They’re letting the computer whitewash the fence for them, which may be quite clever, but they’re never learning how to look at the wood in winter and know if they’ll need to paint it again next summer. They’re ignoring that human craft has only ever been expanded by those who learned the nature of their brushes and colors so intimately that they ventured to imagine new ways of painting.

Who knows what AI will do to our basic workplace skills. My current forecast is bleak. Actual mastery requires doing the hard part. Building deep, generational, transferable knowledge requires harder work still, as well as the passage of wisdom between human hands. We’ve been handed the keys to the most powerful “work smart, not hard” machine of all time, and I worry what it might cost us. Maybe my fear is misplaced. Or, maybe the moments of genius sparked only by rubbing two human brains together are inherently beautiful things that we will not be able to comprehend the value of until they are lost to us for good.

While there might be easier, quicker, “smarter” routes to everywhere, we are already walking around ever more incapable of reaching destinations, contacting our loved ones, and deciphering the cursive script of all of the humans who learned how to be people before us and wrote it down so we could know too. I’m not saying you need to delete your AI or that people should be navigating via sextant instead of Google Maps. But it’s a weird time, and there are centuries of human wisdom held in letters, maps, and stories that we are slowly losing because we've become oh-so-resourceful. In engineering ourselves smarter phones, smarter maps, and smarter houses, we’ve pursued cleverness to its terminus where we need not be smart at all.

I know I’m being existential, but I feel entitled to it. At some point, resourcefulness becomes dependency, and we risk breeding new strains of ineptitude that we’re hubristic to believe we will never pay for. One day, the generation that ChatGPT-ed their way through life will likely eradicate a skill we couldn’t afford to lose, and like a rare spider or seafaring bird we took for granted, we will only learn to appreciate it once it’s gone. They will have found the smartest way to work, and with all their new time, they will stumble into their parties and family dinners with no true wisdom to impart other than how to make the most money with minimal effort.

Is the efficiency worth the risk? Are the extra two or three hours of activity that can be extracted from each day? What about the chunks of shareholder value buried deep in the marrow of workplace behavior that the AI heroes are always about to unlock?

I’m sure there’s material value there. Sincerely. This isn’t a doomsday prophecy. But what scares me is the “efficiency at all costs” mentality and the danger-laced insistence that, as we transcend the age of hard work, the best thing for our souls and societies is to move into the age of “smarter.”

Some Things Are Meant to Be Hard

Stepping off my existential soapbox, what I will acknowledge is that there is no reward for doing things the unnecessarily hard way. You don’t win points or deserve something more because you suffered for it. No one is going to congratulate you on writing by hand when you could have typed or clap for you because you didn’t use AI. While I don’t think you should be working smarter for the sake of it, you also shouldn’t be making things harder than they have to be for martyr points no one’s ever going to hand out.

But some things are meant to be hard. Learning is always a hike up a trail that’s inherently steep. And, sometimes, the hardness is the whole point.

So, if I could program all of us with new advice as we navigate a world of rapid technological change and fraught political times, it would be this:

Smarter is not always better. It is rarely richer, more beautiful, or more human. The world is full of devices and algorithms that are getting smarter by the day, and you don’t need to be doing the same. The richness… that’s in the hard stuff. So go find the things where the hard work expands your mind and your life as you pursue them. Then go work as hard as you can.

Thanks — always — for reading.
Talk soon.
KL

For the past nine months, one of the things I’ve been doing in my ghostwriting job is writing books about companies’ cultures. It’s quite fun: I bury myself in their documentation, quietly lurk in their meetings, and interview dozens of their employees to try to figure out what they’re about and how to explain it.

This culture book writing adventure has been both (1) a delightful post-hoc justification for an ethnographic methods class I took for fun in college (2) a sort of surprising exercise. Two books and over 150+ employee interviews later, I’ve learned a lot of things about what company culture is and is not as well as what keeps cultures strong in the face of time and growth.

The idea I keep coming back to, though, is something a former manager once said to me: that of all the bells and whistles that we dress up as company culture, at the end of the day, culture is what you tolerate.

Company Culture and Its Discontents

Just to get us on the same page, when I say “company culture,” I mean the set of shared values, ideologies, and attitudes that define how people in a company relate to work and each other. Sometimes enshrined in principles or values, a company’s culture is what values it does (and doesn’t) hold, and how those inform behavior. Companies that value candor foster open debate. Companies that value trustworthiness reward reliability. Most company cultures are built on a handful of these values and axioms that, if clear, overdetermine how everyone does everything.

And crucially, I really do mean everyone and everything.

In studying different companies’ cultures, one of the things I’ve had to research is what causes them to break. What makes an employee say that “the culture here isn’t what people think”? The not-so-surprising finding is that cultures break when people start acting out of alignment with the business’s values. The very surprising (at least to me) finding was how minor and infrequent these infractions can be to wreak major havoc.

Consider, for a moment, airport boarding (the subject of many heated debates in my household). Airport boarding is a group activity in which shared norms and values—namely, obedience—govern how people behave. Sure, there’s a process, but there’s rarely an enforcement mechanism, and gate attendants are hardly club bouncers. The system holds because everyone implicitly agrees to play the same way (a cultural agreement). Until one person doesn’t. The second overhead space is tight; all it takes is one person boarding ahead of their boarding zone to justify everyone doing the same. My fiance and I have this fight practically weekly (we fly a lot), and the problem is we’re both right. I’m right that we should board in our assigned zone because duh. He’s right that when we see other people ignoring that guidance, we’re suckers to not do so as well. The whole thing is just a game theory problem (another undergrad course vindicated!) where one defector is all it takes to make defection the dominant strategy. One bad egg may not take down the whole system in one go, but over time, the cultural norm erodes into practical irrelevance. Hence why American Airlines had to roll out enforcement technology to publicly shame and deny the line-jumpers. I digress.

The point is this: company cultures are no different from airport boarding. They are rubber-band-and-duct-tape ecosystems that can be corrupted by singular defectors whose existence alters the incentive structure for everyone else. When someone takes credit for others’ work and faces no consequences, self-promotion becomes the smart play. When passive-aggression goes unaddressed, people learn to hedge and politic because why shouldn’t they? One person visibly getting away with violating the culture is enough to change the math for everyone—and suddenly, your values aren’t a shared commitment anymore. They’re a sucker’s game.

This is the startling thing about company culture: it is wildly susceptible to infiltration. Singular defectors—even singular acts of cultural transgression—can alter the calculus for otherwise dedicated cultural stewards so that doing the hard, tiring work of being “good” just isn’t worth it.

Of course, cultural defectors don’t affect everyone. I think of them like atheists in your church. They might sow some doubt, maybe induce an existential crisis or two, but they’re not going to sway the devout. But in the church of your company, what the presence of nonbelievers will do is factionalize people into the culture carriers and transgressors. And the second you’ve reached that point, even your most devout culture carriers are at risk.

This is an observation that holds across the cultures I’ve studied: when leaders fail to manage the presence of cultural transgressors, the people who best exemplify the company culture end up feeling overburdened and disillusioned.

If you interview 100 people in a company, it is the culture carriers, not the transgressors, who will tell you that culture’s broken. “Leadership only says they care about hard work.” “All of this is lipservice.” I’ve heard so many of these comments, but they only ever come from the employees who are supposed to be exemplary cultural role models. Lots of them can only give one or two examples of why they’re disillusioned, but one or two is enough. Promote them all you want, but you’ve got a big problem when you’ve taken your cultural champions and made them feel like suckers.

