Of all the late night hosts, I have always had a very soft spot for Conan O’Brien. His humor is exactly my type, while I find Letterman to be a bit too awkward, Kimmel to be too stoner-ish, and Fallon to giggle too much (and I simply don’t find Jay Leno funny at all). O’Brien’s humor is that perfect mix of self-deprication and blatant immaturity. But I think why I have always really liked O’Brien is because he, despite his amazing career success, always seems to be the underdog. And in my opinion, the underdogs are the most passionate and hardest working people out there. You want one of these on your team. This is why my favorite commencement speech of all time is the one he gave at Dartmouth in 2011 after the scariest and most exhilarating year in his career.
Of course, O’Brien isn’t your classic underdog in that he attended Harvard, where he wrote for the famous Harvard Lampoon (and met his future NBC boss, Jeff Zucker, who was Editor-in-chief of The Harvard Crimson). After graduating magna cum laude in 1987, he pretty quickly landed a job writing for comedic institution Saturday Night Live. He also worked the improvisational comedy circuit.
Things were going well for old Coney, but then he began to feel burnt out after being at one of the toughest gigs in show business for five years. He also had an engagement broken off and a television pilot he wrote that wasn’t picked up in quick succession. Not so awesome. He left SNL with really no plan.
“I told Lorne Michaels I couldn’t come back to work and I just needed to do something else,” O’Brien said. “I had no plan whatsoever. I was literally in this big transition phase in my life where I decided, I’ll just walk around New York City, and an idea will come to me.” This wasn’t the first time O’Brien would be a little lost in his career.
But he found his footing, landing a writing job for a little show called The Simpsons. He worked there from 1991 to 1993. He prospered there, but we hadn’t seen anything yet. When David Letterman announced he was leaving Late Night, it was up to producer Lorne Michaels to find a new host. Michaels thought of O’Brien in a producer role for the show, but his agent said he was more interested in performing than producing. After auditioning, O’Brien landed the gig and his life changed forever.
So O’Brien lands every comedian’s dream gig and the rest is history, right? Not so much. Late Night with Conan O’Brien struggled horribly in the ratings. O’Brien’s team literally had to fight to keep the show on the air as the network kept making threats. The reviews of the show were not great either. Everything seemed to be going against him, even his height.
“There were so many doubters the first year,” says Jeff Zucker, the president of NBC Universal. “They said Conan jumped around too much in front of the camera, that he was too smart, too East Coast, too sophisticated, too young, and even too tall to be successful. But Conan proved everybody wrong. We learned that you underestimate Conan at your own peril.”
But finally he found his footing and a loyal audience with young men, a coveted demographic in television viewer land. As of October 2005, Late Night with Conan O’Brien had for eleven years consistently attracted an audience averaging about 2.5 million viewers. The jokes became famous, the guests were recognizable, and O’Brien became a household name, on par with Letterman and Leno. And then in 2004, it was announced that O’Brien would take over The Tonight Show when Jay Leno retired in 2009. O’Brien was going to have one of the most coveted jobs in show business.
Again, great news, right? O’Brien did take over the show in 2009 and things seemed to be going well, even though Leno still had his own show. But then when Leno’s ratings dropped, which in turn hurt O’Brien’s, a plan was formed to move The Tonight Show with Conan O’Brien to 12:05 so Leno could go back to his 11:30 spot. O’Brien released a statement saying he was not pleased with this move, and to make a long story short, he left the show and was banned from ever working at NBC again.
In the months that followed—and if you watch the documentary Conan O’Brien Can’t Stop—you got to see O’Brien unravel a bit while at the same time exploring his newfound creative freedom. He went on Twitter. He went on the road with a comedy show called ”The Legally Prohibited from Being Funny on Television Tour.” It was a scary time, but also an amazing time.
In an incredible commencement speech O’Brien gave to the Dartmouth College graduating class of 2011, he spoke about this very scary time in his life, the underdoggiest moment of his underdog life. Though he had “failed,” it was an absolutely liberating time in his career. From his speech:
“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.”
I just love this. I love this speech even more than his Harvard speech in which he had the classic line:
“You see, kids, you’re in for a lifetime of ‘And you went to Harvard?’ Accidentally give the wrong amount of change in a transaction, and it’s ‘And you went to Harvard?’ Ask at the hardware store how the jumper cables work, and hear ‘And you went to Harvard?’ Forget just once that your underwear goes inside your pants, and it’s ‘And you went to Harvard?’ Get your head stuck in your niece’s doll house ‘cause you want to see what it’s like to be a giant, and it’s ‘Uncle Conan, you went to Harvard?’”
Failure has such a negative connotation, and it really doesn’t have to. Failure is really a chance to learn something and figure out your next step. It is so helpful. Sara Blakely, billionaire Spanx founder Sara Blakely, says “failing” at something is what gave her the career boost she always needed.
“I feel that failure is life’s way of nudging you and letting you know you’re off course,” she said at the Women in the World Summit. And in that Harvard speech from 2000, O’Brien also encouraged failure: “Fall down. Make a mess. Break something occasionally. Know that your mistakes are your own unique way of getting to where you need to be. And remember that the story is never over.”
Failure is so scary, but finding yourself adrift is not the worst thing in the world. It seems that way at the time, but if you can keep this in mind, while you watch Cartoon Network in your pajamas and drink wine at 11:00 a.m., you will find yourself again and you will probably be better off. Embrace the failure. O’Brien did, and he is my hero.
How do you embrace failure? Tell us in the comments!
Ask Hala Moddelmog, President of Arby’s Restaurant Group, on how to bounce back from a failure!