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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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.

Do you ever feel behind in life?

What are you comparing yourself to?

Today, Jay shares a powerful reminder for anyone who feels like they’re behind in life. Maybe you’re comparing your career path to a friend’s promotion, your relationship status to someone’s engagement photos, or your lifestyle to highlight reels on social media. Jay explains how natural it is to feel this way, especially after school, when the timelines that once kept us moving together begin to split apart. Drawing on social comparison theory, he shows how easily our self-worth can become tied to where others seem to be, instead of honoring the unique path we’re on.

Jay reframes the idea of being “behind,” not as a failure but an essential part of growth. Through psychology and real-life examples, he emphasizes that endings matter more than beginnings, and that setbacks are not signs of weakness, but proof that we’re actively building resilience. He challenges our attachment to comfort, which can quietly keep us stuck, and reminds us that what feels like delay is really unseen preparation for the skills and foundations that lead to future success. Jay shifts how we measure progress, from chasing empty wins to recognizing that grit matters more than perfection.

In this episode, you'll learn:

How to Redefine Success on Your Timeline

How to Recognize False Progress in Others

How to See Struggle as Strength

How to Turn Setbacks into Resilience

How to Trust That You’re Not Late

The struggles you face today are shaping your resilience, your wisdom, and your strength for tomorrow. You are not late, you are not lost, you are simply on your own timeline.

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

00:52 Do You Feel Behind in Life?

02:37 #1: You Aren't Late, You're on a Different Timeline

06:07 #2: Endings Define the Story

08:42 #3: Comfort is What Really Keeps You Stuck

12:27 #4: Progress Doesn’t Guarantee Happiness

14:01 #5: Struggling Is Proof You’re Growing

17:49 #6: You're not Behind, You're Developing Skills

See omnystudio.com/listener for privacy information.