The Obstacle Is the Way: The Timeless Art of Turning Trials Into Triumph (2014) is a self-help book by American author Ryan Holiday. Holiday identifies three aspects of confronting obstacles: “Perception,” “Action,” and “Will.” Weaving Stoic philosophy with historical and contemporary anecdotes, Holiday argues that people can turn obstacles into opportunities by changing their perceptions of their problems. Holiday points to role models such as former American president and general Dwight D. Eisenhower, American aviator Amelia Earhart, American inventor Thomas Edison, Indian leader Mahatma Gandhi, and more. He argues that calm, strategic thinking and a willingness to embrace challenge can help anyone transform their problems into learning opportunities and new accomplishments.

This guide will refer to the Kindle edition of this book.

Summary

In Part 1, “Perception,” Holiday explores how people can intentionally change their perception of a problem by being objective, thinking critically about their emotional reactions, and analyzing the issue for possible opportunities. In Chapter 1, the author lauds American businessperson John D. Rockefeller for weathering financial crashes in his early career and seeing them as a learning opportunity rather than a permanent problem.

In Chapter 2, Holiday points to American boxer Rubin Carter, who was wrongly imprisoned for homicide, as an example of someone who focused their energy and personal agency on finding solutions in the face of an unimaginable problem.

In Chapters 3 and 4, Holiday details how people such as former US president and general Ulysses S. Grant and American astronauts trained their minds to be resilient to stress. In Chapter 5, Holiday argues that people should focus on observing, which is plain and objective, rather than perceiving, which can include exaggeration, worries, or fantasy. In Chapter 6, Holiday encourages the reader to change their perspective by challenging their fears, which he argues rarely add value.

In Chapter 7, Holiday argues that perception is improved when people focus on what they can control and ignore what they cannot. This helps people understand where to direct their energy, and helps them make better use of their time and effort to overcome their obstacles. In Chapter 8, Holiday asks the reader to resist intrusive and irrelevant thoughts and worries. In the following two chapters he lauds creative and strategic thinking as valuable ways to turn a problem into an opportunity. In Chapter 11, Holiday reiterates that clear perception of a problem does not mean romanticizing or denying it, but accurately assessing risks or opportunities and acting accordingly.

In Part 2, “Action,” Holiday examines the importance of taking action to resolve one’s problems. In Chapter 12, he holds up Demosthenes, an ancient Greek orator, as an example of someone who overcame multiple tragedies to become successful. In Chapter 13, Holiday explains how Amelia Earhart navigated sexist discrimination to become the most famous woman pilot of her time, and credits her ability to take initiative for her success.

In Chapter 14, Holiday coaches the reader to be persistent, pointing to Ulysses S. Grant and Thomas Edison as examples of how persistence can pay off. In Chapter 15, Holiday explains that tech inventors in the Silicon Valley tend to see the failure of their products as learning opportunities, and advises readers to use these lessons as they develop new products. In Chapter 16, Holiday claims that taking action can be as simple as executing everyday tasks well, and knowing that these small steps will add up to larger accomplishments.

In Chapter 17, Holiday contends that people should embrace humble beginnings and find purpose in doing work that no one else wants to do. By prioritizing action over pride, Holiday believes that people will earn respect and feel good about their work. In Chapter 18, Holiday acknowledges that some people face unfair obstacles and may need to be creative, strategic, or rule-breaking to get around them.

In Chapters 19 and 20, Holiday claims that many obstacles can be beaten by approaching them from a new angle, rather than head-on conflict. He points to Gandhi as an example of someone who successfully uses strategic, peaceful action or nonaction. In Chapter 21, Holiday tells the reader to channel their negative feelings about a problem into new energy to stay productive. In Chapter 22, Holiday discusses the benefits of embracing uncomfortable challenges and leaning into failures, rather than avoiding them. He concludes Part 2 with a chapter about how failure happens to everyone and is an opportunity to practice acceptance or forgiveness.

In Part 3, “Will,” Holiday argues that developing a strong inner will is essential for confronting obstacles. In Chapters 24 and 25, he describes how former president Abraham Lincoln endured numerous hardships throughout his life which helped him develop determination and patience, while former president Theodore Roosevelt directed his will to improve his physical strength in spite of severe asthma. In Chapter 26, Holiday explains the Stoic method of “premeditation of evils,” which helps people anticipate failure or disaster and plan for it ahead of time (140). In Chapter 27, Holiday explores the Stoic concept of the “art of acquiescence,” in which people accept obstacles which they have no control over, and direct their energies elsewhere (146). In Chapter 28, Holiday coaches the reader to embrace all events in their lives, even negative ones. In doing so, people can learn to find opportunities or advantages in negative situations.

In Chapter 29, “Perseverance,” Holiday argues that modern people are lacking in perseverance, a key trait in navigating challenges. In Chapter 30, he encourages the reader to embrace a larger purpose and give back to others; this helps keep one’s own problems in perspective. In Chapter 31, he reminds the reader that they have limited time to execute their plans. In his final chapter, Holiday insists that obstacles are an inherent part of life, and should be expected and embraced. He concludes his work with “Final Thoughts” on the subject, telling the reader to face their obstacles with confidence and positivity, to “turn them from disaster to real benefit—from defeat to victory” (178).