What I Wish I Learned in College

Colleges teach you how to think. What they should teach is how to live a life that matters.

On the train up to Yale for an event, I told my friend Cherie, “Whenever I go back, I get this feeling of anxiety. It’s not about other people judging me—it’s about me judging myself. Am I doing enough? Am I worthy of having gone here?”

She didn’t hesitate. “Oh yeah. I have that too. It’s called Yale-ing.”

That was it exactly—the quiet, constant self-surveillance that comes from trying to measure up to an imaginary, idealized version of yourself. Yale searches for the most driven, unconventional, obsessive people it can find and gives them space to run. What looks like drive from the outside is often anxiety on the inside—a constant need to prove themselves again and again. They’re insecure overachievers.

Insecure Overachievers

I once heard someone say, “Almost everyone at McKinsey is an insecure overachiever,” and I laughed—it sounded like the perfect insult. But it turns out the phrase comes straight from research by Professor Laura Empson, who studied high-performing professionals across elite firms and found they aren’t just ambitious, they’re fragile. Brilliant, obsessive, relentless—but powered less by confidence than by a gnawing sense that they’re never enough.

Once you spot this pattern, you can’t miss it. Law firms, investment banks, consulting shops, Silicon Valley startups, elite universities. These people don’t work harder because they want to; they work harder because they have to. They need achievement like a drug—one more hit of validation to keep the insecurity at bay.

That’s great for institutions. Insecure overachievers deliver exceptional results. They’ll grind through the night, take on impossible goals, and keep raising the bar long after anyone else would have stopped.

But here’s the bitter irony: the very thing that makes them valuable to the system is what hollows them out as people. Drive shackled to insecurity becomes a trap that looks a lot like success until you’re the one living it.

The Smartness Trap

We were told: They’re smart, they’ll figure it out. But the smartest kids are often the most fragile. It’s the same problem you see with thoroughbred racehorses—their legs are so finely tuned that a single misstep can shatter bone. All that speed, but no tolerance for imperfection. When your entire identity is built on being exceptional, uncertainty doesn’t just threaten your plans—it threatens your sense of self.

Maybe we should breed students less like racehorses and more like draft horses. A racehorse knows how to explode out of the gate, but a draft horse knows how to carry the load mile after mile. Life isn’t one short, glorious sprint—it’s a long, uneven course that demands resilience as much as brilliance.

A Different Kind of Smart

Yale teaches intellectual flexibility—how to analyze, debate, and deconstruct ideas. What it doesn’t teach is psychological flexibility: the ability to step back from your own thoughts and feelings, see them as mental events rather than absolute truths, and choose actions based on what really matters to you.

Without that skill, many Yalies end up brilliant but brittle. They avoid experimenting where they might not immediately excel, get locked into scripts like investment banking because it’s the “next logical step,” feel anxious when not visibly winning at something measurable, and double down on effort even when goals don’t align with their values.

Laurie Santos’s The Science of Well-Being has become Yale’s most popular course, introducing students to positive psychology tools. But learning to boost your mood doesn’t go deep enough into the pathologies that drive Yale students: perfectionism, self-criticism, the sense that nothing is ever enough.

Psychological flexibility means noticing the voice that says I’m not doing enough, I’m falling behind, I don’t belong and learning to hold it lightly rather than taking it as gospel. It means sitting with discomfort—fear, failure, even boredom—without immediately trying to outrun it with another achievement. Most of all, it’s about aligning your actions with values you choose for yourself, even when it’s hard, even when the outcome is uncertain.

What Yale Should Teach

If Yale really wanted to prepare students for life, it would teach psychological flexibility as deliberately as it teaches critical thinking. This means learning to:

• Step back from thoughts and recognize them as passing mental events, not absolute truths
• See identity as bigger than labels like “smartest” or “future leader”
• Pivot when values or circumstances change, instead of grinding harder at the wrong goal
• Tolerate discomfort and uncertainty without rushing to resolve it through achievement
• Choose based on your own values, not just what looks impressive on a résumé

With real training in psychological flexibility, graduates could handle the identity shock of no longer being “the best,” detect early when goals don’t align with their values and change course, experiment more boldly knowing uncertainty is part of growth, and sustain long-term well-being because their self-worth isn’t tied to one narrow definition of success.

Yale would still produce people who execute at the highest level—but only on goals they actually choose, not just ones handed to them. That’s the kind of smart the world needs: not brilliance without direction, but wisdom with stamina.

Leading a Good Life

The goal should go beyond helping people be smart—it should help them lead good lives. Psychological flexibility allows you to step back from inherited assumptions and choose your path based on what truly matters, not just what looks impressive from the outside.

Without it, intelligence risks becoming a tool for chasing the wrong things faster. With it, intelligence can be directed toward building a life that is not only accomplished, but meaningful. That’s what true wisdom is about—not just knowing more, but knowing what matters, and having the courage to shape your life around it.

If Yale could instill that kind of wisdom alongside brilliance, its graduates wouldn’t just be prepared to succeed in the world—they’d be prepared to live well in it.

References on Psychological Flexibility

• The Happiness Trap by Russ Harris – a practical guide to noticing thoughts, defusing from them, and living by values.
• A Liberated Mind by Steven C. Hayes – the definitive book on psychological flexibility, written by one of the originators of the concept.
• The Extraordinary Gift of Being Ordinary by Ronald D. Siegel – on how strength comes from letting go of perfectionism.
• The Science of Well-Being by Laurie Santos – Yale’s most popular course, a positive psychology foundation and an entry point into this work. You can take it for free on Coursera.