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Howard Hughes, an American businessman and inventor, inherited his father’s company and fortune as a very young man. Hughes purchased his relatives’ shares in the company and took sole charge of it. While Hughes was a “gifted, visionary, and brilliant” man (94), he was unable to manage his different desires and ambitions, and ultimately his company failed spectacularly. Holiday calls Hughes an “egomaniac” whose self-absorption triggered his financial and personal downfall (94). While his life as a billionaire and “eccentric” is easily glamorized, Holiday emphasizes that he “died in an asylum of his own making” and emphasizes that his egotistical behavior interfered with his real talent and genius and killed his potential (97).
Genghis Khan was a successful conqueror because he was able to adapt Mongol culture and policy by observing the societies he encountered and warred against. Khan learned about military organization, walled cities, siege tactics, and insights into each locale he visited, always putting his new knowledge to use. Holiday ponders how as people become more successful, they encounter new, bigger problems and claims that this makes humility an essential quality. By being humble, people can learn new things and continually improve, making them more competitive at their craft.
The author instructs the reader, “It is not enough only to be a student at the beginning. It is a position that one has to assume for life. Learn from everyone and everything” (104). Holiday contrasts amateurs, who stay in their comfort zone of what they already know, and professionals, who “like being challenged and humbled” and consider learning a continual process (105).
In the late 1970s and early 1980s, NFL coach Bill Walsh helped to transform the 49ers from the worst-ranked team in the league to Super Bowl Champions. Walsh did not mythologize his success, however, instead admitting that he was not sure if he could reform the team. Their early failures under his coaching prompted him to consider quitting, and some members of management disagreed with his tactics. Walsh never focused on winning games but on implementing higher standards of behavior and athletic performance, even for seemingly irrelevant things like locker room tidiness. Holiday praises the strength of Walsh’s rules and his humility in acknowledging that he was not certain they would win games.
The author claims that people should fight the impulse to create narratives out of their success that lionize their accomplishments and simplify the real events that took place. Walsh’s “Standards of Performance” were the backbone of the team’s success, but the media dubbed him a “genius” and mythologized his rise (109). Holiday notes that the team lost badly in the following two seasons and only improved once everyone embraced the Standards of Performance again. This demonstrates how overconfidence can ruin success and how everyone must humbly work to overcome those temptations.
Holiday credits investor Paul Graham with his insight that small steps are as important as “sweeping visions” and that it’s helpful for people to keep their identities “small” and put their energy into their work (111-12). This is the opposite of believing in destiny, as Napoleon did, and using the concept to justify grand visions. Similarly, considering oneself a genius, or listening to that flattery, can lead to arrogance.
Holiday laments people’s interest in “labels” that fuse their identity to their profession and can make people assume that they will enjoy success in their field. Holiday coaches the reader to focus on the present moment and the small steps within it: “Instead of pretending we are living some great story, we must remain focused on the execution—and on executing with excellence. We must shun the false crown and continue working on what got us here” (112).
Holiday compares two Civil War generals, William Tecumseh Sherman and Ulysses S. Grant, and their vastly different life choices after the war. While Sherman disliked politics and refused to run for office, Grant embraced the public’s goodwill and successfully ran for President. Holiday claims that Grant did not understand how to play politics in Washington, and although Grant was a good man, his administration was “corrupt, contentious” and generally ineffective (114-15). After his time in office, Grant was humiliated by a disastrous investment he made with a disreputable investor. Bankrupt, Grant spent his final years frantically writing his memoirs in the hopes of leaving his family with the profits.
The author claims that Grant’s downfall is symptomatic of how the ego can lead people to overlook the great things they have and envy what they do not have. He suggests that if Grant had better self-awareness about his own skills and focused on more realistic goals, he could have accomplished much more without experiencing such dramatic financial and emotional consequences. Holiday ponders the irony of Grant becoming a national success story, only to have that success create egotistical temptations that led him to make poor decisions.
While competitiveness is an important force in people’s lives and careers, it only serves people well if they understand who they are competing against and why they are motivated to do so. Holiday recommends identifying one’s priorities and ignoring other opportunities or temptations. By making these compromises, people will overcome their ego’s tendency to chase everything since “[e]go rejects trade-offs […] Ego wants it all” (118). Holiday encourages the reader to see the “emptiness of this illusion” that they can have everything they want (119).
