On Purpose with Jay Shetty

Jay sits down with Eileen Gu, the most decorated freestyle skier in Olympic history, to go behind the resume and into the mindset that built it all. Eileen opens up about the grandmother and mother who shaped her, why direction matters more than raw effort, her “evidence over affirmation” approach to fearless competition, and the devastating personal loss she carried in the very same hour as her Olympic gold medal win.

With Love and Gratitude,

Jay Shetty

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What We Discuss:

00:00 Introduction

01:25 Who Are You Beyond Your Achievements?

03:12 The Childhood Curiosity That Shaped Everything

05:52 What Her Childhood Journals Reveal Now

09:20 Rethinking Masculinity, Femininity & Fashion

11:30 The Weekend Trips That Built an Olympian

14:37 The Two Women Who Shaped Who She Became

17:38 Even Olympians Can Feel “Behind” In Their 20s

19:37 Hard Work Vs. Direction And Momentum

22:38 Finding Direction Amid Unlimited Opportunities

26:29 Learning As A Superpower

31:22 Train Like You’ve Never Won

36:06 Seperating Your Identity From Your Craft

41:34 Evidence Over Affirmation

43:34 The Physics And 4D Visualization of Freeskiing

49:42 Inside the Milan Olympics

55:13 Highest Highs And Lowest Lows

01:00:02 Eileen Gu On Final Five
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Jay explores why our relationship with money is about so much more than what’s in our bank account. He breaks down five lessons, from how childhood shapes the way we spend and save, to what we’re really buying when we make a purchase, what money can and can’t solve, why simple systems work better than willpower, and how to make money work for you instead of letting it run your life.

With Love and Gratitude,

Jay Shetty

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This episode is for general educational and informational purposes only and is not financial, investment, tax, or legal advice. Consider your individual circumstances and consult an appropriate professional before making financial decisions.

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What We Discuss:

00:00 Intro

00:30 Are You Financially Literate?

04:51 Your First Money Lessons Start in Childhood

10:08 What You’re Actually Buying When You Make a Purchase

15:26 Money Can’t Buy Happiness, But It Can Buy Options

17:17 How Much Is Actually Enough?

21:21 Systems Over Willpower

26:50 Money Is Not The Goal
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Jay answers four listener calls about the messy, unresolved side of forgiveness, from custody guilt and bias in parenting, to forgiving yourself after the sudden loss of a parent, uncovering a spouse’s hidden life after they’re gone, and the heartbreak of a friendship betrayal. Jay shares research-backed tools to release guilt, rebuild trust, and move forward for your own peace, without excusing what happened.

With Love and Gratitude,

Jay Shetty

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Access resources from the hotline for individuals and families facing mental and/or substance use disorders here: https://www.samhsa.gov/find-help/helplines/national-helpline

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What We Discuss:

00:00 Introduction

00:24 What Forgiveness Is Really For

00:49 The Guilt Mothers Are Expected To Carry

01:54 Are Mothers And Fathers Held to Different Standards?

07:45 The Guilt That Comes After Losing a Parent

08:40 Forgiving Yourself For What You Couldn’t Control

15:52 When Grief Comes With Betrayal

17:54 The Trap Of “I Should Have Known”

22:05 The 4 Levels Of Trust

25:17 The Pain Of A Friendship Betrayal

26:20 When Healing Doesn’t Feel Like Healing
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Jay sits down with Harvard Business School professor Alison Wood Brooks, author of Talk: The Science of Conversation and the Art of Being Ourselves, to explore what makes great conversations actually work and where most of us get it wrong. Together, they unpack how to choose better topics, embrace the messiness of real dialogue, master the three stages of listening, and give compliments that genuinely connect. Alison also reveals why admitting uncertainty builds more trust than having all the answers, and shares practical conversation games you can start using right away.

With Love and Gratitude,

Jay Shetty

Learn to own the conversations that matter most in Alison Wood Brooks' new class on MasterClass: The Conversation Advantage With Alison Wood Brooks | MasterClass

PURPOSE10 for 10% at altrarunning.com/onpurpose. Free Shipping and Free 30-Day Trial.

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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 Introduction

01:51 Shifting Focus from Yourself In Conversation

05:31 Lowering Your Anxiety with Topic Prep

08:30 Is It Better to Be Interesting or Interested?

09:45 The Butterfly Net Metaphor

13:00 Low-Stakes Practice To Build High-Stakes Confidence

14:00 Debunking Traditional Rules of Persuasion

15:55 Building Conversational Safety Through Validation

17:06 Agenda-Free Relationships vs. Manipulative Networking

20:36 The Power of Follow-Up Questions

24:00 Embracing the Natural Messiness of Dialogue

26:11 Unrealistic Standards Set by Media and Podcasts

27:06 Alison's Top Three Small Talk Techniques

29:22 Balancing Leading vs. Following in Conversation

32:40 Does Your Mind Wander During Conversation?

33:40 The Power of Callbacks

34:00 The Attention Crisis and Screen Disruption

37:09 Strategies for Staying Present

39:00 Reciprocity and the Good-to-Great Question Shift

41:14 Intimate Openers and Stealth Topic-Switching

46:12 How to Respond to One Word Answers

47:35 Game 1: Spontaneous Depth and Sincerity

51:57 Game 2: Breaking Through Reserve

55:56 Talk Time Game: Battle of the Nice Guys

01:01:03 The Compliment Landmines to Avoid

01:04:00 This Is Damaging Your Potential Connections

01:09:48 The Best Way to Receive a Compliment

01:12:30 Talk Time Game: Admitting Uncertainty

01:21:30 Feel More Confident During Conversations

01:22:05 Dating Conversations and the First-Date Pause

01:26:20 Reviving a Dying Date Conversation

01:29:54 Deconstructing the "36 Questions to Fall in Love"

01:31:40 Defusing Heated Disagreements

01:32:22 Preparing for Difficult Conversations

01:34:00 When Distance Is Better Than Talking

01:37:45 Alison Wood Brooks on Final Five
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Jay breaks down the difference between healthy self-reflection and the kind of rumination that keeps you stuck in your own head. He shares four practical shifts to help you break the cycle, from redirecting your attention and resisting isolation to finding purpose through serving others and stepping into what Maslow called self-transcendence. Jay also shares a simple seven-day challenge to help you put it all into practice.

With Love and Gratitude,

Jay Shetty

PURPOSE10 for 10% at altrarunning.com⁠/onpurpose. Free Shipping and Free 30-Day Trial.

Your future is waiting, and Walden is here to help you achieve it. https://WaldenU.edu

JAY’S DAILY WISDOM DELIVERED STRAIGHT TO YOUR INBOX

Join 900,000+ readers discovering how small daily shifts create big life change with my free newsletter. Subscribe here: https://news.jayshetty.me/subscribe

Check out our Apple subscription to unlock bonus content of On Purpose! https://lnk.to/JayShettyPodcast

What We Discuss:

00:00 Intro

00:22 The Rumination Trap

04:00 Four Shifts to Break The Cycle

05:48 #1: The Power Of Attention

10:40 #2: Overcoming The Instinct To Isolate

16:20 #3: Finding Meaning By Being Useful

21:35 #4: Self-Transcendence

25:00 The Seven-Day Challenge

26:48 Healing and Growth as a Gift to Others

28:40 Expanding Your World
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