Zero Tolerance

There’s one company I’ve written for that has been the exception to all this, although not because the same rules don’t apply. But among the three dozen employees I interviewed, not a single one thought the company faced any real culture threat. The ubiquitous sentiment was “everyone lives out our values all the time. Our culture is more than words on the website.” Truly, it’s remarkable to observe.

The secret to their cultural coherence and strength: zero tolerance for defectors.

Now, when I say “zero tolerance,” I don’t mean everyone gets fired at the first sign of trouble. However, I do mean that no transgressions go unnoticed or unaddressed. Sometimes that looks like confrontation; sometimes it looks like confrontation, coaching, and training; and sometimes it looks like exiting people who can’t get with the program. Admittedly, I do think that companies that care about the sanctity of their culture are prone to firing fast. Not unfairly or recklessly, but decisively as soon as it’s clear that a culture issue can’t be fixed. They know--and their leaders will tell you plainly--that the fissures caused by letting cultural defectors linger are often far more costly to a business than the also-high cost of turnover. Even messy goodbyes are cheaper than the slow poisoning of the system.

That’s the other common denominator: leaders at companies with strong cultures take defending those cultures very seriously. I think most leaders think of cultural stewardship as a tenet of their job. Model good behavior, recognize culture carriers, and remind people about the values. I reckon most leaders do this. But stewardship and defense are different beasts, and great cultural leaders are militant defenders, not just shiny exemplars.

Cultural defense requires vigilance. A sort of wild amount of it. It requires anyone with the power to remove bad actors (leaders, managers, anyone with hire/fire authority) to think of cultural defense as a core mandate of their job. Calling people out, coaching them, and having tough conversations is a big part of it. But the actual hard part is being willing to let go of someone good at their job because they’re bad for the culture, with the understanding that the damage they do by staying outweighs whatever value they create.

This is what I’ve learned. That you can model good behavior all you want, reward your culture carriers, and remind people of the values until you’re blue in the face. But if you tolerate exceptions—if you let defectors linger because they’re talented or senior—your culture becomes defined by the delta between what you say and what you do. It becomes defined, in often irreversible ways, by what you tolerate.

You have to fight for your culture. Every single inch of it. You have to stop giving so much attention to where it’s succeeding and hunt ruthlessly for the places where there are cracks. Because if you don’t, eventually, your believers will grow weary too. Then they’ll stop fighting for you.

Thanks—always—for reading. Talk soon.

He was a portrait of stress: purpling undereyes, torn cuticles, and shoulders pulled up to his ears.

Ignoring the fact that I still wasn’t convinced he had a real job at this point (you try going on a date and explaining that you’re a fractional finance executive who works for companies that sell: baby swimsuits, straw hats, and bright orange emergency preparedness kits. And whatever it was that the men he referred to as “the weed brothers” did…) it didn’t take that many weeks of knowing Logan to understand his job was legitimately stressful. Businesses always weeks away from being out of cash, deals that could fall apart with a change in the wind, and lots and lots of numbers that need lots and lots of attention. Personally, it would make me throw up from the pressure.

None of that was what was bothering him.

He was wrapping up a project with a client he’d decided to step away from after trying his best to help them. The team was uncooperative, he wasn’t the answer, and he needed to get out of there. They were not taking it well.

As we walked along the lakefront, Logan chewed on the inside of his cheek and vented. “I don’t have time for it, but I want to rebuild the model for them so they’re set up in the best place I can get them.”

“You don’t owe them that,” I pushed back. “And you do owe your other clients that time.”

“Yeah, but I don’t want them to fail. They’re good people.”

“They’re going to fail anyway. A new financial model isn’t going to fix the problem, it will just make you miserable.”

“Yeah, but…”

I stopped the conversation to offer an unsolicited diagnosis because famously I do that.

“You’re wrong about what you’re afraid of here. You think you’re worried about them failing without you, but you’re actually just worried they’re going to think you’re a bad guy for not doing everything in your power to help them.”

Logan looked slightly offended, which was fair. And, naturally, did not stop me.

“If they want to blame you for their failure, they will, one way or another. You’re just trying to not be misunderstood, and I think you need to get over it.”

Lucky for me, Logan is a kind, patient, low-ego man who took this advice graciously, dropped the client the following Monday, and has never once told me I need to work on my advice delivery.

Also lucky for me, that conversation unlocked new understanding about my career too.

Watching him twist himself up over the opinion of people who no longer mattered, I recognized a thing I’d done my fair share of--chasing after this feeling of relief that someone, somewhere, understands I am always trying my best.

That feeling is so seductive. The comfort of believing that if people understand your intentions, it will insulate you from their criticism. It is also a false comfort, and if you want to have any kind of real power in your career, it’s one you’re going to have to learn to live without.

Here’s the thing no one tells you when you start taking on real responsibility at work: the more decisions you get to make, the less understood you’re going to feel.

Even for the best communicators, responsibility creates an understanding gap that no amount of transparency can close.

And if you want to lead, you’re going to have to get over it.

The Information Gap

The fundamental problem with wanting to be understood as a leader is that you cannot expect people to understand a decision you made based on information they didn’t have.

Most of us learn this (albeit from the other side) in childhood. Our parents tell us we can’t wear something, say something, do something… and we experience it as unjust tyranny. “They think I’m dumb!” “They want to control me!” “They just want to impose the same rules they were subjected to!” Come on, you’ve thought one of these things.

When I was in middle school, and everyone in my class was getting on this cool new platform called Facebook, I begged my parents to let me make an account. They politely said, “Absolutely not.” While I eventually won out years later, I can remember the heat in my chest the first time I asked. How could they not understand that I was going to be a social pariah? How could they be so… mean!

I bring up this memory because it captures a dynamic I’ve now stood on the other side of. My parents weren’t just acting on more experience than I had, though they were. They were acting on an invisible but absolute difference in the quality of our judgment. They knew better than to let a twelve-year-old dive headfirst into some new technology. I knew… nothing about anything, really.

No amount of explaining on their part would have closed that gap because it was based on more than missing explanation. We had a responsibility gap. They were responsible for me, and the only thing I’d ever been responsible for was turning in English homework. That difference—carrying weight versus not carrying it—is something you cannot grasp until the anvil is in your hands.

Now. Leaders are not parents, and workplaces are not households. Let’s be clear about that. But a version of this same dynamic plays out at most people’s jobs. People with more experience, more context, and greater responsibility make decisions that affect dozens, hundreds, sometimes hundreds of thousands of people.

And everyone else is supposed to just... accept it?

Devastatingly, that is not how it usually goes.

“This is secretly about cutting costs.”

“She only promoted that guy because he sucks up to her.”

“They’re not telling us the full truth.”

“He didn’t think this through.”

As someone who ran a company survey for a while, let me tell you… these beliefs are abundant and sometimes crazy. And the bigger a company gets, the worse it is—information silos deepen, truths drift apart, and leaders become abstractions to the majority of people they’re supposed to be leading with fewer opportunities to make themselves known.

What makes this so hard to fix is that even when you distribute information, you can’t distribute responsibility. You can explain the reasoning behind a decision all you want, but it doesn’t close the gap between the responsibility havers and have-nots. You can shrink the gap. Totally. But you can’t eliminate it. You are, at one point or another, going to be misunderstood because of it.

