Podcast Summary: IMO with Michelle Obama and Craig Robinson

Episode: Tell Your Story with Jonathan Capehart
Guest: Jonathan Capehart
Original Release: January 7, 2026
Host: Higher Ground

Overview

This episode features a candid, warm, and insightful conversation with Pulitzer Prize-winning journalist and author Jonathan Capehart. Michelle Obama (Sa), her brother Craig Robinson, and producer Natalie sit down with Jonathan to discuss his bestselling memoir Yet Here I Am, his formative years in the segregated South, the influence of his mother, navigating identity as a Black gay man, and the meaning of chosen family. The episode also addresses a heartfelt listener question about familial acceptance and boundaries, with Jonathan offering practical wisdom rooted in his personal journey.

Key Discussion Points & Insights

1. Memories of the Segregated South and Family Heritage

[00:00–16:47]

• Summers in North Carolina:
  Jonathan recalls his childhood trips to Severn, NC, living with his devout Jehovah’s Witness grandmother, Sister Isla Mae. These summers were crucial in shaping his view of race, heritage, and self.
  • “Going witnessing with my grandmother was this woman ... such a devout Jehovah's Witness ... we'd go witnessing on these country roads.” (Jonathan, 06:47)
  • Vivid descriptions of rural customs, witnessing, and the fashion sense passed down from his grandmother and Aunt Annie.
• Racial Segregation and Small Acts of Protest:
  Jonathan’s mother, Margaret, always drove down “White Street” in their Mercedes—described as “a slow motion protest at 15 miles an hour.”
  • “The black daughter of Severn is back in town. ... I'm home. I'm here with my northern address and my education, and I'm bringing my kid.” (Jonathan, 14:31)
• Miss Betsy Story:
  A touching account of his grandmother’s friendship with Miss Betsy, a white woman secretly practicing as a Jehovah’s Witness due to her racist husband.
  • “Miss Betsy would dive into the backseat and get on the floor ... and then she would get up, and we'd be laughing ... it was so sweet.” (Jonathan, 12:08–12:36)

2. The Unbreakable Bond with His Mother

[19:25–30:14]

• Margaret’s Resilience:
  Jonathan’s father died when he was four months old. His mother worked double shifts, teaching him self-reliance and the importance of education.
  • “She taught me how to iron, how to do laundry ... you have to be able to depend on yourself. And there’s some upsides to that. There are also some downsides.” (Jonathan, 21:40)
• Navigating Race in Predominantly White Spaces:
  Margaret deliberately moved to safer neighborhoods and prioritized Jonathan’s academic readiness.
  • “She would say, ... 'if anyone calls you the N-word, you let me know right away,' and ... 'don’t let them put you in vocational education.'” (Jonathan, 23:54)
• Hard Conversations About Race:
  Margaret offered frank guidance about the inevitable inequalities Jonathan would face.
  • “You and Skip, right now, you’re equals... But as you get older ... Skip is going to climb higher. And he’s gonna climb higher because he’s white.” (Jonathan, 27:30)

3. Coming Out and Embracing Identity

[30:14–36:47]

• College as a Place of Liberation:
  Carleton College provided a nurturing environment where Jonathan could come out and accept his identity.
  • “Coming out at Carleton was easy. I mean, relatively easy.” (Jonathan, 31:16)
  • Matthew Brooks, a peer, moved the gay group from the basement to the student union, symbolically encouraging openness and pride.
• Coming Out to Family:
  Jonathan recounts his carefully orchestrated conversation with his mother after college—her surprise, concern for his career, but ultimately, ongoing love.
  • “Are you gay?”—“Yes.”
    “First she goes, 'Why?' and I said, 'I don’t know.' ... 'It’s not your fault. It’s just me.' ... Next thing she said was, 'Don’t tell anybody. You don’t wanna ruin your career.'” (Jonathan & Natalie, 35:42)

4. The Power of Chosen Family

[41:01–61:37]

• Stepparents and Uncles as Role Models:
  Jonathan’s stepfather was a negative influence, but his Uncle McKinley provided a loving, affirming example of manhood.
  • “From him I learned what it meant to be ... a good dad, a good person, a good man.” (Jonathan, 41:39)
• Navigating Familial Rejection:
  Describes being rejected by his grandmother for wanting to bring a partner home but later discovering it was due to external pressure and experiencing reconciliation thanks to loving relatives.
  • “You are always part of the family ... And Giuseppe.” (Jonathan, 43:19)
• “Shoulders Down” Spaces:
  Importance of finding community (“chosen family”)—from 1990s NYC Black professionals to Martha’s Vineyard—as sanctuaries of affirmation.
  • “When you realize ... you walk into this room and I’m surrounded by people ... and we all have this common cultural ancestry ... that’s why Martha’s Vineyard is such a special place. That is a place where shoulders come down.” (Jonathan, 61:00–61:37)

5. Listener Question: Family Acceptance and Boundaries

[46:47–54:41]

• Dominic’s Dilemma:
  A listener named Dominic, the only openly gay man in his family, struggles with his brothers avoiding gay spaces and feeling unseen.
• Jonathan’s Advice:
  • Assert boundaries within family just as you would with anyone.
  • Find and cherish your chosen family if your biological family cannot fully accept you.
  • “Sometimes I think family uses the family tie to keep you ... in place. ... At a certain point, you are going to have to stand up for yourself, family or no family.” (Jonathan, 49:05–49:22)
  • “When you know who you are, when you are just firm in your belief ... then everything else should flow from that.” (Jonathan, 51:41)
  • Recognize that setting boundaries may require sacrifice and can sometimes limit opportunities or relationships but will ultimately increase wellbeing.

Notable Quotes & Memorable Moments

• On showing up in the South:
  “It was a slow motion protest at 15 miles an hour. ... I don’t have to honk my horn, let the car do the talking. And I’m home.” (Jonathan, 14:31)
• On childhood resilience:
  “I was always going to college. It was just a matter of getting in and where would I go.” (Jonathan, 29:55)
• On coming out:
  “‘Are you gay?’ ... I said, ‘Yes.’ [My mother:] ‘Why?’ ... ‘I don’t know. ... It’s not your fault.’” (Jonathan, 35:15)
• On chosen family:
  “Shoulders come down ... that is my New York. This family was formed in the mid-90s ... and we have these common aspirations.” (Jonathan, 61:17)
• On boundaries and self-worth:
  “Just because they’re family, that does not give them a pass to not treat you with respect or the way you want to be treated.” (Jonathan, 52:41)

Important Timestamps

• Segregated South & Main/White Street:
  [00:00–15:37]
• Childhood, Family, and Educational Upbringing:
  [19:25–30:14]
• Coming out, Self-Acceptance, and Mother’s Reaction:
  [30:14–36:47]
• Listener Question and Guidance on Family Boundaries:
  [46:47–54:41]
• Chosen Family, Cultural Community, and Martha’s Vineyard:
  [59:09–61:37]

Tone & Atmosphere

The conversation is intimate, conversational, and full of laughter and shared reminiscences, grounded in warmth and respect. Jonathan’s openness sets the tone for heartfelt advice and camaraderie, making this episode both moving and practical for listeners navigating identity, family, and self-acceptance.

For More:
Jonathan Capehart’s memoir Yet Here I Am is available now wherever books are sold.