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Reboot: Leadership and the Art of Growing Up

4.10  ·  Rating details ·  376 ratings  ·  57 reviews
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 t
Kindle Edition
Published June 18th 2019 by HarperBusiness
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Average rating 4.10  · 
Rating details
 ·  376 ratings  ·  57 reviews

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Brad Feld
Jun 28, 2019 rated it it was amazing
Shelves: entrepreneurship
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 C
Bartosz Pranczke
Aug 11, 2019 rated it really liked it
Shelves: 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 w
Jun 21, 2019 rated it really liked it  ·  review of another edition
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 a
Apr 11, 2019 rated it it was amazing  ·  review of another edition
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.
Jul 16, 2019 rated it really liked it
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!
Christopher Mahussier
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.
Jun 26, 2019 rated it it was amazing  ·  review of another edition
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 abo
Aug 25, 2019 rated it it was amazing
Not your typical leadership book. In fact, this book is for anyone seeking to live a whole and authentic life.
Barry O'Neill
Aug 19, 2019 rated it it was amazing
Essential reading for entrepreneurs. Or anyone.
Adam Nowak
Aug 25, 2019 rated it liked it
Recommended to Adam by: Bartosz Pranczke
Shelves: audiobook, be-better, 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 peo
J. Pablo
Sep 06, 2019 rated it did not like it
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.
Jun 29, 2019 rated it really liked it
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
Pritesh Pawar
Sep 02, 2019 rated it really liked it
Good book and a reminder that in many ways work and life are not separate. When we are blind to this, we inevitably create conditions that are difficult for us and those around us.

Jerry describes all of this in a way that is unsurprisingly personal and heartfelt. By opening up himself, he demonstrates how radical self-inquiry and having the strength to step into the mouth of our demons and bring our colleagues along with us on this journey, can be an incredibly powerful way to lead.

A book that
Jul 16, 2019 rated it liked it  ·  review of another edition
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
Sep 01, 2019 rated it it was amazing
I heard about Jerry Colonna and this book on one of my favorite podcasts, On Being, in which Jerry was being interviewed about the qualities of effective leadership and the radical self-inquiry leadership requires of those who are in leadership positions.

This podcast and book crossed my path at a time when I was deeply troubled by the question of what does it take to be a good leader for others. I had witnessed so many in leadership positions over the past decade of my life misstep. And I feare
Synthia Salomon
Sep 02, 2019 rated it it was amazing
This review has been hidden because it contains spoilers. To view it, click here.
Steve Heitkamp
Aug 16, 2019 rated it really liked it
This is a great book and reminder that in many ways work and life are not separate, not because it is impossible to disconnect from email, but because the work we do and how we did is intimately formed by who we are, with all of our wrinkles, life experiences, fears, and hopes. When we are blind to this, or refuse to look within, to listen to ourselves and to others, we inevitable create conditions that are difficult for us and those around us.

Jerry describes all of this and much more in a way
Sarah E.
Jul 29, 2019 rated it it was amazing
For those who are in leadership roles or who aspire to "take their leadership seats," Colonna inspires us to look more deeply at the often-hidden patterns that guide our work and personal lives. As we grow into our leadership roles, Colonna helps us (gently) bring a compassionate lens to unconscious patterns that are no longer serving us, in order to shift them and help us live more fulfilled lives. Bringing together research and insights from his personal journey as a tech journalist, VC, and c ...more
Sebastian Gebski
This 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.
Kathryn Morrison
Oct 15, 2019 rated it really liked it
What is this book about? It's hard to say - I described it to a friend as a stream of consciousness on leadership and being a good human, punctuated with highly personal but not comprehensive biographical details about Jerry’s life. Aka, very on brand if you love Jerry's message in general, and the Reboot podcast especially. I wouldn't start with this book if you've never heard of Jerry before.

