Are you curious about how historical figures like General Sherman, Upton Sinclair, Genghis Khan and Angela Merkel managed their ego and ambition? Do you want to understand the power of humility, self-control, and good judgment in achieving lasting success? Interested in learning from the resilience of people like Malcolm X and Katharine Graham, who turned adversity into growth opportunities? Let's embark on a journey that contrasts ego and humility, providing valuable lessons from both ancient wisdom and modern success stories.

Ego Is the Enemy

Let's embark on a journey where ego and humility clash. Our story begins in ancient Athens with Isocrates, a wise teacher who penned a letter to young Demonicus, cautioning him about the pitfalls of ambition. 

Isocrates advised virtues like modesty, self-control, and good judgment, warning against the deceit of flatterers and the dangers of unchecked temper and pleasure. These principles were echoed centuries later by Shakespeare in Hamlet and embodied by General William Tecumseh Sherman.

Sherman, much like Demonicus, faced early loss and was guided by a mentor. Though ambitious, Sherman was unique; he understood his limitations and sought roles that fit his abilities. Even when promoted during the Civil War, he asked President Lincoln to ensure he wouldn't be given superior command prematurely. This humility allowed Sherman to grow gradually, unlike others whose rapid rise led to quick downfalls.

Sherman’s realism shone during the Civil War. While others jockeyed for power, he supported General Grant, recognizing the value of teamwork over personal glory. His strategic brilliance, honed from years of study and cautious advancement, culminated in his famous march to the sea. Sherman’s success was not just military; his humility and refusal to seek public office or bask in praise set him apart.

Contrast this with Upton Sinclair, who, during his 1934 gubernatorial campaign, wrote a book imagining his success before achieving it. This premature celebration sapped his motivation, leading to a significant electoral defeat. Sinclair’s story exemplifies how talk and hype can replace action, a lesson echoed by Emily Gould, a writer who spent more time on social media than on her novel.

The message is clear: Silence and humility are strengths. Sherman’s restraint, Sinclair’s folly, and Gould’s distractions teach us that true work requires focus, not fanfare. This lesson is driven home by John Boyd, a fighter pilot turned strategist, who taught military leaders to choose between being somebody and doing something meaningful. Boyd’s life, marked by significant but quiet contributions, challenges us to prioritize purpose over recognition.

In the world of music, Kirk Hammett’s journey with Metallica underscores the importance of perpetual learning. Despite joining one of the world’s biggest bands, Hammett sought lessons from Joe Satriani, understanding that mastery requires ongoing humility and education. This mindset, shared by martial artist Frank Shamrock, highlights the necessity of continuous feedback and improvement.

Purpose and realism trump passion, as illustrated by Eleanor Roosevelt and John Wooden. Passion, without discipline and clarity, leads to overconfidence and failure. Real greatness comes from deliberate, purposeful action, not impulsive zeal.

Our cultural obsession with passion often blinds us to the virtues of patience and methodical progress. By following the examples of Sherman, Boyd, and Hammett, we learn that true success is built on a foundation of humility, continuous learning, and a focus on purpose over ego.

Can Humility and Realism Trump Passion for Success?

In ancient Rome, artists and writers often served wealthy patrons as "anteambulos"—those who cleared the path, making life easier for their benefactors. This role, although seen as demeaning, actually offered invaluable insights and opportunities. Martial, a famous Roman writer, despised his servitude, but it was this very position that gave him a unique perspective on Roman society, ensuring his legacy.

In today's modern world, we see similar dynamics. Interns and entry-level workers often resent their roles, feeling overqualified and underappreciated. But history shows that those who embrace these humble beginnings often achieve greatness. Benjamin Franklin, for instance, wrote under pseudonyms, receiving no credit for his work, learning the ropes of public opinion and stylistic finesse. NFL coach Bill Belichick thrived on analyzing game film, a task others shunned, and rose to four Super Bowl victories.