The Ruinous Pursuit

And yet, it still hurts so much. Really hurts. In this sharp, specific, soul-poking kind of way that makes us do irrational things to avoid it.

The logical first thing most of us try is to explain more: share the context, make the reasoning visible. That can actually get you pretty far. But when it doesn’t, the pursuit can expand into places it doesn’t belong. One more meeting. Okay, two. A longer email. An even more carefully worded Slack message that comms looked at this time. We’re being good communicators! I have told myself this lie, too.

At some point—and it’s hard to know exactly when—you cross this imperceivably thin line between communicating and performing, and the desire to be understood can push you away from trying to make good decisions and into the land of making decisions that will be well-received. These are, perhaps obviously, not the same thing. My take is that almost any time you’re optimizing for how things look, you’re in trouble. I’ve watched people make an astonishing number of wild and harmful choices in the name of optics.

The tricky part is that it will never feel like performing when you’re doing it. It genuinely feels like diligence and care. Like the client really does need you to build them a new model.

But the hours you spend crafting the perfect narrative and managing reactions to a decision that’s already been made—that is time you’re not spending on the next problem, project, and people who need you. It’s effortful, don’t get me wrong. But we’re so quick to mistake effort with work, and in this case, to succumb to the deluge of twenty-first-century “change management” bullshit that’s rotting our brains (a hot take for a different time). TL;DR, the fact that reputation management is hard does not make it the actual substance of your job.

Last thing I’ll say about the risk of wanting to be understood: when you treat buy-in as a criterion for “good” decisions, you’re implicitly accepting the premise that people are entitled to resist decisions they don’t fully agree with.

I obviously don’t mean to suggest people shouldn’t be able to disagree with and question leaders. I love a vocal skeptic who knows when to push back.

But there is a difference between someone questioning a decision and someone refusing to move forward until they’re personally satisfied with the explanation. When leaders bend themselves into pretzels trying to win over people, they teach the organization that resistance works and that they deserve to agree with choices that they’re not trusted to make. We can accidentally teach people that if they just drag their feet long enough, someone will come back around to explain again, softer this time. That’s a dangerous precedent. Let’s not set it, yea?

Getting Over It

Admittedly, I don’t have an awesome framework or a one-stop tip for “getting over it.” Being misinterpreted sucks every time. But I can tell you what I do (and what I make Logan do) when I find myself spiraling about if people think I’m a cold, wicked person.

First step: stop asking “will people get this?” Under the spell of modern change-management hypnosis, we are so fixated on whether people will accept and understand our decisions. Get over it. Sometimes they won’t. It doesn’t make a decision bad. Sometimes we have to accept things that make us mad (like not having a Facebook account when we’re twelve).

Second step: ask yourself, “Am I confident in the way I reached this decision? Was I rigorous? Am I willing to accept the consequences if I’m wrong?” You owe people that: accountability for the choices you make, whether people liked them or not.

Last step: when you’re sure you’ve made a decision in a way you’re proud of—based on the best information and judgment available to you—move on and go do actual work. Which, I hate to tell you, obsessing over how your choices are received and calling it “change communications” is not.

In practice, that means stomaching some pain. You have to learn to say out loud to yourself, “Someone thinking I was being careless doesn’t mean I was.” You need to be able to watch stories about yourself take hold that don’t match your experience, and decide to move on to your next priority instead of chasing down a correction to the narrative. That is your job, after all: to act well—not to be seen acting well.

That’s the deal. Take it, or don’t.

Thanks--always--for reading. Talk soon.

And by “important”, I mean absolutely fundamental to convincing other people that you are a likeable, intelligent, socially aware human who adds value to conversations.

It’s likely no one has ever told you this (perhaps because they can’t get a word in), but even if you don’t know if you’re interruptible, you’ve probably been victimized by someone who isn’t. But just in case your god’s favorite and you haven’t, allow me to paint you a picture:

Katie, Danny, and Bert are meeting for 15 minutes to review how their project is going. Katie gives a quick update: code’s approved, she’ll update the trackers. She leans back to hear Danny’s update.

Except Bert gets there first.

Bert has decided the campaign collateral needs to go in a slightly different direction, and he’s given it a lot of thought. He leads with the headline “When we put together the original materials, we didn’t have last month’s data yet, but it turns out our audience is responding way better to content without illustrations.” Only use content without illustrations because it performs better. That tracks. Katie and Danny nod. They’re onboard.

But Bert? Bert isn’t finished. Bert came armed with many justifications and a breakdown of why the change won’t affect the launch date. And since he’s been staring at his hands while talking, he has no idea Katie and Danny are already with him. They’re still sitting there nodding. Vigorously.

Bert launches into his explanation.

“Yeah, we’re totally aligned,” Katie tries to interject, but Bert just raises his volume the second she starts talking. She tries two more times, then shoots Danny a pleading look. “Sounds great, dude,” Danny tries. But there’s no reaching Bert. He talks for another eight minutes while Danny discreetly sorts through his email, wondering how someone can talk for so long without coming up for air. Katie tries to remind herself that a homicide would not look good on her performance review.

“Any questions?” Bert asks when he’s finally ready to cede the floor. But Danny and Katie don’t hear him; they’re just nodding on autopilot.

“Great, glad you guys agree. Oh, Danny, did you want to use the last four minutes to go over the ad budget? I heard there might be some big changes.”

Danny slacks Katie, I’ll tell you about it later, before turning back to Bert with a forced smile. “Nah, it’s okay, man. I need to get to my next meeting.”

Common advice would tell us that Katie is the villain of this story. After all, Bert was talking, and interrupting is rude. And she interrupted multiple times, or at least she certainly tried.

But put yourself in this meeting, and you know Bert is the bad guy. In his inability to be interrupted, he has wasted his colleagues’ time, obstructed Danny from giving a valuable update, and pissed off everyone around him.

If you aren’t letting people interrupt you, I promise you’re doing all those things too.

It’s not about what you want to say

I used to lead a training session at work on how to be a better presenter, and it always included this concept: effective communication requires sharing what the audience needs to know, not what the presenter wants to say.

This principle applies to all communication, although I violate this in the newsletter all the time. Do as I say, not as I do.

Whenever you’re explaining something, this “needs to know vs wants to say” gap will exist. Your friends don’t need to know where you bought your Subaru to hear how you crashed it. Your manager doesn’t need the backstory on the eight ideas you scrapped. We over-explain because we’re anxious communicators who have no idea what people need and think more detail equals more clarity. And also because we tend to think we’re a little more interesting than we are.

While I encourage you to exercise restraint, you should expect to yap too long sometimes. We all do. And when you do, make sure the people around you can use the one tool that helps them get you back on track—interruption.

A Taxonomy of Interruptions

There are two types of interruption (according to me): tangents and engagements. And while most of us were scolded as children for interrupting our parents with the former, we have also likely used the latter strategically many times without realizing it.

Tangents are what they sound like: disruptions that yank a conversation away from a topic it’s on and to something entirely new. Saying “Mom, can I have ice cream?” when your mother is in the middle of discussing the carpool schedule is a tangent. So is interrupting a conversation about the budget because you just had an epiphany about the creative. So is basically any idea that you introduce with the word “anyway.”

