Reboot Podcast Episode #144 – The Stories We Tell Ourselves – with Ryan Caldbeck

The Reboot podcast showcases the heart and soul, the wins and losses, the ups and downs of startup leadership. On the show, Entrepreneurs, CEO’s, and Startup Leaders discuss with Jerry Colonna the emotional and psychological challenges they face daily as leaders.


Ryan Caldbeck

Ryan Caldbeck

Founder and Executive Chairman of CircleUp

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Episode Description

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 leaders, how do we manage the cacophony of emotions that we inevitably carry with us to the workplace? What holds us back from opening up, sharing, and being true with our colleagues, especially when we’re struggling? 

Ryan Caldbeck is the Founder and Executive Chairman of CircleUp. In this episode, Ryan opens up about the inherent loneliness that comes with being a CEO and reveals how a particularly challenging period in his life exacerbated those feelings of isolation. He describes how an interaction with his young daughter drove his decision to step back from his role as CEO, the relief that sharing his experience with his colleagues brought, and the grief that comes hand in hand with closing this chapter of his life. Jerry encourages Ryan to see that in his sadness lives an opportunity to turn towards curiosity and inquire deeply about what’s being born and who he wants to become in this next stage of life.

Ryan Caldbeck’s Blog | Writing Down the Bones | Men at Forty | Blessing For One Who Is Exhausted 

Show Highlights

Top Quotes: 

“I wish I had found a management coach earlier in the process because it was an absolute godsend to me.” – Ryan Caldbeck

“I can’t tell you how many CEOs tell me they’re crushing it, and the business closes down four months later.” – Ryan Caldbeck 

“I think I was very afraid of hurting the company by being open about my own struggles.” – Ryan Caldbeck 

“As part of our ability to be in the tribe, to be in a family, we’re socialized to try to anticipate and feel what other people might feel, and then respond to that in advance, but like any superpower, inappropriately applied, it can cause problems.” – Jerry Colonna

“One of the things that can enhance the sense of isolation, one of the things that can hold us back from opening up, and sharing, and being true with our colleagues is assumptions about other people’s internal landscape. Just because you’re CEO doesn’t mean you’re responsible for their internal landscape.” – Jerry Colonna

“If we want to create a world in which people are allowed to be true to one another, then those who have the most power have to go first.” – Jerry Colonna

“All beings own their own karma. Their happiness or unhappiness depend upon their actions, not my wishes. And so we can stay in empathetic connection without getting enmeshed in responsibility.” – Jerry Colonna

“Oftentimes when we open ourselves up and we put ourselves out there, we trigger fear.” – Jerry Colonna

“One of the things about mid-life is that sadness is an appropriate reaction because it’s a grief about the passing of time…and yet, within the sadness is an opportunity. And the opportunity is what am… what is being born with me right now? What am I becoming?” – Jerry Colonna


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