On Purpose with Jay Shetty

Do you ever feel like you need to be funny to be liked? How do you handle pressure to always “perform” for others? In this candid, hilarious, and unexpectedly moving episode of On Purpose, Jay sits down with comedian, actor, and podcast superstar Bert Kreischer—famously known for his shirtless stand-up and his ability to keep audiences laughing nonstop. This conversation goes way beyond the jokes as Jay and Bert dive deep into the real stories behind the spotlight, revealing the layers of vulnerability, self-doubt, and emotional growth that make Bert more than just a party-loving comic. Bert shares what it was like growing up with a tough, old-school dad who believed in powering through pain and never showing weakness. That mentality helped shape Bert’s work ethic but also left him carrying emotional weight for years. In one of the most touching moments of the episode, Bert shares how a simple, unexpected conversation with his dad, while they were both high on edibles, changed everything, helping them finally see each other clearly and connect on a deeper level. With Jay’s thoughtful guidance, they unpack Bert’s real-life struggles with anxiety, chasing approval, and feeling like you’re never enough, things so many of us can relate to. Bert is refreshingly honest about his mental health, his parenting ups and downs, and what it's like trying to stay grounded while raising two sharp, hilarious daughters who aren’t afraid to call him out. In this interview, you'll learn: How to Stay Humble While Chasing Big Dreams How to Raise Kids Who Keep You Grounded How to Keep Showing Up Even When It's Hard How to Use Vulnerability as a Superpower How to Manage Anxiety Without Shame How to Turn Criticism into Growth How to Stay Grateful Through Every Stage of Success This episode is full of laughs, a few tear-jerking moments, and plenty of insight into what it really means to show up, be yourself, and keep going, even when it’s hard.  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].   Join Jay for his first ever, On Purpose Live Tour [http://jayshetty.me/tour]! Tickets are on sale now. Hope to see you there!   What We Discuss: 00:00 Intro 02:45 The Wildest Plane Stories You’ve Ever Heard 04:25 Why a Marriage Built on Laughter Works 06:01 When Your Family Becomes Your Funniest Critics 07:16 Were You Always the Funny One? 09:08 How Bert Mastered the Art of Storytelling 14:35 Growing Up with a Tough-Love Dad 17:56 What It’s Like Seeing Your Parent Cry for the First Time 20:40 Realizing Your Parents Are Human Too 23:36 When Your Dad Realizes He Can Use Your Fame   24:35 What It’s Like to Share Your Success with Your Parents 29:05 The Lifelong Quest for a Parent’s Approval 35:08 How a 6-Figure Deal with Will Smith Changed Everything 37:20 The Moment You Know You Have to Chase Your Talent 42:50 Embracing the Power of Pressure 44:09 Is There a Pain You Can’t Laugh Through? 47:06 Letting Your Kids See You Cry 49:56 Why the Way You Tell a Joke Matters 51:43 How Your Kids Really See You 54:05 The Challenge of Uninterrupted Family Time 56:51 Just Show Up and Do the Work 01:01:33 Success Was Never a Straight Line 01:07:24 Don’t Let Greatness Become Familiar 01:11:12 Living with Anxiety When Life Doesn’t Slow Down 01:17:26 Building a Healthier Relationship with Alcohol 01:19:29 How Tracking Your Fitness Can Change You 01:22:00 Bert on Final Five Episode Resources: Bert Kreischer | Website [https://www.bertbertbert.com/] Bert Kreischer | Instagram [https://www.instagram.com/bertkreischer] Bert Kreischer | X [https://x.com/bertkreischer] Bert Kreischer | YouTube [https://www.youtube.com/@bertkreischer] Bert Kreischer | TikTok [https://www.tiktok.com/@bertkreischer] Bert Kreischer | Facebook [https://www.facebook.com/BertKreischer/] See omnystudio.com/listener [https://omnystudio.com/listener] for privacy information.

