Jay Shetty & Jimmy Kimmel ON The Untold Story of Failure

Do the people who fire you eventually pave your path to success?

In this On Purpose episode, held at The Greek Theatre, Jay Shetty welcomed comedian Jimmy Kimmel. Kimmel is best known for his late-night talk show, Jimmy Kimmel Live!, which he hosts and produces. He was introduced to Jay Shetty's show by his wife, who is a fan, and he excitedly opens up about his career and personal life in front of a live audience.

The Weight of External Judgment

Jay Shetty and Jimmy Kimmel discussed the things that people avoid doing due to fear of criticism and judgment. Kimmel openly confessed that he often feels imprisoned by this fear; he shared a recent experience from a wedding, where he thought he wore a suitable attire, only to arrive at the location and discover that everyone wore a black suit. The situation made him feel like the fool in all the pictures.

Apart from social embarrassment, Kimmel noted the sadness of talented people who refuse to pursue their potential because they fear being proven wrong by their inner circle. In his view, this hesitation often stems from a fear of being validated (or even invalidated) by their inner circle; they worry that by stepping into the spotlight, they may disrupt the comfortable narrative. It's a fear that can lead to a profound sense of loss, especially when choosing to leave their talent unused.

Gradual Evolution and Luck

Looking back on his successful career, Jimmy Kimmel emphasized that he was lucky. He told Jay Shetty that, even if you have a lucky opportunity, seizing it makes the difference. His path was fortunate, because he started working in radio, which allowed him to be partly hidden from the audience.

This semi-anonymity allowed Kimmel to take baby steps. He gradually moved from radio to a game show sidekick, then to a partner on a comedy show, before eventually hosting his own show. He admitted to Jay Shetty that he wasn't sure he could have handled the pressure of that big leap right away.

Commitment to Nonsense

Pranks have always been a cornerstone of Kimmel’s life, even leading him to lose jobs. He admitted to Jay Shetty that he had grown up in a family that always had great reactions when he did something.

Kimmel often included his aunt Chippy in his televised pranks; Aunt Chippy is a loud 85-year-old woman with whom he started by putting explosives in her cigarettes and tying cans to her car. More recently, with the resources of a TV show, he escalated the pranks by using a self-driving car to chauffeur his aunt, leaving her alone in the moving vehicle, a prank his three cousins approved of immediately.

The Hard Lessons of Being Fired

During his radio career, Jimmy Kimmel worked at different stations in many cities, often getting fired for torturing his bosses with pranks. He shared with Jay Shetty stories about incidents such as unlatching golf bags on carts, which led him to run over his boss's golf clubs, and his persistent gag of sneaking a discarded hot dog into his boss's desk drawer every night.

When the boss started locking his office, Kimmel climbed in through the cheap ceiling, causing the desk and shelves to collapse, resulting in great damage. He managed to escape and put the hot dog back before locking the door. Eventually, Kimmel was let go from his job, and while these stories are funny now, they were not funny at the time.

Making only $18,000 a year, he repeatedly had to tell his wife that they were moving again, sometimes to places like Tucson. Eventually, Jimmy Kimmel found a radio station in LA that appreciated his prankster attitude and where he learned important lessons, such as not calling his boss’s wife at home on the air.

Staying True to Himself

Kimmel admitted to Jay Shetty that, despite all his firings, he kept going because of his pure delusion. He acknowledged that many of the things he thought were hilarious weren’t even funny, and he admits he wasn’t always good at his job. He realized his actions were often antisocial, and he was acting like an undisciplined child that adult bosses didn't want to deal with.

Despite the missteps, Kimmel always followed his guiding principle: if he thinks something is funny, surely other people will, too. He maintained this belief and applied it to other talented people around him, as well. He explained to Jay Shetty that his relatives (like Aunt Chippy and his former security guard uncle Frank) were constantly yelling and annoying him until his best friend pointed out that they were, in fact, hilarious. Jimmy Kimmel admits he has successfully operated by that principle his whole life.

Payback Time as a Grandfather

Jimmy Kimmel recently became a grandfather. He told Jay Shetty that his main excitement about being a grandparent is that it's a great means to get revenge on his children. He plans to ignore all the rules they set, and instead, do everything they don't want him to do. He explained he sees this as the circle of life.

Jimmy Kimmel noted that his daughter, Katie, is very funny and an artist with a strange sense of humor. She recently posted pictures of the baby screaming and crying after Kimmel texted her that she wasn't posting enough baby pictures. While he doesn't classify his children's humor as genius, he believes it's an important part of life.

Conquering Anxiety Through Hoarding

Jimmy Kimmel told Jay Shetty that he didn't wish his children to inherit some of his physical traits, but more importantly, his anxiety. He explained that he has always felt anxious, regardless of his financial success. When he was poor, he was constantly worried about tomorrow, about having enough food.

Now that he is famous and wealthy, he is experiencing a different type of anxiety. Kimmel explained that people started relying on him and came to ask for many favors. It's a challenging position to be in, he admitted, because it changes the existing relationship dynamics, and, especially, it makes him see who his true friends are and who sees him as a source of financial support.

Jimmy Kimmel told Jay Shetty that when he was young, he experienced scarcity in his home. When he received a set of art pens for Christmas, he would never use them, for fear they would run out. Unfortunately, they stayed unused until they dried. Growing up knowing what it feels like not to have much, he now buys excess art supplies for his drawing passion. He admitted that he may not even live long enough to use them all up, but it helps his anxiety knowing that he has them and they would never run out.

Maturing in the Relationship

Jimmy Kimmel has been with his wife, Molly McNearney, for about 16 years. He credits McNearney with helping him mature because he believes he wouldn't do great if left to his own devices. He opened up to Jay Shetty about the less enjoyable pranks he played on his wife during their relationship and how they grew together and bonded even more strongly throughout the years.

Molly McNearney shortly joined the stage and told Jay Shetty and the audience that Jimmy Kimmel uses humor to hide his true feelings, as a defense mechanism. She praised his evolution as a man, especially his shift toward greater openness and sharing more of himself with the outside world. McNearey also touched on how Kimmel openly speaks about his life on his show and how bravely he opened up about their son's struggles. He is a known advocate for children's healthcare.

Jimmy Kimmel admitted that he finds it difficult to express himself honestly, much like his father. He told Jay Shetty he is better at writing a nice letter than speaking from the heart. Therapy has helped him access hidden parts of himself and made him see the value in having regular sessions. He strongly suggests that everyone go to therapy, both individually and together, noting that it helped him sort things out, even though he finds it uncomfortable. He also shared that when feeling low or worthless, the best thing to do is to help someone else, as he sees it as an almost selfish act that always makes one feel better.

More From Jay Shetty

Listen to the entire On Purpose with Jay Shetty podcast episode “Jimmy Kimmel: The Untold Story of Failure, Rejection & Fame (And the Rare, Unseen Side of Him as a Husband & Father!)” now in the iTunes store or on Spotify. For more inspirational stories and messages like this, check out Jay’s website at jayshetty.me.