The Reboot Podcast

The Reboot Podcast showcases the heart and soul, the wins and losses, and the ups and downs of leadership. Join Jerry Colonna and Reboot Coaches as they go deep with entrepreneurs, CEOs, and leaders like you, to explore the emotional journeys we all face.

The Reboot Podcast

Podcast Topic: Major Transitions

#177 – What Does It Mean To End Well? – with Randy Goodman

#177 // May 22, 2025

#177 – What Does It Mean To End Well? – with Randy Goodman

How do we navigate seismic shifts in our industries and our lives while striving to remain true to ourselves and those we care about? In this episode, Jerry sits down…

#171 – The Great Midlife Edit – with Chip Conley

#171 // April 30, 2024

#171 – The Great Midlife Edit – with Chip Conley

In this episode of The Reboot Podcast, Jerry Colonna sits down with the insightful Chip Conley, author of Learning to Love Midlife: 12 Reasons Why Life Gets Better with Age.…

Wisdom for Work #16 – The Brightest Bulb Challenge – with Ray Foote & Andy Crissinger

Wisdom for Work #16 // August 1, 2023

Wisdom for Work #16 – The Brightest Bulb Challenge – with Ray Foote & Andy Crissinger

For individuals stepping more fully into leadership roles, the transition from individual contributor to team leader can bring about a myriad of feelings. What happens when you go from making…

Extras #17 – Prep for Career Shifts and Job Changes – with Keith McAllister

Extra 17 // November 23, 2022

Extras #17 – Prep for Career Shifts and Job Changes – with Keith McAllister

Whether we decide to leave our job, make a career move, or unexpectedly find ourselves without a job, the space between secure positions elicits a lot of things–unprocessed fresh feelings,…

Wisdom for Work #11 – Career Transitions at Midlife – with Jim Marsden, Ray Foote, Marty Janowitz & Jerry Colonna

Wisdom for Work 11 // June 22, 2022

Wisdom for Work #11 – Career Transitions at Midlife – with Jim Marsden, Ray Foote, Marty Janowitz & Jerry Colonna

In this conversation, Coaches Jim Marsden, Marty Janowitz, Ray Foote, and Jerry Colonna sit down to explore career transitions at midlife. Together, they describe their unique midlife experiences and share…

#158 – Show Up for Your Life – with Laurie Segall

Episode 158 // June 7, 2022

#158 – Show Up for Your Life – with Laurie Segall

Laurie Segall is an award-winning journalist, author, and the founder of Dot Dot Dot and D3 Network. In this episode, Laurie sits down with Jerry to chat about her tenure…

#144 – The Stories We Tell Ourselves – with Ryan Caldbeck

Episode 144 // May 5, 2021

#144 – The Stories We Tell Ourselves – with Ryan Caldbeck

This being human is a profoundly awesome adventure; our lives are peppered with moments of happiness, joy, and wonder, but our experiences can be messy, exhausting, and heavy too. As…

#140 – From Heartbreak, Through Resilience, To Equanimity – with Chad Dickerson

Episode 140 // January 22, 2020

#140 – From Heartbreak, Through Resilience, To Equanimity – with Chad Dickerson

In this fresh release, Jerry sits down with past client, former CEO of Etsy, and fellow executive coach, Chad Dickerson. In this episode, Chad describes the shift from CTO to…

#136 – Adversity As Opportunity – with Marcus Aurelius Anderson

Episode 136 // November 12, 2020

#136 – Adversity As Opportunity – with Marcus Aurelius Anderson

Joining Jerry on this episode of the Reboot Podcast is Marcus Aurelius Anderson, author of The Gift of Adversity: Overcoming Paralysis and Pain to Find Purpose. While preparing to deploy…

Podcast Topic: Major Transitions