What usually holds you back from starting a conversation? Can you remember a time you avoided someone out of fear of saying the wrong thing? Jay sits down with behavioral researcher and bestselling author Vanessa Van Edwards for a powerful conversation that blends science, honesty, and so many surprising moments. Vanessa, who refers to herself as a “recovering awkward person,” shares how her biggest social struggles became the driving force behind her mission to crack the code on human connection. Together, Jay and Vanessa dive into the fascinating world of charisma, exploring the 97 cues, from eye contact to tone of voice, that quietly shape how we’re seen and understood. Vanessa breaks down why so many of us feel overlooked or underestimated—and introduces “signal amplification bias,” a concept that explains why the signals you think you’re sending might not be landing the way you expect. Vanessa shows us how confidence isn’t always something you’re born with but something you can build, with intention and awareness. The conversation goes even deeper as they unpack the tricky balance between warmth and competence, especially for women in the workplace, and how vulnerability isn’t a weakness, but often your greatest strength. They explore how to create those magic “me too” moments that form instant connections, spot the hidden red flags in communication, and let go of the need to be liked by everyone in order to be truly seen by the right people. In this interview, you'll learn: How to Make a Great First Impression Without Saying a Word How to Break the Ice with a Simple “Hey” How to Balance Warmth and Competence in Any Conversation How to Create Connection Using “Me Too” Moments How to Exit a Conversation Gracefully (Without Offending Anyone) How to Spot a Liar Using Body Language and Micro-Expressions How to Ask Better Questions That Spark Real Conversations How to Recognize the Difference Between Charisma and Manipulation Whether you struggle with social anxiety, want to level up your leadership presence, or are just tired of surface-level small talk, this episode is packed with practical tools and uplifting wisdom to help you connect with more authenticity and power. 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].   Join Jay for his first ever, On Purpose Live Tour [http://jayshetty.me/tour]! Tickets are on sale now. Hope to see you there!   What We Discuss: 00:00 Intro 00:51 From Awkward to Empowered: Overcoming Social Anxiety 02:43 How Do You Really Want People to See You? 06:44 Why Aren’t Your First Impressions Landing? 10:01 Why They’re Not Getting Your Signals (And What to Do About It) 13:33 Want to Be More Attractive? Try Being More Available 15:40 One Simple “Hey” That Can Spark a New Connection 19:16 Your Vibe Teaches People How to Treat You 22:06 Speak with Power: Unlock Your Full Vocal Power 23:47 3 Conversation Starters That Actually Work 29:49 Making Friends Doesn’t Have to Be Hard 31:17 Why Compliments Alone Don’t Build Connection 33:30 Break the Ice Without Sounding Like Everyone Else 38:36 Stop Trying to Be Interesting, Do This Instead 40:48 The Art of a Smooth and Respectful Exit 44:32 Use These Nonverbal Cues to Steer the Conversation 47:41 Spot Inauthentic Behavior Before It Costs You 54:28 Why People-Pleasing Feels Safer But Actually Holds You Back 57:48 How to Tell If Someone’s Lying (Without Saying a Word) 01:00:04 When Narcissists Feel Like the Most Charismatic People 01:03:46 Want to Really Get to Know Someone? Take a Road Trip 01:04:45 How Dopamine Makes You More Memorable 01:08:23 Every Answer Can Be a Gateway to Connection 01:10:51 How Asking Better Questions Inspires Growth 01:13:10 Discover Your Social Battery: Introvert, Extrovert, or Ambivert? 01:15:10 You Might Be an Ambivert and That’s a Superpower 01:19:07 The Two Ways Friendships Evolve Over Time 01:22:30 Choose Friends Who Inspire Awe 01:25:20 The Double Standard Faced by Highly Competent Women 01:33:09 Before You Make That Connection, Ask Yourself This  01:34:34 Life’s Too Short for Shallow Connections, Find Your People 01:36:29 Vanessa on Final Five Episode Resources: Vanessa Van Edwards | Website [https://www.scienceofpeople.com/] Vanessa Van Edwards | Instagram [https://www.instagram.com/vvanedwards] Vanessa Van Edwards | X [https://x.com/vvanedwards] Vanessa Van Edwards | YouTube [https://www.youtube.com/@ScienceOfPeople] Vanessa Van Edwards | TikTok [https://www.tiktok.com/@vvanedwards] Vanessa Van Edwards | Facebook [https://www.facebook.com/vvanedwards/] Vanessa Van Edwards | LinkedIn [https://www.linkedin.com/in/vanessavanedwards] See omnystudio.com/listener [https://omnystudio.com/listener] for privacy information.

