Jerry Colonna was a high-flying New York venture capitalist in the early 1990s, but his life wasn’t as glamorous as most made it out to be. He was anxious, overweight, unhealthy, and unfulfilled. After suffering a panic attack on the streets of Manhattan, he started coaching other executives, giving him a new lease on life and a career as one of the premier executive coaches in the United States. In this episode, Colonna calls on years of experience to discuss his thoughts on resilience, discernment, self-esteem, anxiety, motivation, and the rituals that keep him fulfilled. Colonna also gives Shane a public one-on-one coaching session.

Colonna is the Co-Founder of Reboot.io, an executive coaching and leadership development firm dedicated to the idea that better humans make better leaders. He is also the author of Reunion: Leadership and the Longing to Belong, now available for pre-order.

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00:00 - Intro
01:08 - Why did Colonna feel hollow during the peak of his success?
09:43 - Why do we let what we do define who we are?
17:30 - How are you complicit in creating the conditions you don’t want?
32:42 - How do you forgive yourself?
41:00 - How to get out of the negative self-talk loop
46:00 - How do we learn to come to grips with enough?
54:47 - On the “better angels of our nature”
01:01:47 - Colonna’s journaling routine
01:05:34 - What does it mean to “process your emotions”
01:08:31 - Colonna’s morning rituals
01:11:18 - How to build resilience in yourself
01:17:00 - How stubbornness and psychological safety impacts relationships
01:31:30 - Why we keep toxic relationships (and how to end them)
01:45:19 - What is O.F.N.R?
01:52:50 - What is success for Jerry Colonna?

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Like the mentor you’ve always dreamed of having, The Knowledge Project shares timely yet timeless lessons for work and life. Past guests include Naval Ravikant, Daniel Kahneman, Jim Collins, Angela Duckworth, Seth Godin, Melanie Mitchell, & Esther Perel.

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