EPISODE · Mar 16, 2026 · 57 MIN
Designing the Second Half of Life: Meaning, Curiosity, and Becoming | Bill Burnett & Dave Evans
from The Midlife Chrysalis · host Chip Conley
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 becomingThere is no single “right” life, only many good lives you can designStop solving your life and start prototyping small experimentsCuriosity matters more than certaintyMeaning isn’t found in big answers, but in everyday moments of flowThis 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 is06:55 What is design thinking09:22 Designing yourself as a wicked problem10:20 Gravity problems and anchor problems12:32 Opening the aperture of choice14:03 Applying design thinking to midlife16:49 Creativity and reinvention after success18:03 Are midlifers more stuck than younger people19:14 Permission to change in midlife21:50 Prototyping your next chapter24:08 Self-criticism fear and resistance25:00 Learning to be incompetent again27:49 Personal midlife transitions31:14 Dark night of the soul36:53 Introducing the meaning book38:11 Designing meaning in everyday life40:21 Redesigning midlife as a culture44:01 Rethinking work and education48:25 Reframing midlife identity52:07 Wisdom bumper stickersLearn more about MEA at https://www.meawisdom.com/#MidlifeChrysalis #DesignYourLife #MidlifeTransition #FindingPurpose #SecondHalfOfLife #LifeDesign #MidlifeMeaning #PersonalGrowth #MidlifeReinvention #DesignThinking #CareerTransition #CuriosityMindset #ModernElder #MidlifeWisdom #LifeAfter40
What this episode covers
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 becomingThere is no single “right” life, only many good lives you can designStop solving your life and start prototyping small experimentsCuriosity matters more than certaintyMeaning isn’t found in big answers, but in everyday moments of flowThis 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 is06:55 What is design thinking09:22 Designing yourself as a wicked problem10:20 Gravity problems and anchor problems12:32 Opening the aperture of choice14:03 Applying design thinking to midlife16:49 Creativity and reinvention after success18:03 Are midlifers more stuck than younger people19:14 Permission to change in midlife21:50 Prototyping your next chapter24:08 Self-criticism fear and resistance25:00 Learning to be incompetent again27:49 Personal midlife transitions31:14 Dark night of the soul36:53 Introducing the meaning book38:11 Designing meaning in everyday life40:21 Redesigning midlife as a culture44:01 Rethinking work and education48:25 Reframing midlife identity52:07 Wisdom bumper stickersLearn more about MEA at https://www.meawisdom.com/#MidlifeChrysalis #DesignYourLife #MidlifeTransition #FindingPurpose #SecondHalfOfLife #LifeDesign #MidlifeMeaning #PersonalGrowth #MidlifeReinvention #DesignThinking #CareerTransition #CuriosityMindset #ModernElder #MidlifeWisdom #LifeAfter40
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Designing the Second Half of Life: Meaning, Curiosity, and Becoming | Bill Burnett & Dave Evans
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