Jerry Colonna - The Art of Growing Up
Jerry Colonna - The Art of Growing Up
Today, I’m realizing a dream I’ve had for fifteen years–the first episode of my podcast is out and ready for your listening pleasure!
Where the Road Bends episode one is my conversation with the legendary executive coach Jerry Colonna. He is a unique combination of wisdom, enlightenment, charm, and street smarts, reminiscent of Yoda, the Buddha, Ted Lasso, and a New York City taxi driver all in one person.
Before founding Reboot, Jerry was a Partner at J.P. Morgan Partners, the private-equity arm of J.P. Morgan Chase, and a Co-Founder of Flatiron Partners, one of the most successful venture capital firms in NYC during the dot com era. He’s the author of Reboot: The Art of Leadership and Growing Up and Reunion: Leadership and the Longing to Belong, which is due out later this year.
Jerry is a legend in the tech industry and works with some of the top leaders in the world. He’s also navigated multiple major life transitions himself. Jerry and I met a decade ago after I heard him on an episode of This Week In Startups, and emailed him on a whim. At the time I didn’t know anything about executive coaching, but I was immediately captivated and inspired by his message to founders. While we never formally worked together, Jerry has been an informal mentor and showed me that I could leave the world of venture capital and be ok. As you’ll hear, Jerry has so much wisdom and knowledge to share not just about leadership but about change, transition, and the art of growing up.
In the episode, we discuss why stories unite us, what we can learn from depression, and the 'second adulthood.' We also explored what it feels like when you’re working on something that’s not your calling, how to resist the quiet and discomfort of being alone with oneself, and how to pick up the trail of your life to find clues for what’s next.
I’d be lying if I said I wasn’t nervous to embark on this journey. Podcasting is a new medium for me, so I hope you’ll stick with me as I find my voice and hone the format. Like with any new adventure, there will be a number of stumbles and iterations, but I’m going to work hard to ensure that what I share with you is thought-provoking and impactful. Here’s my promise to you: I’m going to put a tremendous amount of love and attention into every conversation.
Without further ado, I hope you enjoy this conversation with Jerry.
💎 A Nugget of Wisdom
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Here's a quote I’ve been pondering this week about change and transition. If it resonates, feel free to share it with those in your life.
Real change makes way for higher dreams
“Any real change implies the break up of the world as one has always known it, the loss of all that gave one identity, the end of safety. And at such a moment, unable to see and not daring to imagine what the future will now bring forth, one clings to what one knew, or thought one knew; to what one possessed or dreamed that one possessed. Yet it is only when man is able, without bitterness or self pity, to surrender a dream he has long cherished, or a privilege he has long possessed, that he is set free–that he has set himself free–-for higher dreams, for greater privileges.”
—James Baldwin, Nobody Knows My Name
💌 Please Reach Out!
I started WTRB because I live for helping others discover and manifest their next big thing. I can't fulfill this mission alone nor do I want to. Please don't hesitate to email or send me a DM on Twitter if you’d like to provide feedback, suggest future guests, sponsor the show, connect about coaching, or just say hi. I view WTRB as a co-creation, so I’d love to hear from you.
Be well,
Steve