Reboot

Have you ever wondered why some leaders seem to carry a quiet confidence while others burn out chasing success? In Reboot: Leadership and the Art of Growing Up, Jerry Colonna challenges the traditional definition of leadership by asking a deceptively simple question: how can we lead others before we truly understand ourselves? Colonna, an executive coach and former venture capitalist, argues that becoming a great leader is inseparable from becoming a mature, self-aware human being.

His core conviction rings through every story and reflection in the book: better humans make better leaders. Leadership isn’t about mastering techniques or acquiring power—it’s about the inner work of growing up, confronting one’s fears, and learning radical self-inquiry. To lead with congruence, grace, and resiliency, Colonna asserts, you must first take your seat as a full adult—capable of being honest, vulnerable, and grounded in truth rather than performance.

The Inner Work of Leadership

Where most business books emphasize strategic thinking, Colonna emphasizes personal excavation. Leadership begins by peeling back the layers of self-deception. His coaching practice, Reboot, is founded on a central methodology called radical self-inquiry—a process of examining not only what you do but why you do it. The author invites leaders to ask questions that pierce their defenses: How have I been complicit in creating the conditions I say I don’t want? What am I not saying that needs to be said?

He echoes Carl Jung’s observation that “I am not what has happened to me; I am what I choose to become.” Through that lens, Colonna treats leadership as a mirror reflecting our internal state. Our companies, our teams, and even our relationships serve as canvases onto which we unconsciously project unresolved childhood narratives—stories of safety, love, shame, belonging, or fear of abandonment. By turning inward to face the wreck of our own past, we can retrieve the treasure hidden within it. (Comparable thinkers such as Parker Palmer, Sharon Salzberg, and Pema Chödrön have similarly argued that adult wisdom stems from integrating rather than suppressing discomfort.)

Elevating Darkness Into Light

Colonna calls this process “elevating darkness.” Rather than trying to fix ourselves through ambition or distraction, true growth requires standing still—listening deeply to your heart and to the hearts of others. He recounts moments of sitting in silence, from his near‑suicidal days at Ground Zero after 9/11 to his time fasting alone in the Utah desert, when he discovered that stillness is not an absence of action but the precursor to transformation. “Standing still and powering down,” he writes, “allow us to reboot our core operating system.” Leadership is the art of learning to dwell in uncertainty, the “not‑knowing” space that forces us to grow beyond strategy into humanity.

This inner transformation is not easy. As Colonna confides, writing this very book “kicked his butt.” Yet, the act of vulnerability is precisely what makes him a credible guide. He offers no formulaic “five steps to success.” Instead, we see leadership as lived experience—messy, heartbreaking, courageous. Through stories ranging from CEOs fired from their own companies to entrepreneurs confronting shame, he illustrates that only by facing our own wreckage, our pain and fear, can we lead with steadiness and compassion.

From How to Why

One of Colonna’s defining contributions is his “formula” connecting practical skills with inner awareness. He teaches that organizations often fixate on the how—how to hire, how to scale, how to raise capital—but they ignore the why and the who. Practical skills are essential, yes, but without clarity about personal motivation, they become hollow. Radical self-inquiry reveals not only why we pursue success but which unconscious forces drive that pursuit. Sharing experiences with peers removes the lonely isolation that plagues many leaders who fear being “found out.” True leadership, then, arises from the realization: you are not alone.

Leadership as a Journey into Adulthood

Ultimately, Reboot reframes leadership as a spiritual and psychological rite of passage—from adolescent striving to adult equanimity. Growth demands heartbreak; equanimity is born from resilience. Colonna’s Buddhist influences shape his vision of the leader as a broken‑open‑hearted warrior—someone strong‑backed but soft‑fronted, capable of facing reality while remaining compassionate. Through each life story, he teaches that the art of growing up is not linear or comfortable. It is cyclical, messy, and deeply human.

In the chapters that follow, Colonna guides readers through this journey step by step—from understanding the formative stories of money and safety (Chapter 1), through facing failure and loss (Chapters 2–3), to embracing relationships, purpose, and mortality (Chapters 5–9). It’s a manual for anyone who suspects that work can be more than busyness and success can be more than accumulation. If you’ve ever felt like life’s demands are pushing you toward yet another burnout, Reboot reminds you that leadership is the practice of growing up—of choosing every day to become the adult you were meant to be.

At the heart of Colonna’s coaching philosophy lies the practice of radical self-inquiry, an intentional, courageous form of introspection that exposes self-deception with compassion. He defines it as “the process by which self-deception becomes so skillfully and compassionately exposed that no mask can hide us anymore.” If traditional leadership asks what actions will make you successful, radical self-inquiry asks why you feel compelled to act at all.

