Reboot

Reboot Plot Summary

Introduction

The evening light was fading as I sat across from a CEO on the verge of burnout. Eyes hollow from sleepless nights, he confessed, "I've built a company valued at millions, but I feel like a fraud. Like I'm still that scared kid from my childhood, just waiting to be found out." His vulnerability struck a chord with me, as it echoed the journey of Jerry Colonna, whose transformation from venture capitalist to executive coach reveals the profound connection between leadership and personal growth. Leadership is not merely about strategies and management techniques—it's about becoming the adult you were meant to be. Through Colonna's remarkable journey, we discover that the most significant leadership challenges aren't found in spreadsheets or board meetings, but in our internal landscape. The path to becoming an effective leader requires radical self-inquiry: examining our past wounds, confronting our fears, and embracing our whole selves. This journey is not for the faint of heart, but it offers the most rewarding destination—the ability to lead with authenticity, resilience, and equanimity, transforming not only ourselves but those we guide along the way.

Chapter 1: From Brooklyn Roots to Leadership Heights

Jerry Colonna grew up in Brooklyn with a backdrop of family struggles. His mother suffered from mental illness, and his father turned to alcohol to cope with life's pressures. As a child, Jerry would hide under a horse chestnut tree on East 26th Street when family conflicts became too much to bear. This early experience of seeking safety amid chaos would later shape his approach to both life and leadership. Money became synonymous with security for young Jerry. Playing Monopoly with his mother, he developed a unique strategy—keeping his money hidden under the board rather than displayed in front of him like other players. He'd surprise everyone by revealing his wealth only when purchasing properties. This childhood game foreshadowed his approach to business: quietly accumulating resources while developing a keen understanding of financial security. Despite finding success as a venture capitalist and amassing considerable wealth, Colonna eventually found himself standing at Ground Zero in 2002, contemplating suicide. The pursuit of financial security and professional achievement had not filled the emptiness inside. "I was in my life but not really living," he writes. Despite having "all the lemon drops I could ever want"—his metaphor for financial security—he felt hollow and disconnected from himself. This crisis became Colonna's turning point. He began therapy, meditation, and deep self-examination. He discovered that his drive for success was rooted in childhood insecurity—a belief that accumulating wealth would provide the safety and love he craved. His therapist asked a pivotal question: "What will it take? When will you stop?" Colonna's surprising answer was "Bill Gates," revealing how his pursuit of wealth had become untethered from any real sense of enough. The journey from Brooklyn to Wall Street and eventually to becoming a renowned executive coach illustrates a universal truth about leadership: our past shapes our present in ways we often fail to recognize. The ghosts of our childhood—our fears, coping mechanisms, and unmet needs—don't disappear when we take leadership positions. Instead, they often drive our decisions unconsciously, creating patterns that can sabotage our effectiveness and happiness. By examining his own story through radical self-inquiry, Colonna transformed his understanding of leadership. He discovered that better humans make better leaders, and the process of growing into authentic leadership requires us to grow into authentic adulthood. This means confronting our shadows, understanding our patterns, and accepting all parts of ourselves—even those we've long tried to hide or deny.

