Mark: Most leadership books are lying to you. They sell you frameworks, 7-step plans, and productivity hacks. But what if the single most important leadership skill isn't a skill at all, but the courage to face your own childhood trauma? Michelle: Whoa, that's a heavy opening. So you're saying my obsession with color-coded spreadsheets is just a cry for help? Because I feel personally attacked. Mark: (Laughs) It might be! But that's the provocative heart of the book we're diving into today: Reboot: Leadership and the Art of Growing Up by Jerry Colonna. Michelle: I've heard of this guy. Isn't he some kind of legend in the startup world? Mark: He is. And Colonna isn't your typical business guru. He's a former venture capitalist turned executive coach, often called the “CEO Whisperer,” who blends Buddhism and Jungian therapy into his work with founders. Michelle: CEO Whisperer? That sounds intense. So this isn't about spreadsheets and quarterly reports. This is about the soul of a leader. Mark: Exactly. Colonna's whole argument starts with this idea that leadership isn't a performance. It's a crucible.

Michelle: A crucible. That sounds painful. Like something from a medieval blacksmith shop. What does he mean by that? Mark: It is painful. A crucible, in his view, is a severe test or trial that forces you to confront who you really are. It’s a moment of failure, loss, or intense self-doubt that strips away the mask you wear as a leader. And he argues these moments are where real leadership is forged. Michelle: Okay, but getting fired is just... getting fired. How is that a 'leadership lesson'? It sounds like a nice way to spin a painful failure. Mark: That’s the perfect question, because it gets to the core of it. The event itself isn't the lesson. The lesson is in your response to it. He tells this incredible story about Chad Dickerson, who was the CEO of Etsy. Michelle: Oh, I remember when that happened. It was a huge deal. He took the company public, and then suddenly he was out. Mark: Right. And Colonna was his coach through all of it. He describes this night after Chad was let go, sitting on a rooftop in Brooklyn, looking at the bridge. They're sharing beers and tears, and Chad is just broken. He feels like a complete failure. He’s asking, "What did I do wrong? Was I not good enough?" All the things you'd expect. Michelle: Of course. His identity was probably completely wrapped up in being CEO of Etsy. Mark: Completely. But here’s the crucible moment. Colonna says his job wasn't to give Chad a pep talk or a 5-point plan to get his next job. His job was to just sit there and listen. To bear witness to the pain. And in the days that followed, Chad had to announce his departure to the team he'd built over six years. Michelle: That must have been brutal. Mark: It was. But instead of being bitter or defensive, Chad chose to act with what Colonna calls "dignity and grace." He worked late, ensuring a smooth transition, caring for his team even as he was being pushed out. He leaned into the heartbreak. Colonna describes him as a "gentle, brokenhearted warrior." Michelle: A brokenhearted warrior. I like that. It’s such a powerful image. It’s not about being invincible; it’s about being strong enough to be broken and still be kind. Mark: Precisely. That’s what Colonna calls leading with a "strong back and an open heart." The strong back is the discipline, the accountability. But the open heart is the compassion, the vulnerability, the willingness to feel the pain without letting it destroy you. Chad's failure became the source of his strength. He grew more as a leader in his exit than he might have in another five years of success. Michelle: That’s a complete reversal of the "never let them see you sweat" school of leadership. But it makes sense. The leaders I’ve most admired were the ones who were human, who admitted when things were tough. Mark: And that's the point. The book argues that we've been sold a myth of the infallible leader. Colonna says the real work of leadership is the work of becoming a better human. It’s about learning to handle your own suffering so you don't inflict it on everyone else. Michelle: Which I think we've all seen happen. The boss who is terrified of failure, so they micromanage everyone into misery. Mark: Exactly. And that response to failure, that terror, often comes from a place we don't even recognize. Colonna argues we're all haunted by these 'ghosts in the machine' from our past.

