On Purpose with Jay Shetty

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 [https://news.jayshetty.me/subscribe].  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: Jimmy Kimmel | Instagram [https://www.instagram.com/jimmykimmel/] Jimmy Kimmel | Facebook [https://www.facebook.com/jimmykimmel/] Jimmy Kimmel | YouTube [https://www.youtube.com/user/JimmyKimmelLive] Jimmy Kimmel | X [https://x.com/jimmykimmel] Jimmy Kimmel | TikTok [https://www.tiktok.com/@jimmykimmellive] See omnystudio.com/listener [https://omnystudio.com/listener] for privacy information.

What’s the hardest part of parenting for you? Do you think kids today are more anxious than before? Today, Jay sits down with Dr. Becky Kennedy, clinical psychologist, best-selling author, and founder of Good Inside, a global parenting and mental health platform. Named the “Millennial Parent Whisperer” by Time, Dr. Becky is known for her compassionate, practical approach to raising emotionally healthy children while maintaining strong, sturdy leadership as a parent. In this eye-opening conversation, Jay and Dr. Becky explore why modern parenting often swings between dismissing children’s emotions and letting them call the shots, sharing practical ways to find the balance in between. Dr. Becky shares why parenting is a skill you can actually learn, the surprising power of repairing after conflict, and how boundaries and validation work together to help kids feel safe, understood, and supported. Dr. Becky shares how to shift your mindset from “my kid is giving me a hard time” to “my kid is having a hard time,” creating a more compassionate approach to conflict and connection. She explains why constantly optimizing for happiness for your kids can actually create anxiety later in life, why letting kids struggle is key to building resilience, and how to release the heavy burden of “mom guilt” by recognizing which emotions are yours to carry and which belong to your child. In this interview, you’ll learn: How to Repair After Rupture and Strengthen Connection How to Set Boundaries Without Power Struggles How to Validate Feelings Without Over-Coddling How to Build Capable and Resilient Kids Why Not All “Mom Guilt” is Actually Guilt How to Balance Empathy with Leadership as a Parent Parenting isn’t about getting it perfect. It’s about showing up, repairing when things go wrong, and modeling the emotional skills you want your children to have. As Dr. Becky reminds us, the most powerful thing you can give your kids is the confidence to face life’s challenges knowing they are both safe and valid. 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 [https://news.jayshetty.me/subscribe].  What We Discuss: 00:00 Intro 02:49 Should Kids Dictate Parenting Styles? 06:03 Building Tolerance As A Skill 10:43 How To Overcome Mom Guilt 18:27 Becoming a Mom Shouldn't Be Endured Alone 21:50 What is the Best Parenting Strategy?  29:30 The First Step Of Repair  34:18 How to Reconcile with Your Kid 36:54 How to Reconcile with Your Kid 39:17 Your Kid is Just Having a Hard Time 42:04 The Myth Of Always Being Available 44:30 How Do You Set a True Boundary? 48:36 The Communication Skills Every Parent Needs 52:34 What is Your Job As A Parent? 56:48 Your Kid’s Feelings Are Valid  59:12 How Boundaries & Validation Make for Resilient Adults 01:00:40 Should you be Optimizing for Happiness In Childhood? 01:09:45 The Power of Patience & Time 01:12:56 Teaching Kids How To Build Tolerance 01:19:44 Fostering Independence  01:24:36 Teaching Children Self-Reliance  01:30:33 The Value Of Discipline 01:37:56 The Pressure Parents Experience  01:41:52 Independence Vs Dependence  01:50:46 The Fear Of Patterns Repeating Episode Resources: Dr. Becky Kennedy | Website [https://www.goodinside.com/] Dr. Becky Kennedy | Instagram [https://www.instagram.com/drbeckyatgoodinside/] Dr. Becky Kennedy | Facebook [https://www.facebook.com/drbeckyatgoodinside] Dr. Becky Kennedy | YouTube [https://www.youtube.com/@goodinside] Dr. Becky Kennedy | LinkedIn [https://www.linkedin.com/company/goodinside/] Dr. Becky Kennedy | X [https://x.com/goodinside] Dr. Becky Kennedy | TikTok [https://x.com/goodinside] See omnystudio.com/listener [https://omnystudio.com/listener] for privacy information.

