future startup logo

Bookworm #2: Reboot: Leadership and the art of growing up by Jerry Colona

Bookworm is a new book review series from Future Startup where we share actionable ideas and insights from a book to help you improve your life. We aim to publish 3-4 reviews per month.

This week 10 lessons from Jerry Colona’s excellent book Reboot: Leadership and the art of growing up (highly recommended). Reboot is one of those books that comes with packed insight and very little redundancy and exaggeration, which makes it hard for a reader to do justice while doing a review. After completing the book, as I always do, I sent it to a few of my friends and the email subject was simple: “this book has very little bullshit in it.” On to the lessons. 

Learn to sit still. Stillness has transformational power

“Standing still and powering down allows us to start anew and, if you will, reboot our core operating and belief systems. Standing still and listening deeply to our heart as well as to the hearts around us are the necessary first steps toward moving past merely, numbly, surviving our lives. As poet Terry Tempest Williams advises, we learn, then, to speak and “comprehend words of wounding without having these words become the landscape where [we] dwell.” With such comprehending, we elevate the darkness of our lives, lead from the realm of the stars, and continue growing up.”

Radical self-inquiry is the beginning of our journey to growing up

“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.”

Radical self-inquiry makes us resilient people

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.

Radical self-inquiry enables us to become our true self 

“Radical self-inquiry is how we learn to become more of ourselves, more like ourselves, more authentic. More human. And better humans are better leaders. This is what great leaders do. Great leaders look unflinchingly in the mirror and transform untamed hungers and unruly compulsions into moments of self-compassion and understanding. In doing so, they create the spaces for each of us to do the same, turning our organizations into places of growth and self-actualization. They infuse the profanity of work with the sacred duty of Work: the opportunities to lead, to grow into their whole selves while nurturing others, encouraging them to do the same.” 

True listening has the power to change our lives 

“Holder,” he taught me, “listening opens that which pain has closed. “You were not given this life only to lament,” he went on. “Make holy that which you were given: Go and listen.” Listening, I’ve come to understand, is bearing witness to lives unfolding, to lives being discovered. Deep listening, listening compassionately, means guiding, gently nudging, or sometimes shoving people down the path of radical self-inquiry so they can make their way to their own truest selves. Then, and only then, can they lead with the dignity and grace of being human. The goal, then, is to help you listen to the stories of your heart so that, in the end, you can know the why of your leadership journey and become the adult, the full human you were meant to be. Then the simple but hard task becomes clear: Lead from the place of your truest self. Do so not merely for yourself but for those who love and entrust their careers to you.”

The first step of leadership is learning to lead yourself first 

“Learning to lead yourself is the hardest part of becoming a leader. That’s one of the things new CEOs and aspiring entrepreneurs come to me for. They come because they feel lonely; they don’t have anyplace else to put the feelings. They’ll sit on my couch or pace while they talk on the phone, pausing as we grapple with issue after issue after issue. Learning to lead yourself is hard because we are wired to look outward. We feel pain and we look up and out to see who’s hurt us. We feel loss, and the hurt gives rise to anger as we look for someone to blame. Learning to lead yourself is hard because it requires us to look at the reality of all that we are—not to fix blame on ourselves but to understand with clarity what is really happening in our lives. Learning to lead yourself is hard because it is painful. Growth is painful; that’s why so few choose to do it. Moreover, the common denominator in all our struggles is always people. When I first take on clients, I warn them that I don’t have a magic wand. Nevertheless, their wish for some elixir to mend their relationships is heartbreakingly visceral.” 

“Learning to lead ourselves is hard because in the pursuit of love, safety, and belonging, we lose sight of our basic goodness and 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 listing the right way to be. We are inevitably knocked on our asses by the demands of leading. And when we make mistakes—when we fail to lead—our identity; our sense of self; our self-esteem; our deeply held beliefs about what it will take to feel loved and safe and that we belong, as well as that most the basic ability to provide for ourselves and our loved ones, seems to implode. All too often we break down in the work of becoming a CEO, a manager, a leader. But in that breaking is the promise of a making.”

Asking difficult questions is a sacred act

“Tell me what success and failure mean for you and we can use your answers to chart a path. Tell me if, after imagining your children working for your company, you feel shame, fear, or pride, and I’ll tell you if you’re building a worthwhile company.”

Good leaders are, first and foremost, good human beings

“A good man takes care, answers a voice in my head; that of my father, perhaps, or my Grandpa Guido? A good man, as I’ve been repeating lately, builds castles, slays dragons, and, if he’s opened his heart, tends the hearth—building a fire against the cold, empty night so that his loved ones are safe, warm, and happy. Hand-built castles and slain dragons give those he loves safety and belonging.”

Seeing the world as it is, enables us to deal with it better

“Seeing ourselves and the world as they are is a cornerstone of good leadership and the well-lived adulthood. One of the most startling challenges I will put to a client comes from my bastardization of a Zen aphorism: This being so, so what? Things being as they are, what will you do about it? Avoiding havens of self-delusion, maturing with a fierce regard for the truth of who and how we are, allows us the grace and freedom to live with contradictory, confusing, and ambivalent feelings.”

Our lack of understanding about ourselves is the source of most of our challenges

“When leaders fail to look at themselves, they turn their inner turmoil and very human contradictions outward. Further, unable to face their fears, they mask the anxiety with aggression. As my friend and mentor Parker Palmer, teaches, “Violence is what we do when we don’t know what to do with our suffering.”

You can buy the Reboot: Leadership and the art of growing up on Amazon, we don’t get an affiliate fee as yet!


Mohammad Ruhul Kader is a Dhaka-based entrepreneur and writer. He founded Future Startup, a digital publication covering the startup and technology scene in Dhaka with an ambition to transform Bangladesh through entrepreneurship and innovation. He writes about internet business, strategy, technology, and society. He is the author of Rethinking Failure. His writings have been published in almost all major national dailies in Bangladesh including DT, FE, etc. Prior to FS, he worked for a local conglomerate where he helped start a social enterprise. Ruhul is a 2022 winner of Emergent Ventures, a fellowship and grant program from the Mercatus Center at George Mason University. He can be reached at ruhul@futurestartup.com

In-depth business & tech coverage from Dhaka

Stories exclusively available at FS

About FS

Contact Us