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
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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
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