The "Canvas Strategy" advocates for making others look good, clearing their paths, and in turn, creating your own path. This approach, though seemingly self-effacing, is a strategic investment in one's future. It helps in reducing ego, fostering learning, and building invaluable relationships.

Jackie Robinson’s story exemplifies the power of restraint. Known for his temper, Robinson had to endure relentless racism and aggression as the first black player in Major League Baseball. He chose not to retaliate, understanding that his restraint was crucial for breaking racial barriers. His poise and self-control amid adversity were instrumental in his success and legacy.

The danger of living in one's head, illustrated through characters like Holden Caulfield and historical figures like General George McClellan, highlights how ego can impede action. McClellan’s inaction and self-delusion cost countless lives during the Civil War. In contrast, those who curb their ego, like General George C. Marshall, who refused to keep a diary to avoid self-deception, achieve true leadership and impact.

Early pride can be perilous. Benjamin Franklin, after an early success, was warned by Cotton Mather to "stoop" to avoid hard knocks. Franklin’s continuous effort to humble himself despite significant achievements ensured his sustained success and ability to navigate life’s challenges effectively.

Work is the antidote to ego. Edgar Degas, despite his creative genius, couldn’t excel in poetry because he underestimated the labor it required. True professionals, like Darwin with his decades-long work on evolution, understand that success demands relentless effort, independent of immediate recognition or reward.

Success requires humility and relentless work. By adopting the Canvas Strategy, restraining ego, and valuing hard work over early pride, one can navigate the path to true greatness, just as historical figures and modern success stories have shown.

From Anteambulos to Achievers: Unleashing Greatness Through Humility and Hard Work

Success can be as fleeting as the thin air at the top of a hard-climbed mountain. With triumph come new temptations and challenges, and often, it’s our own ego that hastens our downfall. 

Howard Hughes, the legendary aviator and businessman, epitomized this tragic arc. Inheriting his father’s tool company, he quickly abandoned it to chase grand, often reckless ventures. His boldness led to colossal failures: a disastrous film career, a floundering defense contractor, and a failed airplane project that cost millions. Hughes's ego blinded him to his limitations, leading to a life marred by paranoia, addiction, and squandered potential.

His story is a stark reminder that success requires continual learning and humility. Genghis Khan, in contrast, exemplified this mindset. Though a ruthless conqueror, his real strength lay in his openness to learning. He adapted the best practices of the cultures he conquered, which contributed to his enduring legacy.

Bill Walsh, the legendary football coach, also understood the importance of focusing on fundamentals rather than grand narratives. His “Standard of Performance” instilled excellence in seemingly trivial details, leading to the San Francisco 49ers' rapid rise to Super Bowl champions. Walsh resisted the urge to craft a glorified story about his success, recognizing that it was the small, consistent efforts that truly mattered.

Ulysses S. Grant, a Civil War herol, stumbled when he lost sight of what truly mattered to him. Unlike his friend Sherman, who retired contentedly, Grant pursued the presidency and later fell victim to financial ruin, driven by a misguided sense of honor and ambition. His tragic end underscores the perils of not knowing and sticking to what’s important.

Entitlement, control, and paranoia are dangerous companions to success. Entitlement makes us believe we deserve everything; control turns us into perfectionists, exhausting those around us; and paranoia isolates us, making us prisoners of our own fears. Success can intoxicate, but to sustain it, we must remain grounded, continually learning, and humble.

Ultimately, true success lies not in ego-driven achievements but in understanding and focusing on what genuinely matters to us. This clarity allows us to say no to distractions and yes to a fulfilling, purpose-driven life.

Can Ego and Ambition Undermine Your Success? Lessons from Howard Hughes and Ulysses S. Grant

In 1953, President Dwight D. Eisenhower returned to the White House after his inaugural parade. His reaction to being handed confidential letters marked an insightful moment. Eisenhower promptly instructed, “Never bring me a sealed envelope. That’s what I have a staff for.” 

Contrary to seeming snobbish, it was a reflection of his commitment to a well-organized, efficient administration. Eisenhower believed in empowering his staff and focusing on big-picture priorities, a strategy that allowed him to maintain a balance between work and leisure, contrary to his public image of a leisurely golfer. 

