How have I been complicit in creating the conditions I say I don’t want? | Jerry Colonna (CEO of Reboot, executive coach, former VC)

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 — Brought to you by: Eppo —Run reliable, impactful experiments Contentsquare —Create better digital experiences OneSchema —Import CSV data 10x faster — Where to find Jerry Colonna: • X: https://x.com/jerrycolonna • LinkedIn: https://www.linkedin.com/in/jerry-colonna-reboot/ • Website: https://reunion.reboot.io/ — Where to find Lenny: • Newsletter: https://www.lennysnewsletter.com • X: https://twitter.com/lennysan • LinkedIn: https://www.linkedin.com/in/lennyrachitsky/ — 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 (01:05:00) Turning a growth mindset into a fixed mindset (01:11:30) 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 [email protected] . — Lenny may be an investor in the companies discussed. This is a public episode. If you'd like to discuss this with other subscribers or get access to bonus episodes, visit www.lennysnewsletter.com/subscribe