Reboot: Leadership and the Art of Growing Up

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.

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.

...I helped found an executive coaching company, Reboot, to help folks do just that: to share what’s really going on.

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.

Exploring that space between memories and the stories we create allows us to emerge as the leaders we were born to be. 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. Still, when I sit well and quietly, I can see a way through the puzzle, especially when another is blocked. I laugh as I recall that one of my favorite childhood pastimes was completing books of mazes. I like working my way out of mazes; I am good at it.

I plowed to unearth last year’s reasons— 

The farmer plows to plant a greening season - ‘Harrowing’ by Parker J. Palmer

When I was a boy, I wasn’t often seen. I was looked after, cared for. I was held and comforted, especially after some painful experience. But I wasn’t often seen. I was a good boy when inside I wanted to rage. I tried hard, all the time, when inside I wanted not to care. I was compliant, and therefore complicit, in not being fully appreciated.

The smells of coffee, roses, and lemon drops signal I’m safe.

Money was safety. The pursuit of money, then, became a chase for safety and a flight from poverty, chaos, and the streets of my childhood.

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

Over the coming weeks, we’d talk about what was happening to me. Being there but not really being there. Living a life of there-but-not-there hurt like hell.

Ghosts of our pasts—our grandparents and their grandparents as well as the ghosts of their lives—inhabit the frames. They and their beliefs, interpretations of scenes, words, and feelings haunt the frames of lives as surely as the roses, figs, and lemon drops of our present daily lives do.

Tracing forward from these remembrances of things past gives us the chance to re-experience and reframe these beliefs. Doing so liberates us from the confounding forces we label as fate, destiny, or—even more frequently—the other person’s “fault.” We will never sort through them all, of course, but what we don’t sort through impedes our happiness. It tricks us into using the rest of our lives—and the people we love, the professions we choose, the organizations we lead—to try to close the gaping wounds from childhood.

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

I am not what has happened to me,’ taught Carl Jung. ‘I am what I choose to become.

It [choosing] 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?

Radical self-inquiry is how we learn to become more of ourselves, more like ourselves, more authentic. More human.

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.

It would be easy to paint my realization around work as sacred duty as something sprung from some genius within. It was not. It sprang from exhaustion, from being lost myself, from having nowhere else to turn with my own suffering.

My noble truth, I’m humbled to admit, didn’t come from within me. It came from the simple act of choosing to continue to live.

My friend, the poet Pádraig Ó Tuama, says, “To live well is to see wisely and to see wisely is to tell stories.” I’ll go further; telling stories helps us live well. Telling the stories of our lives, telling the stories of the lives around us, helps us make sense of the world and, in the end, be wise.

Wise and sacred. Years ago, as I was beginning to distance myself more fully from that day, in 2002, when I teetered on the edge of my own Ground Zero, I was alone, naked, in a desert in southern Utah. On the second day of a three-night water-only fast, as part of a fourteen-day quest, I settled into the meaning of the true name I’d be given: Holder. Holder of Stories of the Heart. Holder of my stories. Holder of the stories of those I love. Holder of the stories of the brokenhearted leaders who come to me.

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.

I’m sitting on a picnic table while Chad Dickerson sips from a bottle of beer. Of course, of course, of course . . . the night would be sweet and bitter. Tomorrow Chad will announce to the world that he’s been asked to step down as CEO of Etsy, the online marketplace for handcrafted goods he had led for the past six years.

What would Obama do?’ we took to asking each other in moments when his heart flagged. How do you handle yourself on the way out, regardless of whether you were given the respect you deserved?

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.

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.

His [Steve Kane] crucible moment wasn’t merely that he correctly foresaw that going public wasn’t right for Gamesville. And it wasn’t merely that he knew that a bird in his hand was worth more than the millions in the bush. It’s that he had stayed in touch with where he was from and what had formed him. He remembered that he was the son of an entrepreneur, a scrappy, end-the-day with-more-money-than-you-began entrepreneur. His dad and my iceman grandfather would have loved to play cards together.