In stark contrast, John DeLorean’s venture into creating his car company became a classic tale of mismanagement. DeLorean, who left General Motors in rebellion against its disciplined culture, envisioned a creative paradise. Instead, his company spiraled into chaos, plagued by politics, incompetence, and criminality. 

DeLorean’s inability to delegate effectively and his penchant for chasing fleeting ideas led to the company’s downfall and the production of faulty cars. His story underscores the importance of structured leadership over mere genius.

General George Marshall, another exemplary figure, demonstrated the power of selflessness and integrity. Unlike many of his contemporaries during World War II, who were often consumed by ego and political infighting, Marshall focused on the mission. When offered the prestigious command of D-Day, Marshall deferred the decision to President Roosevelt, prioritizing the country’s needs over personal glory. This act of humility and his consistent avoidance of self-promotion made him a revered leader.

John Muir’s experience in Alaska offers a different kind of leadership lesson—one of cosmic humility. Muir felt an overwhelming sense of connection to the natural world, capturing what the Stoics call "sympatheia." This sense of belonging to something larger than oneself is crucial for leaders to remember, especially when material success and ego can cloud judgment and purpose.

Angela Merkel, Germany’s chancellor, epitomizes the balance of power and humility. Known for her plainness and modesty, Merkel’s clear-headed and patient approach has made her a formidable leader. Her story of standing on a diving board as a child, carefully considering her jump until the last moment, reflects her cautious and deliberate decision-making style. Merkel’s focus on results over image and her ability to remain sober amidst power have been key to her sustained success.

These stories illuminate the essence of effective leadership. It’s not just about ambition or talent but about managing oneself, prioritizing the collective good, and maintaining humility and clarity in the face of success and power.

Lessons in Leadership: Insights from Eisenhower, DeLorean, Marshall, Muir, and Merkel

Failure is inevitable on any journey, but it's how we handle setbacks that truly defines us. Ego often blinds us, making failure even more painful. Take Katharine Graham, for instance. Born into privilege, she never anticipated the challenges that lay ahead. Her husband’s mental breakdown and subsequent suicide thrust her into a leadership role at The Washington Post, a position she felt unprepared for.

Despite being a novice, Graham faced monumental decisions—like publishing the Pentagon Papers and investigating Watergate—against advice from her board and legal counsel. Her resolve turned these crises into triumphs, earning the paper a Pulitzer Prize and changing American history. Her perseverance in the face of adversity, from union strikes to hostile takeovers, culminated in an astonishing financial success for the company.

Similarly, Malcolm X transformed his prison sentence into a period of profound personal growth. By choosing "alive time," Malcolm educated himself and emerged as a powerful advocate for civil rights. His story exemplifies how adversity can be a catalyst for significant transformation.

Belisarius, a brilliant but underappreciated general, serves as another example. Despite saving Western civilization multiple times, he was repeatedly undermined by Emperor Justinian. Yet, Belisarius remained steadfast, finding satisfaction in doing his duty well, regardless of external validation.

These stories illustrate a common theme: resilience in the face of failure. Whether it's Graham's navigation through corporate storms, Malcolm X's intellectual awakening in prison, or Belisarius’s unwavering commitment to his duty, each found a way to turn adversity into an opportunity. The lesson? Embrace setbacks as a chance to grow, keeping ego in check and focusing on the journey rather than the destination.

Can Failure Be the Catalyst for Your Greatest Success?

John DeLorean’s rise and fall is a cautionary tale of ambition gone awry. DeLorean’s car company collapsed due to his outsized ambition, mismanagement, and ego. Instead of accepting responsibility, he tried to save his company through a $60 million drug deal, leading to his arrest. His downfall serves as a stark reminder of the dangers of letting ego dictate actions.

Contrast this with Steve Jobs, who, after being fired from Apple, chose a path of reflection and improvement. He founded new companies, learned from his past mistakes, and eventually returned to Apple, leading it to unprecedented success. Jobs’s story underscores the power of humility and the willingness to learn from failure.

