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The Grueling Class
Why Silicon Valley loves Stoicism
Jacob Rosenberg

“The one class is born to obey, the other to command.” —Seneca

Stoicism begins with a wayward merchant. Legend has it that in 312 B.C. a dye salesman named Zeno was shipwrecked in the Aegean Sea. He washed ashore in Athens, read a book of Socratic dialogues, and found philosophical purpose. His brush with misfortune guided him to the idea of self-control in an uncontrollable world. “Man conquers the world by conquering himself,” Zeno is said to have said. He developed a following.

Soon he and his acolytes were convening in the Athenian marketplace on a porch that would become their namesake, the Stoa Poikile, where they were surrounded by others who wished to draw a crowd—fire eaters, sword swallowers, and the like. Zeno’s doctrines of personal mastery would trickle down to Seneca, a sort of philosopher laureate of the Roman imperial period, and Marcus Aurelius, the Roman emperor—and eventually, two millennia later, to an opportunistic writer named Ryan Holiday, himself a kind of wayward merchant.

“At the core of it,” Holiday, a former marketer for American Apparel, is telling me, “I think there’s something in Stoicism that connects to the philosopher mindset”—he catches himself—“or, sorry, the entrepreneurial mindset.” Zeno is “an entrepreneur,” Holiday explains, “a person trying to make their way in the real world.” Then he begins to rattle off the new mantras of the philosopher-entrepreneur: “You’re responsible for yourself. No one’s coming to rescue you. Make the most of this. Don’t get caught sleeping. Put in the work.”

Holiday is, most recently, the author of Stillness Is the Key—not to be confused with The Obstacle Is the Way or Ego Is the Enemy, his two other this-is-the-that Stoicism titles. His book sales number in the millions; last January, Holiday’s 2016 book of meditations on Stoicism sold nearly 33,000 copies, he tells me. He also runs a popular website called Daily Stoic (plus a video channel), and he claims his daily email of Stoic advice reaches hundreds of thousands of people, including senators, billionaires, and “just a lot of ordinary people.” That’s to say nothing of the speaking engagements with nfl players and coaches, Navy seals, and government agencies. There’s Stoic merch, too: a memento mori medallion for $26, a ring for $235. Holiday’s project is straightforward: to boil down the work of ancient thinkers into pithy advice—philosophy as lifehack. “Have Your Best Week Ever With These 8 Lessons of Stoicism,” proclaims one of his video titles.

Along with tech lifestyle guru Tim Ferriss, Holiday is the principal evangelist of modern Stoicism, which is enjoying a vogue these days, especially among the Silicon Valley set. Gwyneth Paltrow’s personal book curator says, “Stoic philosophers are having a moment now.” A mini–book industry has sprung up around Stoicism that includes Holiday, Donald Robertson, and William B. Irvine. Author Elif Batuman took a Stoic turn while living alone in Istanbul. Susan Fowler, the software engineer who blew the whistle on Uber’s sexist culture, said she’d found the courage to come forward from Stoic teachings. Elizabeth Holmes held close a copy of Meditations as her blood-testing company crumbled. Twitter ceo Jack Dorsey is regularly taking cold baths. And there are the hundreds of thousands of people on Reddit and Twitter and Y Combinator’s Hacker News message board, ingesting bite-sized Stoic quotes about indifference and control and holding themselves up as a lonesome but formidable bulwark against “modern-day Oprah culture.”

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January/February 2020