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

Join over 750,000 people to receive my most transformative wisdom directly in your inbox every single week with my free newsletter. Subscribe here.

Join Jay for his first ever, On Purpose Live Tour! Tickets are on sale now. Hope to see you there!

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.

‘The Kylee Cast’ With Kylee Griswold, Ep. 2: Autopen And Super Men