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Jimmy Fallon Spent Years Chasing A Dream That Wasn't Really His. Finding His 'Why' Changed Everything.

How The Tonight Show host built his career and an entertainment empire -- by first identifying his most important mission.

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This story appears in the January 2022 issue of Entrepreneur. Subscribe »

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?”

Image Credit: Brian Bowen Smith |

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.”

Related: To Live the Dream You Have to Schedule Time to Dream

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).

But Fallon’s realization is valuable to any entrepreneur, because it has nothing to do with comedy or 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.

Image Credit: Brian Bowen Smith | NBC

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.”

Related: Why Discovering Your 'Why' Is the No. 1 Business Move

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 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 coanchor 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?

Why ask why? Because we rarely ask it in our successful moments, when the answer seems self-evident. Why? Why not? But what if we don’t know?

So I ask Fallon: “If somebody had asked why that was your goal, would you have had an answer?”

He pauses. Three seconds of silence.

“No,” he finally says. “I’m trying to think, why would that be my goal? Maybe, from all the books and articles that I’d read, the trajectory of someone famous from Saturday Night Live is to do movies. It’s just the path.”

Want to hear the opposite of a self-directed mission? To hear an entrepreneur’s greatest trap? Four words, right there: “It’s just the path.” Not your path. Simply the path, a path, some path, a clearing that other people make for their own purposes, not for yours. That is the path through an unimaginative life and away from the satisfaction of a risk taken.

Fallon made two movies. Both bombed. There was a bright spot in there: He met his future wife on one of them, the producer Nancy Juvonen. But otherwise, his phone stopped ringing. With no why to guide him, Fallon had no sense of what to do next. With Juvonen’s help, he found the first step: Stop focusing on what he does not have and start focusing on what he does. “So now there’s no movies. What can you do, cry about it? I already did that for a year,” he says. “What can I do now? I have to do something. And I have talent. I mean, I could do stand-up. I could sing comedy songs.”

Related: Finding 'Why' You Do What You Do Is Key to Excellence

He started creating and performing again. He rebuilt, slowly. Then he got a call from Lorne Michaels, the creator of Saturday Night Live and producer of Late Night and The Tonight Show. Years earlier, when Fallon was leaving SNL, Lorne said he thought Fallon would make a great late-night host. Now, five years later, O’Brien was leaving Late Night and the job was open. Truth be told, NBC executives weren’t sold on Fallon. “They were like, well, we have other people that might be better for this thing,” Fallon recalls. But Michaels stuck by him. The executives relented.

“That changed my career, changed my life,” Fallon says. “They go, ‘OK, if you really think Jimmy can do it, let’s see what’s up.’ ”

Fallon had a lot to learn, and fast.

Image Credit: Brian Bowen Smith | NBC

How do you do something you’ve never done before? For Fallon, it happened with a finely calibrated mix of cockiness and self-doubt.

“That’s always the way I did stand-up,” Fallon says. As we talk in his corner office at NBC’s headquarters, he pops up from his chair to illustrate, imaginary microphone in hand. Fallon is a mover, an entertainer; he seems most comfortable on his feet. “You’d know, right off the bat, that this joke’s gonna work — but then you’re like, I’m losing them, I’ve got to bring them back, I know what can bring them back.”

Get too cocky, and every little stumble will throw you off. Doubt yourself too much, and you’ll never go out there in the first place. It’s hard to get the balance right, and Fallon remembers hugging his confidence too tightly at first. “To hear anyone say, ‘Oh, you’re so lucky,’ that was almost triggering to me,” he says. He’d felt he earned it; being lucky sounded insulting. “But in my head I’m like, ‘Wait, am I though?’ It’s out of self-doubt. But I think it’s a good mix to have.”

Entrepreneurs are shaped by the challenges they face, and Fallon was too. Hosting a late-night talk show required a pace he’d never worked at before. Back in the SNL days, when a joke bombed, he’d stew about it for a week. But now, he and his team had to move with abandon. They’d write a joke, try it out, and if it didn’t work, there was always tomorrow. “I mean, 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.’ ”

This is a small but critical realization. Consider it: At SNL, Fallon felt like he was being judged solely by his work. A failed joke meant that he failed. But now that he was out there every night, his audience was gaining trust in him. If a joke failed, oh well — they knew he was trying. If you want to figure out your why, this is the place to start: It is a recognition that you (or your brand) are not simply the sum of the things you create. You are something deeper—and that is what people really come to you for. A coffee shop doesn’t just serve coffee; it fosters community. Entrepreneurs don’t just build companies; they solve people’s problems.

Related: 6 Habits That Turn Dreams Into Reality

Fallon’s show was on at 12:35 a.m., which gave him no illusions. “Nobody talks about a show at 12:35. People are just fighting sleep at that point,” he says. So he and his team gave themselves a simple mission — to make people smile as they’re drifting off. The show was joyous and earnest. They played games like “Name That Guy,” where they asked audience members to guess the name of random strangers. There was no point to it. No way to win or lose. People loved it.

