Reboot - Book Summary

Discover Your Inner Leader — Transform Through Self-Inquiry

Have you ever found yourself pausing, mid-step in the hectic pace of leadership, to wonder if you're really mastering the role? It's not unusual to feel a mix of doubt and insecurity, especially when faced with the unyielding demands of the corporate world. The constant pressure to appear unfalteringly competent can leave anyone questioning their leadership abilities.

"Reboot" offers a remedy not through the usual quick-fix management techniques, but by encouraging a journey of radical self-inquiry. This profound expedition within is designed to help you confront and navigate the internal landscapes that shape you as both a human and a leader. By probing deep into the essence of your being — understanding the forces that have molded you, recognizing your irrational moments, and evaluating your responses in times of challenge — you embark on a transformative path.

The wisdom gathered from such introspection empowers you to redefine your notion of leadership. This fresh perspective fosters an environment that is less about survival of the fittest and more about understanding and growth. It advocates for leadership that is not just effective but is also compassionate and humane.

Throughout our exploration, inspired stories and powerful insights will illuminate the way:

- We'll uncover the legendary tale of the Buddhist saint Milarepa, who faced his demons in a cave, teaching us the power of confronting our own fears and uncertainties.

- We'll discover the unexpected virtue of stillness, learning when the most productive action can actually be non-action — a moment of pause.

- And we'll delve into why horses, with their keen sense of who they trust and follow, can teach us a thing or two about authentic leadership.

"Reboot" is not just another leadership book. It is a call to introspection, a challenge to face yourself and grow. By exploring the depth of your experiences and acknowledging your vulnerabilities, you pave the way for genuine leadership. And in doing so, you create spaces of work that breathe forgiveness and understanding, reshaping not just yourself but also the very essence of leadership around you.

Unlocking Leadership Solutions Begins with Self-Exploration

Imagine this scenario: during an intense leadership workshop, a conversation takes a sharp turn as a CEO — overwhelmed by the chaos engulfing her professional life — seeks a lightning-fast solution to end her turmoil. Her plea reverberates with urgency, a cry for the magical "One Quick Trick" to cut through the storm. However, Jerry Colonna, the seasoned guide through these turbulent waters, offers an alternative route — not a quick fix, but a journey into radical self-inquiry.

This recommendation often lands heavily on the shoulders of CEOs and entrepreneurs. After all, reaching the pinnacle of success in the cutthroat business world typically demands an armor of mental fortitude. This armor, while effective in the boardroom, tends to seal away the raw, unfiltered truths of our inner selves, prioritizing the mechanics of management over the profound 'whys' of our endeavors.

Yet, beneath the surface of strategic decision-making and professional achievements, there lurks an undercurrent of unresolved issues. These issues manifest in myriad ways: an overly domineering presence in the office, a palpable disconnect with the team, or decisions that seem to defy logic, driven more by emotion than reason.

The path to understanding — and ultimately resolving — these workplace manifestations begins not with outward strategies, but with a deep, introspective quest to the core of our being. It's about shattering the crafted illusions we've told ourselves and confronting the uncomfortable realities that have molded us.

Through his workshops, Jerry Colonna has witnessed firsthand how the root of a professional's anxiety often traces back not to the boardroom, but to the personal battlefields of their past. Be it domineering parents, the scars of bullying, the grip of poverty, or the sting of isolation, these childhood traumas cast long shadows over the luminous halls of achievement.

Colonna's own journey of self-discovery following a crisis in 2002 brought him face-to-face with his childhood adversities in Queens. Despite his outward success, the specter of poverty — memories of scarcity and familial strife over finances — haunted him. His relentless drive was as much about escaping these shadows as it was about achieving success, a realization that brought clarity to his professional anxieties.

This narrative invites us not to search for answers in the external world of management wisdom but to pause and dive deep within our true selves. It's a call to embrace the transformative power of self-inquiry, to unravel the intricacies of our identity, and in doing so, uncover the pathways to genuine leadership and healing.

Embracing Crisis: The Defining Moment of Leadership

In the unpredictable journey of leadership, there comes a moment — often unexpected — that flips the script on everything. Suddenly, the roadmap you've meticulously laid out is obsolete. Your company faces unprecedented challenges, you're ousted by the board, or abruptly, the lifeline of investment dries up. It's within the chaos of these crises that the essence of true leadership is forged and revealed.