The Whiteboard Formula

In one memorable scene, Colonna sketches a formula on a whiteboard while teaching new CEOs. He writes “Practical Skills + Radical Self-Inquiry + Sharing with Peers = Enhanced Leadership & Resiliency.” At first, everyone expects a checklist of how‑to tactics. Instead, he invites them to admit what’s real—to confess fear, loneliness, and confusion. As each person claims vulnerability, others exhale in relief. This communal honesty reveals a simple truth: the feelings may be true, but the facts may be inaccurate. They are not alone. (Comparable to Brené Brown’s research on vulnerability and connection.)

Knowing the Wreck Itself

Radical self-inquiry is not comfortable analysis. It’s an excavation. Colonna borrows from Adrienne Rich’s line, “Not the story of the wreck but the wreck itself.” You don’t merely describe your pain—you dive into it. Only by revisiting the emotional wreckage of childhood patterns can you locate the forces shaping your adult life. Many leaders, he observes, grew up in households marked by parental absence, poverty, or premature responsibility. As adults, they unconsciously reproduce those patterns at work, hiring others with similar wounds or chasing success as proof of worth.

Courage Over Comfort

Radical inquiry requires courage over comfort. It asks you to face what you’d rather bypass—the shame, the hunger, the hidden grief. When you slow down enough to notice how you really are (Colonna’s signature question: “How are you? No, really, how are you?”) you reclaim your humanity. This authenticity strengthens resilience. Leaders who inquire within discover they can withstand crises not because they’re invincible, but because they’ve befriended their own fears. It’s a continual practice: standing still, listening, sharing honestly, and remembering that transformation begins by telling the truth.

Leadership, as Colonna describes it, is a crucible—a vessel in which pain and pressure transform character. Borrowing leadership expert Warren Bennis’s phrase, he shows how adversity “cooks” us. When life doesn’t unfold as planned—when a company fails or a public firing shatters identity—it exposes who we are beneath ambition. Only by leaning into that heat can we emerge stronger and unbroken.

Chad Dickerson’s Crucible

The story of Chad Dickerson, former CEO of Etsy, grounds this idea. Fired from the company he built, Dickerson sits with Colonna on a Brooklyn rooftop, grieving and questioning his worth. Through months of coaching, he evolves from anxious executive to warrior leader—someone who “takes his seat” with dignity. Dickerson learns to hold both strong back and open heart: the strength of firmness and the softness of compassion. This stance—borrowed from Buddhist teaching—illustrates that true adulthood isn’t armored toughness but resilient openness.

Eat Me If You Wish

Colonna recalls the Tibetan saint Milarepa’s story: when demons fill his cave, he first instructs them, then finally kneels and says, “Eat me if you wish.” That surrender eradicates fear. Likewise, warrior leaders face their own demons—failure, shame, envy—by accepting them fully. The warrior stance transforms fear into clarity. It doesn’t mean abdication; it means recognition: if I’m wrong, I will learn. If I fail, I will grow.

At the crucible’s core, growth arises from integrity. Leaders like Steve Kane (Gamesville) and Alex (a start‑up founder) succeed not by brilliance alone but by moral steadiness—doing what’s right even when risky. Kane accepts a buyout against pressure to go public; Alex halts a failing project, facing investors with honesty. Their resilience and self‑trust come from radical inquiry into why they lead. They act not out of fear or greed but congruency with self. The warrior’s transformation reminds you that pain is not punishment—it’s the heat that reveals the gold.

Most people equate progress with motion. Colonna confesses that he did too—until his body rebelled. From teenage suicide attempts to the cluster headaches that struck him during triumph as a venture capitalist, his story teaches that hyperactivity hides emptiness. The cure is stillness. Standing still, he discovered, doesn’t mean apathy; it means being present enough to hear what life wants to teach.

From Doing to Being

As a young man, he raced through subway rides and workloads until exhaustion. External success masked internal depletion. When illness forced him to stop, his therapist asked the haunting question: “What are you not saying that needs to be said?” That inquiry began his practice of quiet introspection. He realized his busyness had been a survival strategy—a way to earn safety and love through constant proof of worth. Slowing down exposed loneliness but also freedom.

The Power of Stillness

Pema Chödrön’s teaching that “things are always falling apart” became Colonna’s mantra. He recalls sitting in meditation retreats with Ani Pema, hearing her mischievous reminder that even your understanding of impermanence is impermanent. To achieve peace, you must stop the spinning, silence the pitch, and ask why life feels unbearable. Standing still allows “the forest to find you,” as poet David Wagoner wrote. For leaders, this means pausing long enough to notice burnout, fear, or false bravado, so authentic motivation can surface.

