Reboot: Leadership and the Art of Growing Up

by Jerry Colonna

“Where in my body does this story live?”

Relief can come, though, when we gaze at this distortion as if seeing the immense sky containing all our positive and negative traits, as well as those of the Other. What is it about your co-founder’s failures as an entrepreneur that disgust and enrage you? Was it perhaps because she saw in him the fact that not only was he not keeping her safe but that she, like him, was failing?

If I had not encountered Mom’s irrationality, if I had not actively but unconsciously sought out time and again the ability to reenact being in relationship with the Irrational Other, I would not have discovered my deeper self and all the rich resources that are waiting for me to deploy.

Journaling Invitations Why do I struggle 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? What’s being said to me that I’m not hearing?

What if being lost is part of the path? What if we are supposed to tack across the surface of the lake, sailing into the wind instead of wishing it was only at our backs? What if feeling lost, directionless, and uncertain of the progress is an indicator of growth? What if it means you’re exactly where you need to be, on the pathless path?

We live in a world that says anything less is failure. Up and to the right, we’re told, is where the happy people are. That’s where the people who never fear, never fail, never struggle live.

Our economy is driven by the sense that here—down and to the left—is awful and if we buy the right soap, drive the right car, build the right company, love the right way, we’ll be safe and loved and happy forever and ever. And ever.

We look to those who seem serene, content—the embodiment of up and to the right—and fail to see the struggles they have lived through. We project onto them our wishes and expectations of reaching that point where all things are at peace and we never, ever have bodily odor. Everyone else’s journey is so much easier. Everyone else’s business is so much more successful. And ...

But a map is a poor substitute for a life lived. The truest guide isn’t the mind of a guru but your broken, scared and scarred, lonely heart. I just wish br...

The irony, of course, is that up and to the right, as appealing as it is when we’re down and to the left, is a place of separation. It’s a place where, were we to achiev...

“What would it feel like to let go of the need to know?” I asked. He paused and felt what it would feel like in his body, not in his mind, if he let go of not only the need to progress but of the belief in progress.

“What would it feel like, in that body of yours,” I continued, “if incremental progress that was directionally correct were enough? What would it feel like to tack across the surface of that lake instead of heading out for the other side, fully intending to make it in the shortest time possible?”

it feels to me that you’d live in congruency with your truest self, where the meaning of your life was a function of the meaning of each day. And each day, an expression of your life.”

“And aliveness, well, I don’t know how we are fully alive when we spend all this energy damping down and rejecting the various parts of ourselves.”

the pursuit of purpose is really a cover for the pursuit of a feeling, aliveness. But aliveness can come about only after integrating even the most shameful parts of ourselves—even the stories of our misdeeds, mistakes, and missteps. Integrating those and learning to forgive oneself.

Later—much later—I read Shunryū Suzuki’s Zen Mind, Beginner’s Mind and realized that coming back to the beginner’s mind is a do-over. “If I allow myself,” I tell Andrew, “then I can have an infinite number of do-overs.” I explained that we can always return to what is, what is really happening, what is truly present. Even more powerfully, if we do that, then we can let go of the e-mail, let go of the missed quarter, let go of the shame of having eaten all those Oreos.

The mentor, Chris, was a skilled chess player and he’d drawn some analogies between chess and life. “He shared this concept of a strategic retreat.” There are times both in chess and in life, when you’re going down a certain path, and you hit a roadblock. And then you realize that the moves you’re trying to make aren’t working out. “At those times, I have to abandon that game plan and re-strategize, and make a strategic retreat and take a different plan of attack.”

Implicit in the belief that the path is not, in fact, pathless is the belief that there’s a wrong fork and, worse, we may choose unwisely, only to regret our lives.

Aliveness comes from living a life of personal integrity in which our outer actions match our inner values, beliefs, wishes, and dreams. I am living my purpose, living with aliveness, when I write, regardless of whether my words are published. This then defines our life’s work not as a path to be discovered (and certainly not by following someone else’s map) but as a way of being, where each day is a chance to live into the command to live with the inner and outer in alignment. Acknowledging the days, weeks, months, and years when we have not lived that way, giving ourselves the do-over, the freshness of beginner’s mind, to rise again and try again.

Work—our careers, our professions, our jobs—is neither the blissful expression of deep purpose nor the dreadful obligation that stands in the way of being ourselves. Work is an opportunity for a daily realignment of the inner and outer, a daily do-over of life expressed with integrity.

Standing still; leaning in; and listening to our children, our partners, our loves, our employees, our customers, and, most important, our own hearts—that is how we grow.

But seen from the vantage point that all steps are purposeful, all of it becomes worthwhile—a glorious, life-giving retort to those who would question our worthiness and lovability.

Journaling Invitations What’s my purpose? Why do I feel lost while I struggle to move forward? How do I grow, transform, and build a life of meaning?

Only now, in my fifties, have I begun to realize that those critical voices—the ones whispering that we are no good, less than, a fake—are, ironically, meant to soothe us and keep us safe. The voice of the inner critic is meant to protect us from humiliation and shame, from the risks of being found out—from being seen as the impostor, the charlatan, we fear we may be—or think we already know we are.

Sometimes our frustration grows out of boredom—familiarity breeding contempt. We live with our creations, day in, day out, and come to hate them. Seeing only the flaws in the creation, we’re simply, painfully facing our deepest insecurities, our deepest doubts about our right to create anything at all.