Similarly, Dov Charney of American Apparel refused to step aside gracefully, leading to lawsuits, financial ruin, and eventual bankruptcy. His inability to let go exemplifies how ego can exacerbate failure.

Historical figures like Alcibiades also illustrate the destructive power of ego. His shifting allegiances during the Peloponnesian War ultimately led to Athens’ ruin. Ego not only destroys careers but can also dismantle entire civilizations.

The story of Alexander Hamilton offers wise counsel: “Act with fortitude and honor... Have the courage to make a full stop.” This advice highlights the importance of pausing and reassessing rather than continuing down a destructive path.

In contrast, the New England Patriots’ drafting of Tom Brady shows the value of humility and continuous improvement. Despite their success, they focused on their scouting missteps, holding themselves to higher standards. This mindset of constant self-evaluation and striving for betterment underscores the power of humility over ego.

Orson Welles’s experience with William Randolph Hearst over “Citizen Kane” further illustrates the futility of ego-driven vendettas. Hearst’s obsessive campaign to destroy the film only cemented its place in history and tarnished his own legacy. Welles, on the other hand, continued his work without bitterness, showing resilience and grace.

Winston Churchill, Katharine Graham, and other great leaders faced immense challenges but triumphed by keeping their egos in check and focusing on the larger picture. Their stories remind us that failure and adversity are part of the journey, and how we handle them defines our character.

Ultimately, the battle against ego is ongoing. Success, failure, and aspiration are parts of life’s continuum, and ego can derail us at any stage. The key to navigating these phases is maintaining humility, learning from mistakes, and continuously striving to be better. This approach not only leads to personal growth but also to lasting success and fulfillment.

Triumph over Ego: Lessons from John DeLorean, Steve Jobs and Other Famous Personalities

Embarking on a journey where ego and humility clash reveals timeless lessons about ambition and restraint. Ancient wisdom from Isocrates and the disciplined approaches of figures like General Sherman and Bill Walsh emphasize the importance of understanding one's limitations, focusing on small, deliberate actions, and prioritizing purpose over ego. Sherman, for instance, grew gradually and strategically, while Walsh transformed the 49ers with exacting standards and humility.

Contrasting stories like Upton Sinclair's premature celebrations and John DeLorean’s mismanagement illustrate the pitfalls of ego-driven actions. True success, as seen in the lives of Malcolm X and Katharine Graham, often comes from resilience and the ability to turn adversity into growth opportunities.

Learning from historical figures like Genghis Khan and modern leaders like Angela Merkel, we see that continuous learning, humility, and clear purpose are crucial. Merkel’s cautious yet decisive leadership style underscores the value of patience and deliberate action over impulsive zeal.

The "Canvas Strategy" champions making others look good as a path to personal success, encouraging humility and learning. Leaders like General Marshall, who prioritized mission over personal glory, demonstrate the power of selflessness and integrity.

Failure, inevitable on any journey, tests our ability to manage setbacks without letting ego blind us. The stories of Steve Jobs and Malcolm X show that embracing failure with humility and a focus on improvement can lead to remarkable transformation and success.

In the end, maintaining humility, focusing on continuous improvement, and managing ego are essential for lasting success and fulfillment. Whether in personal ambitions or leadership roles, these principles guide us through the complexities of success, failure, and aspirations.

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Ego Is the Enemy

Ryan Holiday

7 Key ideas

18 MINS

4.7 (2.4k)

Are you curious about how historical figures like General Sherman, Upton Sinclair, Genghis Khan and Angela Merkel managed their ego and ambition?

Do you want to understand the power of humility, self-control, and good judgment in achieving lasting success?

Interested in learning from the resilience of people like Malcolm X and Katharine Graham, who turned adversity into growth opportunities?

Let's embark on a journey that contrasts ego and humility, providing valuable lessons from both ancient wisdom and modern success stories.

Key Ideas

#1