Reboot: Leadership and the Art of Growing Up

by Jerry Colonna

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. By growing to meet the demands of the call to leadership, we’re presented with the chance to finally, fully, grow up.

that leadership requires an authentic and vulnerable dive into the wrecks of our lives—would

“Radical Self-inquiry.” “And when they do that, when they look in places they’ve avoided, they often get stuck,” I continued. “They get scared. They get lost in their fears and in old patterns of self-loathing. So, mired in their self-criticism, they think they’re the only one who hasn’t a fucking clue as to what they are doing or how to live.

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.

As you read this book, I’d like you to hold these questions in your heart: How did my relationship to money first get formed and how does it influence the way I work as an adult? What was the belief system around money and work that I grew up with? (Chapter 1.) How can I lead with the dignity, courage, and grace that are my birthright? How can I use even the loss of status and the challenge to my self-esteem that are inherent in leadership to grow into the adult I want to be in the world? (Chapter 2.) In what ways have I depleted myself, run myself into the ground? Where am I running from and where to? Why have I allowed myself to be so exhausted? (Chapter 3.) 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? (Chapter 4.) Why do I struggle so much with the folks in my life? Why are relationships so difficult? What am I not saying to my co-founder, my colleagues, my family members, my life partner that needs to be said? (Chapter 5.) What’s my purpose? Why does it feel I’m lost while I struggle to move forward? How do I grow, transform, and find meaning? (Chapter 6.) How has who I am shaped the ways I lead others and myself? What are the unconscious patterns of my character structure that are showing up in my organizations? (Chapter 7.) How might I survive my life of heartbreak? How might I live in peace? (Chapter 8.) What kind of lea...

Work gives us the means to create the physical safety upon which our lives depend. Work feeds and shelters us and those we love. Work can give us meaning. But work can also be a means of our suffering. By understanding what’s truly happening all around us, the ways our core belief systems influence our everyday experience, we can extract meaning from the suffering, coax the lotus from the mud, as the Buddhists teach. But this will happen only if we use those challenges that the calls to leadership make on us, not only to grow up but also help us discover our why.

Helping people sort through the why of life helps them access all they need to know to answer the hows that work demands. The hows of life and leadership are endless. If you enhance your understanding of the why of who you are, you’ll be able to face the unending uncertainty in the pursuit of the perfectly executed how. Moreover, if such inquiry is done well, with well-asked questions and deeply true answers, you will end up with a tailor-made how. Such work may not feel quite so practical at first, but it is undeniably useful.

My journey as a leader has taught me that my childhood demanded a hypervigilance and that, to stay safe, I learned to work ceaselessly to try to make sense of the world (even as I was confronted with insensible acts and facts). As part of that effort, I listened closely—collecting and holding the stories of those around me as clues to a puzzling life.

The result is that I often see, hear, sense things that others miss. This can be a source of great wisdom. But this sensing can be an impediment to my peace of mind as well, for I can create whole ships of fiction out of the random flotsam and jetsam that float my way.

For the job to be done, we must know that it’s time to let go of the striving to become and allow ourselves the restful grace of simply being. In my effort to simply be, I’ve learned to balance the disquietude of the past with the life-giving excitement of the future, the seedbed for the growing to come.

with the big dogs.” Success and money—and even more important, the busyness needed to create those—became proof of my worth as a human.

But who we choose to be is awakened by the truths we choose to tell.

But choosing requires knowing. It requires knowing how what happened to us influences the choices we made and continue to make. Again and again I ask my clients, “How are you complicit in creating the conditions of your lives that you say you don’t want?”

But even more, in what ways does that complicity serve you? How does it serve my soon-to-be retired client to remain disconnected from himself such that he doesn’t know how he’d like to spend his days?

He goes on to explain that he’d sworn that he was never going to be cold or hungry or alone again. I nod in recognition. I see him as he sees himself more fully. “Who hired the sales guy?” He looks around sheepishly. “I did.” “And who promoted him?” “Me,” says the camper. “There is nothing to be ashamed of,” I tell him. “The problem isn’t his greed. He’s just doing what you hired him to do. You outsourced your need to never be cold and hungry again to someone more acceptable. And he’s doing a great job at that.” “What if you took back your greed,” I ask him, “and instead see it for what it truly is: a desire to be safe, warm, and happy?” Take back the wish, take back the promise you made to yourself, leave aside the shame and own the fear not as something to deny but as something that fuels you. He brightens. I continue: “Let’s expand that view now. Let’s go beyond making sure that you and your family are never hungry again. Let’s see the ways you and your company have made it possible for your employees and their families to not be hungry. To feel safe, warm, and happy.” His body unfolds, and we all bear witness to his taking his seat not merely as a CEO but as a man, capable of providing for the boy under the overpass. 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.