Today, Jay sits down with serial entrepreneur, investor, and powerhouse mom of four, Kim Perell. Known for building her first company from her kitchen table and later selling one for $235 million, Kim shares the raw, behind-the-scenes truth of what it takes to turn failure into fortune. The conversation centers around Kim’s latest book, Mistakes That Made Me a Millionaire, and offers a heartfelt blueprint for anyone feeling stuck, unfulfilled, or uncertain about their next move.  Jay and Kim explore why perfectionism can sabotage progress, how fear often masks itself as procrastination, and why waiting to feel “fully qualified” often leads to missed opportunities. Kim introduces her 70% rule: a concept that encourages action over hesitation and reveals how taking small, imperfect steps helped her overcome self-doubt and build extraordinary businesses. The two also dive into the power of mentorship, the emotional toll of toxic relationships, and why surrounding yourself with the right people is crucial not just for professional growth, but for personal evolution. In this interview, you'll learn: How to Start a Business Before You Feel Ready How to Use the 70% Rule to Make Bold Decisions How to Find the Right Mentor and Build a Real Relationship How to Stand Out When Pitching Yourself  How to Know When It’s Time to Pivot Your Business How to Build a Winning Team Without Doing Everything Yourself How to Audit Your Inner Circle for Growth and Clarity Making mistakes doesn’t mean you’ve failed, it means you’re showing up, learning, and trying something new. No success story is smooth or simple, but all of them prove that progress is always possible. 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 [https://news.jayshetty.me/subscribe].  What We Discuss: 00:00 Intro 02:57 How to Get Unstuck and Move Forward 04:17 When It’s Time to Pivot Your Career 05:50 Is Regret More Powerful Than Fear? 08:06 You Don’t Need To Be 100% Ready To Start 09:52 Are You Ever Really Ready? 11:29 Dream Big, But Start Where You Are 13:09 The Power of Believing in Your Vision 15:24 Be Delusionally Confident  16:29 How Mistakes Help You Iterate and Improve 18:30 How to Silence the People Who Doubt You 22:15 Teaching Kids to Embrace Failure 23:20 Rejection as Redirection  26:02 The Difference Between Innovating and Iterating 29:14 Build a Support System That Elevates You 31:51 How to Find Mentors Who Truly Guide You 33:55 Why Asking for Help Accelerates Growth 34:44 How Books Can Mentor You Too 38:21 The Four People Every Entrepreneur Needs 39:35 Why You Need the Right Peers Around You 41:58 Should You Start a Business with Family? 44:00 How to Audit Your Inner Circle 46:02 How Toxic People Drain Your Energy and Money 47:17 The Power of Taking Initiative  48:56 Don’t Let Your Past Limit Someone Else’s Future 51:19 How to Lead and Manage People Effectively 53:17 What Actually Gets You Hired Today? 57:51 Going the Extra Mile Sets You Apart 01:00:01 The Biggest Mistake Is Not Asking 01:04:03 Why So Many of Us Feel Unqualified 01:07:07 Pivoting Is the Secret to Success 01:10:13 How to Know When It’s Time to Pivot 01:11:53 Kim on Final Five  Episode Resources: Kim Perell | Website [https://kimperell.com/] Kim Perell | Instagram [https://www.instagram.com/kimperell/] Kim Perell | Facebook [https://www.facebook.com/kimperell/] Kim Perell | YouTube [https://www.youtube.com/c/KimPerell] Kim Perell | LinkedIn [https://www.linkedin.com/in/kimperell/] Kim Perell | X [https://x.com/kimperell] Kim Perell | TikTok [https://www.tiktok.com/@kimperell] See omnystudio.com/listener [https://omnystudio.com/listener] for privacy information.

