Can you remember the first time you felt truly in charge of your own decisions?
What’s one thing you picked up from your family that you wish you could unlearn?
In this heartfelt episode, Jay Shetty sits down with former First Lady Michelle Obama and her brother, coach and mentor Craig Robinson, for an intimate conversation centered around family, resilience, and the lasting impact of love and connection.
Michelle and Craig reminisce about the powerful values instilled by their parents, a deep sense of independence and unwavering family loyalty. Even through financial struggles, their parents cultivated a home filled with trust and safety, making it clear that family would always be a source of strength. Memories of birthdays around the kitchen table, houses bustling with extended relatives, and the steady presence of grandparents and cousins all contributed to a lifelong sense of belonging and support that continues to influence their lives.
As they journeyed into adulthood, both Michelle and Craig relied on therapy, genuine friendships, and a strong community to help them face life’s transitions, grief, and the many complexities of growing up. Michelle shares how seeking guidance and embracing self-reflection, especially during moments of change, has been central to her personal growth, demonstrating the value of openness, adaptability, and continuous learning throughout every stage of life.
In this interview, you'll learn:
How to Foster Family Unity During Tough Times
How to Nurture Independence in Children
How to Unlearn Limiting Beliefs from Your Upbringing
How to Create Safe Spaces for Honest Conversations
How to Teach Empathy Through Parenting
How to Balance Protection and Freedom as a Parent
How to Normalize Therapy and Emotional Support
Their conversation is a moving testament to the impact of compassion, authenticity, and purposeful living, a reminder that life’s greatest challenges can be met with empathy, courage, and hope.
With Love and Gratitude,
Jay Shetty
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What We Discuss:
00:00 Intro
02:00 The Kind of Love Only Siblings Understand
04:15 What was the First Secret You Shared With Each Other?
09:53 Raised To Be Independent Children In A Loving Community
14:55 How Different Generations Celebrate Birthdays
17:00 How to Unlearn Your Inner Fears
19:47 The Fear Of What Could Happen Can Hinder Personal Growth
25:28 What a Childhood Encounter with Police Taught Me About Bias
29:35 Being Judged By The Color Of Your Skin
31:54 Racism Is Still An Issue
34:07 How to Raise Resilient Children
35:59 Don't Make Assumptions Based On Your Emotions
38:17 Don't Let Negative Thoughts Dictate Your Actions
40:48 The Power Of Good Parenting
48:41 How To Prioritize Being A Parent While Chasing Your Dreams
52:08 Parents Aren't Responsible For Their Children's Happiness
58:07 Focus On Cultivating Independence in Your Children
01:02:24 What Is Your Form Of Therapy?
01:11:08 Are You Doing Enough?
01:16:10 How To Become A Good Parent
01:37 What Would Your Mother Be Most Proud Of?
Episode Resources:
Michelle Obama | Instagram
Michelle Obama | Facebook
Michelle Obama | YouTube
Michelle Obama | Books
Obama Foundation
The Light We Carry: Overcoming in Uncertain Times
Craig Robinson | Instagram
Craig Robinson | X
IMO with Michelle Obama and Craig Robinson
See omnystudio.com/listener for privacy information.
On Purpose with Jay Shetty 
