Have you ever felt like losing meant your life was over?

When did you realize it’s okay to fail?

Today, Jay sits down with four-time Grand Slam champion Naomi Osaka to explore her journey beyond the tennis court. Naomi, known for her powerful game and quiet resilience, opens up about the challenges of fame, the weight of expectations, and how motherhood has reshaped her outlook on life.

Jay and Naomi discuss the pressure of being a high-performance athlete, the loneliness that can accompany success, and the struggles of maintaining a sense of self in an industry that often reduces people to their achievements. Naomi candidly describes how, for years, her self-worth was tied to her ranking and performance, but becoming a mother has given her a new perspective—one that prioritizes joy, presence, and growth over perfection.

The conversation also dives into Naomi’s evolving relationship with competition. While she once measured her success by titles and trophies, she now finds fulfillment in self-discovery and personal progress.

In this interview, you'll learn:

How to Detach Your Self-Worth from Achievements

How to Cope with External Expectations and Criticism

How to Use Journaling for Self-Reflection and Growth

How to Prioritize Mental Health in High-Pressure Situations

How to Learn from Setbacks Without Letting Them Define You

Success is not just about winning; it’s about growing, learning, and showing up for yourself every day.

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.

What We Discuss:

00:00 Intro

001:39 Open Discussions About Mental Health

02:50 Impulsiveness as an Athlete

05:08 Moving From Japan to USA

07:43 Lifelong Training and Career

09:54 Incorporating Culture in Fashion

12:18 Discipline and Diet

13:34 Indulging in Guilty Pleasures

15:49 Passing Time While Having Impulsive Tendencies

17:39 Winning the First Grand Slam

20:01 Dealing with Public Hate

22:26 A Long-Time Serena Williams Fan

24:09 Experiencing Motherhood

26:31 The Different Facets of Life

28:21 The Power of Journaling

30:47 Loving the Life You're Living

33:49 The Habit Comparing Yourself to Others

35:37 Stop Chasing Your Old Self

37:14 Motherhood Realizations

38:39 Rigorous Training After Giving Birth

40:45 Setting Boundaries During PressCon

42:30 No One Can Predict Someone's Path

43:36 Finding Calmness Through Meditation

46:37 Setting New Goals

49:18 Shamed for Taking a Break

53:10 Getting Support from Fellow Athletes

54:45 Friendships and Camaraderie

56:00 Mentored by Kobe Bryant

58:24 The Haitian Way of Giving

59:56 Who Are You Spending Your Time With the Most?

01:03:22 Loving Yourself and How You Look

01:04:33 Game Day Routine

01:06:24 You're Never Alone

01:07:58 Fear of Being Forgotten

01:11:33 Naomi on Final Five

See omnystudio.com/listener for privacy information.

Have you ever thought about being your own boss?

What kind of business would you start if you could?

In this special compilation episode of On Purpose, Jay Shetty curates powerful insights from five extraordinary entrepreneurs: Emma Grede, Michael Rubin, Codie Sanchez, Brian Chesky, and Suneera Madhani, offering a dynamic, behind-the-scenes look at what it truly takes to build something meaningful from scratch. Each guest brings a unique lens to the entrepreneurial journey: Emma Grede reminds us that the most powerful companies are born by solving real problems for underserved communities; Codie Sanchez breaks down how grit, financial fluency, and deal-making are more crucial than a flashy idea; while Brian Chesky reveals that building a world-changing company like Airbnb starts with seeing your business as a reflection of your inner world.

Jay weaves these stories into a powerful masterclass on purpose-driven entrepreneurship, showing that success doesn’t come from confidence, funding, or perfection. It comes from grit, learning through failure, and showing up again and again. Michael Rubin drives home the power of obsession and adaptability, while Suneera Madhani brings it back to reality, reminding us that the biggest risk isn’t failing, it’s never starting. It’s a powerful reminder that stepping out of comfort and into aligned action is where true transformation begins.

In this episode, you'll learn:

How to Build a Purpose-Driven Brand from Scratch

How to Master Deal-Making and Speak the Language of Money

How to Stay Innovative When Success Hits

How to Start a Business Without Industry Expertise

How to Scale a Company Without Losing Your Values

How to Take Risks Without Letting Fear Lead the Way

The most meaningful work often comes from solving problems close to your heart, staying curious, and showing up even when it’s hard. You are not too late, underqualified, or behind.

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.