Most important, though, the frustration is egged on by a whispery, persistent, critical voice asking, “Who the hell do you think you are, as if you could cause this impossible, glorious song to come into being? Why would anyone want to use something you created? You’re just wrong. Everyone knows you’ve no idea what you’re doing.”

we’re reminded of one of our most complicated and intricate fearful belief systems: We will inevitably fail because we are a fraud; and such failure will prove, once and for all, what we suspected all along—that we are unworthy of love, do not belong anywhere, and are, therefore, wholly unsafe.

The vulnerable child in each of us gets caught between the urge to be himself and the fear that doing so will bring shame and humiliation. The temptation to stay unseen (and, thus, safe) is strong.

There’s only one way we can know if our disowned selves are calling the shots. We must take the radical step of inquiring into our selves, seeking to see ourselves with clarity, grace, compassion, and a fierce commitment to cut through our own bullshit. We open ourselves up to ways we’ve been complicit in creating the conditions we say we don’t want.

Worse still, because our denied attributes live just outside our daily view, our conscious mind is convinced the consequences of that denial of self must come from some outside force. It is not my denial of the totality of who I am that causes me distress; it’s always the Irrational Other.

The key to understanding is noticing the reaction. Dr. Sayres, my once-longtime therapist, would say, “If it’s hysterical, it’s historical.” If there’s an outsized reaction—negative or positive—chances are you’re operating from your shadow. Or, even more precisely, grabbing an attribute out of the long black bag and flinging it onto the people in your life and blaming them for your internal discontent.

For one person, it may be the admonition to always put others before oneself. That’s a problem, of course, when such movement isn’t rooted in a healthy, life-giving altruism but stems, instead, from the belief that anything but the total negation of the self risks incurring the wrath of those around us—those charged with keeping us well and whole. For another, though, it might be to always put yourself first, lest you’ll be left with nothing but scraps from the family dinner.

For many, that place where we’ve come to think we belong has become stultifying; it’s where we are small, unseen, unsure, and unwilling to claim our strengths, our capacities, our courage, our leadership. We are frozen by the belief that it’s just too dangerous to reach into the black bag and grab hold of the disowned, dismembered parts of ourselves.

You survived. You’ve grown into an adult, capable of grasping the ways these successful survival strategies outlived their usefulness. Your Loyal Soldiers did a fine job. They just don’t know the war is over. While the Crow may pester us, he loves us and wants to keep us safe from the pain of humiliation.

In loving the gifts of the Crow, we end up negating the very threat about which he warned. Our soldier, so desperate to make sure we don’t end up alone, told us over and over to hide our doubts. By admitting our doubts, we get to enjoy one of the great gifts of being human: belonging.

In loving his gifts, I learned to love my Crow. In loving my Crow, I’ve begun the painful work of retrieving the parts of me from my black bag. The act of leading and the art of growing up depend on each of us, finally, eventually, repeatedly sorting the unsorted baggage we’ve been traveling with since childhood.

Trace the roots of a leader’s boredom with a well-functioning team and the desire to shake things up, and you may find a fear of complacency that would allow the family’s enemies to catch them off guard. Or explore a CEO’s sexual relationship with her co-founder, and you may stumble upon a commitment to self-sabotage to ensure that she never outdoes her father.

“What would happen if you let go of the belief in your fundamental brokenness?” How would your life be if you didn’t need to believe you were broken to feel loved?

How would the experience of your life change if you could rest and trust that life’s goodness isn’t always necessarily followed by calamity?

How would it feel if we trusted that no matter how bad our actions, those who truly know us—know the person whom we’re convinced only the Crow and our Loyal Soldier know—would love us?

How will our leadership change when we see that there is no “them” and that there is only us? How will our communities shift if we’re able to stop seeing our leaders as objects of our projections but as merely brokenhearted warriors striving to be a little bit better each day?

This, then, is the highest calling of the warrior-leader: to take our seats as humans and build humane companies, communities where it is gloriously safe for others to be human. The leader—the person living into the immense sky of that honorific—is

We get to become the adults we needed when we were children.

“What am I not saying that needs to be said?”

Consider the ways the unsorted baggage of your life has kept you from not only speaking but being heard: What am I saying that’s not being heard? Consider how you’ve silently seethed, waiting to manipulate the team to prove that you were right all along.

The commitment to sort the unsorted baggage turns leadership into a journey of self-actualization. With that, work becomes not the impediment to our lives, not the repeated manifestation of our inner self-loathing, not the thing that gets in the way, but the way we can live out our lives as they were meant to be.

False grit awakens the Crow. One of its implicit messages is that we should persist to prove that we aren’t as unworthy as the Crow claims. Yet a second implicit message is that if we feel like shit after being punched in the face, it must mean that we are shit. The only way to escape the grip of false grit is to recognize its falsity.

True grit acknowledges the potential of failure, embraces the fear of disappointment, and rallies the team to reach and try, regardless of the potential of loss.

Heartbreak is universal. Keeping one’s heart open to the suffering of others, even upon the failure of our companies and the death of a tree, is rare and the truest grit of all.

Journaling Invitations How has my heart been broken? What have I learned about myself as a result of that heart being broken? In what ways do I embody resiliency? What does a life of peace and equanimity feel like?