Have you ever felt pressure to hide a part of who you are? What helps you feel safe enough to open up? Today, Jay chats with renowned celebrity hairstylist Chris Appleton to share deeply personal parts of his life he’s never shared publicly. Known for creating iconic looks for stars like Kim Kardashian, Jennifer Lopez, and Ariana Grande, Chris has built a career around image and transformation. Chris bravely opens up about the journey that shaped him, pulling back the curtain on the private struggles behind his public success. From growing up in a working-class town in England, and discovering his passion for hair was a way to survive, to feel seen, and to express who he really was.  As the conversation unfolds, Chris opens up about the darkest night of his life. The moment he nearly ended his life, a breaking point born from decades of shame, fear, and the belief that being true to himself would hurt the people he loved most. What followed was not an overnight transformation, but a long, honest path toward healing. Chris speaks candidly about coming out as gay in his late twenties, the grief of ending a nine-year relationship with the mother of his children, and the fear of disappointing his kids.  Jay and Chris explore the power of redefining identity, letting go of what no longer serves us, and embracing the possibility of change at any stage in life. With the support of therapy, self-reflection, and a willingness to confront his pain, Chris began a new chapter, one rooted in alignment between his inner and outer world. In this interview, you'll learn: How to Embrace Your True Identity Without Shame How to Heal After Hiding Your Authentic Self How to Rebuild Private Pain in Public  How to Support Your Children Through Major Life Changes How to Start Over When Your Life No Longer Feels Aligned How to Find Peace Through Forgiveness and Self-Acceptance How to Recognize When It’s Time to Let Go and Move On No matter your past, your pain, or how long you’ve carried it, it’s never too late to begin again. The first step is being honest with yourself. With Love and Gratitude, Jay Shetty Find help and support If you or someone you know is struggling or having thoughts of suicide, call or text the 988 Suicide & Crisis Lifeline [https://988lifeline.org/] at 988 or chat at 988lifeline.org [https://chat.988lifeline.org/]. In life-threatening situations, call 911. Join over 750,000 people to receive my most transformative wisdom directly in your inbox every single week with my free newsletter. Subscribe here [https://news.jayshetty.me/subscribe]. What We Discuss: 00:00 Intro 03:13 Your Roots Don't Define Who You Can Become 06:19 Is It Safer to Hide Who You Really Are? 10:11 What It Actually Takes to Become the Best  14:32 Finding Yourself After an Identity Crisis 17:27 Letting Go of Shame to Be Your True Self 20:15 Accepting and Embracing Your Gender Identity 22:46 How to Come Out Without Hurting the People You Love 30:21 Choosing Inner Peace Over the Deepest Pain 33:10 Rebuilding Yourself After Grief and Collapse 36:40 Why the Right Guidance Can Change Everything 39:13 Struggling Doesn’t Mean You’re Weak 39:30 Forgiveness: Freeing Yourself from the Past 41:15 Sharing Your Story Could Save Someone Else 44:29 When a New Environment Heals Your Spirit 45:06 The Unexpected Call That Changed Everything 47:29 The Hair Appointment That Almost Ended His Career 52:23 How to Build Authentic Relationships in Your Industry 55:33 You Don’t Owe the Public an Explanation 59:09 Why Love Is Always Worth the Risk 01:01:48 Give Yourself Permission to Walk Away 01:05:35 How to Protect Your Peace in a Loud World 01:10:35 What Do You Really See in the Mirror? 01:12:28 Being the Father You Always Needed 01:19:01 Chris on Final Five Episode Resources: Chris Appleton | Instagram [https://www.instagram.com/chrisappleton1]  Chris Appleton | YouTube [https://www.youtube.com/c/ChrisAppleton] Chris Appleton | TikTok [https://www.tiktok.com/@chrisappletonhair?lang=en]   Chris is releasing his debut book, YOUR ROOTS DON’T DEFINE YOU: Transform Your Life. Create Your Comeback, on January 20, 2026. The book is available for pre-order now at the link HERE [https://chrisappleton1.wpenginepowered.com/] See omnystudio.com/listener [https://omnystudio.com/listener] for privacy information.