Chapter 2: Resilient Leadership and the Crucibles of Growth

The night was perfect—stars crisp and bright above a New York rooftop in Brooklyn. Jerry Colonna sat with Chad Dickerson, who had just been asked to step down as CEO of Etsy after six years at the helm. Despite doing many things right and growing into a leader with heart and authenticity, Chad was being fired. Through tears, he asked Colonna, "I did a good job, didn't I?" To which Colonna could only honestly reply, "Yeah. Yeah, you did." This moment captured what Warren Bennis called a "crucible of leadership"—a transformative experience that tests a leader and forges them into something stronger. For Chad, this painful transition wasn't merely the end of his time as CEO but the emergence of something more profound—his truest self. Despite the loss of status and position, Chad carried himself with dignity, working late into the night to get data right and care for colleagues even after learning of his termination. When facing similar crucible moments, many leaders seek concrete playbooks or advice on "the five things every entrepreneur should know." They want certainty in uncertainty. But Colonna pushes back against this impulse, explaining that leadership isn't about having all the answers but about "living in the 'not-knowing.'" The real challenge isn't figuring out what to do but learning to be comfortable with uncertainty while maintaining your core values and integrity. Colonna introduces the concept of the "warrior stance"—strong back and open heart. The strong back represents fiscal discipline, clarity, vision, and accountability. The open heart embodies caring about people, purpose, and meaning. This stance creates the conditions for inner and outer aspects of leadership to dance together, allowing leaders to meet reality as it is, not as they wish it to be. He shares the Buddhist story of Milarepa, who returned to his meditation cave to find it filled with demons. After trying unsuccessfully to chase them away, Milarepa asked, "What are you here to teach me?" With this, most demons disappeared. When one large, frightening demon remained, Milarepa put his head into the demon's mouth and said, "Eat me if you wish." With that, the final demon vanished. This parable illustrates that surrendering to our demons—acknowledging how we contribute to problems without descending into self-flagellation—is crucial for leadership growth. When we put our head into the mouth of the demon, when we face our fears and shortcomings directly, we transform the energy that drives our confusion and struggle into wisdom and strength. The crucible moments in leadership aren't just about overcoming external challenges but about bringing forth our whole selves—the glory and the mess. By taking our seat with dignity, putting our heads into the mouths of life's demons, we transcend mere leadership roles to become the adults we were always meant to be. This is the path of the broken-open-hearted warrior, where resilience comes not from denying pain but from embracing it as part of our wholeness.

Chapter 3: Radical Self-Inquiry and Shadow Work

Jerry Colonna experienced a breaking point in January 1982, shortly after his eighteenth birthday. Sitting at his desk in Queens, he traced lines across his wrists with an X-Acto knife until blood appeared. This suicide attempt led to three months in a locked psychiatric ward at Cabrini Hospital in Manhattan. The experience marked both an end and a beginning in his life journey. Before and after his hospitalization, Colonna coped with life through constant motion. Always busy with school, work, and various commitments, he perfected "the art of doing." His most familiar bodily sensations were a racing heart and beads of sweat running down his temples. This frenetic pace continued through college and his early career. When shelves he'd installed as a makeshift closet collapsed on him in the middle of the night, he simply went back to sleep beneath the pile of clothes and twisted metal. The pattern persisted through his rise as a journalist, then venture capitalist. At Flatiron Partners, which he founded with Fred Wilson in 1996, success came quickly. Every investment seemed to make money, and they were celebrated in the press. But internally, Colonna was dying. He described moving through work like Marvel's superhero the Flash, racing from floor to floor, meeting to meeting, imagining his cheeks blown back by the speed of his movement while colleagues seemed to move in slow motion. This constant motion wasn't a job requirement but a strategy to avoid his inner pain. By moving fast and staying busy, Colonna found it easier to live according to others' expectations. Too busy to live his own life, he took direction from the affirmations of others. The world rewarded this way of being with promotions and accolades, but his soul ached under the weight of carrying this inauthentic self. Everything came to a head after 9/11. Having already experienced a physical collapse that landed him in the hospital earlier in 2001, and feeling increasingly alienated from his work, Colonna reached his Ground Zero moment in February 2002. Standing literally at the edge of the smoking hole where the Twin Towers had stood, he contemplated ending his life. Instead, he reached for his phone and called his therapist. This crisis led to a profound awakening. With his therapist's guidance, he began asking himself a crucial question: "What am I not saying that needs to be said?" He took time off, read books on Buddhism and self-inquiry, and began learning to meditate. Eventually, he encountered Pema Chödrön, who taught him that all things are constantly falling apart, and that to expect otherwise invites suffering. She encouraged him to "keep opening" to what was happening inside himself. Through this process, Colonna developed what he calls "radical self-inquiry"—the practice by which self-deception becomes so skillfully and compassionately exposed that no mask can hide us anymore. This isn't merely looking inward but committing to see oneself with unflinching honesty. It means stopping the "bullshitting" and "spinning" that characterizes so much of professional life and instead asking hard questions: Who am I? What do I believe about the world? How have I been complicit in creating the conditions in my life that I say I don't want? This approach to leadership development differs fundamentally from typical advice focused on strategies and tactics. Rather than offering a playbook, radical self-inquiry provides a method for accessing one's own wisdom and authenticity. By standing still and letting the forest find you—as poet David Wagoner suggests—leaders discover that the most powerful answers come from within, not from external formulas or others' expectations. The journey from constant motion to mindful stillness reveals that leadership growth isn't about doing more but about being more present, more authentic, and more attuned to one's true nature. When we slow down enough to feel our feelings and listen to our inner wisdom, we connect to the source of our strength—our core beliefs, values, and hard-earned wisdom. This connection becomes the foundation for leadership that is both effective and life-giving.