I received a powerful lesson in facing reality when something is failing, in trusting the team, and in holding oneself steady. I learned the power of the warrior pose.

There’s a story told of Milarepa, the great Buddhist saint and teacher. It’s said that one day he left his meditation cave to gather firewood. When he returned, the cave was filled with demons. I like to think of them as little bats, flying around the cave, making a nuisance of themselves.

Unsure of what to do, he begins to wave his arms at them, trying to get them to leave the cave so that he can go back to his meditations in peace. But they don’t leave. Instead, they multiply. So, Milarepa becomes very clever. He says to himself, “I will teach them the dharma, the teachings of the Buddha.” And the demons all quiet down and sit still. But Milarepa notices that, while the demons are quiet, they haven’t left, and their number hasn’t diminished.

Becoming slightly wiser and mildly more adult, he asks the demons, “What are you here to teach me?” One by one, the demons disappear.

Pleased with himself, Milarepa goes back to his meditation but realizes that one demon remains, a big, hairy bloodcurdling demon with big green eyes and bloody fangs. Shaking, terrified, Milarepa puts his head into the mouth of the demon and says, “Eat me if you wish.” With that, the demon vanishes.

Surrendering to the demons that torment you and your organization doesn’t mean abdicating your responsibilities to manage. You are still responsible for dealing with the reality of what is. You are still required to have the strong back, for example, of knowing when you’re wrong.

I don’t care who’s right,’ I yelled in frustration. ‘The only thing we have to focus on is what are you supposed to be learning from this.

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.’ - The Gospel of Saint Thomas

The alchemy of becoming yourself is the ultimate magic act and fullest expression of leadership.

Hello to humans who occupy the fullness—the glory and the mess—of their lives. Hello to broken-open-hearted warriors. Hello to the leaders this broken world needs most. Hello to being the leader you were born to be. Hello to warriors with broken-open hearts.

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.

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.

These traits—insatiable curiosity, a driving need for speed, the ability to read people, and the ability to anticipate problems before they arise—led others to view me as a rising star, a wunderkind. Quite a transition for a guy who, only a few years before, had been a psych patient in a locked ward.

And yet, even as I progressed in my career, the beads-of-sweat years continued.

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 knees, writhing in pain.

So much of that time remains indistinct, but I remember the two books my sister, Annie, recommended to me: Pema Chödrön’s When Things Fall Apart and Parker’s Let Your Life Speak. Both books, as well as Sharon Salzberg’s Faith, flew with me to Arizona from New York.

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

... she [Ani Pema] refers to meditation as the act of stripping away delusion and being with what is, simply and wholly.

I spent the entire year eating my lunch in a bathroom stall to avoid the kids who were making fun of me.’ Lunch, for Tracy, meant humiliation, sadness, and pain; and the only way to be safe was to be alone. She wept as she remembered that time. She sobbed as she reentered those feelings. She sat still and felt the past wash over her.

‘Tracy,’ I said, calling her back to the present. ‘Tracy, what does your company do?’ Wiping her nose, she looked puzzled. ‘Tracy, tell me what Chewse does, what’s its mission?’

‘We provide nutritious lunches and snacks to other start-up companies,’ she answered really puzzled. ‘And why is that important?’ I asked. Smiling and laughing, she replied, ‘So that people can get out from behind their desks and gather together for lunch . . . so that lunch isn’t painful but loving. So that no one needs to eat alone to feel safe.

In the months that followed that realization she changed the company’s mission statement to include the word love and added a heart to the logo. She embraced the painful roots of her company’s founding, realizing that Chewse wasn’t merely an attempt to ‘disrupt the food delivery business’ but an opportunity to give others what she herself had lacked: community.

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.

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.

Well, would you rather they stay for a lie?’

He told the truth and they stayed. Not only did they stay, but they volunteered to take pay cuts to help the company manage its cash.

Another of 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.

