Why Being Good at School is Making Us Bad at Work

Over the past few years of hiring young people, something has become increasingly obvious to me: the school-to-work pipeline is broken.

Ask anyone who hires recent grads, and they’ll have some version of this story: candidates roll in with impressive credentials, high polish, and strong interviews... followed by an immediate inability to autonomously solve even simple problems. Across the labor market, employers are souring on some of our country’s best-educated students, managers are declaring that Gen Z is underprepared for the workforce, and even young employees are turning to each other to try to figure out why they’re struggling so much if, just years ago, they were navigating and succeeding in the most competitive academic landscape our country’s ever seen.

Some of this dysfunction is definitely attributable to the cocktail of anxiety, entitlement, social media addiction, ennui, and idealism that afflicts our current batch of twenty-four-year-olds. But I also think there’s something broken beyond the wrinkles in the social fabric. The system that is supposed to prepare us for our launch into adulthood is leaving young people insecure and incompetent.

It’s not just that the school-to-work journey isn’t working for everyone; it’s that it’s not working for anyone. Modern schooling is making young people actively bad at work.

School is not Like Work

If I could reduce the many differences between school and work to one critical distinction, it would be this: at work, your job is to serve a customer, but at school, you are the customer.

Whether you enjoy the experience or not, school is engineered around you and your growth. It feels like work because it's hard, and we use terms like academic “career" to liken it to employment because school is a progressive journey where knowledge compounds into expertise. But whether you're paying for your education through tuition or taxes, you are, in fact, the consumer.

In contrast, the entire premise of work is that you’re part of a system designed to create value for someone else. Your job is to be useful and to create value, regardless of how much value you’re deriving in the process, and being self-interested at work is a surefire way to underdeliver where it counts.

This difference is the core of what trips up many young professionals and causes them to burn out, check out, or simply fail. They’ve built a misplaced orientation to doing hard work and bought into myths about success that felt true for seventeen years, but can’t carry them beyond the classroom.

While I could keep you here all day discussing the ways I’ve seen this show up in young people, here are the three core school-implanted myths that I think young people need to unlearn to succeed at work:

Myth #1: Being Smart Is the Point

In school, intelligence is both the currency and the goal. We test for it, sort by it, and reward it. Education is essentially a prolonged intelligence pageant where the kids who can best convince people they're the smartest reap the prize money. Smart is the whole point.

At work, being smart is table stakes. At best, it makes your coworkers take you more seriously, but it often just makes you a nuisance.

Smartness-obsessed employees over-explain simple concepts, produce overcooked deliverables that are unreadable to leaders who are short on time, and spend hours dressing up decisions instead of actually making them. They overfocus on presenting work that shows off the expansive mindscape of their intellect instead of questioning whether they’re creating work that’s useful to someone else.

Unfortunately, work is not a problem set. You don’t get points for showing your work. The output matters. Your winding, thoughtful journey to get there almost never does.

Instead of trying to prove that you’re smart (you already did… that’s how you got hired), go try to figure out how you can be most valuable. You might just find that in a sea of alleged geniuses, the most valuable person is often the one who is willing to do the elbow-grease tasks that everyone else feels too smart for.

Myth #2: Failure is Fatal

Another misplaced belief that schools instill in young people is that failure is to be avoided at all costs. Always. Some of this comes from the hypercompetitive landscape of American education, but it’s also just baked into the system. A bad test at eighteen is memorialized in the GPA you graduate with at twenty-one. One bad class can be the difference between being eligible for certain jobs and graduate programs, so why would someone risk taking a class they struggle with when all mistakes are archived and averaged?

In the workplace, that mindset is lethal. Most real jobs require making decisions with incomplete information, shipping before you’re ready, and earning wisdom from mistakes your competitors aren’t willing to risk. Different industries and jobs certainly have different tolerance levels for failure (surgeons, this newsletter is, as always, definitely not about you), but in most jobs, getting ahead mandates taking risks that others won’t and often failing in the process.

The young people I see at work today are terrified of this prospect. They’re hesitant to jump into unstructured projects, uninterested in solving problems that they aren’t positive they’ll be rewarded for, and desperate to be told they’re “good.” That’s all fine and well if you want to have a perfectly middling career, but these attitudes invariably cap people’s growth and keep them trapped in solving problems that most other people could also solve. Simply put, the only way to be exceptional at work is to do something that other people either can’t or won’t. You have to be the exception. And the number one thing that will stop you from doing so is fear of failure.

You have to keep moving and keep reaching, even when you don’t feel bulletproof. And while school might keep the score of all the times it didn’t work out, in work, the lessons learned from failures can be serious advantages over time. The only people who get them: the people who are willing to fail.

Myth #3: Progress Always Goes Up and to the Right

In school, progress looks an awful lot like a ladder: each year you advance, climb higher, take more challenging classes, solve more complex problems, cross classes off your requirements list, accumulate more accolades, and keep it moving.

Work is way messier, and the rungs on the metaphorical ladder are often unevenly spaced. While school instills in students an annual cycle of moving forward, careers often involve many consecutive years of moving sideways, stepping backwards to make a switch, or just staying still in one job or on one project without an annual graduation to say “you’re doing great.” Progress is won in small moments and lessons, in better relationships and microscopic battles, and yes, eventually, in promotions and pay raises, but just as often in redirection toward more suitable paths.

One of the hardest things for high-achieving students-turned-employees is adjusting to a world where there’s no guaranteed promotion or gold star waiting at the end of the quarter. At work, doing good work is sometimes its own reward, and great work can go unnoticed, leaving students who were taught to think of success as a steady march forward feeling devastated and stuck in place. Worse, it can trap employees in the cycle of over-fixating on titles, jobs, and chasing validation instead of learning and building a wealth of experience to serve them later on.

Somewhere along the way, we confused measurable progress with meaningful growth. Young employees need to learn to navigate the unmarked, winding path that starts where schools stops.

The kids who played the game exactly right are struggling to play a new one with very different rules and scorekeeping. And while a little deprogramming and re-learning can go a long way for anyone, if we want to help young people feel a little less lost and get a lot more out of them in the workplace, we might have to stop pretending that school was ever the right map to career success.

Thanks, as always, for reading. Talk soon.