What We Discuss:

00:00 Intro

03:06 Start With the Problem Only You Can See

06:40 The Power of Who’s in the Room

08:10 Believe in Your Vision Before Anyone Else Does

10:44 What Really Motivates You Every Day?

13:26 Three Essential Skills for Building a Business

18:33 How to Master the Art of Deal Making

28:03 Redefining What Success Means to You

31:10 Life’s Greatest Lessons Start Within

34:17 Surround Yourself With the Right People

38:54 Can Hustle and Drive Be Taught?

40:46 Learn by Observing Others’ Mistakes

41:30 What is at the Heart of Entrepreneurship?

42:52 Bringing Innovation to What You Love

47:14 Avoid These Common Mistakes when Building a Business

49:44 Pattern Recognition Is a Business Superpower

52:05 Why Hard Conversations Build Stronger Foundations

55:34 Courage Is the First Step Toward Risk

59:46 Start by Solving a Real, Specific Problem

01:03:49 What Got You Here Won’t Get You There

See omnystudio.com/listener for privacy information.

Do you ever feel like who you are is holding you back?

Can you really change your personality — or are you stuck with it for life?

Today, Jay sits down with award-winning journalist and author Olga Khazan, whose groundbreaking book Me But Better explores the science of personality change. As a staff writer at The Atlantic, Olga has spent years investigating what shapes who we are — and whether it’s possible to become more confident, resilient, and fulfilled by intentionally shifting our traits.

Jay and Olga explore the surprising research showing that personality isn’t fixed — and that with consistent effort, anyone can become a different version of themselves. Olga shares how she transformed traits like anxiety and self-doubt by applying science-backed tools and testing them in her own life.

They dive deep into how habits shape identity, why a strong “why” is essential for lasting change, and how the traits we envy in others might point us toward who we’re meant to become. They also unpack the difference between being “authentic” and being stuck — and why growth often looks like discomfort before it feels natural.

In this episode, you’ll learn:

How to Change Personality Traits You’ve Had for Years

How to Shift from Anxiety to Emotional Balance

How to Use Habits to Redefine Who You Are

How to Identify the Traits That Align with Your Goals

How to Stop People-Pleasing Without Becoming Cold

How to Make Growth Feel Authentic — Not Fake

True change doesn’t come from pretending to be someone else — it comes from becoming the person you were always capable of being. This episode is a powerful reminder that you’re not stuck. With intention, action, and the right mindset, you can grow into someone new.

With love and gratitude,

Jay Shetty

What We Discuss:

00:00 Introduction

02:08 Key Takeaways From Olga

03:03 Frustration As A Block

05:22 Research Says We Can Change Our Personality Traits

07:30 Why Do We Get So Stuck?

09:46 Is Personality Change Age Exclusive?

11:47 How Can We Change Our Personality?

17:34 Changing Habits Vs Personality Traits

24:31 How Long Does It Take To Change Personality Traits?

35:09 Gender Effects On Personality Traits

37:36 5 Personality Traits That Make Up Personality

41:35 Feeding Motivation For Change

51:46 How Can We Be More Extroverted?

54:04 Exposure Therapy For Introverts

56:56 How Personality Changes Affects The People Around Us

01:01:43 The Social Investment Theory

01:03:15 How Does The SIT Affect Relationships?

01:06:45 From Pessimism To Optimism

01:09:31 How People Pleasers Can Create Healthy Boundaries

01:14:35 Can Introverts Become Extroverts?

01:18:24 Can People With Depression & ADHD Change Their Personality?

01:21:25 Olga On Final Five

Episode Resources

Olga Khazan | Instagram

Olga Khazan | X

Olga Khazan | LinkedIn

Olga Khazan | Facebook

Me, But Better: The Science and Promise of Personality Change

See omnystudio.com/listener for privacy information.

Today, Jay dives into a feeling many of us know well: the sense that nothing in life is going the way we hoped. Whether your career feels stuck, your relationships feel off, or you’re just not where you thought you’d be by now. Jay reminds us that feeling stuck doesn't mean you've failed, but could be life giving you a moment to pause and reset. Jay explains that the way we experience reality depends on what we choose to focus on. When we're fixated on what's going wrong, we often miss the small signs that things are already starting to move forward.

Jay also challenges the idea that success is supposed to be linear or perfect. He reminds us that the people who seem ahead aren’t more talented, they just started sooner. Rather tha comparing ourselves to someone else’s timeline, Jay encourages us to focus on our own path and let go of the pressure to have it all figured out. Instead of trying to achieve something massive all at once, Jay encourages us to “shrink the vision, save the dream,” and take small, consistent steps that compound into real transformation. He reminds us that a plateau isn’t a setback, it’s a season of quiet growth that often comes right before a breakthrough.

