Reboot: Leadership and the Art of Growing Up

by Jerry Colonna

But in all cases, allowing yourself to be eaten by the demon that remains—acknowledging how you have contributed to the problem without descending into pointless self-flagellation—turns up the heat beneath the crucible. Without heat, there is no alchemy.

“Why?” I asked inelegantly and in a very uncoachlike way. “Why do you need to be right?” She released a deep breath, a sigh, “Because if I was wrong, my Dad would wipe me out.” And the tears flowed, and the sobs took even my breath away. “I was never sure I was safe. I had to prove myself worthy every night. He would grill me over dinner about my day and the choices I had made. I learned early on that the only way to survive was to be right.” Over the next few weeks, on guard for her need to be right, we carefully went to work changing her approach to the co-founder. For her, the crucible moment came in facing her shame, acknowledging who she really had been. As a result, she got to choose how she wanted to manage, what kind of company she wanted to work for, and who she wanted to be as a leader. We forge our truest identity by putting our heads into the mouths of the scariest demons, the realities of our lives. Only by facing our fears, our prejudices, our passions, can we transform the energy that is the source of our aggression, the source of our confusion, the source of our struggle.

It’s a lesser-known teaching from the one of the Gnostic Gospels, the Gospel of Saint Thomas: “If you bring forth what is in you, what is in you will save you. If you do not bring forth what is in you, what is in you will destroy you.”

Jesus taught a truth: the only choice that doesn’t destroy you is to bring forth who you were meant to be. The alchemy of becoming yourself is the ultimate magic act and fullest expression of leadership.

In all these thoughts I read a steady, consistent wisdom: the wisdom of knowing yourself and your own beliefs and living them. Enduring the alchemical crucible requires developing the capacity to reflect, to turn the pain of the everyday life as a leader into lessons. Every wisdom...

That’s the greatest crucible of all: Learning to bring forth not only what is in you but the whole of you, the glory of you as well as the mess of you. Taking your seat, putting your head into the mouth of all the demons of your life and challenging them to eat you if they wish. Taking these steps allows you to take on more than your leadership; it allows you to sit like royalty, like someone who belongs at the table, deserving of having become the person you were always meant to be.

I know now that, despite what my frantic mind told me then, the constant motion wasn’t a requirement of the job I’d chosen. But producing a weekly magazine with daily deadlines was the perfect job for someone who mistook motion for meaning. Everyone thought I was thriving but, on the inside, I was dying. The non-occupation of my body was obvious to those who cared to look closely. I was busy, I was alert and active, but I wasn’t really present in my life. My eyes darting from one person to another, listening without hearing—I wasn’t really attending to my life, and I wasn’t really connecting to the people who mattered most to me. In so many ways, the world affirmed this way of being. I was rewarded with promotions. Years later, and with the benefit of thousands of hours of introspection, I understand why the world affirmed this way of being. When I moved fast, when I spent my days not truly occupying my life, not standing still, not being real, I found it easier to live in accordance with other people’s expectations. By not standing still, I was able to be the object of everyone else’s projections of who and what I should be. Too busy to live my own life, I took direction from the affirmations of others.

Since the world needed an editorial wunderkind to direct a magazine about technology, I’d readily put aside my love of writing and poetry and took on the mantle of being a technologist. My family, I thought, needed someone who was happy, smart, and capable, and I donned the cape of the good student, the fast-rising executive, who was also everyone’s friend.

Over time, hyperawareness became part of my character, part of me. It became, as I’ve often joked, a superpower. Even today, when I work with coaching clients, I track every bob of the Adam’s apple, every pause in the story (where it occurs, what words preceded and followed it, where their eyes move when they pause), to brace for the coming storm or, even more, to discern what they might need, right then, in that moment. If I give them what they need, says my little boy, they will be saved, and if I’ve saved them, then I’ll be safe.

Even today, the questions I ask can be unsettling. When used well, people on the other side of the question can feel an uncanny and unexpected sense of being truly seen. When not used well, they can feel like they’re facing an inquisition, with my hypervigilance creeping back up and threatening to break the fragile connection between us.

Following that incident, she began helping me connect the dots between my waking-world stresses from things such as the busyness, the hyperawareness, and my propensity to shape-shift to fit the scene, often withholding even from myself my most deeply held feelings. In those weeks, she began pushing me to ask myself one simple question: “What am I not saying that needs to be said?”

Looking back, I realize this time as the beginning of my own radical self-inquiry. My pain helped me realize that I was lost. My soul, no longer content to be “bruised and battered,” took charge of my body and grabbed the attention of my conscious mind. The headaches, which continued even as the self-inquiry began, became a way for my body to say, in effect, “Wake the fuck up.”