Chapter 4: Leadership Through Heartbreak and Vulnerability

At one of Colonna's CEO boot camps, a young woman shocked the group with her revelation: "What I wish the people I worked with as well as the investors thinking about putting money into my company knew about me is... that I have a rare blood cancer and, if my treatment over the next six months doesn't succeed, I'll be dead within the year." The room gasped collectively. She had kept this secret to protect her team and investors, carrying the burden alone so that everyone who had believed in her wouldn't be at risk if the company couldn't secure its next round of financing. This moment illustrated what happens when we stop spinning our stories and allow ourselves to be seen in our full, vulnerable humanity. By sharing her secret, this CEO began to feel the shift that comes from taking her seat as an authentic, frightened, deeply feeling adult. The group's response wasn't to pull away but to draw closer, to hold her in her vulnerability. Colonna shares another pivotal moment from his own life. He and his son Michael were watching a film that Michael had been eager to share. As the movie unfolded, Colonna initially saw it as a coming-of-age story about a young man about Michael's age. But near the end, the plot twisted, and suddenly the film spoke directly to Colonna's own childhood traumas. He found himself weeping uncontrollably as the credits rolled. In the car afterward, still emotional, Colonna tried to compose himself. Then his teenage son said something profound: "Dad, you might as well tell me what's going on, because if you don't, I'm going to make shit up and it's gonna be negative about me." In that moment, Michael taught his father that withholding our truth doesn't protect others—it often leaves them to create narratives that can be worse than reality. This insight extends to leadership contexts. Colonna recounts a client who, after weeks of assuring employees that financing was a sure thing, discovered investors were backing away. Terrified to tell his team the truth, he asked Colonna, "What do I tell them?" Colonna's response was simple: "How about the truth?" The CEO feared mass resignations if employees learned investors were bailing. "Well," Colonna countered, "would you rather they stay for a lie?" The CEO told the truth, and not only did the team stay, but they volunteered to take pay cuts to help the company manage its cash. Authenticity creates the conditions for trust and collective resilience. When leaders share their burdens—their fears, their doubts, their struggles—they create space for others to do the same. This doesn't mean indiscriminate transparency or shifting anxiety onto others. Rather, it means dropping the facade of perfection and invulnerability that keeps people isolated in their struggles. Colonna draws on Buddhist teacher Pema Chödrön's encouragement to "keep opening" to what is present. This openness applies not just to our inner experience but to sharing ourselves with others. When we allow ourselves to be seen—not just our strengths but our uncertainties, our heartbreaks, our humanity—we give others permission to do the same. We create communities where people can bring their whole selves, where vulnerability becomes a source of connection rather than shame. True leadership emerges not from having all the answers or projecting unwavering confidence, but from the courage to meet life as it is, with an open heart and a willingness to be real. When we stop the spinning, stand still, and allow ourselves to be seen, we discover that what we feared would drive others away often brings them closer. Our vulnerability becomes not a liability but the foundation for authentic connection and collective strength.

