EP. 1767

05/05/25

Michelle Obama & Craig Robinson

“My motto was, your life is soon gonna be yours, so let’s start now.”

Michelle Obama Opens Up: Her Struggle To Feel Like She's "Enough," Mental Health in the White House & Lessons from Childhood w/ Craig Robinson

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Michelle Obama and her brother Craig Robinson reveal how growing up in a tiny Chicago apartment shaped their values and outlook on life. From Craig “vetting” Barack Obama during a pickup basketball game to Michelle navigating the pressures of the White House, their conversation uncovers how family bonds grounded them through extraordinary circumstances. What makes this sibling dynamic special isn’t just their impressive achievements but their authentic connection – Craig bringing lightness and joy while Michelle delivers wisdom and perspective. Their shared belief that “home is about who’s there, not where you are” resonates deeply as they explain how they raised confident children amid extreme privilege and spotlight by teaching them that success comes from character, not circumstance.

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Michelle’s book Becoming

Michelle’s book The Light We Carry: Overcoming in Uncertain Times

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"Home is about who's there, not where we are."
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And now let’s jump into episode 1767 of The School of Greatness! 

Some Questions I Ask:

  • “What is one lesson each one of you has taught each other as adults that you didn’t learn in school?”
  • “Did you ever lose that when you were in the White House, like being in awe of how far you had come and how far you and Barack had created your lives together?”
  • “Were you able to just be her big brother in the height of all this while she was in the White House or were you trying to coach her like you would your athletes?”
  • “How do you build belief in yourself that you were worthy of the success at such a high level?”
  • “How did you overcome that belief that you don’t belong or that other people are telling you you don’t belong?”
  • “How do you raise healthy conscious kids to be good, loving, generous when they are given more financially, success opportunities, networking?”
  • “Do you feel like you’re more confident now in the last 10 years, the eight years in office, or the kind of four to eight years before leading into the office?”

In this episode, you will learn:

  • Why basketball became the ultimate character test when Michelle asked Craig to play pickup with Barack Obama before their relationship got serious
  • How their parents “coached confidence” decades before it became popular, building them up rather than breaking them down
  • The surprising way Michelle and Barack maintained their mental health during White House stress by coaching their daughter’s basketball team
  • Why Michelle feels more confident at 61 than ever before despite asking herself “am I good enough?” throughout her career
  • The counterintuitive parenting approach that helped them raise grounded children despite White House privilege
  • Plus much more…

Show Notes:

The School of Greatness Podcast
The School of Greatness Podcast

The School of Greatness Show

The School of Greatness shares inspiring interviews from the most successful people on the planet—world-renowned leaders in business, entertainment, sports, science, health, and literature—to inspire YOU to unlock your inner greatness and live your best life.