Stopped in my tracks, I looked around the room and guessed again: ‘How many of you grew up in homes with a lot of yelling?’ Twenty-three of the twenty-five employees raised their hands.

The problem wasn’t conflict avoidance, I pointed out. The problem was fear: leftover childhood fears. Fear of the consequences of anger. And because the most senior people had never acknowledged the ways their leadership styles, the choices they made as leaders, were rooted in old patterns, the patterns were replicated and amplified.

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.

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.

Like everyone, I have millions of lines of such code, operating instructions for how to navigate the world and relationships, which add up to hundreds of ghosts in the machine of my mind.

Her impulse, like the impulse of nearly all my clients, was to analyze the Irrational Other to figure out what was wrong with them so that they could be fixed, changed, made better. That was often a cover for another impulse, which was to figure out what was wrong with the Other so that they could justify the ending of the partnership, overcoming guilty feelings.

As in so many relationships, this complex interweaving of self and Irrational Other relies on a combination of psychological transference. The Irrational Other becomes a stand-in for someone in our lives, usually from our past. They become a screen onto which we project our negative and positive qualities, those we can’t allow ourselves to acknowledge as our own.

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.

We ask: How, indeed, have I been complicit in creating the conditions I say I don’t want? More to the point, what am I willing to give up to stop being complicit?

Radical self-inquiry is the path to seeing habits and patterns. Questions that drive us toward that insight are endlessly helpful:

• ‘What parts of me are being projected onto the other person?’ 

• ‘How do I reclaim those parts of me?’ 

• ‘What do my reactions say about me?’ 

• ‘Why do I do what I do?’ 

• ‘Why do they do what they do?’ 

• ‘What need for love, safety, or belonging might they be trying to meet with their irrational behavior?

See the stories you’re telling yourself about the other,’ I continued. ‘What do those stories reveal about the stories that you might have been holding quietly, silently, for all your lives?

How am I complicit in creating the conditions I say I don’t want?

I suggested she use a tactic I learned from training in nonviolent communications: OFNR. O, for observation of undeniable fact. F, for feeling and assumptions about motivation and other interpretations of facts. N, for needs—individual as well as collective needs. R, for request . . . a request for an alternate way of behaving.

‘Start with the facts,’ I told her. He left the office earlier than expected and he did so without telling anyone. ‘Then,’ I explained further, ‘share how his doing so made you feel’ —in this case, disrespected. ‘Then share with him the collective need . . . that everyone in the company has a need to feel respected. Then,’ I told her, ‘make a request. If he needs to leave early, ask that he let you know in advance.

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 broken-open hearts weren’t so damned painful.

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 achieve it at all, we’d find ourselves utterly alone.

At the end of the rafting trip, we were lifted from the bottom of the canyon by helicopter. Two hours later, I sat at McCarran Airport, stunned by the incessant ding, ding, ding of slot machines, cascading coins, and dreams of a better life. I’d left the canyon, but the canyon never left me.

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?

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 doovers.” I explained that we can always return to what is, what is really happening, what is truly present.

I was speaking by satellite phone with my client and friend, the polar explorer Ben Saunders, as he was trying to retrace his friend Henry Worsley’s path across Antarctica. The sastrugi—the parallel wavelike ridges carved by the polar winds into the surface of icy snow—were tougher than he’d imagined, and he was close to giving up.

The possibility of giving up wears on him. In 2016, his friend, his mentor, Henry, stopped one hundred and twenty-six miles short of his goal of being the first person to cross the Antarctic peninsula unaided and unassisted. Overcome by exhaustion and airlifted out, Henry died in Chile. Ben’s trying to complete the journey, to finish his friend’s quest. He’s been cursing each ridge, he told me; each ridge means he can’t really ski but must painfully step up and over.

The elders in the community would share some insights, some wisdom,’ he continued. ‘There was one that a friend of mine, a mentor, gave that has stuck with me for a really, really long time.’ 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.