Stillness and Creation

Stories like entrepreneur Tracy Lawrence, who transformed childhood shame into business purpose, show the creative power of stillness. When she stopped striving and listened inward, she discovered her company’s mission—to make lunch a moment of belonging, not isolation. Stillness reconnected her to childhood pain and turned it into service. Colonna’s lesson: when you cease fighting impermanence, your leadership gains depth. Movement without stillness is chaos; stillness without movement is death. The art is to balance both—to rest long enough to be real before you act.

Leadership often tempts us to hide behind masks of control. In this chapter, Colonna urges you to remember who you are—not the idealized success persona, but the unfiltered human behind it. Forgetting leads to isolation, fear, and impostor syndrome; remembering restores trust and authenticity.

The Power of Vulnerability

At his coaching boot camps, leaders share truths they’ve never voiced. One woman reveals she’s dying of blood cancer, afraid investors won’t fund her. By speaking her reality, she gives others permission to be real. Her organization responds with compassion—the team rallies, the company survives, and she finds healing. Colonna calls this “taking your seat” as your authentic adult self. True connection arises when leaders courageously tell the truth rather than protect others with lies.

Breaking the Pyramid of Power

Many workplaces still mirror childhood hierarchies—parents atop, children striving below. Colonna draws a triangle and asks who sits at its peak. Most say “the boss.” This pyramid breeds shame, fear, and pretense. When leaders insist they know everything, teams collude in denial and dysfunction. Remembering who you are breaks that illusion. Admitting “I don’t know” transforms authority into humility. In doing so, you create cultures rooted in truth, not fear.

This Being So, So What?

Colonna distills maturity into one Zen-inspired phrase: “This being so, so what?” Life is messy, unfair, and impermanent; accept that, then decide what’s next. Leadership begins with reality, not fantasy. Remembering who you are means seeing life—and your organization—as they are, doing good work, done well, for the right reasons. (Comparable to James Hollis’s emphasis on adult responsibility in Living Your Unlived Life.)

We all wrestle with irrational people—partners, relatives, co-workers. Colonna turns that frustration inward and asks: what if their irrationality mirrors our own? This chapter explores how childhood patterns shape our reactions to the “Irrational Other” and offers a path to transform resentment into understanding.

Ghosts in the Machine

Borrowing from software language, Colonna calls old psychological scripts “ghosts in the machine.” These are memories turned into code—rules like “don’t upset your mother” or “stay invisible to stay safe.” When triggered, we reenact them unconsciously. Conflicts with irrational colleagues often resurrect these ghosts. The solution isn’t to fix others but to debug ourselves: identify what part of us their behavior awakens.

Compassion for the Mirror

Relationships at work or home replay our family dramas. A CEO fights with a co-founder only to realize she’s reliving her father’s withdrawal; a partner tolerates toxicity because it feels familiar. Through inquiry, Colonna helps clients see these dynamics and detach gently. His teacher Sharon Salzberg reminds him, “All beings own their own karma.” Recognizing this frees you from trying to rationalize the irrational. The goal is not to win but to understand.

Forgiving the Irrational Other

When Colonna finally visits his dying mother—the archetype of his “Irrational Other”—he tells her, “I forgive you.” That moment symbolizes liberation: accepting the humanity behind irrationality. Beneath the immense sky, even brokenness is complete. In doing so, you reclaim parts of yourself you exiled long ago. As philosopher Rilke wrote, love means “seeing each other whole and before an immense sky.”

How do you know you’ve lived a meaningful life? Colonna’s answer unfolds as a meditation on purpose, uncertainty, and continuous rebirth. In visits to the Grand Canyon and conversations with peers, he discovers that the path to purpose is not straight but pathless.

The Pathless Path

After a company collapse and spiritual crisis, Colonna explores the canyon where ancient youth left handprints as proof of existence. He asks, “What are my handprints?” His realization: purpose isn’t found; it’s lived. A meaningful life is an accumulation of integrity—moments when your inner and outer selves align. He contrasts the illusion of constant upward motion (“up and to the right”) with the reality of tacking across life’s unpredictable lake. Every detour holds its own wisdom.

Strategic Retreats and Do-Overs

Through stories of explorers, entrepreneurs, and his own mistakes, Colonna reframes failure as strategic retreat. Like polar adventurer Ben Saunders accepting a do-over mid‑expedition, life requires knowing when to pause and reorient. His mantra “bird by bird” (borrowed from Anne Lamott) reminds us that progress is incremental. Purpose emerges from continuous do‑overs, small steps, and beginner’s mind.

