A love letter to Reboot, by Jerry Colonna

I’m not the type to read business books past the third chapter. I’ve found that pretty much all business books get to their point pretty quickly, and then repeat that point, approaching it from infinite angles, for the next 200 pages. It’s exhausting.

There are exceptions, however. And one business book changed my life.

Reboot, by Jerry Colonna, was released in 2019. I picked up the book because Jerry was hailed as “the CEO whisperer”, and one of the top Executive Coaches in the country, which I figured was right up my alley. But then the entire book was the opposite of what I expected in the best possible way.

Through an examination of his life story, interspersed with multidisciplinary perspectives from some of the best thinkers, both contemporary and throughout history, Jerry hits directly at the human side of starting and running a business, which to that point in my life was still pretty well unexamined. He addresses the toll that the specific set of circumstances in which founders put themselves takes on them as human beings. He does this in a way that hit me hard–his perpetual chasing of “lemon drops” as a proxy for feeling whole, for example, which is a feeling to which my entire soul can relate (although lemon drops themselves are meh).

Jerry also cites his sources in many cases, from Jung to Plotkin to Buddha, all experts with various perspectives on the human condition (all “different fingers pointing at the same moon”). I cannot express my gratitude for this choice enough, as it enabled me to go on a months-long, on-and-offline google-deep-dive into the ancient wisdom of how to be a human being, a dive that continues to this day and is responsible for my budding faith (if you can call it that, I’ve been an athiest most of my life so I’m still not sure that’s the right word).

The core hypothesis driving all this–which to be fair he stated in the first three chapters so I could have stopped there, but I’m so glad I didn’t–was that better humans make better leaders. The book, therefore, along with his coaching company of the same name, is intended to help leaders become whole in their humanity, thereby enabling them to lead other humans to become better versions of themselves. It’s a brave approach amongst so many books offering ways to push your humanity ever deeper in the quest for ultimate achievement. I believe it’s also a necessary approach, as there’s no way I would have picked up a book about ancient wisdom and feelings unless it was smuggled in under the guise of productivity, such was my blindness. Jerry Miyagi’d me.

In the guise of a business book, Jerry penned a letter on how to live a life, written specifically for those of us who have already made the decision to prioritize our business over ourselves. It’s full of necessary information for founders which is hard to find elsewhere. Wrapped in a package of productivity, Jerry smuggled in one of the three most profound transformations of my life.

Wax on, my friend.

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