What if the life you built is no longer the one that fulfills you? In this powerful episode, former venture capitalist turned CEO coach Jerry Colonna shares how his midlife crisis became a chrysalis—from collapsing under the weight of outward success to rebuilding a life rooted in meaning, connection, and emotional resilience.

He shares the moment he almost gave up, the books and mentors that helped him begin again, and why real leadership starts with healing yourself. If you're navigating uncertainty or chasing purpose after 40, this is your roadmap. Subscribe for more conversations that honour the complexity—and beauty—of becoming whole.

Timestamps:

00:00 Intro

00:51 Greeting and introduction

02:06 Jerry’s background & career journey

09:36 Fundamentally being broken

12:33 The crash of 2001 and Grand Canyon awakening

15:35 Post-9/11 breakdown and decision to change

18:41 The power of asking “How am I complicit?”

21:41 The pursuit of wealth and inner emptiness

25:57 Childhood trauma and the need to be seen

28:31 The transformation: from ego to true self

33:31 Becoming Buddhist business coach

37:57 Lessons from modern elders: Pema, Parker, Sharon

44:56 What gets better with age

47:10 Midlife wisdom and personal integration

51:34 The ability to enjoy bitter sweetness

52:50 Why do we need midlife wisdom schools

54:37 Collective healing and “you’re not alone”

56:10 Bumper sticker of wisdom

Learn more about MEA at https://www.meawisdom.com/

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From Wall Street to Inner Peace: The Emotional Journey of Jerry Colonna

The Midlife Chrysalis

From Wall Street to Inner Peace: The Emotional Journey of Jerry Colonna