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

Marcus Aurelius was a Stoic philosopher who lived from 121 CE to 180 CE. Aurelius was also the emperor of the Roman Empire from 161 CE until his death in 180 CE. Aurelius did not teach philosophy or author any texts he intended to be published. However, his personal notes and reflections, Meditations, have been preserved and are a major text in the Stoic canon. These writings have been categorized into 12 sections according to different periods of Aurelius’s life. Because of his decision-making and the relative stability that Rome enjoyed during his reign, Aurelius is generally remembered as being one of Rome’s most successful and competent rulers.

Holiday quotes Aurelius many times in The Obstacle Is the Way, emphasizing the value of his Stoic approach to life’s problems. Holiday argues that Aurelius is a role model because of how he managed his emotional reactions to Cassius’s personal and political betrayal. Instead of becoming angry and seeking revenge, Aurelius gave Cassius the opportunity to change his mind. When he did not, Aurelius announced that he would remove him from his post but forgive him, and avoid civil war. Holiday claims that Aurelius made the “obstacle,” Cassius, into a positive by endeavoring to solve the problem without violence. Holiday writes: “As he told his men, if there was one profit they could derive from this awful situation that they had not wanted, it would be to ‘settle this affair well and show to all mankind that there is a right way to deal even with civil wars’” (175).

Eisenhower (1890-1969) was one of the most prominent American generals in World War II; his full military title was Supreme Commander of the Allied Expeditionary Force.

After serving in World War I, Eisenhower was promoted to the position of major and studied tank warfare, a new invention at the time. In the 1930s, he was assigned to serve in Manila, the Philippines, where he helped the Philippine government establish a military. At the beginning of World War II, Eisenhower was assigned to North Africa, where he planned Operation Torch to wrest control of several North African regions from German control. Later in the war he was responsible for planning “D-Day,” formally known as Operation Overlord, the successful Allied invasion of continental Europe.

Holiday uses Eisenhower as an example of how thinking creatively and strategically can help people overcome obstacles. He credits Eisenhower with developing a military strategy which confronted the German army’s use of tanks by exploiting the weakness in their strategy, namely that by advancing with long lines of tanks they left their sides exposed to attack. Holiday praises Eisenhower’s ability to shift his perception of German blitzkrieg, calling his strategy, “[...] a textbook example of the role our own perceptions play in the success or failures of those who oppose us” (54).

Amelia Earhart (1897-1939) was an American pilot. Earhart gained fame as the first woman pilot to fly solo across the Atlantic Ocean in the early 1930s. Earhart was a pioneer for women’s involvement in aviation, which at the time was very male dominated. Earhart disappeared over the Pacific Ocean during her attempt to fly around the world in 1939.

Holiday uses Earhart as an example of someone who overcame discrimination by accepting opportunities and applying herself to her work. He emphasizes how in her early career Earhart was treated as inferior to her male colleagues. When she was given the first opportunity to fly across the Atlantic, she was offered no pay even though her male chaperones were paid well, and she did not get a chance to operate the plane. Holiday praises Earhart for her willingness to take an imperfect opportunity and build on it to create a substantial career.

Mahatma Gandhi (1869-1948) was an Indian political activist who led a nonviolent campaign for India’s independence from Britain. A devout Hindu and a lawyer, Gandhi challenged the British occupation of India through peaceful protest. Holiday uses Gandhi’s example to demonstrate how people can successfully take on more powerful opponents by using their enemy’s strength against them. Gandhi’s strategy was to accept and emphasize his position of military weakness. This forced the British forces to either allow Gandhi to violate their laws, or enforce them violently and look like bullies. Holiday suggests that people can emulate Gandhi by not being intimidated by more powerful enemies, but considering how their opponents’ strength may be turned into a weakness with the right strategy. Holiday uses Gandhi to illustrate how creative and strategic thinking can help people overcome obstacles.