Engagements are less obvious and come in more forms. Often, they’re acknowledgements and agreements: “Yup,” “mhm,” “I got it,” “understood.” These let the speaker know that you get the point, and they can move on. Other times, they are redirects: “Wait,” “hold on,” “hey, but…” which can tell a speaker you need them to pause or backtrack before they continue. And most sneakily, they are skip-aheads: full sentences or new ideas that respond to the place the speaker’s sentence was heading before it finished getting there.

We are taught that interruptions are rude because tangents always are. They say, “What I’m thinking about is more important than what you’re talking about,” and “I am totally not listening.”

But engagements aren’t that easy. While they can feel rude--especially if you’re wrong about where the speaker was going or if you do it every other sentence--this type of interruption is a useful tool for letting someone know how their communication is going.

“I understand” can be a big relief for someone who’s not sure they’re getting the message across, just as a re-direct can help show someone that you’re seriously listening and want to be certain you understand them. Interruptions, when they engage with the speaker, are often just the easiest way to help someone figure out how to communicate what you need to know.

I will quickly admit that I am biased. I come from a proud lineage of engaged interruptors, and I’ve been interrupted this way all my life. Implicitly, I was taught to interrupt this way. My family’s full of sharp, busy people, and we sit around the dinner table, interruptions are as common as speaking.

After decades of trying to be mindful of my interrupting, I’ve found most engaged interruptions help more than they hurt.

Particularly at work.

In social settings where we tell stories for pleasure, interrupting often has no point. Even if you get where the story is going, let someone tell it their way. It’s joyful, and you’re in no rush. Order another drink and chill.

At work, almost all communication serves a purpose to inform, inquire, or instruct. Time is expensive, clarity is important, and information asymmetries abound. In this setting, being joyful is not the point (although is encouraged!), and you often are in a rush. So when Bert decides to filibuster the monthly business review, interrupting him when everyone clearly gets the point isn’t just practical, it’s respectful to other people’s time. Allowing yourself to be interrupted is also respectful.

Being uninterruptible: not respectful.

It’s actually tactless, selfish, and rude. When you prevent others from interjecting with engagements, you’ve done the exact same thing a tangent does. You’ve declared that what you have to say is more important than what anyone else does. That might not be what you think, but it’s what you’ve communicated.

So, unless you’re certain you’re a perfect business communicator, you need to make sure that whenever you speak, you can be interrupted.

Great. Now that I’ve told you all the stuff I wanted to say and you probably didn’t need to know (this newsletter is for pleasure, sorry), I’ll tell you the one thing you need to do to be more interruptible.

In Short: Pay Better Attention

Being uninterruptible, though it may seem like a crime of ego, is usually a crime of ignorance. Bert doesn’t ramble because he’s enchanted with his own explanations; he does it because he wants to convince his teammates of his idea, and he has zero idea that he did it in one sentence. The only thing Bert has to do differently to avoid his meeting faux pas is pay attention while he talks.

Most people, through their faces and bodies, will tell you what they think about what they’re saying. Educators know this better than anyone: a silent classroom doesn’t mean everyone is listening if everyone’s slumped over, staring out the window. When talking at work, think of yourself as a teacher who has to get through to your class. It doesn’t matter how clear the material is if they’re all on their phones, so you need to try to read their cues while you speak.

Head nods: people are following. Good sign.

Really big head nods: they really agree, or they want you to move on. Either way, move on.

Head tilts: people are confused. Bad sign. Pause and give people the chance to ask questions.

Furrowed brows: people are either confused or unhappy

Slyly reading something on their laptop: you’ve lost them

Mouths gaping open and closed like goldfish: they get your point. Let someone else talk.

Your brain already knows how to read these nonverbal cues. You just have to make a point of taking them in.

When you’re speaking (no matter what you’re speaking about), pause. Take breaths. Look around for two seconds. All these things give you the chance to read the room and, even better, the chance for someone to interrupt and help you out.

Let’s say you’ve failed to do this. You have not, in fact, read the room, and now your colleagues are trying to interject. My advice: just try letting them. When you hear someone raising their voice at the same time as you, try to meet it with curiosity. Stop speaking, let them talk, and then assess. If they were off base about where you were headed, you can always just get back on track and finish the thought. If you have to, you can even interrupt to do so.

If they skipped ahead successfully, let them do so. It expedites the conversation so long as everyone else is following too (this is when you scan for furrowed brows and tilted heads).

Worst-case scenario, it’s a tangent. And you interrupt back, try to get back on track, and if you’re really miffed about it, tell the person later that you didn’t like the way they spoke over you.

The one caveat I’ll include: it’s possible to be too interruptible, especially for women and minorities. My guidance is to trust your instincts. You know when you’re being shut down or spoken over because you’re not being taken seriously. I promise you do. When someone’s just repeating you or blatantly ignoring what you were saying, you know. When this happens, I lean on a tactic I learned from an older female debater I admired in high school. She was being aggressively spoken over in a cross-examination, and instead of backing down or raising her voice, she waited until the kid paused and delivered a calm, devastating: “I actually wasn’t finished speaking.”

I cannot begin to tell you the power that phrase introduced into my life.

But for all the moments you are being engaged with, I’ll leave you with this:

Being interruptible is not a speaking skill; it’s a listening skill. If Bert had paid attention—for literally two seconds—he would’ve made his team feel seen, and IT wouldn’t be wondering why Katie googled “how to dispose of a body” during working hours.

Let the people interrupt you, even when it’s mid-sentence. Your meetings will get better, you’ll learn where to start applying restraint, and best of all: you’ll make other people feel heard.

Thanks, always, for reading. Talk soon.

Sure, fair enough. But I wasn’t grasping why that would make our proposal a bad idea.

Well, because Congress was also in the middle of negotiating terms for a new nuclear arms reduction treaty (START) with Russia. Also controversial! And if the congresspeople who would (hypothetically) advocate for withdrawing Marines wasted all their energy and influence on getting people to agree, they’d have no influence left to shape a good START treaty.

“Political capital is finite!” some pimply dude in slacks and an untucked button-down shouted at us. “This argument is so stupid,” I whispered to my partner. And then we swiftly lost.

People write this argument (the “politics disad”) in debate for one reason only: it applies to everything. Accordingly, I went on to answer it hundreds of times over eight years of debating. And just for posterity: I was right the first time. The argument is stupid.

But that one kernel of genius—that it applies to all proposals—really landed with me. I think it’s true: advocating for something always requires dipping into finite reserves of influence. Including at work. Where, whether we know it or not, we’re all participating in an economy of political capital.

Political Capital: The Basics

Think of “political capital” as a person’s ability to influence decisions. You use it every time you raise an issue, advocate for a change, or try to get someone to change their mind. It’s a little north of “trust” and a little south of “power.” And unlike other personal “resources,” such as competence or humor, it doesn’t compound with use. It depletes.

We have other cultural references for this idea: famously, The Boy Who Cried Wolf, a story about how credibility misspent becomes credibility lost. But political capital theory asks us to consider that you can lose influence even when there is a wolf.

This idea matters for everyone… but especially for those of us who think ourselves sharp, incisive, and very good at spotting workplace wolves. It’s obviously a great thing to be able to identify problems at work, but that awareness becomes a liability quickly if you don’t manage your influence wisely (aka: pick your battles). And if you’ve been lobbying constantly without gaining traction, you should perhaps consider that the problem isn’t people misunderstanding your brilliance. It’s more likely you’re just spending your political capital too recklessly.