I think it’s the kind of book I could read at different points in my life and take away completely dif
Xavier Jenkins
Sep 04, 2019 rated it really liked it
Loved this book! However, it took a bit of time to get used to his voice. It seemed just a bit contrived. After a few chapters I realized this is actually who he is. That made the rest of the book better. Interesting concepts for leadership including the Broken-hearted warrior/leader. It's not till the heart is broken that the beliefs sink in. I'm not doing this concept justice at all. But, essentially, we learn then we apply. It's part of why we need to understand more about who we are, what mo ...more
Aug 31, 2019 rated it liked it
I first discovered Jerry through the startup podcast. The way in which he asks questions to lead his clients to new understanding of self is a true gift. I had high hopes for his book to provide new insights. Instead I found it to be a journey through his life and journal. While many aspects were interesting, it was more a journey of self discovery versus stated insights. In many ways the same approach he says he says he takes in his coaching sessions. For someone looking for a journey of self d ...more
Sep 11, 2019 rated it it was ok
Shelves: abandoned, 2019-read
This was abandoned sort of because it was due back at the library, yet by the same token, I read the first section, set it down and didn't pick it back up until due date. I heard this author/coach on the On Being podcast with Krista Tippet and thus requested the book. While I think I probably agree with and/or could benefit from much of what he has written, of what I did read felt extremely privileged and overly simplistic, hence not picking it back up. Perhaps it is just the mood of the moment ...more
Chuck Hardy
Aug 09, 2019 rated it it was amazing
Interesting read. Recommended to me by a friend, was just what I needed at the time. A good next read after Daring Greatly: How the Courage to Be Vulnerable Transforms the Way We Live, Love, Parent, and Lead.
Aug 20, 2019 rated it it was amazing
The bad: Nothing of note.

The good: Although Jerry’s methods are very holistic in nature, with meditation and poetry and other activities I don’t necessarily see myself partaking in, the lessons here are deep and authentic. It takes balls to face the situations Jerry mentions, and although there are more questions than answers, it's a brutal book and a necessary one to evolve as a leader and person.
Oct 09, 2019 rated it did not like it
This book seems very similar to Fierce Conversations, which may be because I just finished that. They both speak to interrogating reality and being vulnerable as a leader, but Fierce Conversations delivers it in a much better way. This book was more like an autobiography than a leadership book and was condescending to those who are not CEOs, venture capitalists or engineers. Did not enjoy his narration.
Jonathan Crabb
Sep 05, 2019 rated it it was amazing
Fascinating book on how leaders can get better, especially through the practice of radical self inquiry. The leadership content has a large Buddhist influence which may turn off some readers, but I found it to be applicable and helpful.

However the largest reason for my five star review was that this book was particularly helpful in thinking through my own leadership journey. I am thankful for both the content and timing.
Nick Armstrong
Sep 25, 2019 rated it really liked it
Shelves: leadership, business
This is the kind of book that takes a few re-reads of specific sections to really grok. The premise is solid and could really be summarized as: if there's something about your company that you hate, it's probably your fault and with a little bit of grace (and some really good mentors) you can help undo the mess just as easily as you created it.
Stevo Brock
Jun 23, 2019 rated it it was amazing
This book was Stevo's Business Book of the Week for the week of 6/23, as selected by Stevo's Book Reviews on the Internet. You can find me at, on my Stevo's Novel Ideas Amazon Influencer page (, on LinkedIn ( or search for me on Google for many more reviews and recommendations.
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“Looking back, I see all those subway rides, all that motion, as an attempt to gather lemon drops. My twisted logic went like this: I didn’t have any lemon drops, and therefore felt exhausted and depleted and constantly battled migraines, because I wasn’t doing enough. The answer, therefore, was simple: Do more, faster.” 0 likes
“foreword, I was honored but uncertain. I asked, “Why not a mogul, a famous business success?” He replied that this wasn’t an ordinary business book—it reconfigures notions of success itself and ideas of who we are and what would make us happy. It teaches us how, above all things, to be real. The journey laid out is a path to equanimity, or peace, which is priceless. The book is genuinely a transmission, heart to heart. —Sharon Salzberg” 0 likes
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