Persian emperor Xerxes is one dramatic example of how power and success can foster paranoia and entitlement. When a flood broke a bridge his army needed, Xerxes executed the military engineers who built it, blaming them for its failure. He even punished the chains that held the bridge together. Holiday attributes Xerxes’s “delusional threats” to his egotistical mindset brought on by his powerful position (121). Holiday considers how this erratic and selfish behavior is typical of rulers throughout history.
The author claims that the same instincts that sometimes bring success can become a liability later on. For instance, a healthy sense of determination and rejection of criticism may help people succeed but could later turn into closed-mindedness and arrogance. Holiday points to President Nixon and businessman Ty Warner as examples of people who lost their positions of power because they began to live in a “bubble” of their own delusions. A sense of entitlement and a desire for control undermine one’s leadership because they overestimate one’s own abilities while undervaluing others’ contributions. They can also hinder progress by creating a perfectionist mindset in which everything must be done perfectly. Paranoia further degrades leadership by creating hostile and suspicious relationships.
Holiday examines the importance of managing others and oneself. President Eisenhower was known for his efficient approach to organization that he brought to the White House. On the other hand, inventor John DeLorean left the company GM to begin his own car company but failed to instill discipline and effective management practices. As a result, the company failed. Holiday acknowledges that DeLorean was a creative “genius” but argues that without personal and professional discipline, he ended up a “power-hungry narcissist” who could not execute his vision (127-28). Holiday laments DeLorean’s egotistical behavior, noting that his ideas were strong but he failed to develop the discipline to make his invention a feasible business. The author claims that there is no one perfect management system or style but argues that egotists may become controlling micromanagers or more broad-minded visionaries who struggle to delegate tasks and follow through on practical steps.
When people experience success, they may become afflicted with “the disease of me”: an arrogant and entitled attitude that makes it difficult to collaborate with others (133). General George Marshall was one of several American generals to serve in World War ll; Holiday praises him for never catching “the disease of me.”
Marshall rejected honors and promotions because he felt they were inappropriate or a distraction from his work. For instance, Marshall had the opportunity to lead the troops on D-Day and coordinate the invasion; however, he encouraged the president to pick whoever he felt was best suited for the job, and he later picked Eisenhower. Marshall was renowned for his humble attitude and did his best to not be distracted by media attention and honors. When Marshall had his official portrait painted, he did not even look at it. Holiday admires Marshall’s humility and modesty.
The American conservationist John Muir wrote vividly about feeling a strong connection to all of the nature around him while on a trip to Alaska. Holiday calls this emotion “sympatheia,” which he defines as a “connectedness with the cosmos” (139). This feeling can be both energizing and humbling but is disrupted by stress, distractions, and the ego. By reflecting on the world’s “immensity,” including its nature and history, people will feel humbled and recognize their small part in things. Holiday connects this feeling with creativity, arguing that people who are self-centered will fail to cultivate the “receptiveness and recognition” that creative insight requires (140). People who have already attained success will have to be especially mindful to not be led astray by their egos. The author encourages the reader to intentionally seek out “cosmic sympathy” by going into nature or putting their problems into perspective (142).
Holiday lauds “sobriety,” or a calm and measured demeanor, over passion and flair. Angela Merkel was a “sober” chancellor of Germany who was known for her modesty and stoic demeanor. Holiday calls Merkel “slow and steady” since she worked as a physicist for years before eventually entering politics in her fifties (145). According to the author, this demonstrates her patience and lack of ego since she was not in a rush to acquire power. This steady approach helped Merkel serve as chancellor for 16 years.
Holiday praises Merkel for her “rational” and analytical approach to problem solving, agreeing with her comment that “[y]ou can’t solve […] tasks with charisma” (147). Holiday encourages the reader to consciously “sober” themselves by avoiding worrying about their image, competing and performing with others, or becoming self-important.
Aristotle was a tutor to Alexander the Great, who went on to conquer large swathes of Europe and Asia. Aristotle taught about the importance of moderation through his concept of the “golden mean,” or the ideal midway point between extremes. For instance, courage is a golden mean between recklessness and cowardice, while generosity is a golden mean between greediness and becoming destitute. Holiday argues that pursuing the golden mean can be a strategy to overcome one’s own ego. For instance, he coaches the reader to avoid the extremes of either hyper ambition or complacency by developing a measured and consistent discipline.
