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Jay Shetty PodcastJay Shetty Podcast

Jimmy Kimmel REVEALS: I Got Fired So Many Times Because of My Behavior..

Have you ever failed at something you really wanted? What did that experience teach you about yourself? Today, Jay chats with late-night legend Jimmy Kimmel for an unforgettable live conversation at the Greek Theatre in Los Angeles. Jimmy opens the episode playfully roasting Jay, showing off his signature, sharp wit right out of the gate. The laughs quickly give way to a candid, wide-ranging conversation about Jimmy’s life, marked by gutsy decisions, constant reinvention, and moments of surprising vulnerability. Jimmy reflects on the emotional cost of self-expression, his early struggles with being misunderstood, and how persistence (and a healthy dose of delusion) helped him find his place in the world. Jimmy shares how anxiety has shaped his life, from growing up without much money to now being someone people rely on for support, advice, and even financial help. From outrageous pranks and career missteps to a touching tribute to his prank-loving Aunt Chippy, Jimmy constantly balances humor with disarming honesty. Jimmy also opens up about the challenges of becoming more emotionally available, how therapy has helped him grow, and how being a father, and now a grandfather, has reshaped his priorities and softened his edges. In this interview, you'll learn: How to Stay True to Yourself How to Use Humor as a Tool for Healing How to Keep a Lifelong Passion Alive How to Stay Grounded When Success Finds You How to Cope With Anxiety Through Creative Outlets How Helping Others is the Key to Healing Yourself It’s not about being perfect, it’s about being honest, showing up, and continuing to try. Whether through meaningful conversations, creative expression, or simply sharing space with others, healing and connection are always within reach. With Love and Gratitude, Jay Shetty Join over 750,000 people to receive my most transformative wisdom directly in your inbox every single week with my free newsletter. Subscribe here. What We Discuss: 00:00 Intro 04:44 Why is Putting Yourself Out There So Hard? 08:00 Discovering What Truly Drives You 09:19 The Origins of Jimmy’s Legendary Pranks 11:56 When the Pranks Never Stop 17:02 Failed Firings and Conversations That Went Sideways 18:30 Staying True to Your Creative Voice 21:42 Becoming a Grandfather for the First Time 25:55 Living With Anxiety: How It Shapes Family Life 27:29 Jimmy’s Take on Managing Anxiety 29:56 What It’s Like to Face Financial Pressure 31:17 How Jimmy Met the Love of His Life 32:31 Is Finding Love in LA Really That Hard? 33:17 The Secret to a Strong and Lasting Marriage 38:19 Why Talking About Your Feelings Is So Tough 39:16 What To Do When You’re Feeling Low 43:05 Jimmy on Final Five Episode Resources: https://www.instagram.com/jimmykimmel/ https://www.facebook.com/jimmykimmel/ https://www.youtube.com/user/JimmyKimmelLive https://x.com/jimmykimmel https://www.tiktok.com/@jimmykimmellive https://www.instagram.com/jayshetty https://www.facebook.com/jayshetty/ https://x.com/jayshetty https://www.linkedin.com/in/shettyjay/ https://www.youtube.com/@JayShettyPodcast http://jayshetty.me

Jimmy KimmelguestJay Shettyhost
Aug 12, 202551mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Jimmy Kimmel on pranks, firings, anxiety, and emotional growth lessons

  1. Kimmel explains why putting yourself out there is difficult, and how starting in radio let him take “baby steps” into bigger public roles while luck and preparedness played major parts.
  2. He recounts a long pattern of prank-driven workplace conflict—often targeting bosses—that repeatedly got him fired, creating real financial and family stress despite the stories being funny in hindsight.
  3. He describes anxiety as evolving from scarcity worries to the pressures and relational complications that come with success, including navigating money requests and shifting social dynamics.
  4. Kimmel credits his wife and therapy with helping him mature emotionally, move from inward to outward focus, and use his platform for advocacy (notably around children’s healthcare).
  5. He offers practical principles: listen more than you advise, avoid lashing out by pausing before speaking, and when feeling low, help someone else to regain purpose and perspective.

IDEAS WORTH REMEMBERING

5 ideas

Lower-stakes exposure can make bold goals achievable.

Kimmel notes radio let him be “half hidden,” reducing the fear of visible failure and enabling gradual moves to bigger stages; designing smaller steps can help others attempt what they’d otherwise avoid.

Being “right” about your creative instincts isn’t enough—timing and context matter.

His pranks felt funny to him and the audience, but bosses didn’t experience them that way; creative ideas still need alignment with the people who control the environment.

Repeated failure can build empathy and better leadership behavior.

Having been fired many times made him hate firing others, and it sensitized him to the human cost behind “funny” stories—especially when livelihoods and families are involved.

Success can intensify anxiety by increasing responsibility and changing relationships.

Kimmel contrasts anxiety about buying lunch with anxiety about being the person others rely on, fielding serious requests, and realizing some relationships are transactional.

Money requests reveal relationship priorities—often painfully.

He describes how people may value access or financial help over the bond itself, and that realization sometimes forces a reevaluation of who is genuinely close.

WORDS WORTH SAVING

5 quotes

Putting yourself out there is hard. I started in radio. You're already halfway hidden, and nobody sees you. You don't have an audience there to not laugh if you're not funny.

— Jimmy Kimmel

Pure delusion.

— Jimmy Kimmel

I have to say, to this day, I, I hate firing people. It crushes me to fire somebody, even if they deserve it, even if they've done something bad, because I've been fired so many times.

— Jimmy Kimmel

It's hard to figure out how to be happy. I mean, there's by, there's no logical reason why we should, should be happy. It doesn't make sense.

— Jimmy Kimmel

When you're really down, when you're, when you're feeling low, and when you're looking for answers, helping other people is always a help. It always makes you feel better.

— Jimmy Kimmel

Fear of judgment and self-presentationStarting in radio and incremental risk-takingPranks, workplace boundaries, and repeated firingsLuck vs preparation in creative careersAnxiety, scarcity mindset, and success pressuresMarriage “check-ins,” therapy, and emotional expressionMeaning, service, and using a platform for advocacy

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