In this episode, you'll learn:

How to Break Mental Overload with Movement

How to Take Action Before You Feel Ready

How to Stop Waiting for the Perfect Time to Start

How to Reframe Feeling Stuck

How to Build Momentum with Tiny Steps

No matter where you are in your journey, remember this: you’re not behind, you’re not broken, and you haven’t missed your chance. Feeling stuck doesn’t mean you’re failing, it means you’re in the middle of growth.

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.

What We Discuss:

00:00 Intro

01:06 Does It Feel Like Nothing's Working?

02:38 What is the Frequency Illusion?

04:39 Step #1: Stop Trying to Feel Motivated

10:04 Step #2: Break the Mental Spiral

12:07 Step #3: There is No ‘Right’ Time to Start

16:14 Step #4: Consistency Outlasts Talent

24:35 Step #5: Shrink the Vision, Save the Dream

See omnystudio.com/listener for privacy information.

Do you struggle with self-doubt sometimes?

What helped you get through a tough emotional season?

Today, Jay sits down with award-winning rapper, actor, and activist Common for a deeply moving live conversation recorded at the legendary Chicago Theater. Known for his poetic lyrics and conscious artistry, Common opens up about his journey from a young boy on the South Side of Chicago to becoming an Academy Award, Emmy, and three-time Grammy winner. In this intimate conversation they explore the emotional and spiritual work behind his success. From heartbreak and rejection to healing and purpose, Common shares what it really took to become the man he is today.

Common shares personal stories of growth and transformation, starting with his childhood dream of becoming a professional basketball player and how he eventually found his voice through writing and music. He reflects on the moments that shaped his purpose, including the story of Emmett Till, which moved him to live with more intention. Common also opens up about the heartbreak that forced him to confront the ways he was dimming his light, and the daily spiritual practices that help him stay grounded today, like reading scripture, praying, practicing gratitude, and staying active.

Jay and Common also dive into what it means to be vulnerable in hip-hop, why self-love is the foundation for every other kind of love, and how trusting the divine plan can turn disappointment into direction. They explore how trusting a bigger plan can help turn setbacks into clarity, and share personal insights on setting boundaries, building real friendships, and staying connected to your highest energy.

In this interview, you’ll learn:

How to Transform Pain into Purpose

How to Stop Dimming Your Light in Relationships

Why Vulnerability is a Superpower in Creativity

How to Build Daily Practices for Spiritual Alignment

How to Trust God’s Plan, Even When It’s Painful

How to Attract Friendships that Match Your Frequency

Whether you're moving through heartbreak, looking for direction, or trying to reconnect with your purpose, this conversation is a powerful reminder that your story matters and you're right where you need to be.

With love and gratitude,

Jay Shetty

What We Discuss:

00:00 Introduction

01:13 Live In Chicago

02:15 Common Before the Fame

06:11 Jay On His Childhood & Upbringing

06:44 Pain As A Catalyst for Creativity

09:01 Proximity To Greatness Is A Motivation

10:11 Living Our Dreams To The Fullest

13:49 How to Trust God's Plan

16:46 Trust That There’s a Bigger Plan

22:19 Transitioning Between Careers

30:15 Attracting & Building New Friendships

36:18 Everyday Routine For Body & Mind Care

40:40 A Poem From the Audience

43:21 My New Favourite Colour

48:49 Pushing Through Fear As A Motivator

53:33 Letting Go and Letting God

55:26 Common On Final Five

Episode Resources:

Common | Website

Common | YouTube

Common | Instagram

Common | X

Common | Facebook

See omnystudio.com/listener for privacy information.

Today, Jay reframes how relationships are built—not through surface-level attraction or blind chemistry, but through clarity, communication, and intentionality. He presents nine transformative questions that often go unasked in modern dating, not because they’re unimportant, but because they’re uncomfortable. Jay explains that avoiding these conversations leads to assumptions, unmet expectations, and unnecessary heartache. He underscores that a healthy relationship isn't defined by constant harmony, but by the courage to ask, listen, and grow together.

Blending personal stories, practical wisdom, and psychological insight, Jay highlights how asking the right questions early can reveal compatibility, values, and emotional readiness. He breaks down how these conversations create a shared language, prevent miscommunication, and ultimately strengthen the foundation of any relationship. Rather than using questions as ultimatums or pressure points, he encourages approaching them with curiosity and empathy.

