Creative Risks, Failure as Experimentation

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

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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

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