Holiday points to previously mentioned historical figures such as Alexander the Great, Napoleon, and Howard Hughes as examples of people whose egos motivated their actions, reminding the reader that they are cautionary tales. Holiday writes, “We know what decisions we must make to avoid that ignominious, even pathetic, end: protecting our sobriety, eschewing greed and paranoia, staying humble, retaining our sense of purpose, connecting to the larger world around us” (152). Holiday claims that failure is bound to follow success and that people should be mentally prepared for adversity rather than buy into the delusion that their success will last forever.
In Part 2, “Success,” Holiday continues to use historical examples to develop his argument that egotistical behavior undermines success and often leads to failure. The broad array of historical figures he analyzes have little in common other than their traits. For instance, Holiday lauds leaders such as President Eisenhower, General Marshall, and Chancellor Angela Merkel for their work ethic and high standards. By including such examples, Holiday argues that genuinely successful people are rarely showy, attention-seeking, or materialistic but instead focus on results. He writes, “As hard as it might be to believe from what we see in the media, there actually are some successful people with modest apartments […] They lack artifice, they wear normal clothes. Most successful people are people you’ve never heard of. They want it that way” (148).
By contrasting people such as Merkel with those like Howard Hughes, Holiday shows that fame, glamor, and ambition do not guarantee success or happiness. Holiday explains, “Howard Hughes—despite his current reputation as some kind of bold maverick—was not a happy man, no matter how awesome his life may seem from history or movies” (154). This recurring point challenges society’s fascination with dramatic life stories and eccentric, creative geniuses and emphasizes the value of stability and lasting contributions.
Holiday expands this point by arguing that there are many historical figures who are perceived as success stories, even though their efforts were destructive and did not bring about a lasting or positive change. For example, Alexander the Great was a successful conqueror during his short life but ignored his tutor Aristotle’s advice to embrace moderation and instead followed his extreme ambition of taking over the world. This, according to Holiday, is likely why he died so young. Similarly, Napoleon had an extremely ambitious vision that fueled his many military excursions, but he ultimately lost his power and empire. As such, Holiday considers Napoleon’s career and leadership a failure since they did not bring lasting, positive effects. He explains, “All that death, that effort, that greed, and those honors—for what? For basically nothing. Napoleon, he wrote, quickly faded away, just like the smoke from his artillery” (151).
These points connect to Holiday’s theme about The Importance of Self-Awareness. He often returns to his argument that in order to overcome their egos, people must concentrate on achieving the best results possible and not worry about being recognized for their work or maintaining a certain reputation. By using General Marshall as an example of a humble and private person who greatly impacted history, Holiday critiques the notion that fame is a good measure of success. He writes,
When it comes to Marshall, the old idea that selflessness or integrity could be weaknesses or hold someone back are laughably disproven. Sure, some people might have trouble telling you much about him—but each and every one of them lives in a world he was largely responsible for shaping. The credit? Who cares (137).
By examining Marshall’s humble habit of avoiding the spotlight, Holiday is able to sharply contrast ego with real confidence, which he believes are very different. He explains, “Ego needs honors in order to be validated. Confidence, on the other hand, is able to wait and focus on the task at hand regardless of external recognition” (134).
In Part 2, Holiday also examines Ego and Delusion, reiterating how success can exacerbate egoic tendencies, which then makes reasoned interpretations and decision-making impossible. Holiday claims that increasing knowledge and success can give people the impression that their hard work is over. He writes, “With accomplishment comes a growing pressure to pretend that we know more than we do […] That’s the worry and the risk—thinking that we’re set and secure, when in reality understanding and mastery is a fluid, continual process” (103). As an antidote to these tendencies, Holiday advocates Continual Learning as a Remedy to Ego, arguing that those who remain successful are those who remain humble and continue to learn and grow.
By examining achievements as a risk factor, Holiday also challenges the perception of material success as a destination that, once attained, is sure to stay the same. According to Holiday, this is a misguided perception that the ego plays a significant part in forming. The author notes that “prosperity holds no guarantees” and that downturns and failures are simply a part of the “facts of life” since “reversals and regressions are as much a part of the cycle of life as anything else” (152). Moreover, he argues that the risks posed by the self-aggrandizing and delusional ego are even more acute once people are successful since there may be many others vying for their position or status. He writes,
It’s during your moment at the top that you can afford ego the least—because the stakes are so much higher, the margins for error are so much smaller. If anything, your ability to listen, to hear feedback, to improve and to grow matters more now than ever before (110).
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By Ryan Holiday