Reboot: Leadership and the Art of Growing Up

Jerry Colonna‘s book, Reboot, came out this week.

He had given me the manuscript to read so many months ago that I had to go back and read it again before I could write about it.

So I bought the book yesterday and read it again over the last twenty four hours.

AVC regulars don’t need any introduction to Jerry. I’ve been writing about him, citing him, and telling stories about him since the very start of this blog.

Jerry is my friend, my former partner and co-founder of the first business I ever started, Flatiron Partners, and one of the best people on planet earth.

Jerry’s book is about two things that are really the same thing, himself and his work to help people, mostly entrepreneurs, discover themselves.

Jerry describes this work as “radical self inquiry”:

But the most challenging piece of the formula—indeed, the most important—is the notion of radically inquiring within. I define it as the process by which self-deception becomes so skillfully and compassionately exposed that no mask can hide us anymore. The notion is to recognize that, if things are not okay, if you’re struggling, you stop pretending and allow yourself to get help. Even more, it’s the process by which you work hard to know yourself—your strengths, your struggles, your true intentions, your true motivations, the characteristics of the character known as “you.” The you behind the masks, the stories, the protective but no longer useful belief systems that have been presented for so long as the “you” that you would like everyone to see.

Invariably such inquiry involves getting to know, as the poet Adrienne Rich says, “not the story of the wreck but the wreck itself.” With help, patience, courage, and guidance, we explore the wreck and retrieve the treasure. Knowing how to survive and understanding what it takes to thrive are skills that come from our childhood. Take any random group of entrepreneurs, for example, and do a quick unscientific survey by asking them to raise their hands if they grew up in an environment where at least one parent had disappeared or left or was never present. Most hands will shoot up. Early promotion into adulthood is often painful and equally often a sign of an early promotion into leadership. Probe a bit further and you may find that leaders who have built their company may have unconsciously stacked the team with other folks who experienced such early promotion.

Radically inquiring within allows us to step back and see the patterns of our lives not as random acts of a willful or even vengeful God but as forces that shape who we are. It’s this understanding that will make us not only better leaders but better, happier, more resilient people.

Reboot, the book, is about Jerry’s radical self inquiry to discover who he is and then his work to help others do the same.

He tells his own personal story over the course of the book and also weaves in the stories of others who he has worked with along the way to explain what the work of radical self inquiry is and why it must be done and the rewards that come from doing it. He is teaching by example.

Jerry started his career as a writer and he is a wonderful one. It is a joy to see him go back to those roots and exercise those muscles again.

Let me put it to you this way. You are reading AVC for a reason. Maybe you are an entrepreneur. Maybe you want to be one. Maybe you work for one. Maybe you are investing in entrepreneurs. Or maybe you are married to one. Or maybe your daughter is one. No matter what the reason, you are here at least in part because you are interested in entrepreneurs and the work they do. And so as part of that interest, I would recommend you pick up Jerry’s book and get inside the head of one. It will flip some switches on for you.