How to Become the Leader Your Community Deserves: Jerry Colonna on Radical Belonging

Healing Our Politics

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Guest: Jerry Colonna, known as the "CEO Whisperer," is the founder of Reboot, an executive coaching and leadership development firm dedicated to the notion that better humans make better leaders. Jerry made a name for himself as one of the world’s top venture capitalists before transitioning into his role as a coach. His books, Reboot: Leadership and the Art of Growing Up and Reunion: Leadership and the Longing to Belong, have deeply influenced leaders around the globe. Jerry’s work focuses on radical self-inquiry, bringing one's whole self to leadership, and fostering a sense of belonging in the workplace and beyond.

About the Episode: In this episode, we challenge the misconception that vulnerability is a weakness in leadership. We explore Jerry Colonna’s practice of radical self-inquiry, how it works, and how you can apply it to enhance your leadership effectiveness in public service. We dive into the importance of understanding your personal triggers and how this awareness can transform your responses to public criticism and internal stress. We discuss actionable techniques for bringing your whole self to your leadership role, even in the face of potential backlash or misunderstanding. Jerry shares his experiences of growing up in challenging circumstances and how these shaped his journey towards becoming a more compassionate and effective leader. By embracing your full humanity, Jerry emphasizes, you can create more authentic connections, foster a sense of belonging, and lead with greater resilience and clarity—learn how to bring deeper purpose and well-being into your leadership in this powerful conversation.

Key Topics Discussed:

· [00:01:48] Guest into

· [00:06:34] Healthy masculine: “Adulthood”

· [00:10:00] Growing up fast (Jerry)

· [00:13:18] Don’t romanticize pain

· [00:15:41] The wounded leader

· [00:17:02] Humans are VERBS

· [00:21:09] Why we wear masks

· [00:22:23] Jerry as coach

· [00:23:00] A broken heart got me here

· [00:24:14] King of the fairies

· [00:26:15] First suicide attempt

· [00:27:25] Rockstar venture capitalist

· [00:32:28] Depression lies

· [00:33:05] The thought that changed everything

· [00:34:04] Your birthright

· [00:34:38] Experience your worth

· [00:38:49] ELC Foundation donors

· [00:39:32] HOP Sponsor - Elected Leaders Collective

· [00:41:38] Become a “better leader”

· [00:44:05] Fear of “doing the work”

· [00:45:31] The longing to belong

· [00:46:26] The inner work comes first

· [00:48:03] “The price of the ticket”

· [00:50:38] Love, safety, and belonging

· [00:51:21] EBITA alone is not leadership

· [00:51:35] Physical safety

· [00:53:48] Summit at Sea

· [00:55:47] Who are you not to speak?

· [00:56:53] Democracy requires belonging

· [00:58:35] The better angels of our nature

· [00:59:33] The benefits of “doing the work”

· [01:01:08] Moral acts are the reward

· [01:02:39] The face of courage

· [01:04:11] The dissonance of belonging and courage

· [01:06:11] “Loving Kindness” meditation (meta)

· [01:07:05] The tradition of non-violence

· [01:09:12] How to de-escalate a public meeting

· [01:10:25] Harden, not your hear

· [01:11:51] Final takeaway: Gratitude

· [01:12:25] Rabbi Tarfun Quote https://www.sefaria.org/Pirkei_Avot.2.16?lang=bi

· [01:13:04] Where to find Jerry (below)

· [01:14:12] “The Leader’s Handbook” newsletter https://leadershandbook.substack.com/about

Key References and Resources Mentioned:

· [00:05:52] Reboot: Leadership and the Art of Growing Up by Jerry Colonna

· [00:05:52] Reunion: Leadership and the Longing to Belong by Jerry Colonna

· [00:05:52] Reboot Coaching and Leadership Development Firm

· [00:09:24] Cry, Baby: Why Our Tears Matter by Benjamine Perry https://www.amazon.com/Cry-Baby-Why-Tears-Matter-ebook/dp/B0B5M7KDHT

· [00:17:02] Naropa University

· [00:31:42] Parker J. Palmer’s Let Your Life Speak

· [00:51:21] What is EBITA?

· [00:53:48] Summit at Sea

· [01:02:59] The Soul of America by John Meacham

· [01:06:11] Lovingkindness: The Revolutionary Art of Happiness by Sharon Salzberg

· [01:07:58] Nonviolent Communication: A Language of Life by Marshall Rosenberg

· [01:07:58]