Living in Congruency

The deeper truth: purpose is not external. It’s living daily with congruency—where actions match values. Every job, relationship, and hardship becomes a chance to embody integrity. Work, Colonna argues, is not an obstacle to selfhood but its expression. Through standing still and listening to your heart’s questions, you leave your own handprints—proof that you lived with authenticity, not perfection.

Everyone has an inner voice that mocks and criticizes. Colonna names his the Crow. This chapter is about making peace with that voice, seeing it not as an enemy but as a misguided protector. To grow up as a leader, you must learn to love your Crow.

The Inner Critic as Guardian

The Crow caws to shield you from humiliation: “Don’t speak; don’t risk; don’t be found out.” Like a Loyal Soldier guarding a deserted island, it believes the war is still raging. Those protective strategies—overwork, perfectionism, avoidance—once ensured survival but now restrict maturity. Colonna helps leaders honor these parts with compassion: thank them for saving you, then release them.

Making the Unconscious Conscious

Following Jung and Robert Bly, he describes the “long black bag” of our shadow where disowned traits hide. When the Crow attacks, it’s signaling what you’ve buried—anger, ambition, creativity. Radical self-inquiry turns that into awareness. Leaders who reclaim their shadow stop projecting their fear onto others and build cultures based on humane truth instead of secret shame.

Loving the Broken-Open Self

To love the Crow is to love your humanity. At one talk, Colonna asks CEOs, “Who here is brave enough to admit they’re terrified?” The laughter that follows dissolves isolation. By accepting imperfection, leaders become “broken‑open‑hearted warriors,” creating workplaces where it’s safe to be human. Loving the Crow means leading with compassion—for yourself first, then for others. (Parallels Brené Brown’s idea that vulnerability is the birthplace of courage.)

Colonna defines adulthood not as avoidance of pain but as the capacity to keep one’s heart open when pain arrives. Every chapter leads here: heartbreak as teacher, equanimity as destination.

The Heartbreak of Everyday

Trees fall, loved ones die, dreams collapse. From the loss of his childhood chestnut tree to his client’s failed expedition, Colonna learns that impermanence is life’s constant. Resilience isn’t about bouncing back—it’s about ceasing to board the roller coaster. True grit, he writes, is kind, not stubborn. It persists not in denial but in compassion—for yourself, your team, and the world’s suffering.

Listening as Healing

Colonna’s encounter with Pema Chödrön reframed forgiveness: include all hearts past, present, and future in your meditation. Listening opens what pain has closed. On a vision quest, he learns from “Grandfather Boulder” that even sorrow can be made holy if listened to. Equanimity arrives when you see heartbreak not as failure but as the ripple of universal suffering—and choose to meet it with lovingkindness.

Just as I Am, I Am Enough

For Colonna, equanimity culminates in radical acceptance: “Everything’s great and I’m okay. Everything sucks and I’m okay.” This peace is attainable only through heartbreak. When you stop resisting impermanence, you hear what life whispers—that your worth was never conditional. The art of growing up is learning to meet every storm with a light heart and an open ear, knowing that this too shall pass.

The final chapter weaves together Colonna’s thesis: leadership is spiritual adulthood. It’s not about managing people—it’s about managing your own capacity for truth. The gifts of leadership mirror the gifts of life: heartbreak, responsibility, and growth.

Better Humans, Better Leaders

Colonna argues that leadership lessons and life lessons are one and the same. When you grow as a human—recognizing your contradictions, embracing your failures—you automatically become a wiser leader. The leader’s first task is self-inquiry: What am I not saying that needs to be said? What am I saying that’s not being heard? What’s being said that I’m not hearing? These questions, taught by his psychoanalyst Dr. Sayres, wield a “flaming sword” of discernment, cutting through delusion.

Leading with Humanity

Drawing from mentor Parker Palmer, he concludes that “violence is what we do when we don’t know what to do with our suffering.” Leadership requires channeling suffering into service. Adult leaders transform organizations into communities of belonging. They embody the calm mare of the herd—leaders chosen not for dominance but for empathy. Taking your seat means leading with fierce reality: strong back, open heart, clear sight.

Becoming the Adult You Were Meant to Be

Colonna’s closing reflections on his father, his children, and his mentors reveal leadership as legacy. Good work done well, for the right reasons, is adulthood in action. To grow up, we must integrate success and sorrow, light and shadow, ambition and care. His final wish: may we each become better humans, so that the world is led by adults—courageous, kind, and fiercely real.