IMO with Michelle Obama and Craig Robinson
IMO with Michelle Obama and Craig Robinson

IMO Live: Swerving Through Life with Michelle and Craig

July 22, 2026

AI Summary

5 min read

Michelle Obama and Craig Robinson sat down for a live IMO event in London to interview each other about the central idea that has shaped both of their lives: the power of swerving. The conversation is built around the argument that a successful life is rarely a straight line, and that the willingness to change direction—often at a financial or social cost—is a skill that can be learned, practiced, and passed down. The episode is less about career advice and more about a specific philosophy of living: staying flexible, trusting the process, and keeping yourself free enough to leap when the moment comes.

The First Leap Is the Hardest

Both Obama and Robinson describe their early careers as exercises in "checking the box." Obama went to Harvard Law because she was good at school and didn't know what else to do; Robinson went into investment banking because it paid the most money. Neither path brought satisfaction. Obama recalls sitting on the 47th floor of a corporate law firm, looking out at the South Side neighborhood she came from, and realizing she was disconnected from it. "Is this who I want to be? Have I even thought about it, or was I just checking boxes?" she asks.

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What you'll learn

  • 1 (00:34) **Episode Introduction & Format Switch** - Michelle and Craig open the live show at SXSW London, explain the IMO podcast format, and announce they will interview each other instead of a guest.
  • 2 (05:00) **Craig’s Career Trajectory: A Case Study in Swerving** - Craig outlines his professional journey from Princeton basketball to pro ball in Manchester, then finance, back to coaching, NBA front office, and finally podcast host.
  • 3 (09:04) **Michelle’s Transition: The Danger of “Checking Boxes”** - Michelle reflects on her own path: good student, Harvard Law, corporate law firm, then realizing she hated law.
  • 4 (12:08) **The Scary Leap: Craig’s Pro Basketball Decision** - Craig explains that his decision to play pro ball in England wasn’t scary for him, but it was for their mother.
  • 5 (15:40) **Overthinking Big Decisions in a World of Too Many Options** - Michelle and Craig discuss how modern life, with its endless information and FOMO, makes decision-making harder.
  • 6 (18:25) **Parenting for Bravery: Letting Kids Try Hard Things** - A tribute to their parents, who pushed them to do things they wouldn’t do themselves, unlike many parents who push for “safe” careers.
  • 7 (23:40) **How Parents Prepared Them to Be Brave** - Their parents taught them to think for themselves and own their lives from a very young age (kindergarten).

+ Full timestamped outline available in the app

Guests on this episode

Michelle Obama Craig Robinson

Show Notes

Live from South by Southwest in London, Michelle and Craig flip the script and interview each other! In a vulnerable and revealing conversation, they discuss their journeys through Chicago's South Side, law school, the Oval Office and share what they’ve learned about one another while working together. Plus, a lightning round of questions on beloved British traditions!

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IMO with Michelle Obama and Craig Robinson

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