What does rejection feel like to you? What do you usually do to move past that feeling? Today, Jay sits down with legendary filmmaker and comedian Judd Apatow for a vulnerable and inspiring conversation on life, creativity, and resilience. Known for shaping modern comedy with films like The 40-Year-Old Virgin and Knocked Up, Judd opens up about the struggles behind the success, sharing how self-doubt, early failures, and rejection shaped him into the storyteller he is today. He reflects on the power of mentorship, the lessons he learned from icons like Gary Shandling, and why finding your voice often requires patience, humility, and a willingness to fail forward. Together, Jay and Judd explore how comedy can be both healing and revealing, born not just out of joy but often out of pain. Judd talks about the risks he took, the creative experiments that didn’t work, and how those “failures” became stepping stones toward lasting impact. He reveals how therapy, mindfulness, and even family dynamics have influenced his work, and why the most meaningful measure of success is not box office numbers, but whether your work truly connects with people. In this interview, you'll learn: How to Find Your Creative Voice How to Balance Ambition with Presence How to Use Mentorship to Grow How to Push Through Self-Doubt How to Create With Authenticity How to Learn From Rejection How to Protect Your Flow State The setbacks you face today can become the foundation of your greatest breakthroughs tomorrow. Stay patient with the process, stay true to yourself, and keep moving forward with faith that your story has meaning and impact waiting to unfold.  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.  Check out our Apple subscription to unlock bonus content of On Purpose! https://lnk.to/JayShettyPodcast  What We Discuss: 00:00 Intro 01:09 What Made You Laugh Out Loud? 03:52 Raising Children Without Pressure 05:22 Never Limiting a Child’s Potential 08:09 The Most Memorable Interview 09:44 Discovering a Personal Path 10:27 From Fan to Friend 11:58 Running a Show Together 14:24 Growing with Creative Peers 15:58 Why Failure Leads to Success 18:00 The Power of Putting Yourself Out There 20:27 Why Success Takes Time 23:21 Creating Something Original 27:00 A Sliding Doors Moment 28:15 Realizing the Power of Choice 30:22 Becoming Part of Another’s Success 31:40 Confronting Creative Blocks 34:06 Inside a Storyteller’s Mind 35:34 Choosing to Be Part of the Solution 38:00 Taking Creative Risks 40:34 Silencing the Inner Critic 43:27 The Real Formula for Comedy 47:26 The Pitfalls of Mocking Others 48:41 The Promise and Peril of AI 51:39 Letting Go of a Problem-Seeking Mind 54:13 Projecting Childhood Trauma at Work 57:47 Separating Emotions from the Work 01:00:09 Choosing the Right Collaborators 01:02:58 Learning to Lighten Up 01:05:27 What Leads to True Success 01:07:30 The Most Impactful Self-Help Books 01:13:13 The Pain Behind Comedy 01:17:14 Defining True Happiness 01:22:33 Exploring an Ayahuasca Experience 01:24:18 The Secret to a Lasting Marriage 01:28:05 Lessons to Share with Children 01:30:07 Being Direct Yet Constructive 01:31:48 Finding Drama in Good People 01:34:07 Why Mentorship Matters 01:38:09 Judd on Final Five Episode Resources: Judd Apatow | Website Judd Apatow | Instagram Judd Apatow | Facebook Sicker in the Head: More Conversations About Life and Comedy Comedy Nerd: A Lifelong Obsession in Stories and Pictures See omnystudio.com/listener for privacy information.