For, if I didn’t wake up, my soul was going to drop me to my knee...

Perhaps it was nothing but some general fear that made him question his worthiness. But, nevertheless, the combination of a devastatingly frightening war and a life-threatening illness left the boy with the only answer his mind could grasp: “I am not worthy.”

But panting through work is a lousy strategy. It feeds the anxiety of never enough; it gets in the way of thinking clearly; and it convinces you to mistake motion for meaning.

When you use your position, power, agency and the resources of a company; when you unconsciously bend colleagues, friends, and family to serve your hunger for love, safety, and a sense of belonging—oh, those longed-for lemon drops—you stand in the way of finding a mission that unites everyone in the first place.

You’re not leading when you spend your time trying to outrun your demons, trying to numb yourself to the hungers that come from within. I understand the impulse. It’s a rush to, well, rush from task to task. Moreover, it feeds a sense of superiority: “Geez, my work must be so important . . . look how fast I’m moving!” But it can also feed distrust and disunity; “Look how fast I’m moving,” when said by one who holds power, implies a profoundly disheartening and negative statement: “Look at how slowly you’re moving.”

A deeper look shows that the view is also fed by a tendency to merge what we do with who we are. “We are nothing,” we tell ourselves, “unless we are doing.” Our value as humans becomes dependent on whether we’ve gotten the A in the class, raised the funds our nascent start-up needs, gotten the right accolades from those above us, married the right partner, purchased the right home. I am what I do, and if what I’m doing is fast and, therefore, important, then I must be...

This is the first step to radical self-inquiry; it starts with the courage to be still in the face of uncertainty.

Pema, with a wide grin on her shaved head, settled into a cushion in the middle of the room, the teacher’s seat. She immediately started teaching on the nature of things falling apart. It’s not just the material world, she noted. All things. All. Things. Our wishes, our dreams, our conceptions of who and what we are supposed to be, our sense of self, our sadness, our joy . . . all of it. Falling apart. All the time. Right before our eyes. And that hurts. It hurts because the ego, the fragile persona we develop to combat the slings and arrows of outrageous fortune and our sense of utter unworthiness, believes that only by keeping things exactly as they are, moment to moment, can we be free of suffering. I nodded knowingly;

Keep opening. Stand still. Keep opening and stand still. Open up, get curious, and inquire within.

radical self-inquiry. The process by which self-deception becomes so skillfully and compassionately exposed that no mask can hide us anymore. Radical in that such inquiry is rare. Radical in that it demands that we stop blaming others for our lives. Compassionate in the way a good teacher is compassionate: stop bullshitting yourself.

Slow down. Stand still. Breathe. Let the forest find you. Then you can begin to ask yourself the hardest questions: Who am I? What do I believe about the world? What do success and failure mean to me (and not to everyone else)? What kind of adult do I want to be? And, most helpful, how have I been complicit in creating the conditions in my life that I say I don’t want?

holy grail, profitability, and closed its largest round of financing. But, most important, Tracy no longer wonders why she cares so much about the business succeeding, why she worries so much about failure. She understands her sacred mission and, therefore, her core as a leader. When you learn to stand still in lost and empty times, then the forest can find you and, what’s more, you can find yourself.

When we stand still, we run the risk of remembering who we are. When we stop the spinning, we run the risk of confronting the fears, the demons who have chased us all our lives. When we stop the bullshitting, the pretending that we’re crushing it, that we’ve got it all figured out, we run the risk of being overwhelmed by the realities of all that we carry—the burdens we’re convinced must remain secret to keep us and those we love safe, warm, and happy.

But the spinning prevents us from being who we really are. And perversely prevents the people whom we love, the people we’re trying to protect, from knowing, trusting, and seeing us. I know the wish to be seen. I know the need to show up to be seen.

The most important part of the story was that the treatment she received worked. She’s alive today. But another development shouldn’t be overlooked: In sharing her secret, she created the conditions in which her colleagues could share her burden. She was no longer the self-appointed guardian of their safety; they came together to care for each other.

When leaders, parents, lovers choose to share the reality of their heart, it gives everyone in their lives the chance to know them, to hold them—to trust each other.

We don’t share what’s really going on because we have misguided notions of dutiful caretaking. These warped, childlike views serve only to exacerbate our isolation and, contrary to what we’ve been taught, destroy trust. I often think of the moment after we’ve chosen to stand still as one in which we’re faced with a threshold, a doorway.

