How have I been complicit in creating the conditions I say I don’t want? | Jerry Colonna
Jerry Colonna (guest), Lenny Rachitsky (host), Guest (OneSchema sponsor segment) (guest), Narrator
In this episode of Lenny's Podcast, featuring Jerry Colonna and Lenny Rachitsky, How have I been complicit in creating the conditions I say I don’t want? | Jerry Colonna explores radical self-inquiry: how leaders stop creating their own misery Jerry Colonna, renowned executive coach and author, explains how radical self-inquiry helps leaders see how they’re complicit in creating the very conditions they say they don’t want. He introduces his leadership “equation”: practical skills + radical self-inquiry + shared experiences = enhanced leadership and resilience. Through personal stories, Buddhist ideas, and live coaching of host Lenny Rachitsky, Jerry shows how attachment to success, busyness, and identity fuels suffering and dysfunctional teams. The conversation ultimately centers on building consciousness, resilience, and kinder leadership so ambition doesn’t come at the cost of mental health or healthy relationships.
Radical self-inquiry: how leaders stop creating their own misery
Jerry Colonna, renowned executive coach and author, explains how radical self-inquiry helps leaders see how they’re complicit in creating the very conditions they say they don’t want. He introduces his leadership “equation”: practical skills + radical self-inquiry + shared experiences = enhanced leadership and resilience. Through personal stories, Buddhist ideas, and live coaching of host Lenny Rachitsky, Jerry shows how attachment to success, busyness, and identity fuels suffering and dysfunctional teams. The conversation ultimately centers on building consciousness, resilience, and kinder leadership so ambition doesn’t come at the cost of mental health or healthy relationships.
Key Takeaways
Use “complicit,” not “responsible,” to reclaim agency without self-blame.
Asking, “How have I been complicit in creating the conditions I say I don’t want? ...
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Leadership growth requires more than skills; it needs radical self-inquiry and shared experiences.
Jerry’s equation—practical skills + radical self-inquiry + shared experiences = enhanced leadership and resilience—highlights that tactics alone fail if leaders don’t examine their inner drivers and process them in honest community.
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Busyness and constant growth often mask deeper fears about worth and identity.
Feeling compelled to stay “crazy busy” or always growing can be a strategy to quiet an inner voice that says you’re not good enough; until that’s faced directly, no level of success will feel safe.
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Attachment to outcomes (money, status, success metrics) amplifies suffering.
Drawing on Buddhist teachings, Jerry explains that when our self-worth depends on maintaining income, status, or growth curves, we live in constant anxiety about losing them, instead of enjoying the work itself.
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Powerful questions are a practical entry point into radical self-inquiry.
Questions like “What am I not saying that I need to say? ...
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Unexamined childhood patterns quietly run teams and companies.
Groups often replay family dynamics—avoiding conflict with jokes, scapegoating, or control—so unless leaders examine their own history and triggers, those “unsorted bags” drive organizational behavior and sabotage performance.
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The more power you have, the greater your moral responsibility to do inner work.
Leaders shape conditions for many others; if they refuse self-examination, their anxieties, attachments, and blind spots scale across the entire team or company, whereas their growth unlocks healthier, more resilient organizations.
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Notable Quotes
“The question that I often ask is: How have I been complicit in creating the conditions I say I don’t want?”
— Jerry Colonna
“Complicit does not mean responsible. You’re driving the getaway car; you’re not sticking up the bank teller.”
— Jerry Colonna
“I get you want to be a great CEO. But what I really care about is you not killing yourself in the process.”
— Jerry Colonna
“Until you make the unconscious conscious, it will direct your life and you will call it fate.”
— Jerry Colonna (quoting Carl Jung)
“If you choose to live an unexamined life, please don’t take a job that involves other people.”
— Jerry Colonna (quoting Parker Palmer)
Questions Answered in This Episode
In what areas of my life do I say I want change, yet my actions suggest I’m complicit in maintaining the status quo?
