Podcast Summary

IMO with Michelle Obama and Craig Robinson

Episode: IMO Live: Choose Yourself with Natasha Rothwell
Date: September 10, 2025
Host: Higher Ground

Episode Overview

This special live episode of IMO is recorded from Martha’s Vineyard as Michelle Obama and Craig Robinson sit down with Emmy-nominated actress, writer, and producer Natasha Rothwell. The conversation is candid, deeply personal, and frequently hilarious, touching on Natasha’s creative journey, the meaning of self-love, neurodiversity, and the importance of community—especially for Black women and creatives. The episode is a celebration of embracing your authentic self and creating your own path, no matter how unconventional.

1. Setting the Scene: Martha’s Vineyard & Introductions

[00:00-07:50]

• Michelle and Craig share banter about vacationing in Martha’s Vineyard and the sense of safety and freedom the island has given their family over decades.
• Warm audience welcome and gratitude expressed for the local film festival team.
• The sartorial choices of the hosts and Natasha are discussed, with Michelle showing off her Ralph Lauren bustier and Craig quipping about his “Oak Bluffs Collection” fit.
• Michelle reflects on the unique Black leisure culture on the island:

  “We leisure, we travel, we leisure—and we leisure all up and down Martha’s Vineyard, don’t we?” (Michelle Obama, [11:39])

• Introduction of Natasha Rothwell, highlighting her career (How to Die Alone, Insecure, White Lotus) and production company Big Hattie Productions.

2. Natasha’s Creative and Personal Background

[08:05-17:02]

• Natasha describes her experiences as a military kid (“Air Force brat”), moving frequently and learning to make home wherever her family was.

  “It really hit home for me that it’s not a place that’s home. It’s the people. And that has always stayed with me.” (Natasha Rothwell, [12:50])

• The challenges and benefits of her neurodiversity:
  • Natasha reveals she was only recently diagnosed with ADHD and as being “neurospicy” (her term for having ADHD and being somewhere on the autism spectrum).

    “I didn’t get diagnosed until last year. My life up until that point has been understanding that I’ve been spicy but not knowing the exact flavor. And now that I do, it’s allowed me to tap into communities who are also ADHD…and advocate for my needs.” (Natasha Rothwell, [16:00])

3. Owning Neurodiversity and Ending Stigma

[17:30-24:02]

• Natasha and Michelle discuss the stigma around neurodiversity and mental health, especially in Black communities.
  • Michelle encourages openness for future generations:

    “Our kids do come in all shapes, sizes, and colors…and there’s no shame in being able to diagnose it, treat it, parent it properly.” (Michelle Obama, [22:04])

  • Natasha on destigmatizing:

    “One, name it to de-shame it, you know. And so for me, I have to be able to talk about my experience.” (Natasha Rothwell, [22:54])

4. Family, Self-Love, and Redefining Success

[24:02-30:00]

• Natasha talks about what her parents’ 47-year marriage taught her about love—both romantic and otherwise.
  • On being “happily single”:

    “I am childless by choice. I don’t want kids. I have two amazing dogs…and so much love in my life…I thought that romantic love was more important than any other kind of love. Platonic, fraternal, familial. As I’ve gotten older…my life is full.” (Natasha Rothwell, [25:45]; repeated throughout)

  • Michelle challenges societal expectations of women, especially Black women, to be “chosen”:

    “I am tired of so many amazing Black women waiting to feel worthy because somebody hasn’t chosen them or they haven’t chosen somebody…Marriage should be a choice.” (Michelle Obama, [28:39])

• Natasha shares her story of taking herself on a date across the Brooklyn Bridge to reclaim her own joy and agency.

  “By the time I left New York, I took my damn self across the bridge and had a great time.” (Natasha Rothwell, [29:27])

5. People-Pleasing, Boundaries, and Growth

[33:17-36:13]

• Natasha talks about her journey unlearning people-pleasing, rooted in her church upbringing and cultural norms.
  • Notable anecdote: Eating chicken enchiladas as a vegetarian rather than be an imposition.
  • Key lesson:

    “My needs are not an imposition. It was recognizing the importance of honoring my needs in the company of other people, not just when I’m by myself.” (Natasha Rothwell, [34:38])

  • Practical advice: Pause before saying yes—check in with your own authenticity.
  • On people-pleasing in Hollywood: “There’s no in the middle. It’s either a hell yes or a hell no.” ([35:08])

6. The Making of an Artist

[36:22-46:37]

• Natasha describes her original dream of Broadway, the unexpected move into TV and comedy, and the spiritual serendipity of her creative journey.
  • On production: “When I realized my career had given me a position of power and influence, that’s when I created my production company…to help others, artists who have stories to tell and give them that platform.” ([38:00])
• She recounts her time in Japan teaching and performing improv, learning about universal humor, and navigating Blackness abroad.
  • Natasha’s lived experience as a Black woman in Japan during Obama’s election was met with surprise and joy—a recurring “Obama!” greeting from locals. ([42:51])
  • Her parents’ unwavering support, even when she originally planned to major in journalism, provided the backbone for her creative risks.

