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The Reboot Podcast

May 5, 2021

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.

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