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.

Timestamps:

03:48 What Designing Your Life is

06:55 What is design thinking

09:22 Designing yourself as a wicked problem

10:20 Gravity problems and anchor problems

12:32 Opening the aperture of choice

14:03 Applying design thinking to midlife

16:49 Creativity and reinvention after success

18:03 Are midlifers more stuck than younger people

19:14 Permission to change in midlife

21:50 Prototyping your next chapter

24:08 Self-criticism fear and resistance

25:00 Learning to be incompetent again

27:49 Personal midlife transitions

31:14 Dark night of the soul

36:53 Introducing the meaning book

38:11 Designing meaning in everyday life

40:21 Redesigning midlife as a culture

44:01 Rethinking work and education

48:25 Reframing midlife identity

52:07 Wisdom bumper stickers

Learn more about MEA at ⁠https://www.meawisdom.com/

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

The Midlife Chrysalis

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