Chapter 5: Navigating Relationships with the Irrational Other

As a teenager, Jerry Colonna often found himself caught between his mother's delusional rants and his father's passive response. One morning at the kitchen table, his mother claimed to have met Art Garfunkel at a bowling alley and insisted she was the inspiration for the song "Mrs. Robinson." Young Jerry, frustrated and desperate to establish some grasp on reality, bluntly told her, "You are not Mrs. Robinson." His father's only response was, "Don't talk to your mother like that... Don't upset your mother." This admonition—"Don't upset your mother"—became deeply ingrained in Colonna's psyche, evolving into a broader rule: "Don't upset the Other." He developed hypervigilance, constantly scanning for emotional cues and potential threats. This survival strategy eventually became what he calls a "superpower"—an ability to read people with uncanny precision, but at a heavy personal cost. At fifteen, overwhelmed by his mother's irrational behavior and his father's enabling response, Colonna ran away to Coney Island. Under the Wonder Wheel, he shouted, "This is not going to be my life!" and fell to his knees, shaking and sobbing. Later, he wrote a note to himself: "It's absolutely irrational to try to argue rationally with someone who is being irrational." This insight would later inform his approach to relationships in leadership contexts. As an executive coach, Colonna frequently encounters leaders struggling with what he calls the "Irrational Other"—colleagues, partners, or team members whose behavior seems incomprehensible or deeply frustrating. One CEO client lamented about her co-founder: "I just can't deal with him. He says he'll do something and then he up and leaves... And when he does finally return, he says nothing about his broken promises." Through his work, Colonna discovered that what makes others seem "irrational" isn't just their behavior but the clash between their unconscious programming and our own. Everyone carries what he calls "ghosts in the machine"—outdated operating instructions from childhood that influence how we navigate relationships. When these invisible programs collide, conflict and misunderstanding are inevitable. In unpacking his client's frustration with her co-founder, Colonna helped her see the deeper dynamics at play. "I think I need him to be disappointing and emotionally distant," she realized. "Oh, fuck, he's my father." Her father had been a man whose emotional presence depended on alcohol, whose drinking led to unexpected disappearances, and whose returns were marked by secretiveness. The co-founder relationship had unconsciously replicated this painful pattern. Colonna introduces three powerful questions to help navigate these challenging relationships: 1. What am I not saying that needs to be said? 2. What am I saying that's not being heard? 3. What's being said that I'm not hearing? These questions invite us to move beyond blaming the "Irrational Other" to explore our own role in relationship dynamics. He shares how another client, Eliza, used this approach with her CTO who seemed to disrespect her by leaving work early without notice. Rather than assuming the worst (that he couldn't stand working for a woman), she practiced nonviolent communication—sharing observations, feelings, needs, and requests. It turned out he'd received an emergency call about his daughter and hadn't mentioned it because he feared appearing weak by putting family ahead of work. The path to healthier relationships lies in what Rilke called seeing each other "as a whole and before an immense sky." This means recognizing that even the most frustrating behaviors often stem from attempts to meet basic human needs for love, safety, and belonging. When we can see both ourselves and others as whole beings—shaped by our histories but not defined by them—we create space for genuine understanding and growth. The most painful gift of the Irrational Other is the opportunity to see ourselves more clearly. Their behavior becomes a mirror, reflecting aspects of ourselves we've denied or projected outward. By examining our reactions with curiosity rather than judgment, we discover the unconscious patterns driving our relationships and gain the freedom to choose different responses. This is not just good leadership—it's the essence of growing up.

