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

Holiday argues that, with the right attitude, people can find opportunities within obstacles. He encourages readers to see how negative events often contain hidden benefits or opportunities, and inspires them to try to emulate historical figures.

Holiday claims that by combining three steps—a rational perception, well-planned actions, and a strong will—people will be able to identify and embrace opportunities that come from challenges: “When one person sees a crisis, another can see an opportunity” (16). He points to a variety of successful people who embraced hardship as an opportunity to learn, or as a personal test they had to pass. For instance, John D. Rockefeller made a conscious decision to not allow his rocky start in business to scare him into a different industry. Instead, he saw his early career as a learning opportunity, and as such experienced remarkable success. Holiday explains:

Of course, many people experienced the same perilous times as Rockefeller—they all attended the same school of bad times. But few reacted as he did. Not many had trained themselves to see opportunity inside this obstacle […] a chance to learn from a rare moment in economic history (16).

Holiday also portrays Steve Jobs as someone who exemplified the ability to transform challenge into opportunity. For instance, Jobs did not back down from his ambitions when others told him they were not possible. Instead, he was confident that he would be the first to develop a certain product or deliver something on a tight timeline. Holiday uses the examples of Jobs rallying his team to make the first iPhones to demonstrate how successful entrepreneurs view obstacles “as an opportunity,” and how “it is often in that desperate nothing-to-lose state that we are our most creative” (52).

Holiday argues that General Eisenhower was also able to shift his perception of a problem, the Nazi military’s dominant tank warfare, to identify an opportunity. Thinking creatively, Eisenhower argued that the Germans were leaving themselves vulnerable to flank attacks, a weakness which the Allies could exploit. Holiday contrasts Eisenhower’s keenness with his less perceptive colleagues:

Striding into the conference room at headquarters in Malta, General Dwight D. Eisenhower made an announcement: He’d have no more of this quivering timidity from his deflated generals. ‘The present situation is to be regarded as opportunity for us and not disaster,’ he commanded. ‘There will only be cheerful faces at this conference table’ (54).

Eisenhower’s strategy was a success and helped the Allies secure victory in the war.