Radical Self-Inquiry: Jerry Colonna on Growing Up Without Feeling Like Crap

Colonna's signature question is "How have I been complicit in creating the conditions I say I don't want?" He chose the word complicit deliberately because it does not mean responsible. Think of the word accomplice: you are driving the getaway car, not sticking up the bank teller. The phrase "I say I don't want" matters too, because it points at the gap between what we claim and what we do.

He insists that the question is not meant to blame people for the bad things in their lives. Its purpose is to evoke agency by looking at the ways we may be deluding ourselves. His example is saying you don't want to feel busy all the time while actually feeling unnerved when your agenda is not jam-packed. Asking how that serves you opens up the chance of getting the same feeling in a more conscious way.

This is the heart of what Colonna calls radical self-inquiry, a way to cut through our own delusions. It is a core part of how he coaches and of how he thinks about the process of growing up.

Colonna tells how the equation was born at a talk at Naropa University, where he grabbed a whiteboard and wrote "practical skills." That, he explains, is what people typically come to a coach for: how to do the job and how to live. He then added radical self-inquiry, the questions about your father, your relationship to money, or your self-worth that tend to drive clients crazy, and a third term, shared experiences.

The equation reads practical skills plus radical self-inquiry plus shared experiences, meaning the practice of talking honestly about the craziness in your head, equals enhanced leadership and greater resilience. He circles resilience as the real purpose. In his late 30s, he says, his lifelong depression had become so bad that despite outward success he was suicidal, and what he cares about is that people do not kill themselves on the way to being great executives.

Lenny notes that many people expect success, money and a beautiful house to make them happy. Colonna calls that the big lie we are socialized with from childhood. He recalls a 19-year-old at a book event summarizing his message as "you don't have to be an asshole to be successful," and adds the corollary that you don't have to feel miserable just because you are building a career.

For people who keep climbing the ladder, Colonna says the pivot is consciousness. Radical questions are the ones we are socialized not to ask: if you say ambition matters, what do you believe success will do for you, how do you define it, and where does that come from? He tells the story from his first book, Reboot, of his "pursuit of lemon drops": his grandfather always had an endless supply, which in his chaotic childhood meant stability and wealth. As a successful venture capitalist he had the lemon drops but still did not feel safe.

Lenny voices the common fear that opening this up means quitting your job and moving to the woods. Colonna points out that this empathy is really Lenny's own question, then agrees the fear is real: if you ask whether a relationship or career is working, you might end up leaving it. But he argues we mistakenly believe that paying no attention to discomfort makes it disappear.

Instead we paste on band-aids, some healthy such as obsessive working out, some unhealthy such as work or substance abuse, and some what he calls spiritual bypassing, such as weekends of ayahuasca or mushrooms. He quotes Bruce Springsteen's autobiography, in which the singer describes 25 years of psychoanalysis and the unsorted baggage of childhood that eventually exacts a price, often in tears. Colonna has seen entrepreneurs sabotage successful businesses because a childhood belief says they do not deserve success. Lenny sums it up as better some tears now than ten times more later, and Colonna agrees.

On how to practice self-inquiry, Colonna notes that journaling has grown popular in his 27 years of coaching, but people often don't know what to write. He offers four questions: how have I been complicit in creating the conditions I say I don't want, what am I not saying that I need to say, what am I saying that's not being heard, and what's being said that I'm not hearing. The middle two also work well for anyone responsible for leading people.

He says you know you are in the right zone when the questions take your breath away, and that the most important person to share the answers with is yourself. Drawing on Buddhism, he names self-delusion and attachment as the biggest contributors to suffering. His summary is that questions that startle us or make us a little afraid of the answer are where the gold is.

The third term, shared experiences, grew out of the early Reboot boot camps for first-time CEOs, where he and co-founder Ali Schultz would pretend to sell practical skills and then ask questions like "who would you be without the story of who you are?" Imagine sitting in a circle of people who care about you and hold space without trying to fix you. In the entrepreneurial world, he says, we are socialized to say everything is moving up and to the right when it isn't, and shared experience is the chance to tell the truth.

Lenny admits he is perpetually busy and keeps taking on more because watching the newsletter grow is fun, quoting Will Smith's line about fame feeling great on the way up and awful when it fades. Colonna asks how he feels about himself when growing and when not growing. Lenny says great when growing, and when stalled, a sense that it might all fall apart and that he may not be as good as he thought.

Colonna suggests that being busy on a growth trajectory may make a persistent imposter voice a little quieter, and offers another possibility: enjoy the puzzle of making something out of nothing without your self-esteem depending on whether it succeeds. He cites his friend Seth Godin's idea of art projects. Lenny says that is how he began, but then it worked, income arrived, and the stakes went up.

Colonna calls this attachment: the real hook is not the money alone but the feeling of "see, I'm not nothing, I'm a somebody." He points out that his wife would love him if the podcast failed, and that as a parent you should convey unconditional love rather than love tied to the A on the spelling test. Your value as a human being, he says, is unshakable, and you can still pursue goals because puzzles and hard work are rewarding.