Chapter 6: Finding Purpose When Lost in Empty Time

"What should I do with my life?" Andrew asked Jerry Colonna during a walk around Wonderland Lake in Boulder. Despite being a coach himself, Andrew felt lost at forty-four, uncertain if he was on the right path. "I know this is absurd of me to ask... I mean, I'm a coach, too, and I'm supposed to be giving other people advice... but, well..." As he struggled to articulate his question, Colonna reassured him: "Andrew, whatever story you're telling yourself is likely wrong. Whatever it's stopping you from speaking is old, tired, and worn out." Andrew burst into tears: "I don't know what to do with my life. I'm forty-four years old and I have no idea if I'm doing the right thing." His questions reflected a universal human yearning: Am I doing it right? Is it supposed to feel this confusing? Will I ever feel safe, warm, and happy? Where do I belong? What do I want from this life? Colonna recognized these questions well, having wrestled with them himself. Years earlier, he'd knelt before Buddhist teacher Pema Chödrön, pleading for her to tell him the path out of his pain. She had lovingly tapped his hand and spoken of the "pathless path"—a concept that left him bereft at the time but later became profound wisdom. "You seem to want to know that you're making progress," Colonna told Andrew. "That there's a path and that you're on it." He suggested a different perspective: "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?" This insight runs counter to society's messages about success and purpose. We're conditioned to believe that anything less than constant upward progress represents failure. "Up and to the right," Colonna notes, is where we're told the happy people are—those who never fear, never fail, never struggle. Our economy thrives on making us feel that where we are is awful and that buying the right products or achieving the right goals will make us safe and loved forever. Yet finding purpose isn't about discovering a straight path forward but about embracing the winding journey. Colonna shares the story of being in the Grand Canyon, looking at handprints left by Havasupai youth who had leaped across a chasm to mark their passage into adulthood. "What are my handprints?" he asked himself. "Some fucking investment? Is this how my passage through and existence in this life is gonna be remembered?" This question led to a memory of walking with his sister Mary when he was seven. She'd asked what he wanted to be when he grew up. After hesitating, he replied, "I think... I think maybe I don't want to be forgotten." The boy in the crack of the tree, wishing to leave handprints, was seeking purpose through impact and remembrance. Purpose, Colonna learned, isn't something external to be discovered but something to be lived into daily. He quotes Joseph Campbell's observation that people conflate the pursuit of purpose with a pursuit of aliveness. "Aliveness comes not from having magically discovered purpose, meaning, nirvana, and a never-ending supply of lemon drops," Colonna writes. "Aliveness comes from living a life of personal integrity in which our outer actions match our inner values, beliefs, wishes, and dreams." This understanding transforms how we view work and purpose. Work becomes neither the blissful expression of deep purpose nor the dreadful obligation standing in the way of being ourselves. Instead, it offers an opportunity for daily realignment of inner and outer, a chance to express life with integrity. Purpose emerges not from grand discoveries but from answering fundamental questions: Who are we? What do we believe to be true? What is the world we wish to create with our actions and hearts? The path to purpose requires standing still, radically inquiring within, and learning to bear the pain of uncertainty. It demands what poet Anne Lamott calls taking life "bird by bird"—step by step, ridge by ridge, with do-overs when needed. When we give ourselves permission for endless do-overs, we release the pressure of finding the "right" path and embrace the wisdom of the pathless path.

