4.8 • 28.5K Ratings
🗓️ 1 August 2025
⏱️ 78 minutes
🧾️ Download transcript
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.
Click on a timestamp to play from that location
0:00.0 | This is an I-Heart podcast. |
0:04.4 | This week on Dear Chelsea with me, Chelsea Handler. |
0:07.7 | Marin Morris is here. |
0:09.3 | You came out of a marriage. |
0:11.2 | You came out of quote-unquote country music. |
0:13.7 | And you had a huge growth spurt from what I can tell. |
0:16.9 | I was expanding and growing at a really fast pace. And yes, you could throw motherhood and the |
0:24.7 | postpartum thing, learning about myself. There were a lot of like identity crises going on, |
0:29.3 | but I realized like I can't look back and slow down for people. Listen to Dear Chelsea on the |
0:35.7 | Iheart radio app, Apple Podcasts, or wherever you get your podcasts. |
0:41.0 | What I was dealing with at the time, feeling ashamed, going against everything an athlete stood |
0:46.9 | for. |
0:47.4 | After I pulled out of the French Open, I flew back home to L.A. |
0:52.5 | And I just stayed in my house. |
0:56.0 | I didn't want to see the outside world. Ranked as number one in the world in women's singles. |
1:00.0 | A four-time grand slam tennis champ, Naomi Osaka. |
1:05.0 | Your dad wanted to train you because he was reading about Richard Williams and what he'd done with the Williams sisters. |
1:12.6 | How aware were you of that when you were growing up? |
1:14.6 | It's me and my sister, my dad on a tennis court at least eight hours during the day. |
1:19.6 | Yeah. |
1:20.6 | I began to think to myself like it would be very weird if I didn't make it. |
1:25.6 | Your vulnerable sharing of your mental health journey, what does it feel like looking back |
... |
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