Why I Love Conan O’Brien (& I Don’t Even Watch His Show)

I recently started following Conan O'Brien on Twitter. I figure it's the least I can do, since I never watched him when he was on at 12:35AM, and I watched a grand total one whole episode of the Tonight Show, AFTER the J-- L--- controversy. I have loved Conan since I read a transcript of his June 2000 commencement speech at Harvard. I remember getting the email of the transcript (this was before YouTube), sent by my Harvard classmate Ann, who was in London about to leave her job at an investment bank and enroll in culinary school in France. I remember printing it out, and highlighting certain passages of it, before posting it on the wall next to my desk, in my Ann Arbor, Michigan apartment. And that's when my love for Conan began. Not only was it unusual to have Conan's brand of humor in the context of a Harvard ceremony, but it was also unheard of (at that time) to hear a person stand behind a podium and talk about his failures. He went in chronological order, covering each stage of his hopeful steps toward being a working comedian on television. At one point, with nowhere else to turn and his fledgling cable show having been cancelled, he even got a temp job at Wilson's House of Leather. As a Harvard graduate. The highlighted passages on my faded print-out still ring like a soliloquy by my beloved Conan:
"Needless to say, I took a lot of criticism, some of it deserved, some of it excessive. And it hurt like you wouldn't believe. But I'm telling you all this for a reason. I've had a lot of success and I've had a lot of failure. I've looked good and I've looked bad. I've been praised and I've been criticized. But my mistakes have been necessary. Except for Wilson's House of Suede and Leather. That was just stupid." "I've dwelled on my failures today because, as graduates of Harvard, your biggest liability is your need to succeed. Your need to always find yourself on the sweet side of the bell curve. Because success is a lot like a bright, white tuxedo. You feel terrific when you get it, but then you're desperately afraid of getting it dirty, of spoiling it in any way. I left the cocoon of Harvard, I left the cocoon of Saturday Night Live, I left the cocoon of The Simpsons. And each time it was bruising and tumultuous. And yet, every failure was freeing, and today I'm as nostalgic for the bad as I am for the good. So, that's what I wish for all of you: the bad as well as the good. Fall down, make a mess, break something occasionally. And remember that the story is never over."
And that message has always stuck with me. I sat on the floor reading it as I entered my fourth year of medical school, wondering how I had ended up there. I pulled it out when I was having thoughts of leaving my job in venture capital, but was gripped with the fear that I would be letting others down. I've since realized that each time I picked up and left, I was still suffering from my own version of the white tuxedo. I wanted to make "clean" breaks with my past each time I left a career. I wanted to shed the identities that I had so carefully cultivated, but I would leave only to start putting on another one. All my life I've desperately wanted to have an identity that other people could understand, while also struggling to be free to understand myself more fully. I always felt that I was more than any job title or industry, but never got comfortable with just being "me". I didn't feel I ever knew my own full potential, and I wanted to live my life trying to find out. It would require embracing my own definition of failure and allowing the possibility, knowing that I would survive. I love Conan more than ever now that he has gone through the storm of being booted out of his Tonight Show gig and emerged as an independent roadshow star. Watching his video at Google shows that he has the resilience of someone who doesn't feel entitled to stardom, but has the steadfast belief to put his craft out there for whomever will receive it. Using his name recognition and social media tools, he has jumped headfirst into the arena of internet marketing, selling out his roadshow within a few hours using only one Twitter link to a website selling tickets. I particularly love his grasp of the whole "smart" crowd that populates the employee ranks at Google, even as he makes jokes at their expense. He can laugh at himself, which is a lesson we can all hope to learn. I love that he continues to live the lessons he talked about way back in 2000. He continues to get into new white tuxedoes, unafraid of getting splashed with mud. Sure, he gets pissed off like anyone of us would if our brand new jacket were soiled, but he's got an inner source to tap into, a humility and humor reserved from all those years of failing. He isn't afraid to pick himself up, and change jackets. Maybe this time around, he'll just be happy wearing a T shirt.

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