Ask Jay: The Right Opportunity Might Not Be What You Expect

Jay answers four listener calls about what to do when the path forward feels uncertain. From career rejection and financial risks to knowing when openness becomes self-abandonment and how to keep going after repeated disappointment, Jay explores how to navigate the moments when what you want isn’t working out the way you hoped. Drawing on Seneca, Pema Chödrön, and Taoist philosophy, he shares how shifting from an outcome mindset to a growth mindset can help you see rejection differently, keep your momentum, and stay open to the right opportunity. With Love and Gratitude, Jay Shetty Mazda crafts cars for people who do more than simply move. Visit Mazdausa.com to learn more. Consumer reports does not endorse products or services. 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 00:30 Navigating Career Rejections 01:31 The Smarter Way To Get Your Foot In The Door 06:32 Jay’s Personal Story With Rejection 08:56 Is The Dream Worth The Financial Risk? 10:24 Before You Take The Leap, Ask Yourself This 14:22 When Does Empathy Become Self-Abandonment? 15:40 Setting Boundaries Without Closing Your Heart 20:44 How To Stop Letting Rejection Kill Your Excitement 21:26 Shift From An Outcome Mindset To A Growth Mindset Learn more about your ad choices. Visit podcastchoices.com/adchoices

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 PURPOSE10 for 10% at altrarunning.com⁠/onpurpose. Free Shipping and Free 30-Day Trial. Mazda crafts cars for people who do more than simply move. Visit Mazdausa.com to learn more. Consumer reports does not endorse products or services. 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 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 Learn more about your ad choices. Visit podcastchoices.com/adchoices

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 PURPOSE10 for 10% at altrarunning.com⁠/onpurpose. Free Shipping and Free 30-Day Trial. Head to https://wayfair.com right now to shop all things home and get your space ready for less. 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. 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 00:30 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 Learn more about your ad choices. Visit podcastchoices.com/adchoices

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 PURPOSE10 for 10% at altrarunning.com⁠/onpurpose. Free Shipping and Free 30-Day Trial. Head to https://wayfair.com right now to shop all things home and get your space ready for less. 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 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 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 Learn more about your ad choices. Visit podcastchoices.com/adchoices

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. Head to https://wayfair.com right now to shop all things home and get your space ready for less. 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 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 Learn more about your ad choices. Visit podcastchoices.com/adchoices

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 Learn more about your ad choices. Visit podcastchoices.com/adchoices

In the very first episode of Ask Jay, a new series where listeners send in voice notes with their biggest questions, Jay explores what it really means to let go when your heart is still holding on. Through four deeply personal stories, he unpacks the difference between love and trauma bonds, the pull of breadcrumbing and relationship amnesia, the anxious-avoidant cycle, and what it takes to rebuild trust after betrayal. Along the way, Jay shares practical tools to help you choose yourself, rebuild self-trust, accept silence as an answer, and recognize when healing needs to come before making a decision about a relationship. 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 Access resources from the Domestic Violence support hotline here: https://www.thehotline.org/ 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 Introduction 01:23 Are You Holding On To A One-Sided Relationship? 03:40 The Law of Reciprocation 06:23 Breadcrumbing And Listening to Your Body 07:34 Trauma Bonds And Relationship Amnesia 09:16 Letting Go Of The “Good Girl” Persona 11:04 Is It Love or A Trauma Bond? 16:07 Why Toxic Relationships Feel So Hard to Leave 16:41 Rebuilding Self-Trust After Abuse 19:11 The Love As Action Test 20:12 Why Avoidant Partners Leave 21:52 What An Avoidant Partner May Be Thinking 23:32 Stop Trying To Read Their Mind 25:38 Redirecting Hope Back Toward Yourself 29:21 Can Trust Be Rebuilt After Betrayal? 31:00 What Was the Purpose Of The Break? 32:58 Should You Give Second Chances? 33:39 Healing Before Making A Relationship Decision 34:36 Building A “Second Marriage” With The Same Person Learn more about your ad choices. Visit podcastchoices.com/adchoices

