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Reboot: Leadership and the Art of Growing Up
One of the start-up world’s most in-demand executive coaches - hailed as the “CEO Whisperer” (Gimlet Media) - reveals why radical self-inquiry is critical to professional success and healthy relationships in all realms of life.
Jerry Colonna helps start-up CEOs make peace with their demons, the psychological habits and behavioral patterns that have helped them to succeed - molding them into highly accomplished individuals - yet have been detrimental to their relationships and ultimate well-being. Now, this venture capitalist turned executive coach shares his unusual yet highly effective blend of Buddhism, Jungian therapy, and entrepreneurial straight talk to help leaders overcome their own psychological traumas. Reboot is a journey of radical self-inquiry, helping you to reset your life by sorting through the emotional baggage that is holding you back professionally and, even more important, in your relationships.
Jerry has taught CEOs and their top teams to realize their potential by using the raw material of their lives to find meaning, to build healthy interpersonal bonds, and to become more compassionate and bold leaders. In Reboot, he inspires everyone to hold themselves responsible for their choices and for the possibility of truly achieving their dreams.
Work does not have to destroy us. Work can be the way in which we achieve our fullest self, Jerry firmly believes. What we need, sometimes, is a chance to reset our goals and to reconnect with our deepest selves and with each other. Reboot moves and empowers us to begin this journey.
Jerry Colonna helps start-up CEOs make peace with their demons, the psychological habits and behavioral patterns that have helped them to succeed - molding them into highly accomplished individuals - yet have been detrimental to their relationships and ultimate well-being. Now, this venture capitalist turned executive coach shares his unusual yet highly effective blend of Buddhism, Jungian therapy, and entrepreneurial straight talk to help leaders overcome their own psychological traumas. Reboot is a journey of radical self-inquiry, helping you to reset your life by sorting through the emotional baggage that is holding you back professionally and, even more important, in your relationships.
Jerry has taught CEOs and their top teams to realize their potential by using the raw material of their lives to find meaning, to build healthy interpersonal bonds, and to become more compassionate and bold leaders. In Reboot, he inspires everyone to hold themselves responsible for their choices and for the possibility of truly achieving their dreams.
Work does not have to destroy us. Work can be the way in which we achieve our fullest self, Jerry firmly believes. What we need, sometimes, is a chance to reset our goals and to reconnect with our deepest selves and with each other. Reboot moves and empowers us to begin this journey.
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First published January 1, 2019
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Displaying 1 - 30 of 211 reviews
June 28, 2019
Jerry Colonna has written a “must read for everyone on planet earth book” titled Reboot: Leadership and the Art of Growing Up.
Jerry and I are extremely close friends and have been for 23 years. I first met Jerry when he was beginning his partnership with Fred Wilson at Flatiron Partners. But, I didn’t meet him through Fred. I met him through NetGenesis, a company I was chairman of at the time that had been started by Rajat Bhargava (who we still work with as CEO of JumpCloud), Matt Cutler (who we still work with as CEO of Blocknative). I won’t repeat the story of Brad, Jerry, eShare, and NetGenesis, but it makes me incredibly happy to reflect on 23 years of friendship, which nicely lines up with my 23 official years of marriage to Amy.
Reboot: Leadership and the Art of Growing Up is extraordinary. It’s 100% Jerry, on every page, and is the book he was put on this planet to write.
If you are an entrepreneur, investor, leader, or human being, do yourself a favor and read Reboot: Leadership and the Art of Growing Up. I’m serious – it will change how you think about yourself, leadership, and life.
Jerry and I are extremely close friends and have been for 23 years. I first met Jerry when he was beginning his partnership with Fred Wilson at Flatiron Partners. But, I didn’t meet him through Fred. I met him through NetGenesis, a company I was chairman of at the time that had been started by Rajat Bhargava (who we still work with as CEO of JumpCloud), Matt Cutler (who we still work with as CEO of Blocknative). I won’t repeat the story of Brad, Jerry, eShare, and NetGenesis, but it makes me incredibly happy to reflect on 23 years of friendship, which nicely lines up with my 23 official years of marriage to Amy.
Reboot: Leadership and the Art of Growing Up is extraordinary. It’s 100% Jerry, on every page, and is the book he was put on this planet to write.
If you are an entrepreneur, investor, leader, or human being, do yourself a favor and read Reboot: Leadership and the Art of Growing Up. I’m serious – it will change how you think about yourself, leadership, and life.
August 11, 2019
The book was not what I thought it would be. And I'm grateful because I'd probably not read it. I didn't even know that I needed such a book.
I needed it.
I've read a lot of leadership books and almost all of them focused on one's external work. How you scale, delegate, have one-on-ones, motivate, what manager's tools you should use, etc. It's all about work focused on other people. Obviously, a very important topic. But the more experience I have the more I think that leaders should primarily work on themselves in order to be better leaders. As a leader, every insecurity, bias, doubt about your life, any voice in your head affects the people you lead. Maybe even more than what "manager's tools" you use.
