
53 segments available
*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 *Transcript:* https://www.lennysnewsletter.com/p/jerry-colonna *Brought to you by:* • Eppo—Run reliable, impactful experiments: https://www.geteppo.com/ • Contentsquare—Create better digital experiences: https://contentsquare.com/lenny/ • OneSchema—Import CSV data 10x faster: https://oneschema.co/lenny *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 (01:04:56) 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 ...References continued at: https://www.lennysnewsletter.com/p/jerry-colonna _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.
Jerry Colonna discusses the societal pressure in the entrepreneurial community to present a facade of success, where every product is thriving and problems are nonexistent. He introduces a powerful self-reflective question: 'How have I been complicit in creating the conditions I say I don’t want?' This question aims to evoke personal agency and self-awareness, challenging listeners to confront their own complicity in their busy lives.
"We're socialized to Not only ourselves, but everybody else. Especially in the entrepreneurial community. All our companies are moving up and to the right. Every product is working. We don't really hav..."
In this segment, Jerry Colonna is introduced as a prominent executive coach and co-founder of Reboot. He emphasizes the importance of self-inquiry in leadership development, sharing his background in venture capital and his belief that better humans lead to better leaders. The conversation sets the stage for exploring deeper themes of leadership, self-awareness, and the challenges leaders face.
"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 hum..."
Jerry Colonna shares his foundational equation for effective leadership: practical skills + radical self-inquiry + shared experiences = enhanced leadership and resilience. He explains how this equation helps leaders navigate their internal struggles and fosters a supportive community, ultimately leading to greater effectiveness in their roles.
"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 fre..."
Colonna challenges the common belief that success equates to happiness, sharing personal anecdotes about his struggles with depression despite outward success. He highlights the societal conditioning that leads individuals to believe that achieving certain milestones will bring fulfillment, urging listeners to reconsider their definitions of success.
"With that, I bring you Jerry Colona. This episode is brought to you by EPO. EPO is a next generation AB testing and feature management platform built by alums of Airbnb and Snowflake for modern growth..."
In this segment, Jerry emphasizes the importance of radical self-inquiry as a tool for personal growth. He explains how asking difficult questions about one's motivations and beliefs can lead to greater self-awareness and agency, helping individuals break free from societal expectations and live more authentically.
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Colonna shares a poignant story from his childhood about the stability he found in his grandparents' home, symbolized by an endless supply of lemon drops. He reflects on how this childhood experience shaped his understanding of safety and self-worth, illustrating the deeper emotional connections that influence our adult lives and career choices.
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Jerry discusses the concept of consciousness as a 'hack' for effective leadership. He encourages listeners to ask radical questions about their ambitions and definitions of success, promoting a deeper understanding of their motivations and the societal pressures that shape their decisions.
"you so much for being here and welcome to the podcast. Well, thanks for having me, Lenny. It's it's really a delight to meet you and to be with you today. I want to start with a a very classic Jerry C..."
In this segment, Colonna warns about the potential pitfalls of a growth mindset, particularly when it leads to burnout and self-neglect. He emphasizes the need for balance and self-care in the pursuit of personal and professional growth, advocating for a more conscious approach to ambition.
"mean responsible. And that's a really important distinction. And as I often say to understand the word complicit think of the word accomplice. Right? As I I will share you are driving the getaway car...."
Colonna highlights the significance of shared experiences and community in developing effective leaders. He explains how connecting with others can provide support and insight, fostering resilience and enhancing leadership capabilities.
"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 you know disconcerted if my agenda isn't jam-packed. And the reason that this is all rea..."
Jerry discusses the necessity of understanding one's intentions in leadership. He encourages leaders to reflect on their motivations and the impact of their actions on their teams, promoting a more intentional and compassionate approach to leadership.
"busy to the point where I feel exhausted? it. And perhaps there's another more conscious way of getting that feeling than feeling like crap all the time. This is a a good segue to something that I hea..."
In this segment, Colonna explores the themes of legacy and purpose, urging leaders to consider the long-term impact of their actions. He emphasizes the importance of living a meaningful life and leaving a positive legacy for future generations.