Alas, some practical guidance on how to build and spend it better.

How to Build Political Capital

While by no means exhaustive, here’s where I would start with building my political capital: be generous, be right, and be predictable.

Be Generous
Counterintuitively, one of the best ways to build political capital is to set aside the power politics and be generous with people. And I really do mean generous: motivated to put others’ interests above your own purely because it’s a good thing to do.

The thing about “advancing your agenda” is that you can’t do it without trust—and no one will ever trust you if you act like a selfish ass.

Admittedly, if you don’t possess some level of innate goodness, I can’t help you with this one. You can’t pantomime generosity. People viscerally feel the difference between being helped and being transacted with. And if you start helping people just to rack up interpersonal debt, it will backfire.

Why you struggle to be generous with others (*cough* your overactive scarcity mindset) is for you and your licensed therapist to discuss. However, if you stop and sincerely ask whether you’re being as good a teammate as you are an individual contributor, you will inevitably find opportunities to earn more trust.

Where can you offer help that you currently don’t because you’re “busy?”

Who could you give more public credit to?

I owe my current career entirely to offering to help executives with their writing—simply because I had the time, and they didn’t. Generosity, even when it’s inconvenient (especially when it’s inconvenient!), always pays off. Even if in unexpected ways.

Be Right
Unfortunately, since influencing eventually requires convincing people you have a good opinion, you cannot solely be benevolent. You also have to actually have good ideas.

To build your credibility as someone who is “right” about things, start by improving your hit rate. People who tell you they’re just “super intuitive” are lying to you. Being right is a skill, not a divine gift. You can build that skill by being attentive, informed, scrutinizing, open to new ideas, committed to truth, and curious (see: how to have good opinions).

Read more, ask more questions, spend more time picking apart your own ideas. The people who are more right than you just do more of these things. And if you build out the foundational behaviors and mindsets that help people be right, you will find your influence grows. This takes time, but “I told you so” (obviously, you never actually say this) is an incredibly effective long game.

Be Predictable
My curveball tip for being influential: be wildly consistent—in what you believe, how you think, how you treat people, and how you work.

Being predictable doesn’t make your ideas better. However, it does make people more likely to hear them because they know how to fit them into your broader POV.

For most people, reliability is as important to trust-building as generosity is. People need to know your interests don’t always trump theirs. They also need to believe that who they perceive you to be lines up with how you actually act. People want to be able to understand how the battles you pick fit into your (metaphorical) war.

If they agree with you on one thing, will you come back asking for more? If they back you, are you going to follow through? Are you simply a hungry little mouse who got fed a cookie and is about to come back for milk? Or a person with clear, consistent, limited motivations that other people can make sense of.

Influencing is a far grander endeavor than just convincing people you’re right. You also have to build a reputation that tells people what to expect when you show up with an ask.

To start: make your values legible. Be vocal about them. Be transparent about how you make decisions. Use your existing political capital in ideologically consistent ways (at least most of it). Explain your reasoning. Never capitulate on things you care about because of who’s in the room. Be persuadable, but not cowardly.

In short, make it easy to answer the question: “What does she care about and believe in?” If the answer isn’t clear, you’re probably a lot harder to align with than you think.

How to Spend Political Capital

Okay, the fun part. You’ve built up some political capital. Let’s spend it.

Consciously Rank Your Priorities.

Before you do anything else, you need to bring more rigor to how you think about your priorities. If you don’t actually know which ones are most important, you risk spending your influence in heated moments or missing the opportunity to be an advocate when it might have mattered.

To avoid that, write down your priorities. Seriously. Grab a pen. Make a list.

Write down the debates you’re trying to win, the problems you’re trying to solve, the changes you want to see, and the opinions you’re hoping to shift. Take all of these together, and then ordinally rank them.

How you establish that ranking is up to you, but I recommend orienting around value for your team/business, not value for you personally. My favorite way to figure out my priorities is to ask myself, “If I could only change people’s minds about one thing this week, what would it be? If I could pick two, what would the second one be?” And so on.

Once you have a list, whenever you’re about to speak up about something, do a quick cross-check to see where it sits on your priority list. If it’s not top five, hold your tongue.

Know the Cost of Your Priorities
You should also account for how much time, energy, and persuasive capital your priorities demand. It is much more costly to convince the CEO that your whole company should have a four-day workweek than to persuade your manager to change the format of your 1:1s.

When you haven’t costed out your priorities, you’re much more likely to pick fights you’re not actually up for. Maybe you think you’re making an offhanded suggestion in a meeting, but you’re actually spending your limited capacity to disagree on an idea you won’t follow through with. Don’t ruffle feathers with no payoff.

Before you decide to try to influence something, even casually, ask if you’re really ready to put up the whole fight. If not, consider that you might not need to say anything at all.

As a rule of thumb, I try not to speak up unless I’m willing to fully own the execution of whatever perspective I’m advocating for. I also, as a rule, never pick “big fights”—ones that require people to shuffle priorities, change plans, deal with massive emotions, or execute highly complex logistics—more than once or twice a year.

And as you’re evaluating cost, be mindful of who you’re spending it on. Most people work with a limited set of stakeholders, so it’s likely your battles are usually with the same people. Just keep tabs on how often you’re clashing with any one person. You can fight many battles on many fronts, even at a high cost, but political capital is audience-sensitive, so when you notice you’re in a recurring battle sequence, give it a rest.

Leverage Alliances
Let’s say you just can’t help yourself—you need to fight one more battle, even when you know you shouldn’t. Then you need to learn how to leverage other people’s capital rather than your own.

It sounds sort of nefarious, but in practice, all I mean is you should form alliances with people who share similar POVs, pool your political capital, and strategically divvy up your influencing pursuits.

Let’s say there’s a project you really care about, but you simply can’t get others to pay attention to it. You can choose to forfeit that priority, OR ask yourself who else the project matters to, who could take the lead on getting it approved.

Unless you actually are a selfish ass, you should never be the sole beneficiary of your ideas. That makes it relatively easy to find these allies. Ask: Who is served by this idea? Who else cares about this?

Identify them, explain your perspective, and then recruit them to spend their political capital.

Even better: influence together. For better or worse, our silly human brains believe there’s truth in numbers. The more people you can get pooling their political capital into the same cause, the easier it is to emerge victorious.

Know When to Ask Instead of Fight

In truth, this advice is mostly here for my sake. A reminder from me to me that while influencing and persuading are great, they are not the only tools at your disposal.

You can also—*gasp*— ask for help.

If that was already obvious and easy for you, congrats, I envy your healthy relationship to personal vulnerability. But if you, like most people, struggle to ask for what you want, it’s easy to become over-reliant on influence and under-reliant on others’ kindness.

When you know you can’t convince someone, consider asking for their trust instead. Ask them to take a leap of faith on the idea. Hit ‘em with a “I know we see this differently, but if you give me the chance, I will work tirelessly to make this work.”

Not every idea is a candidate for this approach, and you also must be able to be gracious when someone says “no.” But I’ve made the mistake of lobbying for opportunities I should have just asked for. Don’t recommend.

Just like you can build your political capital by being generous, you can conserve it by letting others be generous with you.

With that, get out there and be influential!

Thanks—always—for reading. Talk soon.

Truly. Hate. I understand the value and get why it motivates people. I’ve read the studies. Professional goals are good. Yes, yes.

