The Freedom Of Failure

Thanks to Spike for posting a link to Conan O’Brien’s commencement address (2011) at Dartmouth College. As you can imagine, O’Brien covers a lot of ground and makes some great jokes,

“You know, New Hampshire is such a special place. When I arrived I took a deep breath of this crisp New England air and thought, “Wow, I’m in the state that’s next to the state where Ben and Jerry’s ice cream is made.”

Once O’Brien gets to the heart of his message, he manages to keep the humour going, while making a profound point about the way “failure” can liberate us personally and creatively. I’ve quoted the heart of the message below, but if you have the time do check out the video of Conan’s address in full.

“Now, by definition, Commencement speakers at an Ivy League college are considered successful. But a little over a year ago, I experienced a profound and very public disappointment. I did not get what I wanted, and I left a system that had nurtured and helped define me for the better part of 17 years. I went from being in the center of the grid to not only off the grid, but underneath the coffee table that the grid sits on, lost in the shag carpeting that is underneath the coffee table supporting the grid. It was the making of a career disaster, and a terrible analogy.

But then something spectacular happened. Fogbound, with no compass, and adrift, I started trying things. I grew a strange, cinnamon beard. I dove into the world of social media. I started tweeting my comedy. I threw together a national tour. I played the guitar. I did stand-up, wore a skin-tight blue leather suit, recorded an album, made a documentary, and frightened my friends and family. Ultimately, I abandoned all preconceived perceptions of my career path and stature and took a job on basic cable with a network most famous for showing reruns, along with sitcoms created by a tall, black man who dresses like an old, black woman. 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. To this day I still don’t understand exactly what happened, but I have never had more fun, been more challenged—and this is important—had more conviction about what I was doing.

How could this be true? Well, it’s simple: There are few things more liberating in this life than having your worst fear realized. I went to college with many people who prided themselves on knowing exactly who they were and exactly where they were going. At Harvard, five different guys in my class told me that they would one day be President of the United States. Four of them were later killed in motel shoot-outs. The other one briefly hosted Blues Clues, before dying senselessly in yet another motel shoot-out. Your path at 22 will not necessarily be your path at 32 or 42. One’s dream is constantly evolving, rising and falling, changing course. This happens in every job, but because I have worked in comedy for twenty-five years, I can probably speak best about my own profession.

Way back in the 1940s there was a very, very funny man named Jack Benny. He was a giant star, easily one of the greatest comedians of his generation. And a much younger man named Johnny Carson wanted very much to be Jack Benny. In some ways he was, but in many ways he wasn’t. He emulated Jack Benny, but his own quirks and mannerisms, along with a changing medium, pulled him in a different direction. And yet his failure to completely become his hero made him the funniest person of his generation. David Letterman wanted to be Johnny Carson, and was not, and as a result my generation of comedians wanted to be David Letterman. And none of us are. My peers and I have all missed that mark in a thousand different ways. But the point is this : It is our failure to become our perceived ideal that ultimately defines us and makes us unique. It’s not easy, but if you accept your misfortune and handle it right, your perceived failure can become a catalyst for profound re-invention.

So, at the age of 47, after 25 years of obsessively pursuing my dream, that dream changed. For decades, in show business, the ultimate goal of every comedian was to host The Tonight Show. It was the Holy Grail, and like many people I thought that achieving that goal would define me as successful. But that is not true. No specific job or career goal defines me, and it should not define you. In 2000—in 2000—I told graduates to not be afraid to fail, and I still believe that. But today I tell you that whether you fear it or not, disappointment will come. The beauty is that through disappointment you can gain clarity, and with clarity comes conviction and true originality.”