"Better leaders are better humans and better humans are better leaders"
which means that "leadership lessons, then, are, at their core, lessons in humanity".
The book doesn't have answers, but the author did a good job of making me sit still and think about stuff that is very often put aside as less important (which it isn't).
It was not an easy read because just reading it probably won't add anything to your life. It's more like an exercise book. You need to work it through.
I needed it.
I've read a lot of leadership books and almost all of them focused on one's external work. How you scale, delegate, have one-on-ones, motivate, what manager's tools you should use, etc. It's all about work focused on other people. Obviously, a very important topic. But the more experience I have the more I think that leaders should primarily work on themselves in order to be better leaders. As a leader, every insecurity, bias, doubt about your life, any voice in your head affects the people you lead. Maybe even more than what "manager's tools" you use.
"Better leaders are better humans and better humans are better leaders"
which means that "leadership lessons, then, are, at their core, lessons in humanity".
The book doesn't have answers, but the author did a good job of making me sit still and think about stuff that is very often put aside as less important (which it isn't).
It was not an easy read because just reading it probably won't add anything to your life. It's more like an exercise book. You need to work it through.
July 19, 2019
So many gems in this book 💎💎💎
In the introduction, Colonna frames the rest of the book with a series of questions you can ask yourself. Questions like:
💰 How did my relationship to money get formed?
🏃♀️ In what ways have I depleted myself, run myself into the ground? Why have I allowed myself to be so exhausted?
👨🏻🏫 Who is the person I've been all my life? What can that person teach me about becoming the leader I want to be?
👨👩👧👦 What was the story my family told about being real, being vulnerable, being true?
And my favorite question of all, "How am I complicit in creating the conditions I say I don't want?"
Non-fiction books of this kind are often padded in order to meet a word count by the publisher. So many of them have just a handful of nuggets that can be summarized in a few paragraphs, and the rest of the book is filler. That's not the case with Reboot, because Jerry Colonna shares his very personal story in this book, and the stories of some of his clients. Not only are those stories engaging to read, they are illuminating. Sure, one could write a brief summary of key ideas from this book, but they would be missing the deeper point. It would be easy to say something like "radical self-inquiry is important for X Y and Z reasons," but that alone will not emotionally convince anyone to do the often very challenging work of self-inquiry.
The stories, however, might. On the one hand, Jerry uses his own story as a cautionary tale, to show how far off course, how depressed, how lost someone can become in their journey. On the other hand, the story feels so natural. Not easy, but natural in the sense that he seems to have learned the most from the hardships. He has gotten the most healing, the most value, by going through those difficult periods in his life and learning to heal, learning to come home to himself. That's the inspiration, and it's a big reason I enjoyed this book.
In the introduction, Colonna frames the rest of the book with a series of questions you can ask yourself. Questions like:
💰 How did my relationship to money get formed?
🏃♀️ In what ways have I depleted myself, run myself into the ground? Why have I allowed myself to be so exhausted?
👨🏻🏫 Who is the person I've been all my life? What can that person teach me about becoming the leader I want to be?
👨👩👧👦 What was the story my family told about being real, being vulnerable, being true?
And my favorite question of all, "How am I complicit in creating the conditions I say I don't want?"
Non-fiction books of this kind are often padded in order to meet a word count by the publisher. So many of them have just a handful of nuggets that can be summarized in a few paragraphs, and the rest of the book is filler. That's not the case with Reboot, because Jerry Colonna shares his very personal story in this book, and the stories of some of his clients. Not only are those stories engaging to read, they are illuminating. Sure, one could write a brief summary of key ideas from this book, but they would be missing the deeper point. It would be easy to say something like "radical self-inquiry is important for X Y and Z reasons," but that alone will not emotionally convince anyone to do the often very challenging work of self-inquiry.
The stories, however, might. On the one hand, Jerry uses his own story as a cautionary tale, to show how far off course, how depressed, how lost someone can become in their journey. On the other hand, the story feels so natural. Not easy, but natural in the sense that he seems to have learned the most from the hardships. He has gotten the most healing, the most value, by going through those difficult periods in his life and learning to heal, learning to come home to himself. That's the inspiration, and it's a big reason I enjoyed this book.
August 8, 2019
It’s hard to put into words the experience of reading this book. But I’m going to try anyway.
This book was both what I expected it to be but also was not what I was expecting. It is truly "Jerry's book" and therefore one that goes very deep. This isn't your average business book that tells you how to scale your company or one that's handing out tons of unsolicited management and leadership advice on how to do things right.
This book is an exploration of the self and what the self brings to the table when that self is responsible for leading a team or an entire organisation. It's at times uncomfortable to read. It's brutally honest and transparent. As is Jerry and the story he tells about his own path.
