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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