What’s something that really helps you feel energized in the morning? Do you ever give yourself a moment to reset during the day? Today, Jay shares a powerful reminder, rest isn’t something you need to earn, it’s something you absolutely need. If you’ve ever felt guilty for taking a break or felt like you had to justify a vacation, this conversation challenges that mindset and offers a refreshing shift. Rest is not a luxury, it's the fuel for everything we do. Just like your phone needs to recharge, your body, mind, and soul require consistent, intentional recovery. Jay offers simple, practical habits you can start using right away to feel more rested and centered. From scheduling micro-breaks throughout your day, trying out the box breathing method, to practicing the 5-4-3-2-1 grounding technique to bring yourself back to the moment, these tools are small shifts that can make a big difference. You’ll also be encouraged to create tech-free spaces, embrace short daily walks in nature, and carve out intentional pauses in your schedule. In this episode, you'll learn: How to Schedule Micro-Breaks Every 60–90 Minutes How to Redefine Rest as a Need, Not a Reward How to Release Guilt and Shame Around Taking Breaks How to Hydrate and Refocus During Short Breaks How to Reframe Rest as a Tool for Productivity and Creativity Making space to breathe, reflect, and recover won’t just help you feel better, it will help you show up better, think clearer, and live more purposefully. 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]. Join Jay for his first ever, On Purpose Live Tour! Tickets [http://jayshetty.me/tour] are on sale now. Hope to see you there! What We Discuss: 00:00 Intro 01:20 When Was The Last Time You Felt Truly Rested? 03:39 Regular Breaks Increase Productivity And Creativity 06:21 Rest Isn't Something You Earn, It’s Something You Need 07:53 #1: Set The Habit Of A Micro Break 11:15 #2: Practice Intentional Breathing Exercises 12:49 #3: Spend Time In A Mindfulness Practice 15:47 #4: Establish Tech-Free Zones in Your Home 18:55 Rest Is A Necessity, Not A Luxury See omnystudio.com/listener [https://omnystudio.com/listener] for privacy information.

Since the breakup, have there been moments when you actually felt calm, clear, or more like yourself? When you imagine texting them, what are you secretly hoping they’ll say—or make you feel? In this heartfelt and insightful compilation, Jay dives deep into the emotional landscape of breakups, offering a thoughtful and healing space for anyone navigating heartache. With his signature warmth and clarity, Jay brings together trusted voices in emotional wellness and relationships—Lori Gottlieb, Matthew Hussey, Stephan Speaks, Esther Perel, and Mel Robbins—each offering honest, thoughtful perspectives on what it really takes to move on after a relationship ends. Together, they unpack the emotional aftermath of a breakup, from grief and confusion to self-doubt and the search for clarity. Whether you're dealing with the sting of rejection, stuck with unanswered questions, or scared to start over, this episode offers clear, grounded guidance that will leave you feeling both supported and uplifted. Without pressure, it offers a calm, compassionate space to work through the pain with presence, perspective, and hope. In this episode, you'll learn: How to Stop Blaming Yourself After a Breakup How to Know When It's Time to Let Go How to Break Emotional Patterns in Relationships How to Sit With Pain and Still Move Forward How to Choose Peace Over the Past This episode offers more than advice—it brings hope, the kind that encourages self-love, future growth, and a belief that better things are ahead. 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]. Join Jay for his first ever, On Purpose Live Tour [http://jayshetty.me/tour]! Tickets are on sale now. Hope to see you there!  What We Discuss:  00:00 Intro  02:19 Why Breakups Feel Like the Hardest Loss 09:19 “Why Wasn’t I Enough?” Understanding the Root of Self-Blame 20:21 Knowing When It’s Time to Let Go 25:15 Should You Try to Win Them Back? 28:43 Practical Steps to Letting Go After a Breakup 34:41 Do What’s Best For You to Heal 36:56 Everyone Handles a Breakup Differently and That’s Okay 39:30 Shifting Conflict Into Understanding  45:07 What Power Struggles in Relationships Really Mean 47:44 Why Breakups Make You Feel Unlovable 51:25 How to Release Control and Finally Find Peace See omnystudio.com/listener [https://omnystudio.com/listener] for privacy information.