What it does give you is an opportunity to look at the thing that's next to impossible to get actionable advice on without going deep: yourself.
I've been a fan of Jerry's podcast for years yet this book still managed to surprise me and to go deeper, reflect more on the kind of human and therefore leader I want to be.
I do recommend this book wholeheartedly. I'd give it six stars if I could. My caveat here is that as a reader, you should be open to exploring yourself and not just read it from cover to cover. It's a book best taken in slowly, page by page, reflecting on what's being said and on what and who you are in life and at work.
Reading this book is like looking in a mirror page after page, with no way to avoid looking at yourself as you process every single one and explore the depth of Jerry’s words.
This book was both what I expected it to be but also was not what I was expecting. It is truly "Jerry's book" and therefore one that goes very deep. This isn't your average business book that tells you how to scale your company or one that's handing out tons of unsolicited management and leadership advice on how to do things right.
This book is an exploration of the self and what the self brings to the table when that self is responsible for leading a team or an entire organisation. It's at times uncomfortable to read. It's brutally honest and transparent. As is Jerry and the story he tells about his own path.
What it does give you is an opportunity to look at the thing that's next to impossible to get actionable advice on without going deep: yourself.
I've been a fan of Jerry's podcast for years yet this book still managed to surprise me and to go deeper, reflect more on the kind of human and therefore leader I want to be.
I do recommend this book wholeheartedly. I'd give it six stars if I could. My caveat here is that as a reader, you should be open to exploring yourself and not just read it from cover to cover. It's a book best taken in slowly, page by page, reflecting on what's being said and on what and who you are in life and at work.
Reading this book is like looking in a mirror page after page, with no way to avoid looking at yourself as you process every single one and explore the depth of Jerry’s words.
Read
October 12, 2019This definitely ain't a book for me (but that's a conclusion AFTER I've read it).
It's not that I'm not a CEO, the reason is different.
It's a book about leading which looks (sounds, in my case) like it was written by Virginia Woolf - very personal, all about feelings, impressions, moods, etc. Probably there are some people it will resonate with - people of very similar sensitivity, or ones who have similar observations, or ... I don't know, but I guess there'll be some.
In my case it was simply ... irritating. Maybe my emotional side is too dry, maybe I'm too analytical, maybe my empathy level is too low - but this book felt like whining w/o any constructive, practical advises.
I won't dare to put a star rating - maybe the issue here is about the lack of personal "chemistry", but if I really had to, it would be max. 1 star :(
It's not that I'm not a CEO, the reason is different.
It's a book about leading which looks (sounds, in my case) like it was written by Virginia Woolf - very personal, all about feelings, impressions, moods, etc. Probably there are some people it will resonate with - people of very similar sensitivity, or ones who have similar observations, or ... I don't know, but I guess there'll be some.
In my case it was simply ... irritating. Maybe my emotional side is too dry, maybe I'm too analytical, maybe my empathy level is too low - but this book felt like whining w/o any constructive, practical advises.
I won't dare to put a star rating - maybe the issue here is about the lack of personal "chemistry", but if I really had to, it would be max. 1 star :(
September 7, 2019
I pre-ordered the book while listening to Jason Calacanis interviewing Jerry Colonna on his podcast This Week in Startups. That was a very enjoyable episode that felt like it contained a lot of good lessons for people like me, entrepreneurs. Sadly, this didn't happen with the book.
Based on other reviews and the interview, I'm confused. Did I miss something? Did it go over my head? I couldn't get anything from it. It felt like rambling stories with a touch of woowoo.
Based on other reviews and the interview, I'm confused. Did I miss something? Did it go over my head? I couldn't get anything from it. It felt like rambling stories with a touch of woowoo.
March 2, 2020
One of the most frustrating books I've ever read. Frustrating because the genuinely helpful insights about improving as a leader were drowned out by excessively poetic anecdotes.
For example…
“When our employees and colleagues leave our sides and our company, what do we want them to say about our time together?”
vs.
“Fearing broken skis, failed businesses, and the scars that come from skinned knees, we stay small—listening more to our Loyal Soldier’s fear-filled and protective whispered warnings than to the quickening thump-thump, thump-thump, thump-thump of a heart that knows how it’s meant to be.”
For example…
“When our employees and colleagues leave our sides and our company, what do we want them to say about our time together?”
vs.
“Fearing broken skis, failed businesses, and the scars that come from skinned knees, we stay small—listening more to our Loyal Soldier’s fear-filled and protective whispered warnings than to the quickening thump-thump, thump-thump, thump-thump of a heart that knows how it’s meant to be.”
July 3, 2019
Nuggets of wisdom are there, but need to be panned for. Book is far from uplifting and has a flair for the dramatic. Criticizing crow and nobel soldier were good characters to meet.
