Ego Is the Enemy: The Fight to Master Our Greatest Opponent

People with the most ambition and talent are the most likely to become egotistical. Holiday describes this “darker side of the psyche” as a need to be dominant and superior to others (1-2). Ironically, these impulses inhibit people’s ability to be creative, collaborate meaningfully with others, and maintain good relationships and success in general. For this reason, the author considers the ego an enemy of success. The delusional, self-centered nature of the ego provides a sense of comfort for people who are feeling afraid of failure or criticism.

People now have more outlets for boasting and curating a certain self-image, and on social media, this may be rewarded with likes and followers. Mainstream messaging in modern culture emphasizes people’s specialness, and motivational speakers and successful people encourage grand visions and “risk-taking swagger” (5). Holiday considers this misguided and ego-driven, arguing that this encourages people to adopt the “symptoms of success” as if that will guarantee real accomplishments (5). While some successful people have been notoriously egotistical, Holiday argues that their success occurred in spite of, not because of, their egos. Many egotistical people enjoy success for a short time until their arrogance leads to mistakes and failure.

In the fourth century BCE, Isocrates wrote to his friend Domenicus, advising him to always exercise self-control and be wary of people who flatter him. Shakespeare encapsulated some of this advice in Polonius’s dialogue with his son in Hamlet, telling him to not “be false with any man” (16). American General William Tecumseh Sherman was inspired by these lines. A Civil War general, Sherman was unusual because he eschewed a promotion to be top in command because he did not feel ready for the responsibility. While Sherman was higher ranked than Ulysses S. Grant, he invited his colleague to a siege; their collaboration won a victory for the Union. Holiday credits Sherman’s earned confidence, experience, and humility as the foundation for his “march to the sea” military strategy, in which Union forces avoided all-out battles in favor of “maneuver warfare” (19).

After the war, Sherman had celebrity status, but he tried to ignore people’s flattery and continued to do his job. Holiday notes that because Sherman’s confidence was based on real accomplishments, his self-belief led to success. As they aspire to achieve great things, the author warns the reader against basing self-belief or self-esteem on egotistical fantasies rather than real achievements, arguing that the ability to realistically evaluate one’s own abilities is more valuable than vision or emotional investment. Holiday challenges stereotypes about the “self-assured genius” and “pained, tortured artist,” arguing that they are more myth than fact and that neither is truly successful because they are “divorced from reality and divorced from other people” (22).

At the beginning of an ambitious project, it is easier to simply “talk” about one’s ambitions rather than quietly putting in the work. The ego finds it soothing to receive validation and attention, even when it is based on a hypothetical vision rather than a real accomplishment. Anyone can gossip about others or “hype” themselves, but being able to be discreet and “subsist without validation” is a rarity (26). Talking about one’s own plans can feel cathartic, and even productive, which makes it all the more tempting to talk rather than take real action. Holiday asserts, “The only relationship between work and chatter is that one kills the other” (28).

John Boyd was an American military instructor who flew fighter planes in the Korean War and later taught at the Nellis Air Force Base. He later worked at the Pentagon, advised the government, and helped to develop new fighter jets.

Boyd is remembered for his stern advice to younger soldiers, advising them to beware of the temptation to chase promotions and the validation of their superiors when they should prioritize making genuine contributions to the military and maintaining their values of duty, honor, and patriotism.

Boyd phrased this dilemma with the question “To be or to do?”, emphasizing that people often confuse seeming impressive to others with genuinely accomplishing impressive things (31). Boyd never received a high-ranking or visible appointment and lived frugally until he passed away. He never accepted money from private contractors, which he perceived as bribes. Holiday calls him a “great man” for his dedication to his job and his values of honesty, hard work, and accomplishments in his field.

Being a student is inherently humbling, as it imposes an “ego ceiling” on the learner, reminding them that they are still working to become as skilled as their teacher (38). Behaving like a student means acknowledging one’s own weaknesses and limitations, accepting instruction, and putting in the work to improve. Even talented people and professionals can make gains by behaving like students. For instance, when Metallica first hired Kirk Hammett to play guitar, he decided to seek out more guitar instruction and attended weekly lessons to learn everything he didn’t yet know. Holiday credits Hammett’s dedication to his craft with making Metallica such a success.

Holiday argues that “[t]he pretense of knowledge is our most dangerous vice, because it prevents us from getting any better” (38). A student mindset encourages humility, curiosity, and a dedication to ongoing learning, which benefits people from every walk of life. Conversely, ego-driven people are impatient and believe that their raw talent does not need development. Holiday posits that the ego makes people “hardheaded and hostile to feedback” and is therefore the opposite of cultivating a “student mind” (42).