Consider the story of Chad Dickerson, a close acquaintance of the author and the former CEO of Etsy. Faced with the daunting reality of being fired by Etsy's board, Chad didn't succumb to despair. Instead, he spent his remaining time at the company working tirelessly into the night, safeguarding the interests of his colleagues and ensuring the integrity of the company's data. His unwavering commitment, even in the face of personal crisis, exemplified the depth of his leadership.

Such critical moments serve as the ultimate test of leadership — they are, as leadership guru Warren Bennis articulates, our crucible moments. It's under the weight of these challenges that we discover our capacity to lead with courage, humility, and inspiration. Emerging from these trials, we're not only better leaders but better humans, armed with newfound resilience and confidence.

The key to navigating crises lies in confrontation, as illustrated by the ancient story of Milarepa, the Buddhist saint. Upon finding his meditation retreat invaded by demons, Milarepa first attempted to expel them, only to see their numbers grow. He then shifted his approach, deciding to teach them Buddhism, which momentarily subdued them. However, it was not until he confronted them, asking, "What are you here to teach me?" and ultimately offering himself to the most fearsome demon, that they dissipated, leaving him in peace.

Milarepa's lesson teaches us the power of facing our challenges head-on. For instance, in a business partnership marred by toxicity, the path to resolution doesn't lie in avoidance but in confrontation — a metaphorical placing of one's head into the demon's mouth. Such an approach will either mend the fractured relationship or lead to its end, but either outcome clears the path forward, freeing us from the shackles of stagnation.

In leadership, as in life, crises are unavoidable. Yet, it's through these very moments of upheaval that we are given the opportunity to rise, redefine, and demonstrate the true strength of our character. Embracing our challenges, rather than shying away from them, not only defines us as leaders but crafts a legacy of resilience and wisdom for others to follow.

The Power of Pause: Embracing Stillness in a Rushed World

In a world that championed perpetual motion as the hallmark of productivity, we find ourselves ensnared in a ceaseless cycle of tasks. Each day, we dive headlong into a whirlwind of activities — checking emails, spearheading projects, climbing the career ladder. This relentless pursuit leaves little room for reflection, causing us to lose sight of our essence and the profound 'why' driving our endeavors.

It's a troubling truth that our sprint from one milestone to the next often stems from a desire to flee from something lurking in our past.

This phenomenon was starkly illustrated by a case shared by the author, involving a young CEO at the helm of a burgeoning start-up. He sought guidance amidst a pervasive sense of disquiet in his professional life. A deeper exploration revealed a poignant reality: his obsessive work habits had severed the connection with his partner, a significant source of love and support in his life. His relentless drive was not fueled by ambition alone, but by a desperate bid to escape the shadows of a war-torn childhood and a battle with cancer, experiences that haunted him from a country now far away.

Though his story may be extreme, it mirrors a sentiment pervasive in the professional landscape — the notion that stillness equates to regression, that if we cease our forward momentum, even for a moment, we risk being consumed by the darkness of our past.

Yet, this unyielding push forward cultivates a detrimental workplace culture. Leaders, in their fervent rush, inadvertently set a pace that leaves their teams struggling in their wake, breeding an environment of unchecked urgency. As the pace quickens, the collective psyche is plagued by a sense of inadequacy, propelling a frenetic race that sacrifices meaningful connections on the altar of productivity.

This constant state of flux not only strains interpersonal dynamics but also clouds our judgment, leading us to make decisions that, while propelling us forward, may cause us to lose our grounding, dragging those around us into the fray.

The antidote to this maelstrom is not greater speed, but stillness. It demands the courage to halt, even if momentarily, to engage in mindful practices that anchor us to the present. By cultivating moments of quiet introspection, we grant ourselves the opportunity to listen — truly listen — to the whispers of our innermost desires and fears.

In asking ourselves where our haste is leading us, we begin to discern the path that aligns with our true purpose, beyond the shadows of our past or the fleeting accolades of the present. It's within these pauses that we find clarity, foster deeper connections, and rejuvenate our spirit — making stillness not a retreat, but a powerful stride toward a more focused, fulfilling, and humane form of leadership.

The Liberating Power of Truth in Leadership

Reflect on those moments when a tiny fabrication, or perhaps a more significant deceit, spiraled out of control, leaving you fervently wishing for an escape hatch to appear beneath your feet. These moments teach a harsh but invaluable lesson: the truth, no matter how inconvenient or painful, inevitably finds its way to the surface, often at the most unexpected times. This realization underscores a fundamental principle — honesty is a non-negotiable aspect of effective leadership.