Something started to click for Fallon. Sure, this role wasn’t glamorous like being a movie star, but he never had a passion for that anyway. The late-night job came naturally because he was making people happy. And when he looked back at his life, he saw that same instinct: “At the time I was too young to realize it, but I just wanted to make people happy,” he says. His job packing groceries, for example? “I was the best bag packer,” he says. “People would request me!”

He had his realization. “I think my why is, ‘Can it make people happy?’ ” he says.

Now that is something on which you can build a career. It isn’t following a path. It isn’t doing something just because. It is a mission. A purpose. And the blueprint for how to build even bigger.

Image Credit: Brian Bowen Smith | NBC

Fallon always has ideas. That’s not to say they’re good ideas — but how is he to know? It’s why he records them all, typically as voice memos or by jotting things down in Evernote. “I think the last one I wrote down was a magnetized tennis ball that you can stick to your leash when you take your dog for a walk,” he says, “because I always take my dog for a walk and I get to some spots and am like, this would’ve been great if I brought a ball so I could throw it with my dog, but I’m not going to carry a ball in my pocket.”

Can this make people happy? That’s what he wants to find out next. He’s developed a process to test his ideas — and it starts with the person to whom he has the most access: himself. He sets ideas aside to see which ones are memorable. “Usually the good ideas stick with your brain,” he says. Then he takes the best ones, pitches them to himself, and responds to each like a comedian. “I make fun of it in my brain,” he says. “Like, why is it lame? Why is it not good? And I use that to make it more bulletproof.”

If an idea survives, he brings it to people he trusts — often the writers on The Tonight Show, which he’s now hosted since 2014. Fallon hires people based in part on how good they are at collaborating with him, which means they can also share and refine his vision (and he can trust them when they trash an idea). It’s something he learned at SNL; Fallon remembers a time when a producer forced him and another writer to write something together, even though they weren’t planning to. The result was great. Now it’s how he tests new people. “Sometimes it’s best to force yourself and try to write something with someone, just to see if there’s a connection,” he says.

How many ideas make it from his Evernote folder into the real world? Maybe 10% or 20%, he says — which include everything from individual jokes to entirely new TV shows. And if an idea falls flat once, he isn’t discouraged. “I always like to try stuff three times,” he says. “There’s no set rule, but like, I don’t want to just eat a sandwich with mayonnaise on it and go, ‘I don’t like mayonnaise.’ I’d like to try it again and then maybe one more time.” Same with ideas: He’ll try iterations of jokes on his show across multiple nights. After all, he knows his goal is to make people happy, and happiness is an inexact science. Maybe you came close with one idea, but you can’t know how close until you try it again.

And here’s the real beauty of trying out new ideas: They’ll teach you about your audience, but also about yourself. That’s what happened in 2015, when Fallon wrote a book called Your Baby’s First Word Will Be Dada.

It began as all his ideas do. He’d imagined a book that dads could read to their babies, to train them to say “dada” before “mama.” The plot goes like this: A pig says “dada!” and another pig replies “oink.” Same thing with frogs and bees, and so on. Would this make people happy? Yes, he and his team agreed.

They were right; it became a New York Times best seller. But truth be told, Fallon hadn’t considered what would happen next. “People sent me videos of their kids saying their first words, and actually reading the book and understanding that reading is fun, and they’re getting a reaction from people when they read the book, and now they’re learning how to read!” Fallon says, sounding still kind of amazed by the whole thing.

When our jobs are to put things out in the world, it’s oddly easy to forget that the world isn’t one giant blob. Actual people engage with what you make. They absorb your ideas and products and services into their lives. “And you go, wait, there’s something to this that is rewarding for me and you,” Fallon says. He is half-pacing in his office again, thinking this through as he talks, and he has a realization: Maybe he’d only known half of his why this whole time. “Maybe the why is, How do we both get rewarded? How do we make something where you’re happy and I’m happy?”

This makes me think back to the beginning of our conversation. I walked into his office, he greeted me warmly, and then promptly gave me a tour of the room. A detailed, six-minute tour. He offered an explanation for basically every item of interest in there. He showed me the sign next to his door that says, JIMMY FALON, which, yes, is missing an L, and was the first nameplate hung on his door as a late-night host. (“You want to stay humble?” he says. “There you go.”) He showed me family photos. Mementos. A trophy featuring a bust of Rodney Dangerfield that is so heavy, picking it up requires two hands and a groan. (I tried.) He offered tea. Coffee. Pastries. Then he sat down beside a little fish tank, which Lorne Michaels got for him because, at 47, Fallon is now of an age where he needs some calming influences.

“I’ve been trying to put my finger nicely on the glass,” Fallon says, “and I’ve been trying to train them to follow my finger, so they’re not afraid of me.”

He tries it. The fish ignore him. “Look how great it’s working,” Fallon says with a laugh. That’s OK. The fish may need more than three tries. And anyway, this was for my benefit: It was to make me happy, which would make him happy, because that’s what he does and he knows why he does it. It works.

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