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

Theodore Roosevelt overcame adversity in his childhood, such as severe asthma, through determination and effort. Holiday credits Roosevelt’s early challenges with helping him learn how to build up both physical and mental strength in tandem; he had to exercise to build his frail body into a strong one while also becoming more mentally resilient. Holiday claims that by enduring hardship people can build an “inner citadel” of mental strength (136). Holiday encourages the reader to adopt Roosevelt’s view of hardship as good practice for the inevitable battles that life presents.

Holiday lauds the concept of a “premortem,” the practice of anticipating failures and thinking of possible solutions to problems before they arise (139). This practice helps people and businesses develop back-up plans, making them more resilient to the unexpected. Holiday argues that since plans rarely unfold the way people want them to, they should anticipate failure and plan for it as much as possible. The Stoics had a similar method, called “the premeditation of evils” (140), which allowed them to consider all the ways their plans could be ruined and react with less panic when things went awry (140). Holiday warns against becoming attached to idealistic expectations, since “the only guarantee, ever, is that things will go wrong” (141). Holiday compares people who anticipate and plan for the worst to runners who train on tough, hilly terrain and run faster than those who only train on flat, easy courses. 

Holiday argues that acquiescing to fate can be an important part of moving forward and embracing the skill sets or advantages that we do have. For instance, Founding Father Thomas Jefferson accepted that his speech disability meant that he would not be a great orator, and practiced writing instead. Like obeying a stop sign, people can accept certain limitations without taking them personally, and instead choose to go another way. Holiday reminds the reader of the Stoic practice of recognizing what one can and can’t control. When an obstacle is totally outside one’s control, people should practice “the art of acquiescence” and accept it (146). Holiday claims that dreaming about ideal conditions is easy, but accepting imperfect conditions takes strength. This approach does not mean surrendering to obstacles, but acknowledging when a challenge cannot be overcome, and deciding to channel one’s energies elsewhere.

Holiday argues that instead of fighting negative events reactively, people can move on quicker by embracing them and learning to love their fate, or “amor fati” (150). For instance, when Thomas Edison’s laboratory caught on fire and he lost much of his work and workplace, he did not react with anger or grief. While the fire was raging he was calm. He even suggested that his wife and her friends come and watch the fire, since it was so impressively large. He and his employees immediately went back to work afterward and ended up making a great profit that year in spite of the disaster. Holiday attributes Edison’s success to his “unfailing cheerfulness” in the face of disaster (151).

Holiday claims that boxer Jack Johnson showed the same resilience against his opponent and an unfriendly crowd in his famous fight with Jim Jeffries. Holiday instructs the reader: “In your worst moments, picture Johnson: always calm, always in control, genuinely loving the opportunity to prove himself, to perform for people, whether they wanted him to succeed or not” (152). Holiday acknowledges that it is somewhat “unnatural” to cultivate acceptance and gratitude for things that happen to us, but argues that “there are opportunities and benefits that lie within adversities” (154).

Odysseus, the hero of Homer’s The Odyssey, is a mythical example of persistence. He endured his long journey home from the Trojan War in spite of storms, monsters, captivity, and temptations. Holiday claims that modern people are less resilient than our ancestors, and tend to lack perseverance when things are not easy. He feels that without perseverance people are bound to fail, and that “there are far more failures in the world due to a collapse of will than there will ever be from objectively conclusive external events” (158). Holiday argues that without perseverance, people become their own worst enemies by quitting when they should “hold on and hold steady” (160).

James Stockdale, a former US Commander, and John McCain, a former senator, endured imprisonment and torture during the war in Vietnam. They focused on maintaining morale among their troops in prison. Holiday emphasizes how focusing on a larger cause and commitment helps people to withstand challenges because “shared purpose gives us strength” (164). He argues that considering other people’s needs can liberate us from becoming overly focused on our own suffering, and in helping others we can help ourselves. Contributing something valuable to the human family, he says, can be an empowering and purposeful way to overcome one’s own obstacles.

By considering the finite nature of our lives, people can experience renewed motivation to live purposefully. The French writer Michel de Montaigne was violently thrown from a horse and nearly died; ultimately this experience “energized” him and prompted him into a new period of productivity (168). Holiday laments that some people act as though they are “invincible” and take their time and health for granted (168). In reality, death is “the most universal of our obstacles” which everyone experiences eventually (170). Holiday claims that thinking about death helps put life issues into perspective.

Holiday warns the reader against expecting their work or life to become easy once they have overcome their immediate obstacles. Instead, he claims that people usually encounter bigger challenges and that many are “always fighting uphill” (172). He compares life to a marathon rather than a sprint race, and encourages the reader to see their current problems as steps along the way. By using challenges to improve, people will gain confidence and greet new obstacles more competently.

Marcus Aurelius, former emperor of Rome, encountered a significant obstacle when his once-friend and ally Cassius committed treason and claimed power in some Roman provinces. While some senators demanded Cassius’s execution, Aurelius decided to publicly forgive him, and explained that strong leaders should try to avoid civil war and retribution. Holiday argues that by emulating Aurelius, people can perceive negative events in their lives as opportunities to practice their principles, claiming that “under pressure and trial we get better” (179).