One day, an e-mail arrives. ‘I was reading a blog post by Fred Wilson,’ wrote Khalid Halim. In the post, he’d written that I was the best CEO coach he knew. Khalid explained that he wanted to be a coach and wondered if I would be willing to help him. At that point, I was overwhelmed. ‘I don’t have time for another client,’ I said to myself petulantly. My old, old, old sense of too many people wanting too much from me rises. Yet the sincerity of his wish stops me, and I read his note again and again. He wants to help others, I see. I think I see his heart. I say yes to an early-Saturday-morning call, every few weeks. And yet today, he’s one of my partners in this heart-filled enterprise where we take closed, scared, and scarred leaders and help their hearts break open and for warriors to emerge.

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.

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.

The pain of hating our own creation is a consequence of our investing too much of our sense of being into the company, the product, the creation. When we hang our sense of self on the whisper of an idea; when we unwittingly insist that our love, safety, and belonging depend on what we do and, most important, how others feel about our feelings, our actions, and our work; then we leave little space for anything other than bitter, existential suffering.

As Carl Jung notes, ‘Until you make the unconscious conscious, it will direct your life and you will call it fate.’ Jung goes on to assert that humans place the positive and negative attributes of our character—our feelings, beliefs, the things we typically define as strengths and weaknesses; anything that conflicts with our sense of who and what we are supposed to be—into our personal shadow. This allegorical shadow operates the way our true shadow does—behind us, just out of our direct sight, where we have but the vaguest awareness of its existence. We glimpse it only by craning our necks.

... those qualities and aspects that are incompatible with our sense of who we need to be to be loved and to belong get rejected, disowned, and placed in an unlit, unseen part of our consciousness; forever denied and angrily, anxiously, guiltily defended against.

These attributes continue to exist, marinating in our lived experiences, brewing into a cocktail potent enough to knock us and those we cherish onto our asses. In being denied, these attributes grow in intensity; periodically, explosively, often tragically, these attributes step out of the shadow and into the scenes of our lives in troubling and troublesome ways.

There’s the leader whose childhood was marked by poverty and deprivation and, in a bid to feel safe, nurses ambition and desperate cravings to prove all the doubters wrong. But, given the strictures of their childhood or family structures, given the risk of expulsion from the only tribe they may ever have known, they bury that ambition, labeling the wish for money as “greed” and placing it out of sight, in their shadow, over their shoulder, into what the poet Robert Bly dubbed the “long black bag” we drag behind us.

Or the CEO whose brilliant ways threatened her standing in middle school, and so, more than merely denying her intellect, she actively rejects any challenging books or squirms in a classroom seat, lest her light be revealed, her artistry manifested, and her place in the family threatened. Unconsciously she internalizes the isolation caused by the middle-school bullies, remaining cut off from potential allies and isolated from colleagues. All of it—all the positive, all the negative aspects of our character that make us stand out, be different—is thrown into that long black bag.

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.

And, more telling, when does our typical pattern of equanimity get so quickly and readily disturbed?

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.

More important, I explain, it’s proof that you learned the most important skill any human needs: survival.

It was on that trip home that I read depth psychologist Bill Plotkin’s Soulcraft and recognized my Loyal Soldier, who’d dedicated his life to saving me from being cast out, keeping me safe, and making me feel loved.

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.

All Loyal Soldiers then have one basic task: to keep us safe from the wars that raged in our childhood. No matter how awful these strategies have come to make us feel as adults, they were brilliant in their own ways.

By admitting our doubts, we get to enjoy one of the great gifts of being human: belonging.

Power in the hands of one afraid or unwilling to look in the mirror perpetuates an often silent, always seething violence in the workplace. Worse still, when a leader leads from his or her shadow, the dismembering havoc is perpetuated down the line until the company, the tribe, the community simply assumes this is how life must be.

Experimentation creates tension. It carries a risk of failure. Moreover, when such experiments succeed, and companies innovate, people have to integrate change. The potential of failure and the need for change can terrify people. It can feel like the conflicts from their childhood that folks were programmed to avoid.

