Image courtesy

There’s a speech I like listening to on YouTube: Conan O’Brien’s 2011 Dartmouth College Commencement Address. Like most commencement speakers, he talks about failures and following your dreams.

Unlike most commencement speakers, O’Brien explicitly tells us to actively avoid failure because, as he stresses, failure will nearly kill you if it doesn’t actually kill you. But after that, it’ll liberate you.

In Conan’s case, his failure to become host of The Tonight Show meant he got to travel around the country doing comedy shows in a skin tight leather blue suit, tweet his comedy out for free, and land a new show on a new network where he racks up millions of views. I did a lot of silly, unconventional, spontaneous and seemingly irrational things and guess what: with the exception of the blue leather suit, it was the most satisfying and fascinating year of my professional life… I have never had more fun, been more challenged—and this is important—had more conviction about what I was doing.”

I never quite understood that until I experienced a massive failure of my own. Prior to my sophomore year of high school, I was certain of what I was going to do with my life: I was going to become a kickass debater, one of the best on my school’s nationally renowned team and an even better math student and future filthy, filthy rich actuary. I would graduate and easily get into the college of my dreams, Brown. Or Dartmouth. Really any Ivy League, I wasn’t terribly picky. I would fulfill every wish that my parents, my friends, my coaches, hell, probably even my teachers had for me. Rarely did I consider what I may have actually wanted to.

But come sophomore and junior year, things fell apart faster than things did in the book I read in AP Lit this year, Things Fall Apart. I went from being a kickass debater to praying to win just a few rounds and considering myself lucky if my record was neutral. My grade in math slipped from an A…to a B…to a B minus, and I said goodbye to my dreams of becoming an actuary and getting into an Ivy League school. I also started hating math, so not becoming an actuary actually seemed pretty fantastic. But the most painful part was how humiliating it was, and I just couldn’t ask for help because I was so full of pride and so arrogant. I literally thought that even if I struggled a bit now–which I expected–I sure as hell wouldn’t struggle later on because I’d be so damn good that no one could touch me and I’d be that person that I had so badly needed to be, even if I stopped wanting it anymore. So when I started failing, I couldn’t bring myself to admit it.

But once I was able to admit it, it turned out to be the best thing that happened to me, because it liberated me from all preconceived notions of myself and it meant that I didn’t have to be the person that so many people needed me to be anymore–instead I got to be more of…myself. I got to make goals based on my passions instead of my parents’ wishes. I got to dream about working with kids or studying literature instead of planning for a future on Wall Street or in a dreary cubicle with bytes and bytes of data to analyze. I got to research colleges based on how good of an English department they had–and reject the schools whose curriculums focused too much on straight white males!

Failure also humbled me–because of my pride and arrogance I couldn’t even bring myself to ask for help when I struggled and isolated myself, thinking that everyone (or nearly everyone) was doing better than me and wouldn’t understand, and I didn’t want to hear their attempts at reassuring me. Knowing that I could–or did–fail meant that I was actually willing to ask questions and work harder than usual to get a good score: I went into advanced comp, an advanced writing class, thinking that I might fail and that I’d struggle a lot for an A, so I pushed myself into overdrive, polishing and polishing and absorbing all the criticism and double checking requirements to make sure I did well and to make sure I actually improved–or at least learned something.

Failing was an opportunity to succeed, even if it hurt like hell.