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.