Musician and artist Paris Jackson joins Jay for an extraordinarily raw, courageous, and deeply honest conversation on addiction, recovery, and the messy, non-linear journey of healing. Paris reflects on her unconventional childhood, the chronic loneliness that shadowed her early years, and the dark reality of substance abuse that nearly cost her her life and her voice. She opens up about the trauma of adolescent rehab centers, surviving severe mental health crises, and why true recovery requires moving beyond symptom-focused treatment to embrace holistic health, self-grace, and spiritual surrender. Together, Jay and Paris explore the power of inner child work, why pain can be alchemized into medicine, and how finding a conscious connection to something higher can help us feel truly safe in our own skin. Healing is not linear, and growth is not a straight line, it’s a spiral. Every time you revisit a challenge, you are meeting it with more wisdom, more resources, and a deeper capacity for self-forgiveness. Trust that your darkest moments can become your most potent medicine, and that peace begins the moment you give yourself permission to feel it all. 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 1:31 The Meaning Behind 'Happiest Day of My Life' 5:07 Unconventional Childhood and Homeschooling Reflections 6:32 One of Paris’s Most Defining Childhood Memories 8:03 Buddhist Parables, Balance, and Letting Go of Judgment 10:52 Chronic Loneliness and The Roots of Addiction 12:20 Redefining Gateway Drugs and Escapism 14:15 The Severe Consequences of Substance Abuse 19:30 Rebuilding Trust and Finding Authentic Friendship 22:27 Suicide Attempts, Turning Points, and Choosing Sobriety 23:34 Adolescent Rehab Trauma 31:38 Developing a Relationship with a Higher Power 35:17 The Dance Between Spiritual Surrender and Intentional Action 36:37 Analyzing 'Stitched' and Soul Connections 40:22 Inner Child and Inner Teen Healing Work 43:07 The Spiral Nature of Healing and Growth 46:24 ECT Treatment, Western Medicine, and Holistic Health Shifts 54:42 Finding Regulation Through Physicality, Nature, and Animals 59:25 Temporality of Emotions and Embracing Life's Full Spectrum 01:03:17 Paris Jackson on Final Five Learn more about your ad choices. Visit podcastchoices.com/adchoices

Loneliness doesn’t come from being surrounded by too few people, it comes from believing you have to wait for connection to find you. In this episode, Jay shares five powerful mindset shifts to help you build meaningful friendships as an adult by overcoming the fear of rejection, letting go of imagined judgment, and embracing the courage to make the first move. Through practical insights and research-backed wisdom, you'll discover that lasting friendships aren't built through perfect chemistry, but through consistent presence, intentional effort, and the willingness to create the community you've been searching for. With Love and Gratitude, Jay Shetty PURPOSE10 for 10% at altrarunning.com/onpurpose. Free Shipping and Free 30-Day Trial. On Purpose is now Netflix and Spotify exclusive http://www.netflix.com/onpurposewithjayshetty https://open.spotify.com/show/5EqqB52m2bsr4k1Ii7sStc?si=33f7898fb334437c 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: 00:00:00 Introduction 00:02:33 5 Mindset Shifts to Make Friends 00:03:51 Why Making Friends Feels Harder Now 00:06:25 The Fear Keeping You Lonely 00:09:55 People Like You More Than You Think 00:14:35 Why Repetition Builds Real Friendships 00:21:01 Stop Waiting, Start Building Community Learn more about your ad choices. Visit podcastchoices.com/adchoices

Jay sits down with transformational coach Jim Curtis, author of The Book of Possibility, to unpack how our subconscious beliefs, many formed before age seven, quietly shape our careers, relationships, and sense of what we think we deserve. Jim breaks down his Release, Align, Become framework, walks through the four core childhood wounds behind our biggest triggers, and shares practical tools for anxiety and self-doubt, ultimately revealing who you actually are beneath the programming. With Love and Gratitude, Jay Shetty PURPOSE10 for 10% at altrarunning.com⁠/onpurpose. Free Shipping and Free 30-Day Trial. Check out our Apple subscription to unlock bonus content of On Purpose! https://lnk.to/JayShettyPodcast What We Discuss: 00:00 Introduction 01:00 What Are We Getting Wrong About Manifestation? 01:40 Where Our Core Assumptions Come From 04:01 Awareness, Releasing, and Challenging Assumptions 06:57 Deconstructing “I Don’t Know What I Want” 11:45 The Release-Align-Become Framework 17:00 Jay’s Identity Shift: Employee to Entrepreneur 18:16 The Buddha’s Raft Story 20:56 Crafting Affirmations & Laddering Up 24:26 Jim’s Personal Resistance 26:58 Overcoming Self-Doubt and Releasing Shame 29:18 Jim’s Wake-Up Call: Shamans and Kung Fu 31:45 Jim’s Spinal Lesion and the Blackout Walk 34:40 Pain and Suffering as Doorways to Growth 35:20 Demystifying Hypnosis & The Power of Suggestion 44:17 Healing a Lifelong Phobia 46:07 Tools for Anxious and Ruminating Thoughts 48:30 Pre-Patterning for Repetitive Triggers 52:00 The Four Core Childhood Wounds 57:01 The Biggest Mistake in Seeking Love 01:01:46 Rejection Is Protection 01:05:19 Vulnerability: Masks, Mirrors, and Feeling Seen 01:07:23 Breaking Free from “Buckets” 01:09:39 Rebuilding Identity After a Breakup 01:11:55 Connection to Universal Consciousness 01:14:48 Jim Curtis On Final Five Learn more about your ad choices. Visit podcastchoices.com/adchoices