The Obstacle is the Way: The Timeless Art of Turning Trials into Triumph

In the 1960s, boxing champion Rubin Carter was wrongly convicted of a triple homicide and spent 19 years in prison before finally being released after his conviction was overturned. Holiday explains that Carter never considered himself a prisoner and resisted aspects of social control such as wearing a uniform, doing prison labor, or even attending parole hearings. Instead, he dedicated himself to his own legal case. Holiday asserts that Carter’s actions are an example of how people can retain some of their personal agency in spite of challenges that deprive them of most of their power. He instructs the reader to consider how they can change their way of looking at things to shape a situation for the better; he claims that viewing a situation as negative only makes it worse.

Ulysses S. Grant was known for his stoic reactions to disaster, whether on the battlefield or in life in general. He contrasts this steadiness with the “raw nerves” many people feel about everyday challenges (25). Holiday claims that learning to be resilient in the face of stress helps people avoid fearful reactions, which only worsen the problem. Holiday defines having a strong nerve as a mixture of “defiance” and “acceptance;” people can refuse to be intimidated by a challenge, accepting what has happened without reacting fearfully (26).

An essential aspect of American astronauts’ flight training is exposure to different experiences and stimuli that help build the mental resilience necessary to avoid panic while in space. Holiday posits that panicking in the face of stress is a “luxury” which people in dangerous professions don’t have. They must learn “emotional regulation” to be able to deal with real challenges and survive (28).

Holiday does not suggest suppressing one’s emotions. He advises against confusing emotion with dealing with the problem, which he insists are very different things (30). Holiday encourages the reader to consider if their emotional reaction is adding anything constructive to the situation, and to try to put their challenge into the broader perspective of their life.

Holiday borrows Japanese philosopher and swordsman Samurai Miyamoto Musashi’s notion of the “observing eye,” which sees events as they are, and the “perceiving eye,” which “sees more than what is there” (32). The perceiving eye can exaggerate or misinterpret. It is less reliable than the observing eye, which is plainer and matter of fact. Holiday claims that our “animalistic brains” are wired to respond quickly to events, an impulse which we should learn to control to ensure that we aren’t overreacting to perceived threats (33). Holiday compares self-control to a muscle, claiming that it must be developed through practice.

Holiday claims that people are always better at giving advice to others than solving their own problems because in their own lives they lack objectivity. He encourages the reader to consider their problems from someone else’s point of view: “Give yourself clarity, not sympathy” (34).

During the Peloponnesian War, the Greek general Pericles was confronted with a solar eclipse which suddenly darkened the sky, frightening his crew members. Pericles, however, was calm. He compared the sudden darkness to holding a cloak around one’s face, teaching his crew members that “perspective is everything” (36). Holiday lauds Pericles for using “the power of perspective” to overcome fear, which he claims can be “debilitating” and “often irrational” (36).

Baseball pitcher Tommy John was renowned for his work ethic and positive attitude, which helped him overcome a devastating elbow injury through surgery and rehabilitation. Holiday claims that John succeeded in his career for so long because he correctly ascertained what was within his control and worked toward achieving certain results. In doing so, John lived out the Stoic phrase, “ta eph’hemin, ta ouk eph-hemin,” or “[w]hat is up to us, what is not us to us” (43). When people focus on what they can control it “magnifies and enhances our power” (44). 

Holiday asserts that focusing on the present moment helps to prevent people from worrying or overanalyzing the big picture and make steady gains in their lives. He points to the many successful companies which began in recessions or depressions but weathered challenges and later rose to prominence. He claims that entrepreneurs were focused on their own immediate goals, which helped them overcome broader negative distractions and work toward long-term success. Holiday notes that living in the present takes practice; people’s minds naturally wander to thoughts or worries that can be unnecessary and distracting.

American inventor and Apple co-founder Steve Jobs was a pioneering creative. He insisted on thinking differently and eschewed typical perspectives on products and business practices. This gave him a broader sense of what was possible to achieve than many people he worked with. Holiday praises his “adamant” and “malleable” approach to problems, and attributes his success to this brand of confidence (49).

Holiday claims that Jobs applied this high standard to his colleagues as well as himself. For example, he fired an engineer who felt that his mouse design was unbuildable, and encouraged a manufacturer to produce enough glass for the new iPhone design when they felt they couldn’t. This approach to obstacles runs counter to the typical advice people receive to “be realistic” and “compromise” (52). Holiday encourages the reader to adopt a similarly determined mindset in which “obstacles illuminate new options” (52).

During World War II the Allies were flummoxed in the face of German “blitzkrieg,” a military strategy in which the Germans overwhelmed their enemies with rapid invasions of tanks. American General Dwight D. Eisenhower insisted that the Germans’ strategy had a vulnerability which the Allies could exploit, seeing “the opportunity inside the obstacle” (54). Eisenhower helped the Allies devise a strategy which allowed the German tanks to roll through in a line, enabling the Allies to surround them and attack their flanks. Holiday emphasizes that the Allies’ initial perception of the Germans’ blitzkrieg as unbeatable was an emotional reaction which was overcome by calm, tactical analysis.

Holiday argues that if met with the right attitude, adversity can help people develop their skills and self-awareness. He cites a study in which sports scientists found that injured athletes experienced “adversarial growth” by developing better self-awareness, perspective, and altruism because of their challenges (57). Holiday maintains that there is always a silver lining to negative situations if people can change their perception about them. For example, if someone is rude or lazy, people might find that they appear better in comparison.

Holiday reiterates that problems tend to be as bad as one’s assessment of them, and that by changing one’s thinking people can see new ways to overcome obstacles. He claims that clear perception should not mean romanticizing a situation or denying a problem, but accurately assessing the risks and acting accordingly.