Holiday contrasts passion with reason, arguing that people who base their work on reason are more likely to be successful and have sound decision-making compared to those who simply have a passion for their cause. Eleanor Roosevelt, for example, had “purpose” and “direction” that fueled her good works but rejected the idea that she was passionate (45).

While having passion can motivate people, it does not make up for a lack of critical-thinking skills. Holiday compares passion to drunkenness, arguing that it greatly inhibits people’s ability to respond logically to reality. Holiday contends that important work requires “deliberation and consideration” (50), and so keeping one’s enthusiasm in check and recognizing one’s own biases is crucial.

In ancient Rome, there was a position called an “anteambulo,” which literally translates to “one who clears the path” (51). These people, usually thinkers, writers, or artists of some kind, would be patronized by a wealthy person and in exchange would communicate messages and assist them with tasks. One such person was Martial, whose diaries survive today and reveal that he resented helping wealthier people who had more privilege and access than he did. Holiday rejects this perspective, suggesting that if Martial had been grateful for his work and found purpose in it, he could have enjoyed it more and improved himself, rather than feeling bitter.

Similarly, some people today have a similar view of work, feeling hesitant to accept jobs that they are overqualified for or resenting professionals in higher positions than them. Holiday believes that people should not feel demeaned by serving someone in a higher position but focus on helping them do their best work. He coaches the reader to become an “anteambulo” and help others since this will ultimately help them, too.

Holiday points to NFL coach Bill Belichick as an example. His first position with the NFL was as a volunteer, and he let senior coaches take credit for his ideas. He asked for “grunt work” and committed himself to excelling at it (54). Eventually, Belichick’s superiors so valued his contributions that he was offered a paid position. Holiday maintains that “[g]reatness comes from humble beginnings” (56). Holiday compares lower-ranking jobs to creating canvases for others to paint on, and he encourages the reader to develop their own “canvas strategy” in which they allow others to take credit for their ideas and do work that no one else wants to do (57). In the long term, this work should pay off by helping with skill development and creating a network of people who respect one’s contributions.

As a young man, Jackie Robinson was known for his hot temper and had numerous angry outbursts in reaction to racist abuse. However, when baseball coach Branch Rickey scouted him to join the Brooklyn Dodgers team, he specifically told him to restrain his temper and never react to abuse. While this was difficult and grossly unfair, Robinson learned to keep his cool even while being mistreated by other players, coaches, and fans. Holiday attributes Robinson’s success to his ability to manage his emotional reactions as part of his larger career strategy. He points to his spotless reputation and legacy to show that Robinson’s restrained approach paid off.

Holiday argues that becoming absorbed in one’s own thoughts is a symptom of egotism. These thoughts can manifest as self-serving vanity or as self-loathing, both of which are especially common in inexperienced and ambitious people. This type of self-centered overthinking can be paralyzing and prevent people from making decisions and moving forward with their plans.

Psychologist David Elkind argues that teenagers are particularly susceptible to developing an “imaginary audience,” living as though people are following and judging their every move (70). Holiday believes that everyone falls prey to this juvenile perspective, and it is especially relevant now that people are required to market and brand themselves as people and professionals. He concludes this chapter by telling the reader to stop “performing” and focus instead on working and learning (72).

As a young man, Benjamin Franklin learned to be less prideful when he returned home showing off new clothes and money. A distracted Franklin walked into a ceiling beam, and his acquaintance, Cotton Mather, told him to not “hold his head so high” but instead “stoop” as he went through life (73). Holiday argues that pride compromises one’s mind by encouraging a delusional level of self-belief.

John D. Rockefeller tried to limit his pride by keeping a diary and reminding himself to be humble; he knew that becoming arrogant could take him off-course. The author laments that most people steel themselves against criticism and negativity but spend less time reflecting on how false positivity or flattery may be equally damaging. Instead of looking up to the “proud and the accomplished,” Holiday tells the reader to surround themselves with fellow “strivers” (78).

The ego is pleased with big dreams and great plans, but these alone do not result in accomplishments. Without following practical steps, working hard, and dealing with failure, people do not achieve their goals. Holiday argues that hard work is the difference between a real professional and a dilettante, noting that it's easy to fantasize but challenging to make those fantasies a reality.

Charles Darwin worked on his theory of evolution for years without sharing his vision with anyone, instead focusing on perfecting his ideas. Holiday urges the reader to delay gratification and work hard even without quick rewards or validation.

The author acknowledges that starting out in any profession can be hard and that recognizing that one’s craft does not meet one’s standard can breed insecurity. Acting in an egotistical way can assuage these inner fears while also projecting a sense of confidence that others may interpret as bravery or ambition. Caving to the ego means acting with arrogance while taking an easier path, like Lance Armstrong using performance-enhancing drugs to win the Tour de France. The author hints that becoming aware of one’s own ego is an essential lesson early in life because the ego is a “wicked sister of success” (87).