Michelle: Ghosts in the machine. I love that phrase. It sounds like we’re about to start a detective story. What are these ghosts? Mark: They’re the old, outdated patterns of belief and behavior that are deeply embedded in our minds, usually from childhood. They were survival strategies that helped us feel safe, loved, or seen when we were kids. But as adults, especially as leaders, they run in the background and cause all sorts of chaos. Michelle: Okay, give me an example. How does a childhood thing turn into a leadership problem? Mark: Colonna is incredibly vulnerable and uses his own life as the primary case study. He talks about growing up in a chaotic home in Brooklyn. Money was tight, his mother struggled with mental illness, and he felt unseen. So, he would play Monopoly with her for hours. Michelle: Monopoly? The game that destroys families? Mark: (Laughs) The very one. But for him, it was a way to feel safe and in control. He was smart, he was cunning, and he could win. He learned very early on that accumulating property, accumulating money, equaled safety. It was his way of building a fortress against the chaos of his family life. Michelle: I can see that. So that becomes his 'ghost'? The belief that money equals safety? Mark: Exactly. And it drove him his entire life. He became a successful venture capitalist, made a lot of money, achieved everything he thought he wanted. And then one day, standing near Ground Zero after 9/11, he was overwhelmed with a profound sense of hollowness and a desire to die. All the money, all the success, hadn't filled that hole. It was a ghost from a childhood that no longer existed, running a program that was now obsolete and destructive. Michelle: Wow. That's heavy. And it makes you wonder how many of our own career motivations are just... ghosts. The need to be the smartest person in the room, the fear of asking for help, the obsession with a promotion. Mark: He argues that almost all of our professional dysfunctions are. And he has this incredible story from one of his leadership bootcamps that illustrates it perfectly. There was a CEO who was incredibly frustrated with his head of sales. He said the guy was "greedy," "disruptive," and just rubbing everyone the wrong way. Michelle: Okay, a classic difficult employee situation. Mark: That's what it looked like on the surface. But Colonna, in his 'CEO Whisperer' way, doesn't give him advice on performance management. Instead, he asks the CEO a question: "How are you complicit in creating the conditions you say you don't want?" Michelle: Oof. That is a tough question. No one wants to hear that. Mark: No, they don't. The CEO got defensive at first. But Colonna kept probing gently, asking about the CEO's own feelings around money and security. And the story that came out was staggering. As a teenager, the CEO had run away from home and lived under an overpass for a while. He was cold, hungry, and alone. And he made a vow to himself that he would never be in that position again. Michelle: Whoa. So what does that have to do with his head of sales? Mark: He realized, in that moment, that he had unconsciously hired someone to be the embodiment of his own deep, terrified need for security. He was ashamed of that desperate, hungry part of himself, so he "outsourced" it to his head of sales. He hired a shark to make sure the company, and by extension himself, would never be hungry again. The sales guy wasn't being greedy; he was just doing the job he was unconsciously hired to do. Michelle: My mind is blown. So he hired a guy to be the part of himself he was ashamed of? That's wild. It's like your brain is running on old, buggy software from when you were ten. How many leaders are doing this without even knowing it? Mark: Colonna would say, "all of them." To some degree. We project our disowned parts—our fears, our needs, our anger—onto our teams and our companies. And until we do the work to see those ghosts, we're just stuck in a loop, wondering why the same problems keep happening over and over. Michelle: If we're all run by these ghosts, it sounds hopeless. How do you even begin to fix that? It feels like you need years of therapy before you can even think about leading a team meeting. Mark: That's the beautiful pivot in the book. He says the goal isn't "fixing." It's "integrating." It's about learning to see those parts of yourself with compassion and understanding. It's the art of finally, truly, growing up.