"And as is often the case, I'm kind of winging it as I go and I'm walking around probably without shoes on because that's what I do. And there was a dry erase board behind me and I was trying to explai..."
Colonna discusses the therapeutic benefits of writing for self-discovery and reflection. He shares how writing can help individuals process their thoughts and emotions, leading to greater clarity and understanding in their personal and professional lives.
"inquiry. And I said in that moment I said people will come and ask me how and I will drive them crazy because I will say something like tell me about your father right or tell me why you chose to be i..."
Jerry reflects on the implications of artificial intelligence for leadership and humanity. He discusses how AI can be a tool for self-inquiry, helping individuals uncover blind spots and enhance their self-awareness in a rapidly changing world.
"leadership plus greater resiliency. And so the equation is practical skills plus radical self inquiry plus shared experiences. That is the process of actually talking about the craziness that goes on ..."
In this segment, Colonna warns about the risks of a growth mindset becoming a fixed mindset, particularly when it leads to self-judgment and pressure. He encourages leaders to maintain flexibility and openness in their growth journeys.
"really marked most of my life had gotten so bad that despite my outward success I was suicidal and lost. And I would I will turn to the audience and I say, "I get you want to be a great CEO. I get you..."
Colonna concludes with reflections on the role of radical self-inquiry in leadership. He emphasizes the importance of continuous self-examination and the courage to ask difficult questions, encouraging listeners to embrace this practice for personal and professional growth.
"there's this uh huge implication here that a lot of people think that when they reach a certain point, become successful, you know, make a certain amount of money, get a beautiful house they'll be hap..."
Jerry Colonna shares a personal story from his childhood about the stability he found in his grandparents and how it shaped his understanding of success. He reflects on the chaos of his upbringing and how his relationship with money influenced his career choices and sense of self-worth. This segment emphasizes the importance of understanding our past to navigate our present ambitions.
"certain kinds of questions. So for example, someone says I feel really it's really important for me to be to be ambitious and achieve a particular goal. What's radical a radical question to ask is and..."
In this segment, Jerry discusses the fear many people have about asking tough questions regarding their relationships and careers. He emphasizes that confronting these fears is essential for personal growth and self-awareness. Jerry encourages listeners to embrace the discomfort that comes with radical self-inquiry, highlighting the potential consequences of avoiding these critical reflections.
"So longw weeded response to your question. What I encourage people to do is to ask themselves these kinds of questions so that they can raise their level of consciousness. so that they can be in the d..."
Jerry Colonna references Bruce Springsteen's insights on the unsorted baggage from childhood and its impact on adulthood. He explains how unresolved issues can manifest in various ways, including depression and self-sabotage. This segment underscores the necessity of addressing our past to prevent future emotional turmoil and to lead authentically.
"If I pause and ask myself, is this relationship working out for me? I might end up leaving this relationship if I pause and ask myself if this career isn't working for me. I might leave my career. And..."
Colonna discusses the dangers of spiritual bypassing and the tendency to ignore emotional discomfort. He warns that neglecting to confront our issues can lead to greater pain later on. This segment serves as a reminder that facing our fears and sorting through our emotional baggage is crucial for long-term well-being.
"Now this is Bruce Springsteen talking about this, okay? This is not some airy fairy transpersonal jury colona coach, right? And the reason I I draw that out is we as children are socialized not to dev..."
Jerry introduces powerful questions for radical self-inquiry, encouraging listeners to explore their true feelings and motivations. He emphasizes the importance of journaling and self-reflection in understanding one's desires and fears. This segment provides actionable insights for those looking to deepen their self-awareness and confront uncomfortable truths.
"So, coming back to this equation, uh I think I want to give people some things to do now that they're maybe likely convinced, okay, I should really rethink what I'm doing. So, back to the equation, pr..."
In this segment, Jerry discusses the significance of shared experiences in personal growth. He highlights the value of authentic conversations and community support in fostering vulnerability and truthfulness. Colonna emphasizes that creating safe spaces for open dialogue can lead to deeper connections and understanding among individuals.