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.

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 process of radical self-inquiry into one’s own leadership journey is supported by standing still and taking the time to ask oneself open, honest questions around the rules we carry.

“Listening,” I remember, “opens that which pain has closed.”

How do you attract a CFO, a general counsel, or a head of marketing when the culture finds such functions an anathema? How do you hold the heart of what is special, embracing the rebels and misfits who define the greatness of your organization, while creating a tolerant and caring space for those who’ve built their career on doing well at more traditional companies?

Years before, I’d given him the metaphor I often use with clients: “Take your seat.” “Sit like royalty in your leadership seat,” I say. “Sit as if you’ve the right to be there.”

“How the hell do I do this job?” they ask either implicitly or explicitly. They act as if there’s a playbook, a secret handbook that will teach them everything they need to know about leading.

Peggy: What’s the job? Don: Living in the “not-knowing.”

Clients come to me because the “not-knowing” is so unbearable. I often make them crazy when I tell them the answer isn’t in a book. “There’s no book,” I say, often nearly preaching. “There’s no ‘way,’ no ‘path,’ that’s been kept hidden from you.” Some of them get angry when I ask them about their past or what’s in their heart.

But I know that the truest path, the only way, for a warrior to emerge is through the path of radical self-inquiry, the process by which the mask is compassionately stripped away until there’s no place left to hide.

He’d become not merely the man he’d always intended to be, the man he chose to be, but a gentle, brokenhearted warrior who leaned into his own pain to find the strength to do what is right.

The back of the warrior is strengthened by knowledge of knowing the right thing to do. The soft, open heart is made resilient by remembering who you are, what you have come through, and how those things combine to make you unique as a leader. “What would Obama do?” became both a rallying cry and an inside joke. What standards of dignity do you hold yourself to, regardless of how things unfold? What do the people who have counted on you to lead them need from you at this moment?

Indeed, the simple act of asking, “What kind of leader am I?” implicitly acknowledges that there is no one way to lead.

Again, I thought of Carl Jung: “I am not what has happened to me. I am what I choose to become.”

Warren Bennis put it: “Some magic takes place in the crucible of leadership. . . . The individual brings certain attributes into the crucible and emerges with new, improved leadership skills. Whatever is thrown at them, leaders emerge from their crucibles stronger and unbroken.” That’s the arc. We’re smacked in the head by the realization that life isn’t unfolding as we’d hoped, that all our careful plotting hasn’t protected us from the shock of failure and disappointment. Our lives falter. Our companies stagger. We are in that alchemist’s crucible, and the heat of loss and pain is turned up. We’re being cooked.

What conditions are our lives in and, radically as important, how have we been complicit in creating the conditions we so steadfastly declare we do not want? From that place, the warrior leader emerges.

Learning to lead yourself is the hardest part of becoming a leader.

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 wh...

Like so many, they have been seduced by the notion that being a leader means having all the answers, solving all the problems, and telling everyone else what to do.

Self-doubt convinces us that there’s a magic path and if we can only find and follow the yellow-brick road, we’ll end up safe, warm, and happy—successful leaders, beloved adults, retiring in Millionaire Acres at the end of The Game of Life. And we’ll never be hungry, cold, alone, or afraid again.

One of the most profound teachings I’ve ever received came from a simple sutra from the Buddha: we are basically, unalt...

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.

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.

‘Never be ashamed to make a profit.’

‘The goal is to buy low and sell high, not buy lowest and sell highest.’”

That experience taught me something else about the crucible moment: when the leader moves through that moment, it enables those around them to grow as well.

The only answer, the only balm against the inevitable, existential pain of becoming the leaders we were born to be is to see the lessons implicit in the practice of becoming

That’s the true message of Warren Bennis’s crucible. The magic, the alchemy, occurs when what we do mixes with who we are and is cooked by the heat of what we believe.

The Buddhists teach that for the steadfast warrior to emerge, we’ve got to break op...

Exactly so. Strong back and open heart. This is warrior stance, I tell him. The strong back of fiscal discipline. The strong back of clarity and vision, of drive and direction. The strong back of delegating responsibility and holding people accountable. The strong back of knowing right from wrong.

But it’s also the open heart. It’s giving a shit about people, purpose, meaning. It’s working toward something greater than merely boosting your ego, greater than just soothing your worries and chasing your demons away. It’s leading from within, drawing on the core of your being, on all that has shaped you.

The toughest aspect of being a leader—hell, of being an adult—is meeting the world as it is and not as we wish it to be. The demons of the world, the demons of your soul, require just one thing: your broken-open heart.

In some cases, as at Alex’s start-up, the demon is that you have the wrong vision for the company. In others, it may be that you’ve hired the wrong people. In still others, it may be your own failings—like an inability to admit that you’re wrong.