Michelle: Okay, 'integrating' not 'fixing.' That sounds less daunting. But what does it mean to 'grow up' in this context? Is it just about being more mature? Mark: It's deeper than that. For Colonna, growing up means moving beyond mere resilience to a state of equanimity. Resilience is about bouncing back from the roller coaster of life. Equanimity is about realizing you don't have to get on the ride in the first place. You can appreciate it from a distance, with a calm and balanced mind. Michelle: I love that. So it’s not about getting better at handling stress, it’s about creating a life where the stress has less power over you. Mark: Exactly. And that comes from integrating all the parts of your story, especially the painful ones. He tells this heartbreaking story from his own childhood about a giant horse chestnut tree near his home. It was his sanctuary, the one place he felt safe from the chaos inside his house. Michelle: I think we all had a place like that as a kid. A fort, a secret spot. Mark: We did. And one day, he came home and the city was cutting it down. The tree was just gone. He describes weeping into his mother's apron, just utterly devastated. The symbol of his safety was destroyed. Michelle: Oh, that's so sad. I can feel that little-kid heartbreak. Mark: But the insight he draws from it as an adult is profound. He says that heartbreak is inevitable. Life will always fell your chestnut trees. You'll lose the job, the relationship will end, the company will fail. You can't avoid the pain. Growing up is about learning how to hold that pain with an open heart, to find comfort not in an external tree, but within yourself. Michelle: So 'growing up' isn't about getting tougher, it's about getting softer? About accepting the broken parts and realizing they're actually your strength? That's a complete reversal of how we think about leadership. Mark: A total reversal. And it can be a superpower. He tells another story about a CEO he coached named Julie. She was building a company to deliver high-quality food to economically disadvantaged people. Her mission was deeply personal. Michelle: Why was that? Mark: Because she grew up poor. She remembered the shame of being mocked for her unfashionable clothes, of her parents struggling to pay bills. For years, she tried to hide that part of her story, to project an image of a tough, polished CEO. Her pitches to investors were perfect, but they often fell flat. They felt…impersonal. Michelle: She was hiding the 'why.' Mark: She was hiding her heart. So, before one huge pitch meeting, instead of psyching herself up with power anthems, she meditated. She let herself feel the fear and shame of that seven-year-old girl. And then she walked into the boardroom filled with powerful, wealthy men. Michelle: What did she do? Mark: She threw out her script. She started not with market projections, but with a simple declaration: "I grew up poor, and I don’t think poverty should stop anyone from receiving nutritious food. That’s why I launched my company, and that’s why we should partner." Michelle: Wow. I have goosebumps. Mark: The investors were captivated. They didn't just find a company to back; they found a leader to believe in. She didn't hide her 'broken' part; she led with it. She integrated her ghost. That, for Colonna, is the art of growing up. It's loving all the parts of yourself, even the ones you're ashamed of, and realizing they are the source of your greatest power.

Mark: It all comes back to that core idea we started with: better humans make better leaders. The book is really a roadmap for that journey, from facing the crucible of failure, to exorcising the ghosts of your past, to finally finding peace not by winning, but by accepting who you are. Michelle: It really reframes the whole idea of a career. It's not a ladder to climb, but a journey inward. The work you do in the world is just a reflection of the work you're doing on yourself. And it’s a bit terrifying, because it means there are no excuses. You can't blame your boss or the market if the real problem is a ghost from your third-grade classroom. Mark: It's terrifying, but it's also incredibly empowering. It means you have the agency to change your life by changing yourself. You stop being a victim of your circumstances and start becoming the author of your story. Michelle: The book has some critics, though. Some readers find it a bit too "woowoo" or poetic, and that it lacks concrete, actionable steps. They want the 7-point plan, and Colonna gives them a Zen koan. Mark: And that's a fair critique if you're looking for a traditional business manual. But that's not what this book is. Colonna's point is that the "how" is easy once you understand the "why." The real work is the deep, messy, internal work of self-inquiry. The answers aren't in a book; they're inside you. Michelle: It's a challenging read, but it feels like an important one. It makes you ask yourself: what old story am I still telling myself, and what would happen if I finally let it go? Mark: A question every leader—and every human—should probably ask. Michelle: A powerful place to end. Mark: This is Aibrary, signing off.