Jimmy Kimmel has been one of America’s most recognizable late-night hosts for over two decades. With Jimmy Kimmel Live! cementing his place in comedy and television history, it’s easy to look at his career and assume it was a straight shot to success. But during a candid and often hilarious conversation with Jay Shetty at the Greek Theater in Los Angeles, Kimmel revealed just how much failure, risk, and “pure delusion” it took to get there — and why fear of failure may be the single biggest thing holding people back from their own potential.

The Cost of Playing It Safe

Kimmel, who began his career in radio before moving into television, spoke passionately about the people he’s met over the years who have talent but never put it to use.

“Sometimes for them, you saying they’re good at it is enough,” Kimmel explained. “They don’t want to threaten that idea. They don’t want you to ever think, ‘Oh, you weren’t good at that.’ So they leave it. And I think that’s so sad… they don’t use [their potential] because they don’t want to be proven otherwise.”

For Kimmel, this mindset is tragic. It’s a defense mechanism — the idea that if you never try, you can never fail — but it robs people of the opportunity to discover what they’re truly capable of.

He insists that the only way to break through that fear is to actually do the thing you’re scared of, even if it’s terrifying.

From Radio to Television: Taking Baby Steps

Kimmel’s own journey was not an overnight leap into hosting a network show. He credits his career growth to a series of small steps that gradually built his confidence.

“I started in radio, where you’re already halfway hidden,” Kimmel recalled. “Nobody sees you. You don’t have an audience there to not laugh if you’re not funny. You just kind of have to assume you were, and you keep going.”

From there, he moved into being a sidekick on a game show, then a partner on a comedy program, before finally landing his own show. “I’m not sure if I would have been able to take that big leap,” he admitted. “I was fortunate — genuinely fortunate — to take those steps one by one.”

Still, Kimmel acknowledges that even with preparation, luck played a major role:

“A lot of it is luck… but you have to be ready when you get that moment. When you have that moment of fortune, you have to be prepared.”

The Prankster Who Got Fired — Repeatedly

Throughout his early radio career, Kimmel developed a reputation as a relentless prankster. While his mischievous sense of humor has served him well on late-night TV, it got him fired more than once.

He recounted planting explosives in his Aunt Chippy’s cigarettes, tying cans to her car, and eventually escalating to elaborate televised pranks. Before he had the resources of a TV show, though, these antics often targeted his bosses — and cost him his job.

“I thought bosses would be on board with the idea that listeners would think it was funny if I was torturing them,” Kimmel said. “They never liked it at all. They’d tell me they would when they hired me, and then when it happened, they hated it.”

In hindsight, he admits it wasn’t just bad luck — he was young, stubborn, and, in his own words, “kind of crazy.”The Value of Delusion

When Shetty asked how Kimmel kept going despite being fired so many times, Kimmel didn’t hesitate:

“Pure delusion.”

He explained that he held onto a simple belief: if he thought something was funny, surely other people would too. That stubborn confidence kept him moving forward even when people told him his ideas were terrible.

Over time, Kimmel also developed an eye for spotting talent in others — a skill he still values. Whether it was putting his eccentric relatives on TV or elevating behind-the-scenes staff to on-camera roles, he’s always followed his gut about what and who would connect with an audience.

Anxiety Never Disappears — It Just Changes Shape

Kimmel also opened up about anxiety, both in his early days and now as a successful host. When he was young and broke, his worries were straightforward: could he afford lunch, or get $20 out of the ATM?

Now, the anxieties are more complex. “A lot of people rely on you for a lot of things,” he said, noting that he’s often approached for help — financial or otherwise.

The pressure to manage relationships while also being a public figure can be tricky, and sometimes those relationships change when money is involved. “It can be a lot,” Kimmel admitted. “Your relationship with people changes. And you have to figure out when that relationship is more important than money — and sometimes, you realize it’s not.”

Learning Emotional Openness — With Help

Kimmel readily admits that expressing emotions has always been difficult for him. He credits his wife, Molly McNearney, with helping him grow in that area over their 16-year relationship.

“She’s definitely maturing me in that area,” Kimmel said, before joking, “I haven’t matured — I was lying. I just wanted to fit in with the podcast.”

McNearney, who joined the conversation on stage, praised her husband for becoming more outward-focused over the last decade — especially in his advocacy for children’s healthcare, inspired by their own son’s heart condition.

Therapy and the Benefits of Talking

Though he’s naturally private about feelings, Kimmel endorses therapy for anyone who’s willing to try it. He sees it as a tool not only for self-discovery but also for strengthening relationships.

“I find it very uncomfortable,” he said, “but I’m never not glad I did it afterwards. I think a lot of guys don’t like to go to therapy, but… I recommend it, both individually and together.”

On Happiness: Stop Just Worrying, Start Doing

One of Kimmel’s more striking observations came when the conversation turned to happiness.

“It’s hard to figure out how to be happy… There’s no logical reason why we should be happy. It doesn’t make sense. There’s so many people suffering, so many sad and bad things happening, and it feels selfish sometimes to be happy.”

His solution? Action. “If you really want to do something, do something. Don’t just worry about it.”

He believes helping others is not only good for the world, but also for your own mental state:

“If you’re feeling worthless or unloved, the best thing you can do is help someone else — for yourself, not even for them.”

The Takeaway: Your Fear of Failure is Wasting Your Potential

Kimmel’s career is a testament to resilience in the face of rejection. He was fired repeatedly, told his ideas wouldn’t work, and often felt the sting of embarrassment. But he never let fear of failure stop him from trying again.

His advice for anyone holding back because they’re worried they won’t succeed is simple but powerful:

Do it anyway. The people telling you it’s a bad idea might be wrong — and even if they’re right, you’ll learn more by trying than by doing nothing.

Take small steps. Don’t wait for the perfect leap; build your skills and confidence incrementally.

Be ready when luck comes. Preparation ensures that when opportunity appears, you can seize it.

Don’t waste your talent. Believing you have potential but never testing it is the surest way to regret.

Jimmy Kimmel’s story is proof that failure isn’t the opposite of success — it’s the path to it. For him, “pure delusion” was just another word for believing in himself when no one else did. And for anyone stuck in self-doubt, he has a clear message:

Your fear of failure isn’t protecting you. It’s wasting your potential. The only way to find out what you’re capable of is to try — even if you crash a few times on the way up