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Is Midlife a Crisis or a Chrysalis? What Chip Conley Discovered After Dying Nine Times | The Tamsen Show

August 13, 2025

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Is Midlife a Crisis or a Chrysalis? What Chip Conley Discovered After Dying Nine Times | The Tamsen Show

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What if your midlife crisis isn’t a breakdown, but a breakthrough?

That’s the question Chip Conley explored after a near-death experience left him literally seeing visions nine times over 90 minutes. What he saw, he said on  The Tamsen Show were flying birds whispering the words: “Slow down. Beauty and awe can only be seen when you slow down.”

This moment changed everything. Conley left his identity as a luxury hotel founder and began to explore what it meant to be in “the in-between.” He calls it middle-essence, a term to mirror adolescence, a time of transition, uncertainty, and opportunity.

He isn’t alone. Research shows that life satisfaction tends to dip in our late 40s but climbs again into our 50s and beyond, a pattern known as the “U-curve of happiness.” Social scientist Brené Brown describes this midlife shift as an “unraveling,” where we release the scripts and expectations of our youth to author something new.

For Conley, it meant creating the Modern Elder Academy, a “midlife wisdom school” helping others navigate transition. “Anticipated regret,” he says, “is a form of wisdom.”

Want to rethink what midlife can look like and learn how a brush with death became a guide to living fully? Tune in to the full conversation on The Tamsen Show.

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