Jerry Colonna, renowned executive coach and author, explains how radical self-inquiry helps leaders see how they’re complicit in creating the very conditions they say they don’t want. ...
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Which success metrics (money, growth, status, followers) am I secretly attaching my self-worth to, and what would it look like to loosen that attachment?
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What am I not saying in my key relationships or on my team that I most need to say—and what am I afraid will happen if I do?
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How might my family-of-origin dynamics be replaying themselves on my team or in my company culture?
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If I imagined my legacy or eulogy honestly, what would I want people to say—and what would I need to change now to make that true?
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Transcript Preview
... or socialize the bullshit, not only ourselves but everybody else, especially in the entrepreneurial community. All our companies are moving up into the right. Every product is working. We don't really have any problems 'cause we're crushing it. And that's just lie. The question that I often ask is how have I been complicit in creating the conditions I say I don't want? The purpose of this question is actually to evoke your own agency. A perfect example of that would be, I say I don't want to feel busy all the time, but the truth of the matter is, I feel really unnerved and disconcerted if my agenda isn't jam-packed. So if you want to create a high functioning team, do your work. And it starts with the person who has the most power.
(instrumental music) Today, my guest is Jerry Colonna. Jerry is one of the most well-known and respected executive coaches in the world. He's co-founder and CEO of Reboot, an executive and leadership development firm, grounded in the belief that better humans make better leaders. Prior to coaching, Jerry co-founded Flatiron Partners with Fred Wilson, which ended up being one of the most successful early stage investment funds in the world. He's also a partner at JPMorgan Chase and is the author of two books, Reboot and Reunion. As you might expect, this ended up being a very real and very open conversation about being busy and self-inquiry and the dangers of a growth mindset, and the reasons that leaders and teams most often fail, and it's not what you think. Also, we talk about a very simple equation that Jerry and his team use to cultivate great leaders. This is an episode that everybody should listen to and spend time with. It'll make you a better person, a better partner, and a better leader. If you enjoy this podcast, don't forget to subscribe and follow it in your favorite podcasting app or YouTube. Also, if you become an annual subscriber of my newsletter, you now get a year free of Linear, Superhuman, Notion, Perplexity, and Granola. Check it out at lennysnewsletter.com and click Bundle. With that, I bring you Jerry Colonna. This episode is brought to you by Eppo. Eppo is a next generation A/B testing and feature management platform built by alums of Airbnb and Snowflake for modern growth teams. Companies like Twitch, Miro, ClickUp, and DraftKings rely on Eppo to power their experiments. Experimentation is increasingly essential for driving growth and for understanding the performance of new features, and Eppo helps you increase experimentation velocity while unlocking rigorous deep analysis in a way that no other commercial tool does. When I was at Airbnb, one of the things that I loved most was our experimentation platform where I could set up experiments easily, troubleshoot issues, and analyze performance all on my own. Eppo does all that and more with advanced statistical methods that can help you shave weeks off experiment time, an accessible UI for diving deeper into performance, and out-of-the-box reporting that helps you avoid annoying prolonged analytic cycles. Eppo also makes it easy for you to share experiment insights with your team, sparking new ideas for the A/B testing flywheel. Eppo powers experimentation across every use case, including product, growth, machine learning, monetization, and email marketing. Check out Eppo at geteppo.com/lenny and 10X your experiment velocity. That's geteppo.com/lenny. This episode is brought to you by ContentSquare, the analytics platform that helps companies build better digital experiences. Ever wonder why customers drop off before converting or why some pages perform better than others? ContentSquare takes the guesswork out of digital experiences, giving you real-time insights into how users interact with your site or app. With AI-powered analytics, automatic frustration detection, and clear visualizations, you'll know exactly what's working and what's holding your customers back. Whether you're optimizing an e-commerce checkout, refining a B2B lead flow, or improving a mobile app experience, ContentSquare pinpoints exactly what needs fixing and why. ContentSquare powers better customer journeys across 1.3 million websites and apps. Discover the insights you've been missing at contentsquare.com/lenny. Jerry, thank you so much for being here and welcome to the podcast.
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