Your Biggest Failure Will Set You Free

Conan O’Brien’s best career advice after 25 years in comedy

“Don’t be afraid to fail” might be the most common success tip there is. Arnold Schwarzenegger, J. K. Rowling, Denzel Washington, famous people constantly remind us to be bold, try, and worry about being hurt only after we’ve actually crashed.

In 2000, Conan O’Brien gave that same advice to the graduating class of Harvard, having returned to his alma mater an accomplished comedian and talk show host with millions of fans:

“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.”

As inspiring as this advice is, it leaves one big question unanswered: What do you do with your failure once you have it? And what if that failure is really big — and hurts really bad?

It would take O’Brien eleven more years to find the answers to those follow-up questions, which he shared in his second commencement speech, given at Dartmouth in 2011.

Two years earlier, O’Brien had taken over The Tonight Show, the world’s longest-running and most esteemed talk show, from Jay Leno. After only seven months, O’Brien was ousted in a public relations disaster, with Leno taking back his seat.

O’Brien received a million-dollar settlement but was barred from TV for several months. In that time, he “abandoned all preconceived perceptions of [his] career path and stature,” shared his comedy on social media, recorded an album, made a documentary, and went on national tour.

“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 does that work? How can someone suffer the highest fall from grace in their industry and emerge with utter confidence from the incident? According to O’Brien, it is facing his ultimate failure that eventually set him free:

“There are a few things more liberating in this life than having your worst fear realized.”

O’Brien thought hosting The Tonight Show — the holy grail of entertainment — would define his career and forever make him successful. Failing to achieve this goal taught him that, actually, no goal can do that for you. “No specific job or career goal defines me, and it should not define you,” he said.

Instead of having a fixed idea of where your career is supposed to go — a common trait in high achievers and Ivy League graduates — accept that your dreams will change. Sometimes, they might have to. That’s okay. Shoot as high as you can, but don’t wrap your identity around any specific outcome. Use your failures as “a catalyst for profound reinvention,” as O’Brien calls it.

Describing the succession of famous comedians from Jack Benny to Johnny Carson to David Letterman to his own generation, he asserts that, “It is our failure to become our perceived ideal that ultimately defines us and makes us unique.” No matter how well you emulate your heroes, you’ll never become an exact replica — which would also miss the point. What we should really be after, according to O’Brien, is our true, unique self.

Often, we’re only able to invent this version of ourselves once we’ve hit rock bottom. For O’Brien, it meant losing the show he had worked towards for 25 years. For you, it might mean getting fired, giving up a startup that’s not working, or starting from scratch in a new country.

Whatever the big failure that stings right now, in the long run, it will set you free. Unburdened with expectations from yourself and others, you’ll be able to try different things, break with convention, and assemble a new self-image. Ironically, this next version of yourself is exactly who you’ll need to become to achieve new heights.

“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.”

“Don’t be afraid to fail.” That’s solid advice. But, “Don’t be afraid to face your biggest failure?” That’s both inspiring and comforting. Remember it in tough times. Remember that, even after 25 years and achieving your dreams, it still has the power to set you free.


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