Michelle Obama served as the First Lady of the United States, entering the White House alongside Barack Obama. In this candid conversation, she joins Steven with her brother Craig Robinson, a former college basketball coach turned executive, to open up about everything from Trump’s inauguration to marriage challenges, grief, and rediscovering her purpose.

Widely regarded as one of today’s most influential voices on leadership, identity, and social progress, Michelle offers a rare, intimate look at her personal journey.

Together, they discuss:
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How their parents instilled empathy, discipline, and resilience growing up amid racial tension.
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Michelle’s journey through elite schools and corporate law, driven by a need to tick society’s boxes.
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The evolution of Michelle and Barack’s relationship, from colleagues to lifelong partners.
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Fertility struggles, parenting tips, and what it really takes to sustain a long-term marriage.
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Navigating life in the White House, grief, personal boundaries, and rediscovering her true calling.

00:00 Intro 
02:11 Michelle and Craig's Childhood 
04:48 Values Learned from Their Parents 
08:45 Michelle Skipping Second Grade 
12:16 The Role of Race in Their Childhood 
15:19 What "White Flight" Means 
17:01 Coping with Racism 
20:55 Overcoming Being Underestimated 
26:33 Michelle's Search for Identity 
30:20 Meeting Barack 
31:59 Introducing Barack to the Family 
33:48 Why Michelle Initially Rejected Barack 
37:28 Michelle's Career Change: Pursuing Joy 
40:52 Relationship with Barack 
44:56 Going to Counseling with Barack 
49:34 Pregnancy Struggles 
56:27 Hardest Moments in Their Marriage 
57:31 Barack Obama Runs for Public Office 
01:03:28 What I Should Have Said to Barack 
01:07:11 Being the First Black First Lady and Facing Scrutiny 
01:14:09 Reflections on a Sad Time 
01:15:17 Remembering Your Mother 
01:16:53 The Death of Your Mother 
01:18:36 Processing the Grief 
01:20:41 Not Attending Trump’s Inauguration 

Listen to Michelle & Craig's new podcast IMO:
⁠https://bit.ly/3YnxIUg⁠ 

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Follow Michelle:
Instagram - <a href="https://bit.ly/3Ymxs7W">https://bit.ly/3Ymxs7W</a> 
Twitter - <a href="https://bit.ly/4cYXiVC">https://bit.ly/4cYXiVC</a> 

Follow Craig:
Instagram - <a href="https://bit.ly/4lThkVB">https://bit.ly/4lThkVB</a> 
Twitter - <a href="https://bit.ly/4lTGJ1f">https://bit.ly/4lTGJ1f</a> 

You can purchase Michelle’s book, ‘Overcoming: A Workbook', here: <a href="https://amzn.to/4jTqcsi">https://amzn.to/4jTqcsi</a> (UK) / <a href="https://amzn.to/3SbbelM">https://amzn.to/3SbbelM</a> (US) 

100 CEOs: Ready to think like a CEO? Gain access to the 100 CEOs newsletter here: <a href="https://bit.ly/100-ceos-megaphone">⁠⁠https://bit.ly/100-ceos-megaphone⁠</a>

The 1% Diary is back - limited time only:
<a href="https://bit.ly/1-Diary-Megaphone-ad-r%E2%80%A6">https://bit.ly/1-Diary-Megaphone-ad-r…</a> 

The Diary Of A CEO Conversation Cards (Second Edition):
<a href="https://g2ul0.app.link/f31dsUttKKb">https://g2ul0.app.link/f31dsUttKKb</a> 

Get email updates: <a href="https://bit.ly/diary-of-a-ceo-yt">⁠https://bit.ly/diary-of-a-ceo-yt⁠</a> 

Follow Steven: <a href="https://g2ul0.app.link/gnGqL4IsKKb">https://g2ul0.app.link/gnGqL4IsKKb</a> 

Sponsors:
Airalo -  <a href="https://try.airalo.com/TheDiaryOfACEO">https://try.airalo.com/TheDiaryOfACEO</a> with code DOAC3Vivobarefoot - <a href="https://vivobarefoot.com/DOAC">https://vivobarefoot.com/DOAC</a> with code DIARY20 for 20% off Learn more about your ad choices. Visit <a href="https://megaphone.fm/adchoices">megaphone.fm/adchoices</a>

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Former First Lady (Michelle Obama): This Is A Scam! People Were Running From Us Because We Were Black! I Was Bitter About The Racism I Received!

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