Consider the high-profile scandals rooted in deception, such as the Volkswagen emissions fiasco, where deliberate misinformation about diesel emissions not only misled regulators but also betrayed the trust of customers worldwide. Or envision the devastating impacts of corporate shortcuts, like oil spills that wreak havoc on marine ecosystems, all stemming from a failure to adhere to safety standards. These are stark reminders of the far-reaching consequences when leaders choose deceit over transparency — consequences that ripple through societies, affecting lives, livelihoods, and the environment.

The genesis of such deceitful practices is a leadership culture marred by avoidance of truth. It's a culture that, if left unchecked, guides organizations toward calamity, much like the Titanic's slow, oblivious journey toward its doom. To redirect this course requires a profound shift at the leadership helm — a shift that begins with the individual leader's bravery to confront reality and discard the illusionary aspirations leading them astray.

This call for a new ethos of authenticity in the workplace is what the author terms "broken-open-hearted warriorship" — a leadership model that embraces vulnerability, truthfulness, and resilience in equal measure. This philosophy advocates for leaders who, in recognizing their own imperfections, forge a path of genuine connection and mutual respect within their teams.

A stirring example of this principle in action emerged during one of the author's leadership workshops. A young woman, a leader in her organization, shared her recent diagnosis of a rare blood cancer — a reality she feared disclosing to her investors, apprehensive that such vulnerability could erode their confidence and support. Initially, only her closest circle was privy to her struggle, but motivated by a newfound commitment to transparency, she gradually opened up about her condition to her colleagues and, ultimately, to her investors.

Contrary to her fears, her honesty did not trigger a withdrawal but galvanized a wave of support from her professional community. This courageous step not only liberated her from the weight of secrecy but also laid the groundwork for a culture of "broken-open-hearted warriorship" within her organization. Her experience exemplifies the transformative potential of truth in leadership — how, by embracing our authentic selves and our realities, we can foster a more compassionate, resilient, and truthful business landscape, one in which honesty isn't just a policy, but the very foundation of success.

Embracing Our Inner Quirks: Navigating Irrationality in Ourselves and Others

Have you ever found yourself in the heat of an argument, voices raised, only for the tension to suddenly dissolve into laughter? It's in these moments, amidst the absurdity, that we're reminded of the inherent irrationality present not only in our interactions but within ourselves.

This irrationality can be likened to what software developers, borrowing from author Arthur Koestler, refer to as "ghosts in the machine." These are essentially remnants of outdated code, once useful in earlier versions of a program but now lying dormant, potentially interfering with the system's current operations. Similarly, within each of us are remnants of our past — emotional and psychological behaviors shaped in our youth that continue to influence us in subtle, often puzzling ways.

Take, for example, the author's personal anecdote from his childhood in Queens. He recalls his father meticulously correcting typos in the newspaper, an act of asserting control in a life otherwise marked by the vulnerability inherent in poverty. This left a lasting impression, manifesting in the author's adult life as a penchant for pedantically correcting others, a trait that, while occasionally beneficial, has also been a source of tension in professional settings.

This concept of "ghosts in the machine" suggests that irrational behaviors, with their roots entrenched in our past, are not anomalies but a universal aspect of the human experience. We are, by nature, complex and somewhat unpredictable beings. Recognizing and accepting this reality — in ourselves and those we interact with — is crucial for navigating the professional landscape.

The author's experience coaching a business partnership provides a striking example of this. The partnership, fraught with personal tensions, was teetering on the brink of dissolution. However, beneath the surface conflict lay deep-seated psychological patterns; each partner, unbeknownst to them, mirrored characteristics of the other's parent, evoking unconscious reactions forged in childhood. Their professional alliance, initially drawn together by complementary skills and mutual needs, had unintentionally become a battleground for unresolved familial dynamics.

Instead of succumbing to these ingrained behaviors, the partners embarked on a journey of mindfulness, recognizing their shared complicity in the perpetuation of these dynamics. This acknowledgment and subsequent effort to understand their irrational responses allowed them to transcend past patterns, demonstrating that even the most deep-seated "ghosts" can be acknowledged, addressed, and ultimately overcome.

