Dreams of Things that Could Have Been

A few nights ago, I stayed up way too late drawing up a CV of my various professional failures. For most of America’s existence, we’ve made a point to celebrate risk-taking, boldness, and even sometimes failure, and I wanted to get a sense of how I stacked up. But what I learned from that exercise was absolutely not what I had expected: While I make a lot of mistakes and get rejected from a lot of opportunities, in the grand scheme of things, I frankly don’t think I’ve failed enough.

The man who popularized the idea of a “CV of failures,” Princeton professor Johannes Haushofer, chose to publicly admit his disappointments and shortcomings because he understands that “Most of what I try fails, but these failures are often invisible, while the successes are visible.” Just look at his actual CV—it’s a holy terror. By any account, he is one of the most highly educated men on the planet. But as his anti-CV demonstrates, he went through a lot of failure to get to where he is now.

In fact, if a CV of failures seems small, it’s almost certainly because you haven’t dared to push yourself to your limits. And if your CV is big but bland, like mine, it’s probably because you haven’t allowed yourself to fully pursue your dreams. Haushofer notes, correctly, that failures are the product of trying. In a preface to his anti-CV, he writes, “[I]f it’s shorter than yours, it’s likely because you have better memory, or because you’re better at trying things than me.”

“Better at trying things than me.” What’s that supposed to mean?

And then I understood.

Before coming to law school, my last four jobs were in political policy, a political campaign, an investment firm, and then another political campaign. The jobs I’d been rejected from were almost entirely government-centric, with a few finance and consulting positions thrown in. The schools I hadn’t gotten into were almost entirely analogous to the schools I actually attended. I had to ask myself: What about the failures that don’t show up in my anti-CV because I never even tried?

And while I think it’s good to know exactly what you want to do, I also think you should be skeptical—relentlessly so—when looking at an anti-resume like mine. In particular, you should continually ask whether the person you’re dealing with simply has a one-track mind.

A great school expands your field of possibilities, but the pressure it places on you to perform in a particular way is psychologically limiting. As a country, we want people who go to great schools (and generally graduate with little or no debt) to follow their dreams—to make decisions independent of concerns about salary or prestige. Yet our alumni—and this is hardly unique to Harvard—generally take the path of least resistance. They don’t normally become authors, activists, or military officers. A military lawyer did try to recruit me a few days ago, but the truth is that I myself won’t be doing any of these things. They’re not what I want to do for a living. But I also have to consider the fact that around here, they’re also simply not the done thing.

Part of this is unavoidable, and not unique to a university. Sometimes, the world eliminates possibilities for you. Growing up, I wanted to be Dodgers ace Kevin Brown, but life eventually taught me that I couldn’t throw a strike. Some things you realize you don’t want to do forever—for me, journalism, travel writing, scripting for the silver screen. And to a certain extent, making money is important—the only shame would be in denying it. But some of my interests I’ve never taken the time to fully explore.

Specialization is unavoidable, but we can try to be thoughtful about the inevitable. I don’t regret the path I’ve taken. Given my particular skills, interests, and obsessions, it’s hard to imagine doing something substantially different. But where we as a university fall short is in the very act of imagining itself. And yet, in life, we rarely regret the things we tried; we always, however, seem to regret the things we never dared to do.

So here’s my suggestion. Harvard is the second-most-cramped school in the Ivy League. People here are everywhere in a way that is truly difficult at times for a California kid to conceptualize. So carve out some time for yourself. Take a moment to be alone.

Few here have the time to meditate like monks. But you can still get out of the Harvard bubble. Bring a beach chair to Boston Common, take a trip to Cape Cod, or even find your own secret spot on campus—trust me, there are a lot of them. Think about where you came from and the person you want to be. Erase the pressure, the distractions, the deadlines, if only for an afternoon. Reclaim your right to think about the big picture.

Your mind will always point you in the rational direction. But don’t let the chaos and clamor of ordinary life completely foreclose the possibility of following your heart.

Winston Shi is a current first-year at Harvard Law School. His column appears on alternate Tuesdays.