I’m speaking with co-founder of Reboot Jerry Colonna. Jerry is one of the most infamous executive coaches in the world — with a reputation for making CEOs cry and asking devastatingly poignant self-reflection questions.

In this conversation, we explore:

🕷️ Jerry's inner journey discovering his mythopoetic identity and how that has informed the coaching work he is so known for
🙇‍♂️ The idea that one measure of a leader is the numerous of people who feel safe enough to belong
🌍 The root causes of the global intimacy disorder that our culture is experiencing
❤️ The very human tension between longing and belonging that we all experience on some deep level.

I walked away from this conversation deeply moved by Jerry’s sincerity and hope that some of his wisdom is passed on through this audio artifact that we are miraculously able to partake in.

Official Links

📚 Jerry's latest book Reunion
🙋‍♂️ Executive Coaching Company Reboot

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🫁 Episode Sponsor — Nervous System Mastery

This is my flagship 5-week bootcamp designed to equip you with evidence-backed protocols to cultivate calm and emotional regulation. Our 8th cohort will run in Fall 2025 ~ and applications are currently open. My sense is that if this conversation resonates with you, then you'd likely be a great fit for our upcoming cohort. This curriculum represents my attempt to distill everything I've learned in recent years about creating the conditions for our nervous system's flourishing. It's run in an intensive cohort-based way since this is, in my experience, the most efficient way to embody and practice the protocols.

Previous students have shared how partaking improved their sleep and quality of relationships and tapped into deeper states of joy, clarity, and confidence in their lives. We've had over 1000 students have completed this training, and many have said that it has been the most impactful thing they've ever done for their personal growth — so if you're intrigued at all, you can find more details and apply to join this year's cohort over at nsmastery.com

Further Ways to Support the Podcast:

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Tearful Gifts And Concerts Not For Kids