July 21, 2019
As I started reading the book, I thought to myself "If Pema Chodron had written a business book, this would be it". By chapter 3, the author introduces Pema as his teacher. Ok, adds up.
The most valuable part of the book was the list of questions at the end of each chapter. They offer a great lattice for self-exploration. If you make the effort to write down answers to those via a deep and visceral examination of yourself, they can be edifying.
In general, I am not a fan of pop Buddhism - I find the simpler, original texts of Buddhist philosophy a lot more elegant and enlightening than some of the popular interpretations. Also, the over-generalization of "all problems stem from childhood experiences" left me cold. Surely, adult experiences can be as life-shaping and powerful for those with a peaceful childhood?
The tl;dr is that to be a better leader, you need to be a better human. The book has the same pros and cons as a Pema Chodron book. There are powerful nuggets of wisdom buried deep within layers of dramatic and fanciful stories. IMHO, the book could have been 1/3rd the length and 3X as powerful.
The most valuable part of the book was the list of questions at the end of each chapter. They offer a great lattice for self-exploration. If you make the effort to write down answers to those via a deep and visceral examination of yourself, they can be edifying.
In general, I am not a fan of pop Buddhism - I find the simpler, original texts of Buddhist philosophy a lot more elegant and enlightening than some of the popular interpretations. Also, the over-generalization of "all problems stem from childhood experiences" left me cold. Surely, adult experiences can be as life-shaping and powerful for those with a peaceful childhood?
The tl;dr is that to be a better leader, you need to be a better human. The book has the same pros and cons as a Pema Chodron book. There are powerful nuggets of wisdom buried deep within layers of dramatic and fanciful stories. IMHO, the book could have been 1/3rd the length and 3X as powerful.
April 11, 2019
I had the privilege and great chance to work with Jerry both as a member of a leadership team and individually and he has helped me/us break open our hearts, radically inquire within, and create strong backs with an open heart. Jerry has made me a better leader and I am grateful that he now shares his wisdom and personal story with the world through this book. Thank you, Jerry.
July 17, 2019
If you have questions about your life, this book will invite you to ask even more.
I found myself drifting off and then rewinding as questions sparked thoughts.
I think any business owner or leader will find thought provoking questions here and develop a desire to attend a Reboot boot camp!
I found myself drifting off and then rewinding as questions sparked thoughts.
I think any business owner or leader will find thought provoking questions here and develop a desire to attend a Reboot boot camp!
January 25, 2022
To be a good leader, we must be a good human. To be a good human, we need to face the ghosts in our machines and crows on our shoulders.
Appreciate the personal journey Jerry shares. To be a good coach, we need to bring our full selves to the work we do.
Appreciate the personal journey Jerry shares. To be a good coach, we need to bring our full selves to the work we do.
September 10, 2020
Vulnerable, authentic, refreshing take on what it means to be whole, to practice radical self-inquiry, and to be a human.
August 6, 2024
Great read, it opened up new vocabulary for a founder’s journey!
February 29, 2020
Initially when I had picked up this book, I must have been closed minded to the idea that it would have much relevance to me as I am not a leader in my field, my family or friends. But I was intrigued by the 'Art of Growing up' section on the title and from some reviews that I had read, it was enough for me to purchase this book.
By having this initial projection of myself not being a leader, I read the book not being able to relate to many of the stories, and thinking... 'he still has some good points that can be used in every day life'. As I continued to read though, Colonna really does practise what is being preached in his book, and even with my closed mind, he opened up my heart to his, his stories, the stories of the people he coaches, and the imaginary entities that surround us, the Crow, the Ghosts of the Machines, our Lone Warrior etc. (I love how he weaves each of these into the story and they all come together so beautifully at the end).
It became such a beautiful experience reading this book, It no longer became a curiosity in 'how to do the right thing to become the right person' but it evolved into a humbling acceptance of having questions, and not necessarily having been told an answer, but rather than to continue to question until you have reached a unique answer to yourself, one that comes from your authentic being, through the lens of your upbringing, your experiences and your heart.
I've began reading the book a second time, this time with love and appreciation towards how brave and courageous Colonna has been in sharing his life story and wisdom in becoming not only a better leader, but a better human. Leadership comes in many forms, but first and foremost it comes in leading your own life.
By having this initial projection of myself not being a leader, I read the book not being able to relate to many of the stories, and thinking... 'he still has some good points that can be used in every day life'. As I continued to read though, Colonna really does practise what is being preached in his book, and even with my closed mind, he opened up my heart to his, his stories, the stories of the people he coaches, and the imaginary entities that surround us, the Crow, the Ghosts of the Machines, our Lone Warrior etc. (I love how he weaves each of these into the story and they all come together so beautifully at the end).
It became such a beautiful experience reading this book, It no longer became a curiosity in 'how to do the right thing to become the right person' but it evolved into a humbling acceptance of having questions, and not necessarily having been told an answer, but rather than to continue to question until you have reached a unique answer to yourself, one that comes from your authentic being, through the lens of your upbringing, your experiences and your heart.
