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: How their parents instilled empathy, discipline, and resilience growing up amid racial tension. Michelle’s journey through elite schools and corporate law, driven by a need to tick society’s boxes. The evolution of Michelle and Barack’s relationship, from colleagues to lifelong partners. Fertility struggles, parenting tips, and what it really takes to sustain a long-term marriage. 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 Follow Michelle: Instagram - https://bit.ly/3Ymxs7W  Twitter - https://bit.ly/4cYXiVC  Follow Craig: Instagram - https://bit.ly/4lThkVB  Twitter - https://bit.ly/4lTGJ1f  You can purchase Michelle’s book, ‘Overcoming: A Workbook', here: https://amzn.to/4jTqcsi (UK) / https://amzn.to/3SbbelM (US)  100 CEOs: Ready to think like a CEO? Gain access to the 100 CEOs newsletter here: ⁠⁠https://bit.ly/100-ceos-megaphone⁠ The 1% Diary is back - limited time only: https://bit.ly/1-Diary-Megaphone-ad-r…  The Diary Of A CEO Conversation Cards (Second Edition): https://g2ul0.app.link/f31dsUttKKb  Get email updates: ⁠https://bit.ly/diary-of-a-ceo-yt⁠  Follow Steven: https://g2ul0.app.link/gnGqL4IsKKb  Sponsors: Airalo -  https://try.airalo.com/TheDiaryOfACEO with code DOAC3Vivobarefoot - https://vivobarefoot.com/DOAC with code DIARY20 for 20% off Learn more about your ad choices. Visit megaphone.fm/adchoices