105 Episodes

  1. What’s it like being married to an entrepreneur? [Anonymous]

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

    Published: 1/9/2025
  3. 50 insights that will change your life [Khe Hy]

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

    Published: 12/26/2024
  5. Should you move out of the US? [Tiago and Lauren]

    Published: 12/19/2024
  6. How do you conduct an annual review? [Khe Hy]

    Published: 12/12/2024
  7. Why are teens so stressed? [Jennifer Wallace]

    Published: 12/5/2024
  8. What is your love language? [Sunil Arora]

    Published: 11/28/2024
  9. My recent psychedelic journey [Khe Hy]

    Published: 11/21/2024
  10. Does the dream job exist? [Jack Purdy]

    Published: 11/14/2024
  11. How do you survive working at a hedge fund? [Carrie Sun]

    Published: 11/7/2024
  12. Is Khe a dilettante? [Khe Hy]

    Published: 10/31/2024
  13. Does work have to suck? [Paul Millerd]

    Published: 10/24/2024
  14. How do you navigate mid-life? [Erin Cochran]

    Published: 10/17/2024
  15. The truth about online businesses [Khe Hy]

    Published: 10/10/2024
  16. How do you retire early? [Diania Merriam]

    Published: 10/3/2024
  17. How do you find meaning after an IPO? [Rick Foerster]

    Published: 9/26/2024
  18. Should you buy or rent your house? [Khe Hy]

    Published: 9/19/2024
  19. Should you read more fiction? [Anna Gat]

    Published: 9/12/2024
  20. How do you become great at networking? [Mo Bunnell]

    Published: 9/5/2024

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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.