But an equally dangerous conceit keeps us from taking our seats as broken-open warriors. That is, an insidious need to see ourselves as the only one capable to lead. So, there we sit, alone in our struggles, burdened by the weariness of all the intellectual and externally generated demands, decrying the inability of anyone else in the organization, the family, the state, or—dare I name it—the relationship, to make a damn decision.

On the one hand, those voices know that, often, we haven’t a clue as to how to proceed. In that knowledge, we live with the fear of being unmasked as an impostor. But, on the other hand, the shame of our not knowing leads us to believe that everyone else does know; everyone else has it all figured out. Then we do something particularly clever: we turn our shameful fear into further evidence of our failings as leaders, as adults, as humans.

We sit atop the pyramid, pretending we know. Our colleagues outwardly bemoan our inability to delegate and share authority and inwardly revel in the relief that that they don’t have to bear the consequences of a poor decision. And everyone plays the shell game.

Carl Jung’s admonitions reverberates: “Until you make the unconscious conscious, it will direct your life and you will call it fate.” We look at our organizations and logically conclude that they are fated to be dysfunctional messes. That we, because of our lack of skill, are fated to fail as leaders. To never feel safe enough, warm enough, or happy enough.

And there we all are, collectively pretending that the product works, the company’s future is bright, and that we all love and trust each other.

Until the leaders embrace the entirety of their pasts, until they acknowledge the collective wish to sweep all conflict under the rug, the conflicts will be driven underground. That doesn’t mean they’ll stay buried. Instead, they reemerge, with others voicing these roles, proxies for others’ resentments and frustrations.

are. As I often say with my clients, a good first step to figuring out where you want to go is remembering how you got here.

This being so, so what?

We need dreams. But willfully ignoring what is true is not the same as dreaming. It’s delusion; and delusion leads to terrible decisions and, even worse, the destruction of trust.

The first act of becoming a leader is to recognize this being so. From that place, we get to recognize what skills we need to develop and who we really are (and are not) as leaders, and to share our truth in a way that creates authentic, powerful relationships—with our peers, colleagues, and families. Grant us leaders who can do this and we just may create institutions that are less violent to the self, our communities, and our planet. To open to the reality of life as it is—this is the greatest challenge of all.

Like so many of us, I cared for both of my parents. So much so that I inherited my father’s gut-clenching fear. “Don’t upset your mother,” entered my body and came out as “Don’t upset the Other.” It manifested as an obsessive vigilance wherein I learned to watch the Other’s every step, every breath, every pause, or furrow of a brow for clues as to what they might say or do next. The vigilance was honed until it became, if you will, a skill, a superpower, all in service to not upsetting the Other.

To belong, to be a member of the tribe, safe from being thrust out of the only home we know, we internalize the task of making sense of the Other. Then, when the Other acts irrationally—or, importantly, with a rationale that we can’t discern, we get ensnared in a logical trap: It’s dangerous to upset the Other. So, our “job” is not only to keep the Other from becoming upset but to bring the Other back to making sense, to not being upset. We become the guardians of those who should be protecting us. We task ourselves with being the firm ground upon which they can stand despite their unsteadiness.

To be free, each of us must come to understand the causes and conditions of our childhood. For these gave rise to the rules by which we, as adults, live—the rules whose original purpose was to keep us safe and that create the conditions we desperately want to change.

Usually, the lack of awareness, the lack of understanding of why we do what we do—coupled with our inability or unwillingness to explain the roots of our rules—convey the sense of irrationality.

In my attempt to feel safe and that I belong, I may inadvertently drive away the very people who could best help me feel loved, safe, and that I belong.

These ghosts in the machine maintain themselves; the coding replicates and mutates, embedding deeper and deeper in the relationships that define our loves and our lives.

The challenges for business partners who are also life partners have a unique expression of this conscious/unconscious dance. One or both partners may feel both manifestations of the partnership (life and business) affected by ghosts from the family of origin, past romantic relationships, and/or past work experiences. One client, a woman

One partner’s understandable impatience and focus on effectiveness strike us as “irrational” because it reminds us of the ways we constantly disappointed a parent. That “irrational” behavior then triggers our shame, causing us to withdraw, hide, or make a process overcomplicated, increasing the Other’s sense of impatience.

buried deep within us is the belief that however miserable the complex may make us, at the very least it tells us we’re alive.

To the child who lives within us and according to the ghosts in the machine, these complex duets feel like home. The drama and the misery tell us we’re safe. We know this pattern because we’ve been tracing it all our lives.

Not only is it completely irrational to argue with the Irrational Other, it’s irrational to try to alter them so that they make sense to me.