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