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

01:47 Open Discussions About Mental Health

03:10 Impulsiveness as an Athlete

05:28 Moving From Japan to USA

08:02 Lifelong Training and Career

10:13 Incorporating Culture in Fashion

12:38 Discipline and Diet

13:53 Indulging in Guilty Pleasures

16:48 Passing Time While Having Impulsive Tendencies

18:46 Winning the First Grand Slam

21:09 Dealing with Public Hate

22:39 A Long-Time Serena Williams Fan

25:16 Experiencing Motherhood

27:39 The Different Facets of Life

29:07 The Power of Journaling

31:55 Loving the Life You're Living

34:57 The Habit of Comparing Yourself to Others

36:27 Stop Chasing Your Old Self

38:21 Motherhood Realizations

39:46 Rigorous Training After Giving Birth

41:18 Setting Boundaries During PressCon

43:01 No One Can Predict Someone's Path

45:21 Finding Calmness Through Meditation

47:44 Setting New Goals

50:25 Shamed for Taking a Break

54:17 Getting Support from Fellow Athletes

55:52 Friendships and Camaraderie

57:08 Mentored by Kobe Bryant

59:31 The Haitian Way of Giving

01:00:58 Who Are You Spending Your Time With the Most?

01:04:29 Loving Yourself and How You Look

01:05:29 Game Day Routine

01:07:33 You're Never Alone

01:09:04 Fear of Being Forgotten

01:12:40 Naomi on Final Five

Episode Resources:

Naomi Osaka | Instagram

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.