42 pages • 1 hour read
Ryan HolidayThe Obstacle is the Way: The Timeless Art of Turning Trials into Triumph
Nonfiction | Book | Adult | Published in 2014A modern alternative to SparkNotes and CliffsNotes, SuperSummary offers high-quality Study Guides with detailed chapter summaries and analysis of major themes, characters, and more.
Background
Authorial Context: Ryan Holiday
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. These demonstrate how historical figures embodied Stoic principles, whether they identified as Stoics or not. Holiday has also explored Stoic thought in his books The Daily Stoic: 366 Meditations on Wisdom, Perseverance, and the Art of Living (2016), a daily devotional with Stoic quotations, and his book Lives of the Stoics: The Art of Living from Zeno to Marcus Aurelius (2020), which he coauthored with Stephen Hanselman and which includes brief biographies of major Stoic thinkers.
Historical Context: Ancient Stoic Thinkers
Holiday credits ancient Stoic thinkers for articulating the principles and practices he draws on and which form the foundation of his advice. Stoicism was founded in about 300 BCE in Athens, Greece by the philosopher Zeno of Citium (334-262 BCE). Zeno’s Stoicism focused on three main schools of thought: physics, ethics, and logic. Over time, this approach changed as Stoics worked less on physics, and focused on how people could live stable, productive, and moral lives. This school of philosophy became known for its pragmatic approach to life’s problems. Its best known thinkers, Seneca (4 BCE-65 CE) and Epictetus (55-135 CE), focused on finding practical solutions to personal and moral problems, and putting them into action.
Stoic philosophy spread from Greece to ancient Rome, where many Romans embraced it. However, Stoics were sometimes persecuted by the Roman government. For example, emperors Vespasian and Domitian banished some Stoic thinkers from Rome in an effort to quell criticism of their regimes. Eventually, Roman emperor Marcus Aurelius (121-180 CE) embraced Stoic thought; his personal journal, Meditations, is one of the key texts in Stoic literature. In the middle ages Stoicism faded into obscurity. It is currently enjoying a renewed popularity with scholars and authors such as Holiday, who repackage Stoic thought for a modern audience.
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