Established 2014 · London
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Biography
American

Ryan Holiday

1987

Ryan Holiday is the author who brought Stoic philosophy to a mass audience. The Obstacle Is the Way (2014) — which applies Marcus Aurelius, Seneca, and Epictetus to modern challenges — became an underground bestseller adopted by NFL coaches, military commanders, and Silicon Valley executives. His Stoicism books — including Ego Is the Enemy (2016), Stillness Is the Key (2019), and the four-volume Lives of the Stoics series — have collectively sold millions of copies and made ancient philosophy commercially viable in the twenty-first century.

Past sales0
PeriodContemporary
NationalityAmerican
1. Biography

A short life of the author

Ryan Holiday (b. 1987) was born on 16 June 1987 in Sacramento, California. He dropped out of UC Riverside at nineteen to apprentice under Robert Greene (author of The 48 Laws of Power). He became the director of marketing for American Apparel and a media strategist before turning to writing.

Life and Career

Trust Me, I’m Lying: Confessions of a Media Manipulator (2012) — an exposé of how online media is exploited and gamed — was his debut. It was cynical, confessional, and influential.

The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph (2014) — which distils Stoic philosophy (particularly Marcus Aurelius’s Meditations) into a framework for overcoming adversity — became an underground bestseller. It was adopted by the New England Patriots, the Seattle Seahawks, and numerous Silicon Valley executives. The book launched the modern Stoicism movement as a popular self-help genre.

Ego Is the Enemy (2016) and Stillness Is the Key (2019) completed a Stoic trilogy. Lives of the Stoics (2020) was a biographical survey. Discipline Is Destiny (2022) and Right Thing, Right Now (2024) continued the four-volume virtue series.

Holiday also runs the Daily Stoic brand — newsletters, podcasts, journals, medallions — which has become the largest Stoicism community in the world. He owns a bookstore in Bastrop, Texas.

Key Works

  • The Obstacle Is the Way (2014)
  • Ego Is the Enemy (2016)
  • Stillness Is the Key (2019)

Collecting Holiday

The Obstacle Is the Way (2014, Portfolio) brings $10–$30. Trust Me, I’m Lying (2012, Portfolio) brings $10–$25.