I've began reading the book a second time, this time with love and appreciation towards how brave and courageous Colonna has been in sharing his life story and wisdom in becoming not only a better leader, but a better human. Leadership comes in many forms, but first and foremost it comes in leading your own life.
September 13, 2020
It’s easy to tell that Colonna is an amazing coach and mentor. That much comes through in this book. But the style and anecdotes simply didn’t gel for me. I think it can work for people who are more well-known–where readers have a pre-existing interest in the author’s life–but for most of us, I don’t think we have that. As a result, the anecdotes weren’t enjoyable.
I appreciate that it’s not a tactical leadership book but he still adds helpful self-inquiry questions along the way. The problem for me is that the chapters and anecdotes tied to them didn’t actually feel connected. And because I didn’t find much interest in the anecdotes, nothing in this book stuck with me.
My advice is that if you really like the first chapter, keep going. If not, bail.
I appreciate that it’s not a tactical leadership book but he still adds helpful self-inquiry questions along the way. The problem for me is that the chapters and anecdotes tied to them didn’t actually feel connected. And because I didn’t find much interest in the anecdotes, nothing in this book stuck with me.
My advice is that if you really like the first chapter, keep going. If not, bail.
July 1, 2019
Very interesting book, a strange mix of management philosophy, traditional belles-lettres and autobiography. I have “read” it as an audiobook, narrated by the writer. As usual in this case, it gives much more personal touch to the whole experience.
So many different layers could be found in its chapters that it requires several re-reads to fully digest their messages. The questions at the end of each chapter promote self-study. Highly recommended, though four stars only as I did find it time to time difficult to follow and fully engaging.
So many different layers could be found in its chapters that it requires several re-reads to fully digest their messages. The questions at the end of each chapter promote self-study. Highly recommended, though four stars only as I did find it time to time difficult to follow and fully engaging.
June 13, 2021
Summary
Many leadership books focus on tools and tactics: how to hire, how to build strong teams and 1:1’s, how to leverage your time, how to drive alignment, where and when to delegate. This book focuses more on how to “lead yourself”; inner state and reflective intelligence.
It’s equal blend:
1. Stoicism: modern framing of the same wisdom.. Buddhism, zen, acceptance, etc.
2. Therapy: Cognitive distortions, false-narratives we tell ourselves, childhood imprints.
3. Leadership: leading people, leading organizations, leading through challenge.
Don’t expect a lot of answers. Instead, expect a series of rhetorical questions that will slow you down and might help you connect the dots between different parts of your life, your inner dialogue, and your leadership responsibilities.
4 stars for the uncommon approach, thoughtful prompt, and generally fast pacing.
TLDR: “I believe that better humans make better leaders. I further believe that the process of learning to lead well can help us become better humans.”
Jerry’s Story
- Born one of 7 kids in a two-bedroom in queens, 1963
- Mother had a sad and spiraling history of mental illness that eventually left her committed
- Dad worked as a union man for years, but lost his job and economic security
- Jerry grew up deeply anxious, and in his head. Big reader.
- Ended up in VC and investment banking in the 90’s, super successful, but lost a lot in the economic crash and sep 11.
- Wake up call. Leaned into his anxiety as a strength (empathy, seeing and untangling patterns)… instead of just a distraction of (making up fictions and noise).
- Now one of the top exec coaches in the country with focus on startup ceo’s
On Chasing the Right Questions
Busyness (particularly career/capital) can be a crutch, slowing down is hard. “Don’t mistake motion for meaning”.
“Learning to lead ourselves is hard because in the pursuit of love, safety, and belonging, we twist ourselves into what we think others want us to be. We move away from the source of our strengths—our core beliefs, the values we hold dear, the hard-earned wisdom of life—and toward an imagined playbook describing the right way to be.”
“Give me the steps, Jerry. How do I get customers? How do I convince people to hire me? How do I build a business? How do I raise money? How do I hire people? How do I fire people?” All genuine, important questions but, really, all a proxy for the deeper existential questions: Am I doing it right? Is it supposed to feel this confusing? Will I ever feel safe, warm, and happy? Where do I belong? What do I want from this life? Am I worth it? Have I earned my place on the planet, in this life? And, of course, If my life isn’t unfolding as I expected, then what am I doing?
We came to realize that the only answer to the existential question of “Does my life have meaning?” is, again, another set of questions: “In what ways have I been brave?” And “How have I been kind?”
On Internal Dissonance
“If you bring forth what is in you, what is in you will save you. If you do not bring forth what is in you, what is in you will destroy you.”