"we'll point people to the book for many more of these questions and in the worksheets for the third part of the equation, shared experiences. Can you explain what that is? You we were talking about so..."
In this segment, Lenny discusses the common tendency to equate busyness with productivity and self-worth. He shares his personal journey of managing a growing newsletter while grappling with feelings of impostor syndrome. Jerry responds by exploring the emotional implications of growth and the pressure it creates, encouraging a shift in perspective towards enjoying the creative process.
"Let's go back to the the busyiness point and I'll talk about myself a bit to kind of get it real again and because I think it's also something a lot of people struggle with that listen to this are jus..."
Jerry Colonna challenges the notion that self-esteem should be tied to external achievements. He discusses the importance of recognizing one's inherent value regardless of success or failure. This segment delves into the psychological impacts of attachment to outcomes and how it can lead to suffering, urging listeners to find joy in the creative process itself.
"feel about yourself? about myself. Uh like there's this sense that it's all over. Like, oh, maybe it's all going to fall apart and maybe I'm not as uh not as good at this as I thought. And maybe Okay,..."
In this heartfelt segment, Jerry reflects on the messages we send to our children about love and achievement. He emphasizes the need for parents to convey unconditional love, independent of their children's successes. This discussion highlights the importance of nurturing a sense of self-worth in children that is not contingent on external validation.
"much a part of what has driven me is I I was always a very shy kid early growing up. And I don't think people expected a lot of me except my mom and dad I guess. Uh, and so I always had the sense like..."
Jerry introduces Buddhist teachings on suffering and attachment, explaining how our desires can lead to increased suffering. He discusses the Four Noble Truths and how they relate to our attachment to material success and the fear of losing it. This segment encourages listeners to reflect on their motivations and the deeper implications of their pursuits.
"Right. I don't know how I feel about getting parenting advice from Tik Tok but okay. I'm excited to have Andrew Luo joining us today. Andrew is CEO of One Schkeema one of our longtime podcast sponsors..."
Colonna explores the relationship between attachment to material possessions and the suffering it can cause. He reflects on how our fears about losing what we have can lead to a tenuous sense of self-acceptance, urging listeners to consider the motivations behind their desires.
"focus on the the second noble truth because that's really what you're talking about. When we acquire that nice couch, when we buy that nice house that stretches our income to its maximum, if we're doi..."
In this segment, Jerry shares his personal journey of writing as a means of self-discovery. He emphasizes that the act of writing helps him crystallize his thoughts and find answers to his questions, regardless of external validation or commercial success.
"what we're doing. Now, to be clear, this is hard for me. I think it's hard for everybody. When when my first book came out, Dan Harris, who's a really good friend and client, I'm 10% Happier, said to ..."
Colonna discusses the importance of focusing on meaningful work rather than solely on financial gain. He encourages listeners to pursue interests that resonate with them personally, suggesting that this approach can lead to greater fulfillment and success.
"questions that I have. For example, Captain Chaos is running the country right now. What is it that the world is going to need two or three years from now? and what's my contribution to that world. No..."
Jerry reflects on the significance of legacy and the questions we should ask ourselves about the impact we want to leave behind. He emphasizes the importance of considering how we want to be remembered and the values we wish to instill in future generations.
"implicitly asked a how question a few minutes ago. How do I do this? How do I this radical self inquiry? And you know I asked I I responded by an by offering a few questions. Let's build upon that for..."
In this heartfelt segment, Colonna shares his desire to be remembered as someone who cared about the world and acted with kindness. He discusses the moral responsibility he feels to contribute positively to society and the importance of empathy in today's challenging world.
"and and you just paused. I can tell from the Adam's apple jumping up and down that that question landed for you. It's a question of legacy. It's a question of meaning and purpose. At the end of my day..."
Colonna addresses the current societal challenges and the moral implications of our actions. He reflects on the legacy he wishes to leave and the importance of striving for a world characterized by kindness and safety for all, regardless of identity.