But they’re so frustrating. Most people’s goals are some variation of “get promoted” or “make more money.” Both great things that I hope you’ll achieve this year. And yet, the goal-setting authorities would tell you they’re “bad goals” -- not specific, measurable, or what have you.

I would also tell you they’re bad goals because they’re just woefully beyond your control. You can make yourself promotable and work so hard that it would be ludicrous not to pay you more and still find yourself unpromoted. You can do everything “right” and still have everything go wrong. Alas… bad goals.

So, as we head into the new year, what I offer you instead is a few non-monetary goals for your consideration. Goals that have nothing to do with getting promoted and may actually help you have a better work year:

1. Identify a lesson you learned last year — and apply it.

At some point in the past 12 months, your job taught you a lesson worth learning. The great thing about that: you already learned it. The bad thing about that: it’s stupidly easy not to truly internalize the lessons our lives throw at us.

For a simple, wonderful work goal: reflect on one important lesson you learned in 2025 and make a plan for how you’re going to consciously apply it. Identify what scenarios it might come up in and decide how you’re going to integrate your knowledge. Easy.

2. Be more fun to work with.

The goal-setting authorities would certainly hate this one since there’s nothing specific or time-bound about it, but if you want to have a better year, make a point of being more fun to work with.

What counts as “fun” will feel different in different workplaces, but if you need inspiration, here are some of the ways my friends and I have made work more fun over the years:

• Write secret messages into low-stakes PowerPoints in the same font color as the slide background

• Write meeting notes like a screenplay

• Give your meetings sillier names

• “White Elephant” lunches, where everyone orders someone else something absurd for lunch

• Team listening sessions for new Taylor Swift album releases

• Create (kind-spirited) Slack reactions of everyone on the team

You can be excellent at your job and a source of delight at the same time. I imagine you’ve been trying really hard to be excellent. Perhaps this is your year to be delightful.

3. Solve problems nobody asked you to.

This is the closest goal to “get promoted” or “make more money” that I’ll offer. Because if you keep getting skipped for promotions or raises, I’d be willing to bet that you’re not doing this: solving essential business problems without being asked to.

Simply put, doing a great job at everything you’re told is a low-value professional skill. Sorry. Millions of people are more than half-decent at executing someone else’s solution to a problem. Millions of people are also above average at solving obvious problems. Very few people excel at solving problems other people can’t see. If you want to get promoted and make more money, you have to be able to do that.

I’ve learned over time that “find problems to solve” can really stump people. How do you find a problem? How do you find a problem that matters? Ah!

My best advice for achieving this goal is to start asking yourself questions like the following:

• Where does what we say we’re doing differ from what we’re actually doing? How can I close the gap?

• What processes/ways of working are mysteriously harder than they should be?

• What decision keeps getting deferred without explanation?

• Where are we confusing loyalty/satisfaction with inertia?

• What wastes the most time at this company?

Non-exhaustive list, but you get the picture.

If you want to become more valuable at work, make it your goal to solve at least one big problem this year that nobody asked you to.

4. Find something that lets you feel more emotionally balanced at work.

I won’t belabor my personal thesis that most people are bad at work because they’re dysregulated, not unskilled… but seriously. So much of your professional success is built outside of the office.

Instead of spending your year becoming more skilled at your work, make it your goal to become more balanced, regulated, and satisfied. In turn, I promise you’ll find it easier to succeed at work.

Recommendations for where to start: therapy, baking, intramural beach volleyball, a soothing nighttime routine, more regular phone calls with your long-distance friends, reading fiction, meditation, 8 hours of nightly sleep, breaking up with your boyfriend who makes you feel small, stand-up comedy specials, morning walks.

Find what helps you feel in control of your emotions, and make it your goal to turn it into a consistent pillar in your life.

5. Leave.

There are few things I believe more strongly than this: you are never stuck. But that feeling of being trapped, the sense of terminal helplessness we all get caught in… that feeling will swallow you whole if you let it.

So many of us feel this in our jobs, and it’s easy to underestimate how much that helplessness bleeds into the rest of our lives.

If you’re headed into 2026 in a job that’s sucking the life out of you, I want your goal for 2026 to be finding a way out. That can mean quitting into joblessness or finding a new job. Whatever your situation demands. But, my friend, you’ve got to get out.

It doesn’t matter why you’re leaving, and you don’t need other people to validate that it’s a good enough reason. I don’t care what your job is or how you’re rationalizing staying in it. There is no job you need as much as you need your self-respect. There’s not a job on the planet that will do more for you than giving yourself proof that you are the captain of your own life and can walk away from the wrong thing.

If your job is making you feel helpless, know that you’re not. And make it your one and only goal of 2026 to find your way out.

6. Let stuff go (weekly).

My final goal for you for 2026: let more stuff go.

It is so easy to get bent out of shape about things that happen at work. Your friend gets promoted and you don’t. Your coworker won’t stop tapping their pen on their desk. Your coworker always gives you attitude in meetings. Someone else gets credit for your idea.

The things that rile us at work come in all shapes and sizes, and while some of them may be worth your angst, many of them aren’t.

It is a wonderful, noble thing to want to solve all the problems, and address all the issues you have with people, and make everything as good as it can be. Truly. But also… it’s just not that serious. It can simultaneously be true that your work is purposeful, important, and the substance of your life, AND that you let a few more things slide.

So just do it once a week. You can get it out of the way on Mondays if you want. But for just this year, make it your goal to just let it be and keep moving. You’ve got intramural volleyball to get to.

Happy 2026. Wishing you the fullest, bravest, and most exciting year yet. Talk soon.

I get it. We have this nifty new tool that can simulate the act of thinking. And since thinking is notoriously hard and time-consuming, why not outsource? I mainly see it at work. You ask ChatGPT “What am I supposed to make of all this?” or want Claude to tell you what you should conclude from a meeting. You think you’re saving yourself time and getting ahead, and if you’re careful, you might be. But you also might be outsourcing the most basic element of having a personality: forming beliefs and opinions.

The way this happens can be so subtle. As subtle as asking AI to write the meeting agenda instead of coming up with one. But embedded in the task of making an agenda is the work of deciding what’s worth talking about and in what order. Similarly, summarizing a meeting isn’t just making the notes more skimmable -- it’s a discernment task where you form and act on an opinion about what was relevant.

At least in my circles, this idea that discernment is a critical workplace skill is starting to get more airtime. But what we’re not talking about is how discernment skills are built and earned. Devastatingly, to become more discerning, you have to actually practice deciding what matters and what doesn’t. You have to practice forming an opinion.

For those of you who don’t know me, I’ll gently insert that having an opinion is kind of my thing. Not because I have a ton of them (I do), but because I spent eight years competing in a rigorous format of competitive debate and seven years teaching it. I’ve spent over a third of my life literally being trained to form fortified opinions and communicate them to others. If I’m qualified to teach you anything, it’s probably this.

Being able to form a smart, fact-based argument is also the main reason why anyone invites me into a room — and it’s gotten me into a lot of rooms.

As you dive into this novella of a how-to guide, my encouragement for you is that it’s hard but worthwhile. Forming great opinions will get you into those rooms too.

Without further ado: how to form an opinion.

Step 1: Figure out what the question is.

All opinions are answers to questions, but the different questions you have to form opinions about can be quite distinct.