Aliveness comes from living a life of personal integrity in which our outer actions match our inner values, beliefs, wishes, and dreams. I am living my purpose, living with aliveness, when I write, regardless of whether my words are published. This then defines our life’s work not as a path to be discovered (and certainly not by following someone else’s map) but as a way of being, where each day is a chance to live into the command to live with the inner and outer in alignment.
I’d said that equanimity boils down to this: “Everything’s great, and I’m okay. Everything sucks, and I’m okay. Through years of radically inquiring within my broken-open heart, sitting still with that pain and its universal nature, I’ve been able to experience the occasional true equanimity.”
On Interpersonal Conflict
“Do you see it?” my therapist asks. “Do you see that the more you plot, the cleverer you feel? And the cleverer you feel, the more hooked on the anger you become? You nurse and feed that anger until you’re operating purely out of your shadow.” I look up startled, ashamed, feeling caught with my true feelings—my anger—revealed. My oh-so-clever facade of brilliant plotting and analysis was laid bare.
Slow down when you get in fights. Notice the bodily sensations and narratives you are telling yourself.
Many leadership books focus on tools and tactics: how to hire, how to build strong teams and 1:1’s, how to leverage your time, how to drive alignment, where and when to delegate. This book focuses more on how to “lead yourself”; inner state and reflective intelligence.
It’s equal blend:
1. Stoicism: modern framing of the same wisdom.. Buddhism, zen, acceptance, etc.
2. Therapy: Cognitive distortions, false-narratives we tell ourselves, childhood imprints.
3. Leadership: leading people, leading organizations, leading through challenge.
Don’t expect a lot of answers. Instead, expect a series of rhetorical questions that will slow you down and might help you connect the dots between different parts of your life, your inner dialogue, and your leadership responsibilities.
4 stars for the uncommon approach, thoughtful prompt, and generally fast pacing.
TLDR: “I believe that better humans make better leaders. I further believe that the process of learning to lead well can help us become better humans.”
Jerry’s Story
- Born one of 7 kids in a two-bedroom in queens, 1963
- Mother had a sad and spiraling history of mental illness that eventually left her committed
- Dad worked as a union man for years, but lost his job and economic security
- Jerry grew up deeply anxious, and in his head. Big reader.
- Ended up in VC and investment banking in the 90’s, super successful, but lost a lot in the economic crash and sep 11.
- Wake up call. Leaned into his anxiety as a strength (empathy, seeing and untangling patterns)… instead of just a distraction of (making up fictions and noise).
- Now one of the top exec coaches in the country with focus on startup ceo’s
On Chasing the Right Questions
Busyness (particularly career/capital) can be a crutch, slowing down is hard. “Don’t mistake motion for meaning”.
“Learning to lead ourselves is hard because in the pursuit of love, safety, and belonging, we twist ourselves into what we think others want us to be. We move away from the source of our strengths—our core beliefs, the values we hold dear, the hard-earned wisdom of life—and toward an imagined playbook describing the right way to be.”
“Give me the steps, Jerry. How do I get customers? How do I convince people to hire me? How do I build a business? How do I raise money? How do I hire people? How do I fire people?” All genuine, important questions but, really, all a proxy for the deeper existential questions: Am I doing it right? Is it supposed to feel this confusing? Will I ever feel safe, warm, and happy? Where do I belong? What do I want from this life? Am I worth it? Have I earned my place on the planet, in this life? And, of course, If my life isn’t unfolding as I expected, then what am I doing?
We came to realize that the only answer to the existential question of “Does my life have meaning?” is, again, another set of questions: “In what ways have I been brave?” And “How have I been kind?”
On Internal Dissonance
“If you bring forth what is in you, what is in you will save you. If you do not bring forth what is in you, what is in you will destroy you.”
Aliveness comes from living a life of personal integrity in which our outer actions match our inner values, beliefs, wishes, and dreams. I am living my purpose, living with aliveness, when I write, regardless of whether my words are published. This then defines our life’s work not as a path to be discovered (and certainly not by following someone else’s map) but as a way of being, where each day is a chance to live into the command to live with the inner and outer in alignment.
I’d said that equanimity boils down to this: “Everything’s great, and I’m okay. Everything sucks, and I’m okay. Through years of radically inquiring within my broken-open heart, sitting still with that pain and its universal nature, I’ve been able to experience the occasional true equanimity.”
On Interpersonal Conflict
“Do you see it?” my therapist asks. “Do you see that the more you plot, the cleverer you feel? And the cleverer you feel, the more hooked on the anger you become? You nurse and feed that anger until you’re operating purely out of your shadow.” I look up startled, ashamed, feeling caught with my true feelings—my anger—revealed. My oh-so-clever facade of brilliant plotting and analysis was laid bare.
Slow down when you get in fights. Notice the bodily sensations and narratives you are telling yourself.
