Reboot: Leadership and the Art of Growing Up

Jerry Colonna has essentially written a manual for the soul that every entrepreneur needs to keep on their nightstand. Instead of the usual dry advice on how to scale a SaaS company or manage a board meeting, this book dives deep into the internal work required to actually survive the journey. The central thesis—that we cannot be great leaders until we become better, more self-aware humans—hit me like a ton of bricks. It is a vulnerable baring of the soul that asks you to engage in radical inquiry rather than just checking off a list of KPIs. While the prose is certainly more poetic than your average business book, I found the storytelling to be the perfect vehicle for such heavy emotional lessons. It isn’t an easy read, not because the language is difficult, but because it forces you to sit with your own insecurities. Truly transformative stuff for anyone willing to do the work.

Ever wonder why certain professional hurdles feel like massive personal failures? This book provides the answer through a lens of 'growing up' that most business authors are too afraid to touch. Jerry’s willingness to be open about his own depressions and failures makes the advice feel earned rather than preached. I particularly loved the focus on how our internal biases and doubts affect the people we lead every day. The truth is, our teams are reflections of our own psychological health. It’s a profound realization. The book doesn’t offer quick fixes or 'hacks,' but rather an exercise in humanity. It is beautiful, haunting, and necessary. I’ve read dozens of leadership books this year, but this is the only one that actually made me change how I talk to myself during a crisis.

This isn't just a book; it's an invitation to radically inquire into who you are when the title of 'CEO' is stripped away. Jerry Colonna has bared his soul here, and in doing so, he gives us permission to do the same. The chapters on facing our fears and the 'art of growing up' are some of the most profound things I’ve read in years. It’s rare to find a business book that focuses so heavily on the internal landscape of the leader. Most people focus on scaling their companies, but Jerry reminds us that we have to scale our own capacity for empathy and self-awareness first. The storytelling is rich and deeply moving. It’s a slow burn, but the payoff is a much clearer understanding of why we do what we do. An absolute masterpiece for the modern entrepreneur.

Look, if you are looking for a tactical guide on scaling or delegation, you are going to be disappointed. But if you want to understand why you are standing in your own way, buy this immediately. Jerry writes with a level of honesty that is rare in the startup world. He doesn't just talk about success; he talks about the scars and the brokenness that come with it. The 'Loyal Soldier' concept was a total epiphany for me. It helped me realize that the very traits that made me successful early on are the ones now causing friction with my leadership team. This book isn't a quick read—it's an exercise book for your character. It requires you to sit still, listen to the voices in your head, and finally grow up. It’s easily the most important leadership book I’ve encountered.

The concept of the 'Loyal Soldier' alone was worth the price of admission. This book helped me realize that my leadership style was being driven by fears I hadn't acknowledged since I was a teenager. Jerry doesn't just coach you; he walks through the fire with you. The writing is incredibly soulful and personal, which might turn off people who want a spreadsheet-style approach, but for me, it was exactly what I needed. It turns leadership from a set of tasks into a lesson in humanity. I’ve recommended this to every founder in my network because we all suffer from the same insecurities. We all need to 'reboot' our internal operating systems occasionally. It’s a profound, emotional journey that will undoubtedly make you a better person and, by extension, a more effective leader. Truly a must-read.

After listening to Jerry on the This Week in Startups podcast, I knew I had to grab this, though the experience was different than I anticipated. This isn't a tactical guide. Frankly, if you come looking for a play-by-play on delegation, you will be disappointed. However, the way Jerry turns his coaching experiences into narrative stories is genuinely moving. He explores how our childhood baggage follows us into the C-suite, often manifesting as self-sabotage. I gave it four stars because the pacing can feel a bit meandering at times, especially in the middle chapters where the metaphors get a little thick. Still, the self-inquiry questions at the end of the sections are gold. They forced me to stop and reflect on my own 'Loyal Soldier' and how that protective instinct is actually holding my team back. It’s a solid, heart-centered approach to professional growth.

Picked this up because I wanted to understand the psychological side of being a founder, and it delivered in spades. The way the author links our adult behavior to our 'Loyal Soldier'—the parts of us that developed to protect us as children but now limit us—is brilliant. It’s a very different kind of leadership book, one that values heart over hustle. My only gripe is that the tone can occasionally skew toward the depressing side, which makes it a heavy read to get through in one sitting. You have to take it in small doses. Despite that, the wisdom here is undeniable. It’s helped me recognize how my own insecurities were creating a glass ceiling for my company. Better leaders really are better humans. It’s a must-read, even if the poetic style isn't always my cup of tea.

To be fair, the core philosophy that better humans make better leaders is something I wholeheartedly support. However, the execution in this book was a mixed bag for me. The anecdotes are very personal, which is great if you already feel a connection to Jerry’s work, but they didn't always gel with the broader points he was trying to make. I found myself skimming the more flowery sections to get to the actual substance of the coaching inquiries. It’s a very Buddhist approach, which is fine, but it can feel a bit high-level and abstract when you’re looking for a path from A to Z. It’s more of a 'vibe' book than a 'method' book. If you enjoy a slow, reflective read that feels like a therapy session, you’ll love it. If you’re a busy executive looking for efficiency, this might irritate you.

Gotta say, I really struggled with the 'woowoo' vibe that permeates these pages from start to finish. I appreciate that Colonna is a legendary coach, but the writing style felt excessively poetic and, at times, incredibly frustrating to parse. One minute we are talking about business failure, and the next we are diving into metaphors about broken skis and the 'quickening thump-thump' of a heart. It felt like the actual leadership insights were being drowned out by a memoir that didn't quite know what it wanted to be. To be fair, there are some decent questions about self-reflection, but they are buried under layers of rambling anecdotes. If you aren't already a fan of his specific brand of Buddhist-influenced coaching, this might just feel like a lot of whining without enough practical application.

In my experience, a leadership book should provide actionable frameworks, but this felt like a collection of depressing stories with no clear direction. I found the audiobook particularly hard to stomach; the narrator’s voice sounded so victim-based and heavy that it was a struggle to stay engaged. It felt like someone crying for 200 pages about how much they’ve suffered, rather than offering constructive advice for entrepreneurs. There’s a fine line between being vulnerable and just whining, and for me, this book crossed it repeatedly. I was expecting something along the lines of the podcast interviews which were great, but the book is just rambling and disjointed. I honestly don't understand the hype. If you want to feel sad about your life, read this. If you want to grow your business, look elsewhere.