In essence, our journey within the professional realm and beyond necessitates a readiness to confront and coexist with our own irrationalities and those of others. By acknowledging the complex tapestry of our pasts, we pave the way for more empathetic, understanding, and ultimately productive relationships. This acceptance doesn't erase our quirks but empowers us to navigate them more consciously, transforming potential sources of conflict into opportunities for growth and deeper connection.

Charting the Unmarked Trails: The Art of Embracing the Unknown

Life often presents itself as a neatly arranged narrative—climbing the ladder of success, building a family, acquiring a picturesque home. Yet, this mirage can shatter, leaving us to confront the unsettling feeling that there’s something more, something transcendent beyond the contours of daily routine and societal expectations. What do we do when the life we meticulously constructed feels confining, when the path we're on seems too worn and familiar?

The answer lies in the courageous act of embracing the unknown.

Consider the remarkable journey of the author. His professional life was a showcase of achievements, transitioning from journalism to magazine editing, and eventually to venture capitalism. On paper, his trajectory was the epitome of success, marked by non-stop progression and the accumulation of wealth. Yet, despite this outward success, a profound emptiness gnawed at him. Standing at the brink, both literally and metaphorically, outside Ground Zero in 2002, he was a man contemplating the void—a life that, while filled with meetings and milestones, felt devoid of personal significance.

But it was at this precipice that transformation began. Instead of succumbing to despair, the author chose exploration—physically, emotionally, and spiritually. He ventured across glaciers, navigated Chilean rivers, and delved into the discipline of meditation. This journey wasn’t about running away but rather about embracing "not-knowing," a willingness to step into the vastness of each moment without a blueprint. This shift marked a departure from a life lived according to plans and expectations to one open to the myriad possibilities that each new day brings.

An essential aspect of this profound transformation was the concept of the "do-over"—a principle borrowed from childhood games. This simple, yet powerful idea encapsulates the essence of forgiveness, of letting go of past mistakes and regrets to start anew. It’s a declaration that no error is too great to overcome, no misstep so grave that it can’t be left behind.

This ethos of continual renewal, of embracing the pathless path, is a call to all of us feeling trapped by the linear narratives of achievement and societal validation. It’s a reminder that we possess the agency to reinvent our lives, to step off the well-trodden path and forge our own way through the terrain of the unknown.

For those tethered by the predictability of their professions or stifled by the apparent orderliness of their lives, the message is clear—transformation is not only possible, but necessary. As poignantly expressed by Rainer Maria Rilke, "You must change your life." Through the act of embracing the pathless path, we open ourselves to the boundless potential of the present, ready to welcome the serendipitous, the unforeseen, and the truly transformative experiences that lie just beyond the horizon of the known.

Navigating Life with Your Crow and Loyal Soldier by Your Side

Doubt is a near-constant companion throughout our lives, often leaving us feeling as though we fall short of others' achievements or that we don't quite measure up to our own expectations. But how do we combat these pervasive feelings of inadequacy?

First, we must come to terms with our "Crow."

During his college years, the author, under the guidance of poet Marie Ponsot, became acquainted with the concept of the Crow. This metaphorical bird perches on our shoulder, incessantly spewing negative thoughts like, “That’s nonsense,” or “How could you write that?” Ponsot’s advice to her students was to decisively “Shoot. The. Damned. Crow.” This Crow represents the unrelenting voice of self-doubt that whispers we’re unworthy of success, love, or belonging.

Contrary to Ponsot’s advice, however, the author chose not to eliminate his Crow. He understood that the Crow’s persistent self-criticism stems from a place of deep concern about our actions and their impact on the world. This voice of doubt is not an enemy, but a part of our complex human nature, indicating our investment in the quality and integrity of our work and relationships. Instead of seeking to silence this aspect of ourselves, we should learn to live with it, recognizing it as a sign of our fundamentally good, yet imperfect nature.

Next, we embark on the journey of embracing the "Loyal Soldier."

This metaphor, crafted by the author, illustrates another facet of our psyche. Imagine a soldier, isolated and steadfast, guarding a desolate outpost, convinced that a distant war rages on. He remains vigilant, adhering to survival rules that dictate remaining inconspicuous, avoiding risks, and suppressing mistakes. The Loyal Soldier symbolizes our ingrained survival tactics—the cautious voice urging us to blend in and avoid drawing attention.

Like the Crow, the Loyal Soldier is an innate part of our being. It represents our instinctual urge for self-preservation, akin to a protective figure cautioning us against potential harm. Rather than dismissing or fighting against this part of ourselves, embracing the Loyal Soldier with acceptance allows us to understand our tendencies toward caution and self-protection as expressions of care.