Roughly speaking, there are four types of questions: empirical (what is true?), value (what is right?), practical (what is possible?), and strategic (what should we do?). For this piece, we’ll talk about strategic questions, since they’re the ones that matter most at work, but note that along the way, we’ll end up dissecting several empirical, practical, and value-based questions.

All said: you need to understand what type of question you’re answering.

Let’s do an example.

Your boss approaches you one day and says, “The Director of Learning wants our team to do a mandatory communication training. Should we push back?”

If you take the ask seriously instead of saying “trainings, yuck,” the first thing you need to figure out is what they’re really asking. Are communication trainings important? Does our team need one? Do we have time for one? Is it worth it to argue?

You’re being asked all of these things to some degree, but having an opinion about any one of them on its own won’t answer the question. The question requires you to consider all these concepts, and at the core, what you’re actually being asked is:

“Given all considerations that you think are relevant, is the benefit of doing communication training now greater than the benefit of pushing back on it?”

Simple enough. Except a sneaky amount is going on there.

To answer this question helpfully, you’ll have to assess what all the risks and benefits at stake are. You’ll have to assess what all the “relevant considerations” are that interplay with those risks and benefits. To reach a conclusion, you need to form a synthesized take on how all those things affect and compare to each other.

Not actually so simple. But let’s start.

Step 2: Figure out the stakes.

In policy debate, we call the consequences of policy proposals “impacts.” They range from nuclear war to the loss of Amazonian biodiversity and beyond, but every debate has them. At the heart of every debate is just a comparison of one team’s impacts vs the other’s.

When figuring out your POV, naming the risks and benefits—aka the impacts—is always a good place to start.

What’s at stake if you agree to the training? Lost time, project delays, angry cross-functional partners, and maybe an overburdened and frustrated team. What if you push back? Damaged relationships with the Learning team, persistent bad communication, a team that feels pressured but not invested in?

That list isn’t necessarily exhaustive, but don’t stress about that. Honestly, don’t stress at all. I’m describing this whole internal process in great detail, but it’s also a rather casual thing. You’re just asking, “What types of good/bad outcomes might result from pushing back on the training or not?”

Step 3: Compare the stakes (AKA weigh the impacts).

Now we compare those outcomes! Enter: value question.

People assume value questions are always moral ones, but they can also take deceptively practical forms. To answer a value question, you will have to assign relative importance rankings to different forms of “good” and “bad.” Do not be tricked into believing this is ever a merely practical question. The reason hot-button topics like controversy are so intractable is that people are fundamentally disagreeing about what matters most to them. There’s a whole conversation about how to handle value-based disagreements that’s beyond the scope of this piece, but for now, just realize that your opinions always have values buried within them.

Anyhow.

Let’s say your team is already stretched thin. Deadlines are slipping, stakeholders are annoyed, and leadership is worried that another missed deadline will affect revenue. We might decide that making sure the team gets their work done on time is the most important outcome because delivering on the company’s revenue goals is priority one. It matters more than keeping the Director of Learning happy. More than improving how the team communicates.

The thing to notice here is that to answer the value question, you had to call on context. A lot of it. What if you didn’t know leadership was worried? What if you didn’t know the team was already overworked? I’ll spare you another rant on why context is everything—but it really is. Having rich, current context speeds up opinion-formation and makes all of the thinking feel so much easier.

When you don’t have it, the best opinion is often “I don’t know enough to weigh in.”

Step 4: Form a hypothesis.

OK. Now that you’ve decided what the question is and what matters, you can determine how to answer the question.

The way you’re going to do this is by forming a hypothesis.

NOTE: NOT AN OPINION.

A hypothesis. A provisional theory about how you might answer the question based on your initial assessment.

For example: “Yes, we should push back because the training will interfere with finishing critical work that affects revenue.”

Excellent. Now, we test it.

Step 5: Ruthlessly try to prove your hypothesis wrong.

This step is the whole point of debate as an activity—that you never get to argue for one side of an issue. You will always have to switch sides. You must. Because it is in the switching that you learn to build ironclad arguments.

For your non-debater self, the goal of this process must be proving your fledgling hypothesis wrong. Not right.

As humans, we’re remarkably good at coming up with reasons our intuition is right. I won’t overexplain confirmation bias to you. TL;DR—we’re vain, weak little things who yearn to be right. That nasty proclivity means that in order to form a really good opinion, you need to give yourself a success condition that discourages confirmation bias. Your mission must be to take your hypothesis and pummel it.

Hypothesis testing is also fun (IMO). It’s our turn to ask the questions. Namely: what are all the reasons this hypothesis could be wrong?

Quickly: when I say all, I—once again—don’t want you to waste your life being exhaustive. The goal is thorough, not wastefully meticulous. Opinions can be overbaked just as easily as underbaked. You’ll get better at finding the sweet spot with practice.

But back to our example… what are all the reasons we could be wrong?

Well, what if the training actually wouldn’t take that much time and affect project timelines? What if missing the deadline wouldn’t impact company revenue one way or another? What if the whole reason the team is overworked and missing deadlines is that they’re terrible communicators? What if putting up a fight is a nice thought, but you’d just end up getting overruled? What if the Director of Learning has a ton of influence over the CEO you need something from?

As you were forewarned, to resolve all these questions, you’re going to have to formulate a ton of sub-opinions about all the practical and even empirical questions that could prove your hypothesis wrong or right.

I won’t torture you with working through all of these (although if you’re just delighting at this exercise and want to… literally message me any time). But we’ll do one question as an example:

What if the training won’t affect project timelines?

When you formed your hypothesis, you probably assumed that training was a big burden. Maybe that was with good reason. The last training the team did took three whole days. And wasn’t any good. Are trainings intrusive? Empirically, yes.

But answering the empirical question does not a reasonable opinion maketh. You don’t know how much time this one would take. You, my friend, need more info.

Realistically, if the training is short, it probably won’t jeopardize a project or team morale. It could if you’re on a really tight turnaround, but for this hypothetical project, we’ll assume that as long as the training is under two hours, it’s not actually disruptive.

So we need to revise our hypothesis to a conditional statement: if the training is over two hours, we should push back because it will interfere with finishing critical work that affects revenue.”

Step 6: Test more, and more, and more.

Now… we just test again. We’ve resolved the question of whether it’s going to waste time; now we tackle everything else critical. It’s rinse and repeat from here, friends.

Pose more questions and resolve them. If you find that you’re info to answer lots of them, maybe suggest everyone hold off on a decision and go learn more.

In debate, we call all these causal steps between an action and an impact “internal links,” but in real life, they’re just practical questions. Still, I’ve always loved this debate language because it helps convey the point that if the consequence depends on a set of assumptions, sometimes all it takes is one false assumption to break the whole chain. Sometimes one test is enough.

The more you practice this hypothesis testing process, the better you’ll get at figuring out when you have to test it all and when one well-placed inquiry can get you to a decent opinion.

Again. Don’t get all Sisyphean about this. There’s a fine line between thorough and stupid.

Final Step: Communicate your opinion.

Once you’ve done all the testing necessary to feel confident in your opinion, the last thing left is to figure out how to share what you think.

I wish I could give you a script for this. So many people can reach this stage, have well-thought-out beliefs, and still feel shackled by the fear of speaking out. That makes me so sad.

If that’s you, all I can offer you is the promise that if you’ve truly gone through such meticulous steps to form an opinion, you can handle whatever you’re worried will happen when you share.