Chapter 7: Equanimity and the Path to True Warriorship

"I hate the fucking product," Maria, one of Colonna's clients, declared as she curled into the corner of his office couch. "I wake, grab the app, and feel sick. I want to tear everything apart and start all over." This profound dissatisfaction with one's creation is familiar to many leaders and creators. We labor intensely to bring something into being, only to find ourselves disgusted by the result days or months later. Colonna explores this common phenomenon through the metaphor of "the Crow," borrowed from poet Marie Ponsot. The Crow sits on our shoulder, cawing criticisms: "That sucks," "How could you write that?" and "Are you kidding me?!?" This inner critic isn't merely annoying—it's connected to our deepest fears about worthiness and belonging. Each time our work fails to meet our expectations, the Crow reminds us that we are frauds, unworthy of love and belonging. But Colonna offers a surprising perspective: rather than shooting the Crow, we might learn to love it. Our inner critic, like many aspects of ourselves we disown and place in what Carl Jung called our "shadow," was originally meant to protect us. The voice that tells us we're not good enough is trying, in its misguided way, to keep us safe from humiliation and rejection. One client, Patrick, received a devastating 360-degree review where colleagues described him as "bullying," "toxic," and "enraging." Rather than encouraging Patrick to disown his anger, Colonna invited him to explore it as an old friend. Patrick recalled being repeatedly told how wrong he was for being angry throughout his childhood. "Well, I think you have a right to your anger," Colonna told him. "You should be pissed off, given your childhood. But the question now is, what will Patrick, the adult, choose to do with that anger?" This approach—integrating rather than rejecting the parts of ourselves we've banished to the shadow—is essential for mature leadership. When leaders fail to examine themselves, they project their inner turmoil outward, creating toxic workplaces. A CEO's boredom with a well-functioning team might stem from childhood fear that complacency would allow family enemies to catch them off guard. A leader's sexual relationship with a co-founder might reflect a commitment to self-sabotage to ensure they never outdo their father. "Just because you feel like shit," Colonna tells his clients, "doesn't mean you are shit." Our feelings of inadequacy are often old programming, ghosts in the machine, whose purpose was to ensure belonging. By recognizing these patterns, we can stop externalizing responsibility for our inner state and create organizations where people can be fully human. Colonna shares a profound experience of his own transformation. In a desert in Utah, under the gaze of what he calls "Grandfather Boulder," he vomited the heartbreak and pain of his childhood wounds until his throat was raw and his stomach empty. In that vulnerable state, he heard wisdom: "You were not given this life only to lament. Make holy that which you were given: Go and listen." Through listening—to ourselves, to others, to the Earth—we break the chains of shame and fear. By welcoming home the "Loyal Soldier" (the protective part of us still fighting childhood wars) and loving the Crow, we release ourselves from the lacerations of guilt and shame and allow our inner warriors to emerge. The highest calling of the warrior-leader is to take our seat as humans and build humane companies and communities where it is gloriously safe for others to be human. This isn't a soft-bellied approach to leadership. "Namaste my ass," Colonna says. "Try entering the cave, walking to the dark recesses, and retrieving the treasure wa-a-a-y in the back. Then come tell me about being soft." True warriorship emerges from facing our deepest fears and retrieving the treasure—the disowned parts of ourselves that, once integrated, become the source of our greatest strength and wisdom. By sorting the unsorted baggage of our lives, we turn leadership into a journey of self-actualization and work into a way to live out our lives as they were meant to be.

Summary

Jerry Colonna's journey from a boy hiding under a Brooklyn chestnut tree to a venture capitalist standing at the edge of Ground Zero to becoming one of the most sought-after executive coaches reveals a profound truth: leadership is inseparable from the art of growing up. Through stories of broken-open hearts and hard-won wisdom, he shows that our greatest leadership challenges stem not from external obstacles but from our internal landscape—the ghosts in our machines, the shadows we refuse to face, and the wounds we've carried since childhood. The path to authentic leadership requires radical self-inquiry—asking ourselves uncomfortable questions like "What am I not saying that needs to be said?" and "How have I been complicit in creating the conditions I say I don't want?" This process isn't about self-flagellation but about compassionate understanding of how our past shapes our present. By standing still in moments of confusion, by putting our heads into the mouths of our demons, and by embracing our full humanity—both our glory and our mess—we grow into leaders with strong backs and open hearts. Perhaps the most powerful insight from Colonna's work is that we don't need to strive for perfection to lead well. Instead, we need the courage to be real—to drop the pretense that we have all the answers, to share our vulnerabilities when appropriate, and to create spaces where others can do the same. By loving the Crow on our shoulder, by welcoming home our Loyal Soldiers, and by integrating the parts of ourselves we've long denied, we become not just better leaders but more whole humans. And that, ultimately, is the greatest service we can offer those we lead—the permission to be fully, gloriously, imperfectly human.

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Jerry Colonna

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