June 26, 2019
To be a better leader, and human, read this book
Have you ever you come across a book that provides just the spiritual nourishment you were craving at the moment you needed it? To me, this is that book. I cannot express my gratitude to him to have written it. Jerry is an old friend and former colleague so I have a little personal experience with the magical insight he brings to his work as well as the forces that plagued him at the peak of his career in finance. He was always more honest about this than anyone I’ve ever met. And one of his gifts is recognizing these conflicts in other leaders, and showing them, through gentle but firm inquiry, how their patterns may be replaying in their leadership relationships, and what work it takes to resolve them with honesty and integrity. In this hugely readable book, he opens up even more to show the incredible path he’s been on to reconcile his childhood demons and through reading, retreats, therapy, and writing, find ways to break open his heart and become a warrior of radical self-inquiry. I’ve spent the last few years on my own self-inquiry journey, wrestling with similar issues and lightly dipping into some of the touchstones he discovered, along with a few others (Salzburg, Rohr, Katie). I felt like this book, more than any I’ve read lately, helped bring various strands of the inquiry together into sharp focus. He includes questions at the end of each chapter, and I started journaling with them after the first 10 pages. I’ve also worked with hundreds of entrepreneurs, and agree with Jerry that people in that role often discover patterns that once drove them and helped them succeed may not work forever. This book helps you see those patterns in others, and then in yourself, through easy to understand analogies-the Crow, the Loyal Soldier, and others.
Jerry is a master coach and teacher, and you can literally use this book to benefit from his coaching, to explore what is holding you back, and to start to disentangle what it means for you to be a better leader, and more importantly, a better human. Or you can just enjoy the ride of wonderful writing and insight that knit together the personal with the pressures of modern entrepreneurial leadership. Either way, this book is a gem.
Have you ever you come across a book that provides just the spiritual nourishment you were craving at the moment you needed it? To me, this is that book. I cannot express my gratitude to him to have written it. Jerry is an old friend and former colleague so I have a little personal experience with the magical insight he brings to his work as well as the forces that plagued him at the peak of his career in finance. He was always more honest about this than anyone I’ve ever met. And one of his gifts is recognizing these conflicts in other leaders, and showing them, through gentle but firm inquiry, how their patterns may be replaying in their leadership relationships, and what work it takes to resolve them with honesty and integrity. In this hugely readable book, he opens up even more to show the incredible path he’s been on to reconcile his childhood demons and through reading, retreats, therapy, and writing, find ways to break open his heart and become a warrior of radical self-inquiry. I’ve spent the last few years on my own self-inquiry journey, wrestling with similar issues and lightly dipping into some of the touchstones he discovered, along with a few others (Salzburg, Rohr, Katie). I felt like this book, more than any I’ve read lately, helped bring various strands of the inquiry together into sharp focus. He includes questions at the end of each chapter, and I started journaling with them after the first 10 pages. I’ve also worked with hundreds of entrepreneurs, and agree with Jerry that people in that role often discover patterns that once drove them and helped them succeed may not work forever. This book helps you see those patterns in others, and then in yourself, through easy to understand analogies-the Crow, the Loyal Soldier, and others.
Jerry is a master coach and teacher, and you can literally use this book to benefit from his coaching, to explore what is holding you back, and to start to disentangle what it means for you to be a better leader, and more importantly, a better human. Or you can just enjoy the ride of wonderful writing and insight that knit together the personal with the pressures of modern entrepreneurial leadership. Either way, this book is a gem.
February 9, 2021
There were some elements of this book I really liked. The journaling invitations were very good and were by far my favourite part. Not sure I would have kept going otherwise. I found it difficult to make connections between all the different stories used and after a while I tuned out. There were some really interesting insights in among the stories, but they were sometimes hard to find.
The other disconnect I haven't quite worked out is the combination of Buddhist philosophy and a fairly capitalist approach to life essentially defined by work.
The other disconnect I haven't quite worked out is the combination of Buddhist philosophy and a fairly capitalist approach to life essentially defined by work.
November 24, 2019
If you want to be a better leader, work to be a better person. This book explains why and how, through a deeply personal and affecting series of vignettes that unfold like a long walk with an old friend. I was both moved and challenged by it, the only questions left are the ones I need to answer for myself.
April 5, 2024
A surprisingly moving read. For myself, and perhaps many others, this book at first smacked a bit of the musings of an overly poetic finance-bro-turned-yogi. But once I let Colonna’s words permeate beyond my defences, the generosity of his raw vulnerability shared in this book was striking, and many of his familial anecdotes felt disturbingly (but somehow also comfortingly) familiar...
I will note that many of the concepts central to this book feel to me basically those at the core of the Vipassana experience, and given Colonnas repeated reference to Buddhism, I suspect that such an experience was highly influential to his journey, despite there being no explicit mention of it.
The book also makes repeated references to the Jung quote “Until you make the unconscious conscious, it will direct your life and you will call it fate”, and I’m genuinely not sure if psychoanalysis has ever contributed a more poignant and compelling explanation. In many ways, this book is largely an expansion of that idea.
