On Purpose with Jay Shetty
Michelle Obama and Craig Robinson: Break the Generational Patterns Holding You Back (How to Build Confidence, Responsibility, and Emotional Resilience)
Mon, 28 Apr 2025
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 RobinsonSee omnystudio.com/listener for privacy information.
Chapter 1: What unique bond do siblings share?
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But then some of the biggest things were the biggest hits, like Vindication, remember? Listen to More Better with Stephanie and Melissa on the iHeartRadio app, Apple Podcasts, or wherever you get your podcasts.
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Chapter 2: How did childhood experiences shape their independence?
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To whom much is given, much is expected. The guilt comes from, am I doing enough? Me, Michelle Obama, to say that to a therapist. So let's unpack that.
Former First Lady Michelle Obama and someone who knows her best, her big brother, Craig, will be hosting a podcast called I Am Oak.
What have been your personal journeys with therapy?
We need to be coached throughout our lives. My mom wanted us to be independent children. And she would always tell me, stop worrying about your sister.
Having been the first lady of the entire country and representing the country in the world, I couldn't afford to have that kind of disdain.
What would you say has been the most hardest recent test of fear? I'm going to make him start so that I don't start crying.
The number one health and wellness podcast. Jay Shetty.
Jay Shetty. The one, the only Jay Shetty. Ha ha.
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Chapter 3: What lessons did they learn about family loyalty?
And I was holding on because I was worried.
I don't know what they're going to do to my sister. But that picture epitomizes our relationship. He has always been my quiet protector. And that sweet little face. He is the ultimate big brother. And he's been by my side holding my arm like that for my entire life.
Wow. I love that. And do you actually remember, do you remember the moment or it's the picture that you remember?
It's like yours. It's the picture. And I remember back to when I was three and four, some things, but that when I don't, but when I see the picture, it just warms my heart every time I see it.
Yeah, I love that. I mean, sibling relationships, as I said in mine as well, my sister and I are so close. And we haven't lived in the same country for nine years now. But we talk and stay in touch and we're constantly connected. And I wanted to start by asking you this question for both of you that I feel like the first time me and my sister got close is when I shared a secret with her.
And I was wondering what was the first secret that you ever told each other? As early as it was, as silly as it was, that you remember sharing something in confidence in the beginning, early days of your relationship.
Okay, now you did this to me when you came on our show. That is a question I've never been asked. I love it. I love it. You got me back. You got me back. Okay.
A secret.
A secret.
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Chapter 4: How can parents foster resilience in children?
Chapter 5: What fears must we unlearn as we grow?
Jay Shetty. The one, the only Jay Shetty. Ha ha.
hey everyone welcome back to on purpose the place you come to become happier healthier and more healed today's guests are two of my favorite people i'm so grateful and excited to welcome one of them back and one of them for the first time ever i'm speaking about none other than michelle obama and craig robinson welcome
The dynamic duo. The dynamic duo. I always say it's like my most favorite interview ever, period. Oh, my gosh. That's saying a lot.
Oh, my gosh. Wow, you're going to make me cry. I'm like, that's so sweet.
She's the one who turned me on to you. So this is like old home week. I know.
Thank you both. But honestly, I'm so grateful. I was just thinking when I was preparing for this, I was like, I wish my sister was in town because then we could have double interviewed.
All right. We're going to play it next time. We can do that.
She would have killed me if I did that to her because she's not on camera. She's an optometrist in London. The best. Yeah.
She could have checked your eyes for you happily.
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Chapter 6: What does therapy mean for personal growth?
Chapter 7: How do societal biases impact personal experiences?
Chapter 8: What strategies can help us overcome fear?
She would have killed me if I did that to her because she's not on camera. She's an optometrist in London. The best. Yeah.
She could have checked your eyes for you happily.
She's four and a half years younger than me. And I still remember the moment. Well, I don't remember the moment. It's interesting. I've seen a picture of me holding her when she was born and I was like four and a half, five years old. And so I have this memory that I held her when she was born. And we've been inseparable ever since.
Yeah.
and we can just ambush her. Oh, I love that.
Yeah, she will kill me.
But we have one of those pictures too, my favorite family picture. I was a newborn. I was maybe 10 months, but I was one of these big, fat, round, puffy babies and a bonnet and a white dress. And my dad was in a suit and a bow tie. And our mom had the most beautiful tunic dress on and Craig sat on her lap. I was on my dad's lap.
And I have this little fat arm, and he's in a little bow tie, and he's holding onto my arm and looking at the camera like, you better not. You know, he seemed so concerned. You know, he was about two years old.
Craig, can we get the look? I was worried. I had this...
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