But what do we do to our organizations when we define ourselves by the existence of the Other? When we presume that the competitor in the lane next to ours is wrong, bad, or a threat, we are allowing our deepest fears about our own inadequacy to stand in as our ‘vision statement’ and ‘strategic plan.’ An unintended, whispered consequence is that our colleagues—our friends down the hall with whom we built this thing, this product, this service, this company—may fear that they, too, are ‘them.

What if, instead of projecting the best of ourselves onto the Other, we took back that part of ourselves with love and laughter? What if, instead of projecting our banished dangerous rage onto the Other, we were to take it back and welcome it in? What if we saw the Other as a mirror and a pathway to our growth?

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 called to use the gifts of inquiry to see which dragons we may be running from and which princesses we may be running toward. To notice with loving attention if we’re over-indexing on either the soft, open front of the warrior or the strong back. For humane organizations are those that sit still, staying firmly in that place between the strong back of good processes, fiscal clarity, firmly held beliefs and values and the soft, open heart of wisdom, empathy, and fierce gentleness.

His question in response to my exploration of how those things we’ve tossed into our shadow have a deep power that, when accessed with compassion and skill, can drive our creativity. He cried quietly when I noted that his struggle must be so painful.

While heartbreak is the early step on the path to equanimity, fear is the stumbling block leading to the sin of inaction. Fearing the dark rides of the Coney Island of the mind, we choose not to act. Fearing Paris, we stay close to home. Fearing broken skis, failed businesses, and the scars that come from skinned knees, we stay small—listening more to our Loyal Soldier’s fear-filled and protective whispered warnings than to the quickening thump-thump, thump-thump, thump-thump of a heart that knows how it’s meant to be.

As leaders, our task is to feel our way through the heartbreaking, fear-inducing roller-coaster rides, learning not to vomit with each rise and dip. Then, just as we’ve built up the resiliency needed to recover from each nauseating dip, we find that we no longer have the need for it. The little train that makes up the Cyclone comes to a stop and we finally, wisely, get off the ride.

When her pillar-of-the-community father left the family (no doubt in pursuit of his own love, safety, and belonging), she took on the burden of caring for her mother and brother. Yet another hallmark of the entrepreneur; yet another instance of premature promotion into adulthood.

In one of the many songs that define his teachings, a student asks the master, ‘I can contemplate the sky, but clouds make me uneasy. Milarepa, tell me how to meditate on clouds.’ Tell me, in effect, how I can achieve equanimity when the clouds get in the way of my seeing the empty, immense sky.

The student goes on and asks again about the difficulty he has in meditating on the calm beauty and serenity of the sea when all he can see is the waves.

Wise Milarepa, the young boy who turned his suffering into violence only to learn how to truly be with his pain, answers, ‘If the sky’s as easy as you say, clouds are just the sky’s play.’ He then adds that ‘waves are just the sea’s play.’ We can’t separate the clouds from sky or the waves from the sea. There is no space between our thoughts, however painful they might be, and our mind. ‘Let your mind stay within the sea,’ he advises, and so, too, ‘Let your mind stay within your mind.

So much of what I’ve learned about growing up came from learning to lead.

In fact, the process of becoming me made me a better leader. The two processes, becoming a leader and becoming ourselves, are intertwined and interdependent; better leaders are better humans and better humans are better leaders. Leadership lessons, then, are, at their core, lessons in humanity.

Sometimes the belief systems that are most difficult to overcome aren’t the ghosts in the machine of our childhood. Sometimes the most difficult belief systems fall under the rubric of “conventional wisdom.” Conventional wisdom, for example, dictates that, in our process of becoming warrior-leaders, we focus on the hard things. Big rocks, folks say knowingly. ‘Break down the big rocks and then focus on the little rocks.’ But how do you discern a big rock from a little rock?

What makes all of life complicated, and not just hard, is this unwillingness to do the work that’s ours to do; our unwillingness to live the examined life.

