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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