"Tyson. I don't know what's behind his response, but I can tell you what's what's true for me. Okay. I made oblique reference to Captain Chaos in the world as it is right now. The world's a tough place..."
Jerry emphasizes the importance of using one's unique abilities to create a better world. He discusses his commitment to leveraging his skills in writing and communication to foster kindness and empathy, highlighting the moral imperative to act.
"oppose that feel immoral, if not directly immoral. Why does this come up for me? I can't shake the feeling that someone down the line in my lineage is going to ask of me, "And what did you do Grandpa?..."
Colonna shares a personal anecdote about grappling with self-doubt regarding his character and legacy. He reflects on the importance of striving to be a good person and the impact of our actions on those around us.
"see. A world of kindness and empathy. A world where um poverty is diminished. a world where people feel safe however the they identify. I don't give a damn. So, is that my legacy? Yeah. And maybe ther..."
In a poignant metaphor, Jerry likens himself to a toppled oak tree, reflecting on the complexities of life and the importance of living with purpose. He emphasizes the value of providing shelter and support to others throughout one's life.
"moment. And in this moment, I I'm I'm in Marin County. My wife Ally and and I are together and and I'm once again torturing myself with this question. Have I been a good man? I drive myself crazy with..."
Colonna discusses the ongoing process of contemplating one's legacy and the questions that arise as we age. He shares his thoughts on what he hopes to achieve in his later years and the importance of being a voice of comfort and sanity in a chaotic world.
"earth, having done the best job I could of being purposeful. I feel better. My suffering is eased when I can lean into that which then makes me able to be present for the other person. Whether it's a ..."
Jerry addresses the rising concerns surrounding AI and its implications for the future. He shares insights on how to navigate these uncertainties and the importance of open discussions about the role of technology in our lives.
"we've ended up here because I think that I'm still working through those questions. You know, as I said before as we both connected with, I use my writing to find my way to answers to questions. So, p..."
Colonna discusses the unsettling impact of AI on people's careers and skills. He shares insights on how to address these worries and emphasizes the importance of open conversations about the future of work in the context of AI.
"legacy will be. I'm not 100% sure. Is this uh maybe a hint at the new book you're working on? Is this the topic you're thinking about or is this not? Yeah. It and other things. That's right. That's ri..."
Reflecting on technological advancements, Jerry compares the current AI revolution to past transitions in technology. He emphasizes the need for humans to find their role amidst these changes and the potential for AI to enhance human connection.
"I had. You remember I'm old enough to remember when not everything had an IP address. Now our refrigerators have IP addresses, right? I mean it's freaking crazy. I'm old enough to remember when you ha..."
Colonna highlights the enduring value of human presence and connection in a technology-driven world. He expresses hope that AI will help eliminate distractions, allowing people to focus on what truly matters in their interactions.
"experience. You know, my signal is bouncing up into the sky onto a satellite. I won't name the company. It's coming back down. I don't know what your access is. We're using this platform, Riverside, t..."
Jerry discusses how AI tools like ChatGPT can serve as partners in self-inquiry. He shares examples of how these tools can help individuals uncover blind spots and improve their coaching practices.
"connection, humanto human contact strategic thinking, formulation you want to talk about in terms of engineering the the conceptualization that that gets elevated and our skills get better at doing th..."
Colonna emphasizes the significance of asking powerful questions for self-discovery. He encourages listeners to regularly reflect on their thoughts and actions, particularly regarding complicity in undesirable conditions.
"what are what are blind spots in the way I see the world that I'm not seeing. You could also upload all your chat transcripts from your meetings and ask it like what do you what do you what could you ..."
Jerry discusses the ongoing practice of self-inquiry in leadership, contrasting it with the misconception of a fixed growth mindset. He advocates for a flexible approach to personal and professional development.
"thinking partner in a way that I did not have before. And I'm still using my live real human writing buddies which are really important to me. Where does this all end up? I have no idea. You know, it ..."
Colonna critiques the concept of a growth mindset when it becomes rigid. He warns against the ego's tendency to create fixed beliefs that can hinder adaptability and growth in both personal and business contexts.
