The drive that made you successful may not be meant to lead you forever.
In this Wisdom Wednesday episode of The Midlife Chrysalis, Chip Conley and Derek Gehl explore the shift from ego to soul, the defining transition of the second half of life. Drawing from his personal journey, his role as a “modern elder” at Airbnb, and insights from Richard Rohr and Connie Zweig, Chip reflects on what happens when achievement stops being enough.
In this conversation, you’ll learn:
- Why ego builds the first half of life but can limit the second
- How to move from performer to elder
- What generativity really means
- Why awe and space are essential for soul growth
If you’ve felt a quiet nudge that there’s something deeper beyond success, this episode will resonate.
Tune in and consider who’s driving your life now.
Timestamps:
01:13 Gehl’s Proud Dad Moment
04:17 Enneagram and Early Identity
06:20 Coming Out and Authenticity
09:40 The Ballroom Dance Metaphor
11:47 Richard Rohr and Falling Upward
14:14 Living Stuck in Ego
15:24 Ego, Generativity, and Aging
18:22 From Frontman to Guide
19:30 Reincarnation & Evolving Conciousness
21:32 Where People Get Stuck
25:07 Spirituality & Seeking Awe
26:06 Practices to Soften the Ego
27:26 Richard Rohr Workshop in Santa Fe
Learn more about MEA at https://www.meawisdom.com/
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