In The Obstacle Is the Way: The Timeless Art of Turning Trials Into Triumph, Holiday explores how Stoic principles can be applied to modern life. This work marks the beginning of Holiday’s foray into writing about Stoic philosophy, and is part of a series of self-help books which illustrate life lessons through historical anecdotes. It marks a notable departure from Holiday’s initial books, which were centered on his experience working in marketing, media, and business. Holiday’s first book was a memoir about his career as a marketer and media strategist, Trust Me, I’m Lying: Confessions of a Media Manipulator (2012). In his second book, Growth Hacker Marketing: A Primer on the Future of PR, Marketing, and Advertising (2013), he distills his approach to media strategy in the digital age.

The Obstacle Is the Way soon became a bestseller, selling over 1 million copies, and has been translated into over a dozen languages. Holiday followed this success by exploring other principles and themes in Stoic thought in his books Ego Is the Enemy (2016), Stillness Is the Key (2019), Courage Is Calling: Fortune Favors the Brave (2021), and Discipline Is Destiny: The Power of Self-Control (2022). Instead of analyzing Stoic quotes or the lives of Stoic philosophers, Holiday centers his works around anecdotes.