Of all the things I learned in debate that profoundly impacted my life, it is this one that mattered most: being told you’re wrong is not the same as being told you’re bad. People might and certainly will disagree with you sometimes. They might even think you’re dumb. But that doesn’t make you bad, and you can’t let it deter you.

Even if you can’t convince others, sharing well-formed opinions elevates the level of rigor for others around you. We work hard to form our beliefs because it earns us the right to express them. That is why you go through the tedium at all.

If all of that was lost on you because you’re wildly confident in your right to share an opinion, the final tip I’ll leave you with is to share less of it than you think you should.

When we do the hard work to formulate our POV, it’s hard to resist the desire to show that work. You want credit! You want to display your brilliance!

You have to learn not to. No one needs to hear the whole journey of how you got from A to B. And if they do need to, they’ll ask.

When communicating to peers, leaders, and frankly… almost anyone who you aren’t actively trying to develop or mentor, keep the altitude high: “I think we should X because Y, even if Z.” If they have questions or need to know more, just give them space to ask.

OK! If you made it this far...

You might have really enjoyed competitive debate. (Although probably not. Recreational interpersonal aggression takes its toll.)

Whether you’ve never felt confident in your beliefs or you’ve just become a little too AI-reliant, I hope you give this process a spin. Like all good things, it takes practice. But becoming someone with thoughtful, informed, hard-earned opinions is worth every effort.

Well, at least in my opinion.

Thanks for reading. Talk soon.

P.S. -- if you happened to like some of the debate stuff in this, do me a favor and let me know. There’s a lot more of that rattling around in my brain. I’m just unsure if it’s useful and engaging to others.

Every time I’ve started a new job, there’s been at least one brief, first-day moment when I thought I was going to throw up. No actual carnage so far… but the nerves have also never abated. Leaving the cozy enclosure of a familiar job is exciting, except for the whole trading in all your known relationships and ingrained habits for new people, places, and things part. I would do unspeakable things to avoid ever entering a new office again and awkwardly asking where to sit.

While I do think you (I mean “I”) should get over the fear of not knowing where to sit, it is worth worrying a little bit about your first day. Not in a neurotic way. Just enough to make you take the opportunity in front of you seriously.

Starting a new job is one of the only opportunities most of us get in our adult lives to truly start from scratch. Sure, January 1 rolls around each year, but moving from one job to another is the single most common and holistic way for a person to uproot their day-to-day life without having to move cities or have a weird Eat Pray Love moment.

Really, how often do you get to hit the reset button on what you do and who you do it with every day of the week? The magnitude of the reset is sort of wonderful.

It also warrants giving some thought to how you want to approach a new job. And thus, I offer you a listicle. While there are loads of good (and bad) pieces of advice out there that this piece doesn’t cover, here are five of my best-used tips on how to set yourself up for success at your new gig.

Decide who you want to be.

The easiest way to muck up a first impression is not knowing what type of impression you’re trying to make. Maybe that sounds obvious, but I’m intrigued by how many people stress about others’ opinions of them while simultaneously having no idea what opinion they want those people to have.

Start your first day of work preparations by deciding what impression you’re trying to make. Do you want to show people you’re fun? Hardworking? A subject matter expert? Humble? All of the above? Great. Pick a few of the things you’re most eager to showcase about yourself in this new role, and commit to them.

One of my favorite pieces of general self-improvement exercises is to write down (in detail) what type of person you want to be. What qualities do they have? What habits? Then, let the question, “What would that version of myself do?” guide your choices.

This exercise works wonderfully for starting a new job. Write down the impression you want to make and ask, “What would someone who is X, Y, Z do in a meeting? At lunch? After work?” Then… commit to doing those things until they become your new habits.

Try as hard as you reasonably can.

The operative word is “reasonably,” but I really think there are very few times it’s more important to work your butt off than when you first start a job. I know I find a way to say this in nearly every newsletter, but there is genuinely no substitute for hard work. The “work smarter, not harder” people are lying to you. Yes, be maximally efficient. Duh? But there’s a reason you don’t hear people extolling the virtue of “smart work” the same way they do “hard work.”

When you start a job, demonstrate your commitment to the team and showcase your capabilities by taking on as much volume as you can without compromising quality. Showing up and doing great work is important. Showing up and doing a lot of great things tells people you care and you’re ready to be a great teammate.

Be valuable, not just helpful.

Unless you are an associate or admin and “be helpful” is the basic mandate of your job, my forewarning—to women, people of color, and early-to-mid-career generalists especially— is that “trying as hard as you reasonably can” does not mean jumping at every little task to prove yourself.

This has been wildly challenging for me. It’s hard to recognize when you cross the “what got me here won’t get me there” threshold at work, but eventually, the type of “say yes to every opportunity” behavior that’s critical to opening up learning opportunities as an early-career employee becomes a troublesome signal that you lack discernment and self-awareness of the value you bring.

This advice is particularly important for new leaders and managers.

While you’re out here trying your absolute hardest, still remember to ask yourself what you’re teaching people about yourself through your behaviors. Stretch onto a cross-functional project or pick up some low-difficulty tasks because you think they’ll help you gain context? Go for it. Ingratiating yourself by reflexively offering to make slides, format docs, and take on high-tedium/low-impact work? Skip it or delegate it (if appropriate—don’t take stuff on that sandbags your team). You teach people how to treat you and what your time is good for.

(For a full diatribe on being valuable v helpful, see: guide to being an advanced generalist).

You don’t need to super-sleuth. Just ask for context.

One of the hardest parts of starting a new job is figuring out where your experience is enough to let you dive in vs where you need more context. It’s easy to assume that everything requires a month of onboarding to understand or to err in the opposite direction and assume you’re ready to start changing big things on day one, since you did similar work at your last job.

Critical thinking will help you figure out which problems you’re ready to tackle, but so will the devastatingly simple and underutilized tool of “just ask someone.” You can (and probably should) read as much of the company intranet as possible, comb through years of docs, and try to show off all your fancy reasoning skills, but also just ask people for more information and guidance. I would kill for a direct report to ask me “what knowledge do I need beyond my past experience to do X?” Everyone wants you to be asking more questions! Here are some things you can always just ask instead of playing detective:

• Why is this [process/product/norm] the way it is? What’s the story?

• What are the 2-3 most important things to know about this project before I start on it?

• At my last job, I assumed “X, Y, Z” was important when doing this type of work. Is that what matters here?”

Focus on building trust with teammates, not making friends.

Maybe a controversial take, but I despise a random coffee chat. Maybe that’s just the introversion talking, but I’ve never understood why it’s a good use of anyone’s time to exchange abbreviated autobiographies with people you’ll never work with. I know you want friends, and it’s not bad if you find them. But don’t let the initial loneliness of starting a new job distract you from which relationships matter.

The beautiful thing about strong work friendships is that they’re usually forged naturally by working together. You don’t have to trawl the business for people with the same taste in music and beg them to have lunch. Show up, be generally pleasant, and let the friendship-inducing effects of proximity and collaboration take hold.

I know this can be lonely for a minute. Some people’s jobs are also more insular, and you might find it takes longer to find your people than it might take others. But be patient. The easiest way to poison your chance at friendships is to disappoint people early so that others won’t want to work with you. Do a great job, have people’s backs, chill with the fifteen random intro meetings a week, and you’ll find connections. You have my word.

So, whenever and wherever this next phase takes you—good luck. I’ll be cheering for you.