"question like what am I not saying that I need to say? That question, you can ask yourself that question every single day. The question of how have I been complicit in creating the conditions I say I ..."
Jerry explores the balance between ambition and non-attachment, drawing from Buddhist teachings. He encourages listeners to pursue goals without becoming overly attached to outcomes, fostering a healthier mindset.
"mindset. I know that you're not a big fan of this term that there's kind that it's used in a in a I don't know harmful way a lot of times. Can you just talk about that? why you find that growth mindse..."
Colonna addresses the fear of complacency and its roots in childhood experiences. He discusses how self-compassion can serve as a powerful motivator, allowing individuals to pursue their passions without fear.
"me is that everything's falling apart all the time. even our growth mindset. When we get too fixed on the proper way to do things, we're setting ourselves up for attachment and therefore suffering. So..."
Jerry identifies unresolved childhood issues as a primary cause of team dysfunction. He explains how group dynamics can mirror family patterns, leading to challenges in communication and collaboration.
"challenge the assumptions that made you rich in the first place. So think about it in our experience of starting a business. We have what the Zen Buddhists would say is beginner's mind. All things are..."
Colonna emphasizes the necessity of radical self-inquiry for effective teamwork. He shares a personal anecdote illustrating how awareness of group dynamics can lead to healthier interactions and improved team performance.
"and hold mindset a little loosely. I love that. There's a It reminds me of advice. I I did a meditation retreat once and there's always a sense with Buddhism and it's interesting how often Buddhism an..."
Jerry Colonna discusses how unresolved issues from childhood can impact team dynamics and performance. He emphasizes that the real problems in teams often stem from emotional baggage rather than lack of talent or strategy. By recognizing these patterns, teams can avoid repeating dysfunctional behaviors and create a healthier work environment.
"a hallmark of my adulthood. Right? It's um to get satisfaction out of hard work for me is a much greater motivator than fear of complacency. As I've sort of slips my way into that place, I have found ..."
Colonna highlights the importance of radical self-inquiry in leadership. He shares a story illustrating how unconscious patterns can disrupt team discussions, leading to avoidance of painful topics. By making these unconscious dynamics conscious, leaders can foster healthier team interactions and break free from repeating negative patterns.
"Teams are groups and there are group dynamics that always happen. There is the scapegoat. There is the truth teller who has to say, "Let me tell you what's really wrong with everything that's going on..."
In this segment, Jerry Colonna explains how leaders' unresolved issues can affect their teams. He stresses that leaders must engage in self-examination to avoid creating dysfunctional environments. The discussion emphasizes the moral responsibility of leaders to understand their impact on team dynamics and the importance of fostering a culture of accountability.
"Let's apply it here. Until you make conscious the unconscious patterns operating in the group, the group will continue to repeat those patterns and you will blame somebody in the group. romantic relat..."
Colonna poses a critical question for team members: 'How have I been complicit in creating the conditions I say I don’t want?' He encourages individuals to reflect on their roles in organizational dysfunction and to seek personal growth through understanding their contributions to team dynamics.
"this has comes up a number of times on this podcast just yeah the the the the impact the leaders issues have on the rest of the team and al also just this idea that the conditions they're trying to av..."
This segment focuses on the challenges leaders face in empowering their teams to make decisions. Colonna discusses the importance of allowing team members to make mistakes and learn from them, highlighting that leaders must tolerate decision-making that may not align with their preferences to foster growth and independence within their teams.
"power. You were using the word leader. I will talk about power. And you threw out well should they get a coach? Let's put it into larger context. Should you examine your life with radical self inquiry..."
Jerry Colonna concludes with reflections on the significance of radical self-inquiry for leaders. He emphasizes that true leadership success is rooted in self-awareness and understanding one's motivations. This segment encapsulates the essence of the conversation, encouraging leaders to embrace self-examination as a pathway to resilience and effective leadership.
"growth mindset. That's your growth edge. How can I be with the people in my life making boneheaded decisions about something that I care so much about and what is the best way for me to be in relation..."