The Importance of Setting Boundaries and Mentorship

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:

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Twitter - https://bit.ly/4cYXiVC 

Follow Craig:

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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) 

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