Late one night in 1993, all of America had the same collective thought: just who the heck is THAT guy?

We were watching the Late Show, and instead of seeing David Letterman, favorite beloved, cantankerous Hoosier, we found ourselves staring at an awkward, tall, gangly guy sporting a ginger pompadour.

That guy was Conan O’Brien, and there was very good reason we were all wondering who he was. We’d never seen him before. He was a comedy writer who had never before been featured in front of the camera. And yet, television executives at NBC in all their wisdom had decided he was the guy to take over David Letterman’s spot.

It turns out those TV executives were right. O’Brien won us over with his slightly off-center, self-effacing brand of humor, and more than a quarter of a century later he is still on television making us laugh.

It takes moxie to come out of nowhere and become a cultural fixture, and Conan O’Brien has it.

People with moxie sometimes fall up.

Call it the “luck of the Irish,” but O’Brien’s origin story doesn’t follow the celebrated “humble beginnings, rags-to-riches” narrative template. He was born to a solidly middle class East Coast family and raised in Brookline, Mass. His father was an epidemiologist who taught at Harvard, and his mother was an attorney and partner at a Boston law firm.

O’Brien went to Harvard himself and found much success there, including serving as editor of the Harvard Lampoon. After graduating magna cum laude, O’Brian embarked on his comedy writing career, eventually landing a gig writing for Saturday Night Live. After a successful run with SNL, O’Brien was recruited to write for The Simpsons, where his absurdist style also found much success.

Success is often a combination of moxie, talent, networking, attitude and lucky breaks. Throughout his career you can see evidence of all those things in O’Brien’s life. He had a strong foundation for success, and his talent and moxie positioned him well to build on that foundation.

Having moxie doesn’t mean things come easy.

It would be a mistake to think that success just fell into O’Brien’s lap, however. He suffered notable setbacks and disappointments along the way.

The start of his tenure at the Late Night was met with much skepticism. It took months for O’Brien to find his footing. Through harsh criticism, cancellation threats and growing pains, O’Brien matured into his role as late night host and built a solid following.

O’Brien helmed Late Night for more than a decade before his dream job came calling, and he was tapped by NBC to take over The Tonight Show. By now, O’Brien’s comedic chops and skill as a late night host were well established. It should have been an easy win, right?

Only it wasn’t. O’Brien’s reign at Johnny Carson’s desk was doomed to failure from the start, and it had nothing to do with his talent or moxie. O’Brien had landed in the spot due to some fouled up deal-making on the part of NBC. O’Brien had been promised The Tonight Show years before as part of contract negotiations, despite the fact that it was successfully helmed by Jay Leno. When it came time to fulfill that contract, Leno was still going strong, and NBC had to find a way to keep both its stars happy. A public relations disaster with a lot of hurt feelings all around followed.

O’Brien’s turn at The Tonight Show never achieved great ratings, in large part due to the fiasco created by executives and a lack of support by the network. O’Brian left the show after just a few months. His decision to leave was prompted by his fear that the ongoing battle over the show would ultimately lead to its demise, and he couldn’t bear to see that happen.

It takes moxie to sacrifice your own dreams to save something you love, and O’Brien has it. He had public opinion on his side (remember #TeamCoco?) but victory was coming at too great a cost. O’Brien acted with integrity and humility.

People with moxie refuse to be cynical.

O’Brien’s farewell from The Tonight Show, and the network that had nurtured his career for decades, was graceful. While acknowledging that his relationship with NBC was splitting up, he expressed gratitude to the network for giving him a chance and supporting him for so many years. He also expressed gratitude to the fans who had enthusiastically rallied around him.

“All I ask of you is one thing: please don’t be cynical. I hate cynicism — it’s my least favorite quality and it doesn’t lead anywhere,” he said. “Nobody in life gets exactly what they thought they were going to get. But if you work really hard and you’re kind, amazing things will happen.”

O’Brien could have made a franchise around hating NBC, or hating Leno, or being bitter about being forced out of late night television. Instead, he’s launched into new opportunities. He has a show on TBS, comedy tours, and podcasts. In many ways, being unshackled from the late night desk has freed him to explore new comedic ground.

It takes moxie to accept life’s twists and turns with grace, and to even embrace challenges as an opportunity for greater things, and O’Brien has it.

Are you on #TeamCoco?

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