Lenny asks how people let go of the comfort that income brings. Colonna retells the Buddha story and the four noble truths, focusing on the second: that which we do to push away suffering increases suffering. If we buy a nice house or couch to enjoy it, that is fine, but if we do it to push away the fear of not being good enough, loved or safe, we create new fears of losing it.

He says it comes down to why we do what we do, and that it is hard for him too. After his first book came out, Dan Harris advised him not to read Amazon reviews, and he has read only two. He now focuses on the experience of writing, where he tries to answer his own questions; whether a book sells is secondary, and he has to do the work regardless.

Lenny says that is how he started too, writing to crystallize his own thinking, and that focusing on what is interesting and useful tends to work better than chasing money. Colonna builds on this, saying that asking the questions takes you back to your why, your core principle.

Colonna says what animates him now, with his children grown, is what kind of ancestor he wants to be. What he'd like descendants to believe is that he gave a damn about the world, cared, tried and was kind. When Lenny cites Mike Tyson saying legacy is made up, Colonna respectfully disagrees: he feels a moral responsibility to use his ability to help create a world of kindness and empathy, where someone down his lineage might ask what he did.

He recounts a passage at the end of Reboot in which he torments himself over whether he has been a good man, and his wife Allie tells him to stop. On a walk he finds a toppled oak with torn roots, and thinks "Here lies a good man." The tree lived 75 or 80 years with gnarled limbs from good and bad choices but mostly provided shelter and shade. Thinking this way eases his suffering and helps him be present for others.

Asked how to work out your legacy, Colonna says he is still working through those questions. He turns 62 this year and is thinking about what he wants his elderhood to be, and enjoys being a voice of comfort and even sanity in a difficult time.

Asked about AI anxiety, Colonna says it is unsettling. A year ago he compared it to the move from modems to the web, but now thinks this is different. In the coaching world people fear ChatGPT will replace them; he finds it is like putting on a sharp, helpful pair of glasses, which is both disturbing and a challenge to the question of our role as human beings.

What he comes back to is that he and Lenny are talking through a mediated connection and are still present with each other heart to heart. His hope is that what does not matter in the human experience gets burned away by AI, while presence, connection, human contact and strategic thinking get elevated. He admits he could be wrong and we could all be oiling robots.

Lenny mentions people using ChatGPT's memory to ask about their blind spots. Colonna says a colleague uploaded ten years of journal entries to Claude and asked it what he is not saying that he needs to say, and it has made him a better coach. Colonna uses ChatGPT as a writing and thinking partner while still relying on human writing buddies, and says it may supply more questions to ask yourself. Growing up, he adds, is a practice of continuous inquiry.

Colonna says a growth mindset is very helpful, but the ego can turn it into a fixed mindset by sorting everything into growth and not growth, good and bad. Buddhism has taught him that everything is falling apart all the time, even our growth mindset. If you can hold a mindset loosely, have fun, but once you nail it to the floor as how things ought to be, you have become fixed.

In a business context he quotes Peter Senge that it is nearly impossible to challenge the assumptions that made you rich in the first place. Founders start with beginner's mind, get a little success, and the ego decides this is the way to do it. His summary is to stay attached to the growth and hold the mindset a little loosely.

Lenny raises the fear that detachment makes you less ambitious, and recalls a retreat teaching to point your cart in a direction without attaching. Colonna calls that the fear of complacency, which we are socialized to ward off with anxiety, perhaps because we believe achievement earns love. Self-compassion, he says, can be a powerful motivator, and getting satisfaction from hard work is a much greater motivator than fearing complacency; he works seven days a week because he enjoys it.

When teams fail, Colonna says it is rarely lack of talent, strategy or execution but the unresolved demons from childhood. Groups have dynamics such as the scapegoat and the truth-teller, and without individuals' self-inquiry they repeat patterns from their families of origin. He tells of an executive team he coached where every time they approached something painful someone made a joke and the energy vanished. The CEO responded that it was just like his family.

He quotes Carl Jung: until you make the unconscious conscious, it will direct your life and you will call it fate. In teams as in romantic relationships, we unconsciously find foils for our own unresolved issues. To build a high-functioning team, he says, do your work, starting with the person who has the most power; if that person refuses, the group becomes a manifestation of early dysfunction. He cites Parker Palmer: if you choose an unexamined life, please don't take a job that involves other people.

For those with less power, he suggests asking what drew you to this position and how you have benefited from the dysfunction, which may simply mean it feels familiar. For those with more power, he says there is a greater moral responsibility to examine your life. He recalls a 15-person-company CEO asking why nobody could make a decision without her, and his reply that to build a scaled leadership team you have to tolerate boneheaded decisions, which is her growth edge.

Lenny concludes that if you're struggling as a leader, the answer is usually not more skills like public speaking or email, but self-awareness and understanding what drives you. Colonna says that is the wisdom of his 40 years as an adult, after about 15 to 17 years as a venture capitalist and a couple of decades coaching. He says radical self-inquiry leads to a little less suffering and a lot more resilience.

Asked for a last piece of wisdom, Colonna says his hope for intimate conversations is that people walk away thinking they are not alone. It is always a hard time, he says, and what makes it hardest is feeling that you are the only one going through it. Lenny adds that he thinks of these as Trojan Horse episodes, where people come for tactical advice and get something they really need to hear.