By recognizing and accepting the presence of both our Crow and Loyal Soldier, we learn not to chastise ourselves for every critical thought or moment of hesitation. This approach enables us to be more comfortable with our complexities, allowing us to face the world with a sense of openness and bravery. Acknowledging these aspects of our persona as essential components of our journey helps us navigate life’s challenges with grace, understanding that both the Crow and the Loyal Soldier play vital roles in our continued growth and self-awareness.

Cultivating Authentic Spaces: The Essence of Inspirational Leadership

Imagine a workplace where the mere presence of a CEO fills the room with tension, compelling employees to immediately adjust their behavior, an environment reminiscent of scenes from corporate dramas on the silver screen. While these authoritarian figures have long been celebrated in Hollywood narratives, it's worth pondering whether such leadership models are truly effective, or if they belong to a bygone era.

Let's envision a different kind of leadership — one that, rather than evoking fear, fosters an environment where team members feel free to express themselves and grow. Picture the warmth of a family home, where parents provide a nurturing space that allows children to explore their identities, make mistakes, and indulge their curiosity without the dread of being rebuked. Similarly, consider the dynamics of a supportive partnership, where there's room for both the light and the shadows of our beings, affirming that our complicated, sometimes irrational selves are altogether embraced and valued.

Translating this level of openness and acceptance into the corporate realm may seem daunting, yet it's precisely this courageous approach that can transform workplaces into arenas of genuine growth and fulfillment. The most effective leaders are those who not only encourage individual team members to blossom but also nurture the collective, enabling the group to function as a well-integrated whole.

This concept of intuitive, compassionate leadership is perfectly embodied in the natural world by the dynamics within a herd of horses. Known for their heightened sensitivity and perceptive abilities, horses possess an uncanny knack for understanding the emotional states of their herd and even anticipating changes in their environment. When choosing their leader, they don't prioritize strength, intelligence, or physical prowess. Instead, they invariably gravitate toward a mare characterized by her deep, intuitive connection to the group — a leader who can instinctively soothe and guide the herd, acknowledging and addressing the needs of each member.

Applying this model to human leadership represents a radical shift away from the competitive, individualistic ethos that dominates much of the corporate landscape. However, embracing this more holistic, empathetic approach could pave the way toward eradicating workplace toxicity and fostering a culture of genuine cooperation and understanding. In seeking leaders who prioritize the collective well-being, who champion authenticity and connectivity, we may just find the blueprint for creating more inclusive, engaging, and human-centric organizations. This, perhaps, is not just an alternative but the very direction in which the future of leadership is headed.

Embracing Humanity: The Core of Transformational Leadership

The essence of true leadership transcends conventional paradigms of authority and management. As we've uncovered, the journey to becoming impactful leaders is deeply intertwined with our own journey toward mindfulness and introspection. It is through understanding the forces that have sculpted our behaviors, desires, and fears that we unlock the potential to meaningfully connect with others and lead with genuine empathy and effectiveness.

Key to this transformative process is the recognition that leadership is not about wielding power over others but about nurturing spaces where individuals and teams can flourish. By fostering environments of trust, openness, and acceptance — much like the nurturing spaces of a family home or a supportive partnership — leaders can encourage authenticity, creativity, and growth.

Moreover, the leadership journey demands the courage to confront our internal landscapes, to embrace the shadows and lights within, and to navigate the complexities of human emotion and irrationality. It is in the weaving together of our personal narratives, our struggles, and our moments of enlightenment that we gather the wisdom to guide others.

This call for a more humane approach to leadership challenges us to shed toxic workplace cultures and competitive individualism in favor of collective well-being, collaboration, and mutual respect. By embodying the qualities of empathy, understanding, and intuition — akin to the discerning leader of a horse herd — we can inspire a sense of belonging and community, laying the groundwork for organizations that are not only successful but also conscious of their impact on employees, communities, and the planet.

At its core, the message is clear: the path to exceptional leadership is forged through becoming more humane and courageous individuals. This transformation entails a deep engagement with our inner selves, the courage to face our vulnerabilities, and the wisdom to navigate the intricacies of human relationships. By embarking on this path, we can create workplaces that are not just less toxic but are vibrant ecosystems of innovation, solidarity, and shared purpose.