101 Episodes

  1. How do you become a millionaire? [Sam Dogen]

    Published: 5/8/2025
  2. Should men fear mid-life? [Greg Scheinman]

    Published: 5/1/2025
  3. A parent’s worst nightmare: losing a child [Mary Anne Keegan]

    Published: 4/24/2025
  4. How do you get your parents to be vulnerable? [Dorothy Chow]

    Published: 4/17/2025
  5. Is it 2008 all over again? [Khe Hy]

    Published: 4/10/2025
  6. I was wrong about the FIRE movement [Khe Hy]

    Published: 4/3/2025
  7. Should you be weird and manipulative at work? [Jenny Wood]

    Published: 3/27/2025
  8. When should you quit? [Annie Duke]

    Published: 3/20/2025
  9. Is it time to sell? [Khe Hy]

    Published: 3/13/2025
  10. How do you navigate career uncertainty? [Anne-Laure Le Cunff]

    Published: 3/6/2025
  11. What’s next after a brain tumor? [Steven Mallouk]

    Published: 2/27/2025
  12. What if your job actually kills you? [Lou Marchetti]

    Published: 2/20/2025
  13. What the heck happened to the Internet? [Khe Hy]

    Published: 2/13/2025
  14. Is the 40 hour work week dead? [Elle Griffin]

    Published: 2/6/2025
  15. How do you create leverage as an entrepreneur? [Bart Egnal]

    Published: 1/30/2025
  16. Can Money Buy Happiness? [Khe Hy]

    Published: 1/23/2025
  17. What’s it like being married to an entrepreneur? [Anonymous]

    Published: 1/16/2025
  18. How do you prepare for retirement? [Christine Benz]

    Published: 1/9/2025
  19. 50 insights that will change your life [Khe Hy]

    Published: 1/2/2025
  20. How do you find purpose? [Jordan Grumet]

    Published: 12/26/2024

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Here’s a scary fact about adulthood. We stop asking questions. We lose the playful curiosity and creativity that we had as children. And it’s a shame. Questions are gateways to our deepest desires, insecurities and dreams. Reflecting on a deep question takes us one step closer to a life well-lived. Each week, we’ll ponder and debate one of life’s thorniest questions. We’ll explore ambition, careers, money, relationships, productivity and psychology — all in the pursuit of living an Examined Life.