As my friend and mentor Parker Palmer, teaches, ‘Violence is what we do when we don’t know what to do with our suffering.’ Violence to our planet, violence to our communities, and violence to ourselves are what we do when we refuse to look inward and work with the heartbreak of the everyday.

...I’d say that a leader’s subject is himself and the world and ‘it requires every ounce of stamina he can summon to attempt to look on himself and the world as they are.

My co-founder, Ali Schultz, taught me the wisdom of horses. Horses, with their supernatural ability to use their limbic nervous systems to discern truth and congruency, do not base their choice of the leader of their herd on strength or intellectual wisdom. Nor is their choice based on which member might keep the herd safe from a predator wolf. They choose the one who feels the group best and who cares the most. They choose the horse— usually a mare—who is most capable of holding that care in a way that calms the whole group. They’re marked by the attunement to the inner and outer needs of those they have the honor to serve and lead.

This being fierce with the reality of what is requires the bravery to ask of oneself three challenging and yet powerfully liberating questions:

• What am I not saying that needs to be said? 

• What am I saying (in words or deeds) that’s not being heard? 

• What’s being said that I’m not hearing?

Here are your spades, questions to ask yourself so that you might reboot your leadership and move forward on your journey of growing up.

• How would I act were I to remember who I am? 

• What choices would I make, what actions would I take, if I regularly said the things that needed to be said? 

• Who would I become were I to be fully, completely, and wholly heard? 

• What is it that I wish the people in my life understood about me? 

• Who would I be without the myths I’ve told about myself; the stories that took hold when I was yearning to feel love, safety, and belonging?

So often I’m called in to help lead conversations about mission, value, and purpose. When, really, the only questions that matter are those that tell us who we are and wish to be.

• How would our organization respond were we to hear all the things that are being said, regardless if they are being said with words or deeds? 

• What does it mean to be a leader at our organization? 

• What does it mean to be grown, a fully actualized adult? 

• How would we feel if our children were to work for the company we’ve created or the team we lead? 

• How has the unsorted baggage of what has happened to us shaped who we are as leaders? 

• When our employees and colleagues leave our sides and our company, what do we want them to say about our time together? 

• What do we believe to be true about the world? 

• What do we, as a community of people working toward a common goal, believe the world needs?

For me, this has meant integrating words into my daily life. For the man I am meant to be is someone who understands the liberating power of words; others’ as well as mine.

Writing,’ notes the poet Terry Tempest Williams, ‘requires an aching curiosity leading you to discover, uncover, what is gnawing at your bones.

I can’t think of a sadder way to die than with the knowledge that I never showed up in this world as who I really am. I can’t think of a more graced way to die than with the knowledge that I showed up here as my true self, the best I knew how, able to engage life freely and lovingly because I had become fierce with reality. –Parker Palmer, On the Brink of Everything.

Such remembering, the late poet John O’Donohue reminds us, is an essential element of adult leadership. ‘When someone fails or disappoints you,’ he writes, ‘May the graciousness with which you engage / Be their stairway to renewal and refinement.

The goal of this book was to act on you as a coaching session might. The goal was to give you something more useful than answers: the ability to work with the questions, the uncertainties, and the doubts that spring from the dips in life. To show you that you could arrive at your own answers; answers that would be authentic and true to you. At some point you may find doubts arising. At some point, if you’re at all like the rest of us, you may ask yourself if you’re even able to participate in that true adventure of growth. If so, know that the answer is a resounding yes. But there’s a catch. It’s yes, but only if you’re willing to put your head up to the mouth of the demon. In this case, the demon is the underlying lack of belief in your capacity to lead. The demon’s teeth are powerful questions, the answers to which frighten and startle you, accelerating your growth.

Here’s to the imperfection of memory. Here’s to the way we ‘fiction and fable our lives,’ as the poet Pádraig Ó Tuama, says, ‘in order to tell of things that are more than true.