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Jerry Colonna is a world-renowned executive coach, a former venture capitalist, and the co-founder and CEO of Reboot, an executive coaching firm that combines practical leadership development with deeper self-inquiry. With over 27 years of coaching experience, he has guided countless leaders through the challenges of scaling companies, building teams, and navigating the emotional complexities of leadership. Known for his radical-self-inquiry approach, Jerry helps leaders uncover the unconscious patterns that hold them back and empowers them to lead with authenticity, compassion, and clarity.

In our conversation, we cover:

1. A powerful question that unlocks self-awareness: “How have I been complicit in creating the conditions I say I don’t want?”

2. Jerry’s foundational equation for leadership success: practical skills + radical self-inquiry + shared experiences = enhanced leadership and resilience

3. Why teams most often fail (hint: it’s not lack of talent or strategy)

4. How busyness often masks deeper issues of self-worth

5. Why a “growth mindset” can be problematic

6. The importance of legacy and what it means to live a meaningful life

7. The role of AI in self-inquiry and how tools like ChatGPT can help uncover blind spots

8. Jerry’s advice for navigating the unsettling rise of AI and its implications for leadership and humanity

Some takeaways:

1. Ask yourself this question when you’re complaining about things not going the way you wanted: “How have I been complicit in creating the conditions I say I don’t want?”

2. Practical skills + radical self-inquiry + shared experiences = enhanced leadership + greater resiliency. The ultimate goal is resilience, not just leadership skill.

3. The path to success without misery is consciousness—understanding your true motivations, rather than following socialized patterns that lead to achievement without fulfillment.

4. Pay the price of personal growth early: “If you continue to bypass sorting out your baggage, there’s going to come a day where you’re gonna have to pay that price.”

5. Ask yourself these breakthrough questions: “What am I not saying that I need to say? What am I saying that’s not being heard? What’s being said that I’m not hearing?”

6. Create spaces for shared experiences where people can authentically “tell the truth” without fixing or judging each other—this transforms teams and reduces isolation.

7. Constant busyness often masks deeper questions about self-worth—understanding what drives your need to be constantly productive can lead to more meaningful work.

8. “When we become attached to the outcome, we inadvertently fuel our own suffering”—learning to enjoy the process rather than fixating on results leads to greater happiness.

9. Use legacy as a personal compass by asking, “What would I like those who follow after me to believe to be true about me?” to clarify your values and guide decisions.

10. Team dysfunction often stems from unresolved personal issues: “Teams are groups where we unconsciously find the perfect foils to work out our own issues.”

Where to find Jerry Colonna:

• X: https://x.com/jerrycolonna

• LinkedIn: https://www.linkedin.com/in/jerry-colonna-reboot/

• Website: https://reunion.reboot.io/

In this episode, we cover:

(00:00) Introduction to Jerry Colonna

(04:12) Jerry’s key question

(06:55) The equation for great leadership

(09:37) The big lie of success and happiness

(12:12) The consciousness hack

(15:56) Getting over the fear of consequences

(20:23) The problem with bypassing our childhood baggage

(23:22) Radical self-inquiry: asking the tough questions

(27:05) Shared experiences: the power of community

(30:25) The trap of busyness and attachment

(40:45) Understanding our own intentions

(46:58) Legacy and purpose

(55:43) Writing for self-discovery

(57:12) The impact of AI on humanity

(01:04:56) Turning a growth mindset into a fixed mindset

(01:11:28) The role of radical self-inquiry in leadership

(01:19:24) Final thoughts and reflections

Referenced:

• Naropa University: https://www.naropa.edu/

• Fitler Club: https://fitlerclub.com

• Chris Fralic on LinkedIn: https://www.linkedin.com/in/chrisfralic/

• Will Smith on the price of fame: ‘I have been deeply humbled and deeply inspired’: https://www.today.com/popculture/news/will-smith-fame-rcna127830

• Seth Godin’s best tactics for building remarkable products, strategies, brands, and more: https://www.lennysnewsletter.com/p/seth-godins-tactics-for-building-remarkable-products

• The life of Buddha: https://www.britannica.com/summary/Buddha-founder-of-Buddhism

• 10% Happier with Dan Harris podcast: https://podcasts.apple.com/us/podcast/10-happier-with-dan-harris/id1087147821

• Simon Sinek’s website: https://simonsinek.com/

• Mike Tyson Gives Morbid Response to Young Interviewer’s Question About His “Legacy”: https://www.vibe.com/news/entertainment/mike-tyson-morbid-response-young-interviewer-legacy-1234944054/

• Dan Shipper’s post on X about asking ChatGPT for blind spots: https://x.com/danshipper/status/1910387987487318318

• Evernote: https://evernote.com/

• Claude: https://claude.ai

• Peter Senge on X: https://x.com/petersenge

• Carl Jung’s quote: https://www.goodreads.com/quotes/44379-until-you-make-the-unconscious-conscious-it-will-direct-your

• Parker Palmer on LinkedIn: https://www.linkedin.com/in/parker-j-palmer-5a92b110/

• The unexamined life is not worth living: https://en.wikipedia.org/wiki/The_unexamined_life_is_not_worth_living

Recommended books:

• Reboot: Leadership and the Art of Growing Up: https://www.amazon.com/Reboot-Leadership-Art-Growing-Up/dp/0062749536

• Reunion: Leadership and the Longing to Belong: https://www.amazon.com/Reunion-Leadership-Longing-Jerry-Colonna/dp/0063142139

• Born to Run: https://www.amazon.com/Born-Run-Bruce-Springsteen/dp/1501141511

• 10% Happier: How I Tamed the Voice in My Head, Reduced Stress Without Losing My Edge, and Found Self-Help That Actually Works—A True Story: https://www.amazon.com/10-Happier-Self-Help-Actually-Works/dp/0062265431

• Soldiers and Kings: Survival and Hope in the World of Human Smuggling: https://www.amazon.com/Soldiers-Kings-Survival-World-Smuggling/dp/0593298586

• The Giving Tree: https://www.amazon.com/Giving-Tree-Shel-Silverstein/dp/0060256656/

Production and marketing by https://penname.co/. For inquiries about sponsoring the podcast, email podcast@lennyrachitsky.com.

Lenny may be an investor in the companies discussed.