Have you ever thought about starting a business? What would you do if money wasn’t a problem? Today, Jay sits down with bestselling author, entrepreneur, and investor Alex Hormozi for a practical and eye-opening conversation about money, business, and what it really takes to succeed. Alex has built and sold multiple companies and now runs Acquisition.com, where he helps scale businesses to over $10 million in revenue. In this episode, Alex breaks down why so many people feel stuck when trying to grow a business. Alex and Jay dive into the common mistakes that hold people back, like chasing passive income too early, mistaking passion for a plan, or seeking freedom without first building discipline. Alex shares the real steps you need to take to start making money now. He explains how to create active income by offering your time and skills, how to craft offers people can’t refuse, and why direct feedback is the fastest path to growth. Jay and Alex also explore the mindset traps that stop people from moving forward, including fear of judgment, comparison, and the pressure to get it perfect the first time. Together Jay and Alex highlight the importance of showing up consistently, being willing to fail, and choosing long-term growth over short-term comfort. In this interview, you'll learn: How to Start a Business with Zero Capital How to Create an Offer People Can’t Refuse How to Increase Your Income by Trading Your Time Intentionally How to Sell Without Feeling Manipulative How to Get Unstuck from the Passive Income Trap If you're ready to stop guessing and start building something real, this episode gives you the clarity, structure, and confidence to move forward. 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 [https://news.jayshetty.me/subscribe].  What We Discuss: 00:00 Intro 00:40 Get Clear on the Exact Actions That Drive Success 02:10 Why Most People Misunderstand How to Build a Business 04:26 Is the ‘Get Rich Quick’ Model Really Possible? 07:41 The Five Emotional Stages Every Entrepreneur Goes Through 10:52 Start Here to Learn the Skills That Actually Make Money 13:36 Should You Follow Your Passion for Income? 23:30 How to Make Your First Dollar from Nothing 27:57 The 10 by 10 Strategy to Build Proof and Confidence 32:27 Your Product Must Solve a Real Problem 35:37 What No One Tells You About the Trade-Offs of Business 39:40 How to Turn Your Job Experience into a Business 52:27 Redefining Success: It’s Not About the Outcome 56:07 Listen to People Who Are Where You Want to Be 01:02:18 Overcoming the Fear of Selling Ourselves 01:04:23 How to Influence Without Manipulating 01:10:17 The Difference Between Criticism and Insults 01:17:28 How to Break Repetitive Negative Behavior 01:26:15 When to Keep Pushing and When to Pivot 01:28:46 The Four Ingredients of an Irresistible Offer 01:37:02 Focus on Who You Want to Become Not Just What You Want 01:38:40 What Would You Do If You Weren’t Afraid? 01:42:46 The Simple Formula Everybody Has But Nobody is Doing 01:45:53 The Most Important Step Is Just Start 01:47:05 Is Work Life Balance Really Achievable?  01:50:35 Be More Productive by Eliminating Everything Unnecessary 01:55:17 Alex on Final Five Episode Resources: Alex Hormozi | Website [https://www.acquisition.com/] Alex Hormozi | Instagram [https://www.instagram.com/hormozi/] Alex Hormozi | Facebook [https://www.facebook.com/ahormozi/] Alex Hormozi | YouTube [https://www.youtube.com/c/alexhormozi] Alex Hormozi | LinkedIn [https://www.linkedin.com/in/alexhormozi/] Alex Hormozi | X [https://x.com/alexhormozi] Alex Hormozi | Books [https://www.amazon.com/stores/author/B099H3YM3R/allbooks?ingress=0&visitId=adba95de-62aa-4ede-887a-9da62c58165f] See omnystudio.com/listener [https://omnystudio.com/listener] for privacy information.