Episode 81

March 16, 2026

Bill Burnett, Dave Evans

Designing the Second Half of Life: Meaning, Curiosity, and Becoming | Bill Burnett & Dave Evans

Designing the Second Half of Life: Meaning, Curiosity, and Becoming | Bill Burnett & Dave Evans

Most of us try to solve midlife. What if that’s exactly the wrong approach?

In this episode, Chip Conley sits down with Bill Burnett and Dave Evans, the minds behind Designing Your Life, to rethink one of the most misunderstood seasons of adulthood. Drawing from design thinking, human curiosity, and decades of real-world experimentation, they offer a refreshing alternative to the pressure of “figuring it all out.”

Instead of chasing the right answer, Bill and Dave invite us to prototype our way forward gently, curiously, and without fear of getting it wrong.

Key insights from the conversation:

  • Midlife isn’t a crisis. It’s a chrysalis, a space for becoming
  • There is no single “right” life, only many good lives you can design
  • Stop solving your life and start prototyping small experiments
  • Curiosity matters more than certainty
  • Meaning isn’t found in big answers, but in everyday moments of flow

This is a hopeful, grounding conversation for anyone who feels stuck, restless, or quietly ready for what’s next.

👉 Click to watch and discover how to design the next chapter of your life without pressure, panic, or pretending.

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