7. Representation, Authenticity, and “Insecure”

[46:37-51:10]

• Natasha discusses the contrast between being the only Black writer at SNL and joining the open, validating “Insecure” writers’ room.
  • On being cast as “Kelly” in “Insecure”:

    “I went from some place where I was screaming to be seen to another place that saw all of me and acknowledged all those parts.” ([48:14])

  • Real-life bonds with fellow cast and showrunner Issa Rae strengthened her sense of belonging.
• On awards and validation:

  “I’ve already won…The nomination is just an acknowledgment from my peers that I’ve done good work. The moment the award becomes more important than the work, I’ve lost the plot.” (Natasha Rothwell, [51:00])

8. Advice for Creatives, Hollywood, and the Next Generation

[53:24-56:14]

• Reflections on collaboration, the joy of team creative work, and how military/large family background fostered this spirit.
• Encouragement for young, especially marginalized, creators:

  “Do not wait for someone else to give you permission to live your dream. Do it now…Be prolific, not perfect. Create work enough that your bad gets good, your good gets better, and your better is the best.” (Natasha Rothwell, [55:14])

9. Listener Question: Stability, ADHD, and Finding Your Path

[62:34-67:06]

• Listener Sophia (28, Los Angeles): Asks Natasha for advice on building career and personal stability with ADHD and uncertainty.
  • Natasha: Break big dreams into small steps, reach out to peers (not just “up”), and find your people.

    “All the people that are on the grind with you are the people that are going to be there later…Building that community is so important.” ([63:19])

  • On ADHD: Seek resources and medication if needed; it was life-changing for her.
  • Michelle: “Have grace with yourself. Be okay with not knowing anything at 28. Life is really a journey.”
  • Natasha adds: “Don’t be afraid to suck. Do it anyway.”

10. Lighthearted TV Talk & Closing Reflections

[69:04-72:30]

• Natasha, Michelle, and Craig share favorite TV shows (The Office, Severance) and the guilty pleasure of reality TV’s sociological insight (“Love Island”).
• Differences in childhood play for boys and girls discussed as a way to understand why women love reality TV’s psychological games.
• Michelle closes the live show with gratitude for Natasha’s honesty, humor, and talents:

  “You are smart, funny, honest, vulnerable. It shows up in the work that you’ve done. And I can’t wait to see everything that you will do. And please tell your parents that you made them proud.” (Michelle Obama, [71:50])

Notable Quotes & Moments

• Self-Validation & Agency:
  “Don’t wait for someone else to give you permission to live your dream. Do it now…Pull up a chair." (Natasha Rothwell, [55:14])
• Love & Singleness:
  “Romantic love…has to match this amazing life that I’ve worked so hard to build.” (Natasha Rothwell, [26:01] and recurring)
• Destigmatizing Neurodiversity:
  “Name it to de-shame it.” (Natasha Rothwell, [22:54])
• Process Over Perfection:
  “Be prolific, not perfect.” (Natasha Rothwell, [55:14])
• On Awards:
  “The moment the award becomes more important than the work, I’ve lost the plot.” (Natasha Rothwell, [51:18])
• Black Joy & Community:
  “We leisure, we travel, we leisure—and we leisure all up and down Martha’s Vineyard, don’t we?” (Michelle Obama, [11:39])
• People-Pleasing Recovery:
  “There’s no in the middle. It’s either a hell yes or a hell no.” (Natasha Rothwell, [35:08])

Key Timestamps

• [08:05] - Natasha welcomes, talks about her time on the Vineyard.
• [12:50] - Natasha on being an Air Force brat and how that shaped her.
• [16:00] - Natasha discusses late-in-life ADHD diagnosis and “being neurospicy.”
• [22:54] - Destigmatizing neurodiversity in Black communities.
• [25:45] - Insights from her parents’ 47-year marriage and being happily single.
• [29:27] - “Took my damn self across the bridge”—reclaiming self-love milestones.
• [34:38] - The internal battle and triumph over people pleasing.
• [48:14] - How Natasha became Kelly on “Insecure” and finally felt seen.
• [51:18] - On Emmy nominations, validation, and what truly matters.
• [55:14] - Advice to young creators: “Be prolific, not perfect.”
• [63:19] - Listener question about ADHD, stability, and Natasha’s guidance.

Tone & Takeaway

The episode is a mix of heart, vulnerability, belly laughs, and tough love. Natasha’s honesty about neurodiversity, people-pleasing recovery, and the value of all kinds of love is deeply empowering for listeners, especially Black women and underrepresented creatives. Michelle and Craig’s sibling banter and supportive energy set the tone for a conversation that is both intimate and universally resonant.

If you’re navigating uncertainty, craving creative affirmation, or just in need of a boost—this episode will lift you up, make you laugh, and remind you to choose yourself, unapologetically.