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

EPISODE · Jun 2, 2025 · 56 MIN

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

from The Midlife Chrysalis · host Chip Conley

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 Intro00:51 Greeting and introduction02:06 Jerry’s background & career journey09:36 Fundamentally being broken12:33 The crash of 2001 and Grand Canyon awakening15:35 Post-9/11 breakdown and decision to change18:41 The power of asking “How am I complicit?”21:41 The pursuit of wealth and inner emptiness25:57 Childhood trauma and the need to be seen28:31 The transformation: from ego to true self33:31 Becoming Buddhist business coach37:57 Lessons from modern elders: Pema, Parker, Sharon44:56 What gets better with age47:10 Midlife wisdom and personal integration51:34 The ability to enjoy bitter sweetness52:50 Why do we need midlife wisdom schools54:37 Collective healing and “you’re not alone”56:10 Bumper sticker of wisdomLearn more about MEA at https://www.meawisdom.com/#MidlifeTransformation #JerryColonna #CEOCoach #EmotionalResilience #MidlifeAwakening #MentalHealthMatters #LeadershipWisdom #SpiritualGrowth #BurnoutRecovery #Psychoanalysis #BusinessAndSpirituality #RebootYourLife #ModernElders #LifeAfterSuccess #YoureNotAlone

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 Intro00:51 Greeting and introduction02:06 Jerry’s background & career journey09:36 Fundamentally being broken12:33 The crash of 2001 and Grand Canyon awakening15:35 Post-9/11 breakdown and decision to change18:41 The power of asking “How am I complicit?”21:41 The pursuit of wealth and inner emptiness25:57 Childhood trauma and the need to be seen28:31 The transformation: from ego to true self33:31 Becoming Buddhist business coach37:57 Lessons from modern elders: Pema, Parker, Sharon44:56 What gets better with age47:10 Midlife wisdom and personal integration51:34 The ability to enjoy bitter sweetness52:50 Why do we need midlife wisdom schools54:37 Collective healing and “you’re not alone”56:10 Bumper sticker of wisdomLearn more about MEA at https://www.meawisdom.com/#MidlifeTransformation #JerryColonna #CEOCoach #EmotionalResilience #MidlifeAwakening #MentalHealthMatters #LeadershipWisdom #SpiritualGrowth #BurnoutRecovery #Psychoanalysis #BusinessAndSpirituality #RebootYourLife #ModernElders #LifeAfterSuccess #YoureNotAlone

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

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This episode was published on June 2, 2025.

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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...

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