Jimmy Fallon, At Your Service
Entrepreneur|January - February 2022
He spent years chasing a dream that wasn’t really his. But when the biggest opportunity of his career came knocking, he realized he had to find his “why,” or fail trying.
By Jason Feifer, Photography by Brian Bowen Smith / NBC

Jimmy Fallon became a talk show host in 2009 when he replaced Conan O’Brien as the face of Late Night. Fallon had never done anything like it before. So as he prepared to take over, he turned to the man who knew the job better than anyone.

“Any advice?” Fallon asked O’Brien. “I can’t give you any advice,” O’Brien replied.

“You just have to do it.”

“I didn’t love that—I mean, that’s not great advice,” Fallon says now. “But I was talking about it with someone and they said, well, he’s right— because he found who his character is and who he is. Who are you? Who is Jimmy Fallon as a show?”

In that moment, Fallon realized he did not have a good answer. Sure, he had ideas for what would be in his show—the silly games and unbridled joy that would come to define his brand. But why should someone care about him? Who is Jimmy Fallon?

“When you actually get that question, you’re like, uh, um, uh, well, I have brown hair,” Fallon says. “I love this type of humor. I love rock music, but I also like, uh, classical. It makes no sense.”

It makes no sense because it’s not how we tend to think. People talk endlessly about the things they do at work, but they don’t always reflect on the reason they’re doing it. What motivates them? What gives them purpose? What is their measurement of success, and what will guide them when things go wrong? You could call all of this a person’s why—it is the reason for anything they do, and the core of who they are. Knowing this is transformative; it makes people more versatile and intentional. People who know their why are people who never feel lost.

Fallon didn’t have a why, and O’Brien couldn’t give him one. Nobody could. In fact, Fallon realized, he’d have to find it on the job. “The more you do it,” Fallon says, “it forms who you become.”

This process takes time. It should take time. It is the most important thing we can know about ourselves or our work. Fallon would spend years figuring it out for himself—and the breakthrough he had would transform him from a late-night jokester into a cultural force, helming The Tonight Show, writing best-selling children’s books, creating a roller coaster for Universal Studios, developing a range of kooky products for brands (like pajamas called P’Jimmies for Alex Mill), and co-running the production company Electric Hot Dog that produces new shows including That’s My Jam (for NBC), Clash of the Cover Bands (for E!), and The Kids Tonight Show (for Peacock).

"I try to get the script the best it can be," Fallon says, "and if it works, it just works. If it doesn't work, people can say, 'Oh, well, he gives it his all.'"

But Fallon’s realization is valuable to any entrepreneur because it has nothing to do with comedy or entertainment or hosting one of the most storied brands on television. It is simply this: He stopped focusing on the stuff he wanted to make, and he started focusing on the reason people need it.

As a high schooler, Fallon didn’t wonder why he worked. That was clear: His dad already worked two jobs, and his family needed the money.

“As soon as I could work, I worked anything,” Fallon says. His first role was as a bag boy at a local supermarket. Later, he sorted bottles and cans at a recycling facility. These jobs had their indignities. The supermarket made him wear a bow tie, an apron, and boots—especially embarrassing when he’d see a girl he had a crush on. And the recycling center just stunk of garbage. But he tried to see the best in both positions. David Letterman ran a “best bag boy” bit on his show, and young Fallon imagined himself competing in it. At the recycling center, he got to hang out with adults. “I got along with kids my age,” he says, “but I think I was more of an old soul.”

The path from there was steep and upward. Fallon discovered comedy, learned stand-up, and dreamed obsessively of being on Saturday Night Live. He quit college, dove into improv, failed an SNL audition in 1997, and then nailed it in 1998. He was 23 years old. “You just feel like you run the city,” he says. “It was so fun.” He rose to become co-anchor of “Weekend Update” alongside Tina Fey, and in 2004, Fallon was rightfully proud and ready for more. He left SNL for his next big thing.

“My goal was just to be in movies—be like a rom-com guy or something,” Fallon says.

This sounds reasonable. Lots of people dream of being a movie star—and unlike most of them, Fallon was in a position to do it. But this was also the perfect kind of moment to step back and ask that simple question: Why?

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