Have you ever been seen in a way that didn’t feel true to who you are? Who do you feel truly sees you for who you are? Today, Jay sits down once again with the incredible Khloé Kardashian to talk about growth, healing, and what it really means to evolve on your own terms. It’s been six years since Khloé first sat down with Jay, and a lot has changed. Now in her 40s, Khloé reflects on the defining moments of her 30s, the clarity she’s found in this new chapter, and how her journey has shaped the woman she is today In this honest and heartfelt conversation, Khloé opens up about what it really took to move through heartbreak, public judgment, and her own self-doubt. She shares how she learned to forgive herself, let go of shame, and step into a deeper sense of self-awareness. Khloé talks about navigating the pressures around motherhood, relationships, and success — and how therapy, journaling, and her unwavering faith helped her rediscover her worth and inner peace. Jay and Khloé also dive into what it looks like to slow down, make room for solitude, and intentionally choose joy. She offers a glimpse into her daily routines, the spiritual practices that ground her, and how she’s creating a loving, mindful environment for her children, one rooted not in perfection, but in presence and authenticity. In this interview, you'll learn: How to Set Emotional Boundaries Without Losing Your Kindness How to Forgive Yourself and Heal from Past Mistakes How to Use Solitude as a Tool for Self-Discovery How to Stop Comparing Your Journey to Others How to Build Emotional Resilience After Betrayal How to Raise Emotionally Aware and Grounded Children How to Find Peace Through Faith and Daily Rituals Through her candid storytelling and unwavering humility, Khloé offers hope, wisdom, and an empowering message of self-acceptance to anyone navigating their own inner transformation. 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].   Join Jay for his first ever, On Purpose Live Tour [http://jayshetty.me/tour]! Tickets are on sale now. Hope to see you there!   What We Discuss: 00:00 Intro 03:33 Aging Doesn’t Have to Be Scary 05:17 Visualizing Your Life in Your 40s 06:23 It’s Okay to Be Unsure 07:39 How Maturity Brings Stability 09:35 Why We’re Always Chasing More 12:09 The Truth About Success 13:55 Practice Self-Intentionality 16:42 Stop Letting Validation Control You 19:47 Balancing Accountability and Forgiveness 21:42 Learn to Be Patient with Yourself 23:10 Everyone Learns on Their Own Timeline 24:30 A Path to Self-Forgiveness 27:20 When You Might Be the Problem 29:24 You Are Not Your Mistakes 31:39 The Work Only You Can Do 36:00 Rewiring a Negative Mindset 38:18 Why Therapy Can Be Transformative 41:11 Finding the Courage to Trust Again 43:17 Getting Comfortable with Being Vulnerable 46:19 It’s Brave to Let Yourself Cry 48:28 Understanding Your Love Language 52:02 We All Love Differently 54:21 The Beauty of Giving Love 55:31 Reuniting with Lamar After 9 Years 59:51 Leaving What No Longer Serves You 01:03:46 Releasing Residual Negativity 01:05:15 Why We All Need Empathy 01:09:04 What I Want My Kids to Remember 01:11:35 Why Kids Don’t Need the Internet 01:14:24 Dating as a Mom in Your 40s 01:15:28 How to Date More Intentionally 01:17:31 Embracing Alone Time 01:19:05 Leaning Into the Discomfort Episode Resources: Khloé Kardashian | Instagram [https://www.instagram.com/khloekardashian/] Khloé Kardashian | X [https://x.com/khloekardashian] Khloé Kardashian | YouTube [https://www.youtube.com/channel/UCJy0RHFC64EC-kqWOfhCb_g] Khloud Foods [https://khloudfoods.com/] Khloé in Wonder Land [https://podcasts.apple.com/us/podcast/khlo%C3%A9-in-wonder-land/id1785985876] See omnystudio.com/listener [https://omnystudio.com/listener] for privacy information.