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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