In my opinion, this is not a book for those seeking quick fix organisational leadership hacks, but rather a book to prompt awareness, understanding and compassion for one’s own operating manual, an aide to decoding and maybe even un-entrenching those ‘ghosts in the machine’ buried within. All written in such a beautiful, powerful, and heart-breakingly-open way. Highly recommend.
I will note that many of the concepts central to this book feel to me basically those at the core of the Vipassana experience, and given Colonnas repeated reference to Buddhism, I suspect that such an experience was highly influential to his journey, despite there being no explicit mention of it.
The book also makes repeated references to the Jung quote “Until you make the unconscious conscious, it will direct your life and you will call it fate”, and I’m genuinely not sure if psychoanalysis has ever contributed a more poignant and compelling explanation. In many ways, this book is largely an expansion of that idea.
In my opinion, this is not a book for those seeking quick fix organisational leadership hacks, but rather a book to prompt awareness, understanding and compassion for one’s own operating manual, an aide to decoding and maybe even un-entrenching those ‘ghosts in the machine’ buried within. All written in such a beautiful, powerful, and heart-breakingly-open way. Highly recommend.
August 19, 2019
Essential reading for entrepreneurs. Or anyone.
August 25, 2019
Not your typical leadership book. In fact, this book is for anyone seeking to live a whole and authentic life.
August 25, 2019
"To be a better leader, you need to be a better human!"
The thing I liked the most about this book was "Journaling Invitations" section at the end of each chapter. My favourites:
* What am I saying that’s not being heard?
* What am I not saying that needs to be said?
* What’s being said to me that I’m not hearing?
Self-reflecting on them has great power (stop for a minute and try to answer them), but I feel that sharing the answers and thoughts with other people is going to make the real difference (simple, but not easy!)
The thing I liked the most about this book was "Journaling Invitations" section at the end of each chapter. My favourites:
* What am I saying that’s not being heard?
* What am I not saying that needs to be said?
* What’s being said to me that I’m not hearing?
Self-reflecting on them has great power (stop for a minute and try to answer them), but I feel that sharing the answers and thoughts with other people is going to make the real difference (simple, but not easy!)
December 24, 2020
This was the audio book, and his voice was so victim based and depressing as if he was the only person in the world who suffered. Terrible.
November 22, 2020
To grow as leaders, we need to be more mindful human beings who pay close attention to the things that have shaped our present behavior. This will improve and deepen the way we interact with colleagues and how we lead the team as a whole.
Above all else, it pays to become more humans, courageous people, because that is the path to less-toxic workplaces and companies that act responsibly regarding their employees, communitites and the environment.
So, take time for yourself outside of work.
Above all else, it pays to become more humans, courageous people, because that is the path to less-toxic workplaces and companies that act responsibly regarding their employees, communitites and the environment.
So, take time for yourself outside of work.
March 17, 2024
A thoughtful book on rebooting and reconsidering life and leadership at critical points in life. it was open, honest and did not sugar coat the author's challenges. If I could have, I would have given it a 3.5
January 16, 2020
The kindest and gentlest book about leadership
It just tore my heart open. True, clear messages, based on amazing storytelling by the kindest author. I was in tears many times. Absolutely happy I’ve found this gem. As a CEO of a 70+ people startup, there was a lot of insights for me.
It just tore my heart open. True, clear messages, based on amazing storytelling by the kindest author. I was in tears many times. Absolutely happy I’ve found this gem. As a CEO of a 70+ people startup, there was a lot of insights for me.
May 24, 2024
A book that focus on seeking the why we are moved to be leaders, and finding balance on that process. The author tells his own story, as well as that of some people he has coached (or invested on) over the years. In a nutshell, it highlights that we can frequently be driven by hollow obsessions (like being Bill Gates-wealthy, something he confesses to having been his own target earlier in life) and, in the process, be very unforgiving to ourselves and others.
He drives home the importance of equanimity: we should face the good and the bad as equal building blocks of the people we are. And that we are all works in progress and victims of biases that we need to acknowledge. Sometimes his writing can have religious overtones that may or may not land with different readers.
I did like the book (I'd rate it a 3.5/5), but it did read more like a self-help tract. I certainly feel it's a book best read later in the life of an entrepreneur than as a first read because, sometimes, you DO need to pay the devil his dues and some grinding is needed to succeed.
He drives home the importance of equanimity: we should face the good and the bad as equal building blocks of the people we are. And that we are all works in progress and victims of biases that we need to acknowledge. Sometimes his writing can have religious overtones that may or may not land with different readers.
I did like the book (I'd rate it a 3.5/5), but it did read more like a self-help tract. I certainly feel it's a book best read later in the life of an entrepreneur than as a first read because, sometimes, you DO need to pay the devil his dues and some grinding is needed to succeed.
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