In this episode, you'll learn:

How to Ask What a Healthy Relationship Means to Your Partner

How to Talk About Fears Around Commitment Without Pressure

How to Discuss Conflict Styles Before an Argument Happens

How to Know If Someone Is Truly Ready for a Relationship

How to Align on Boundaries and Independence in Love

Love doesn’t have to be a guessing game. The more willing we are to ask real questions and embrace honest conversations, the more aligned, peaceful, and fulfilling our relationships can become.

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.

What We Discuss:

00:00 Intro

02:03 The Conversations We Avoid in Modern Dating

03:36 #1: What Defines a Healthy Relationship?

08:17 #2: What are You Afraid of When It Comes to Commitment?

12:30 #3: How Do You Handle Conflicts?

19:44 #4: What are Your Long-Term Intentions?

22:02 #5: What Does Emotional Availability Mean to You?

25:10 #6: Do You Prefer to Recharge Alone?

27:49 #7: What Does Being Ready Mean to You?

31:30 #8: What Does Independence Look Like to You?

32:52 #9: What Are You Still Healing From?

See omnystudio.com/listener for privacy information.

Today, Jay sits down with author, artist, and creative mentor Amie McNee for a heartfelt conversation about reconnecting with the artist inside all of us. Known for her honest take on creativity and self-expression, Amie opens up about her journey, from battling self-doubt and shame to finding her voice as a writer and artist. Amie shares real stories of rejection, depression, and learning to embrace imperfection, reminding us that art doesn’t need to be perfect, it just needs to be real.

Jay and Amie explore the common myths that hold people back from creating. The idea that creativity has to be profitable, that art must be perfect to be valuable, or that we need permission to begin. They discuss how shame, perfectionism, and fear of judgment often silence our creative instincts, and how practices like journaling, self-mothering, and small daily acts of creativity can help revive them. They also reflect on the emotional vulnerability of sharing your work, the importance of protecting your inner artist, and the delicate balance between wanting to be seen and creating for the pure joy of expression.

In this interview, you'll learn:

How to Reclaim Your Creativity Without Shame

How to Make Art When You’re Struggling with Self-Doubt

How to Start Creating Even If You Don’t Feel Ready

How to Deal with Fear of Judgment and Being Seen

How to Turn Jealousy into Creative Motivation

How to Promote Your Art Without Selling Out

Whether someone is writing a novel, posting their first poem, or simply daring to call themselves an artist, this conversation is a gentle yet powerful reminder—they are on the path, and their voice matters.

With Love and Gratitude,

Jay Shetty

What We Discuss:

00:00 Intro

00:49 Are We Born Creative or Can It Be Learned?

02:12 Why Everyone Is an Artist in Their Own Way

03:50 What Happens When You Suppress Your Creativity

06:37 How Journaling and Self-Compassion Can Heal You

08:30 You Owe Everything to the Past Version of You

13:03 How to Move Through the Fear of Being Judged

16:07 Why Art Exposes Both Light and Darkness

17:25 Let Go of Needing External Validation

19:30 Everyone Just Wants to Be Seen and Heard

24:31 Stop Dismissing the Parts of You That Want More

26:28 Stuck in the Wrong Job? Try Small Creative Steps

30:56 How Perfectionism Fuels Procrastination

33:11 Embrace the Beautiful Chaos of Art

34:17 What the 30 Circles Test Reveals About Creativity

36:44 How to Share Your Art Without Losing Yourself

39:07 Real Artists Are Meant to Break the Rules

40:29 What to do When No One Sees Your Art

41:54 If You Hate It, Stop Doing It

44:19 Don’t Chase Virality, Make Meaningful Art

46:40 Yes, You Can Make Money from Your Art

50:10 Every Creative Act Has Value So Honor It

53:12 Charging for Your Art Is Not Selling Out

57:39 Oversaturation Is a Myth, There’s Room for You

01:00:53 Your Voice Is One of a Kind Use It

01:02:25 Use Jealousy to Guide, Not Derail You

01:03:49 How to Inspire Others by Owning Your Path

01:07:12 Amie on Final Five

Episode Resources:

Amie Mcnee | Website

Amie Mcnee | Instagram

Amie Mcnee | Facebook

Amie Mcnee | TikTok

Amie Mcnee | Books

We Need Your Art: Stop Messing Around and Make Something

See omnystudio.com/listener for privacy information.