He has sold 5m books about this ancient Greek approach to life – and been feted by sports teams and CEOs. What makes this former PR man so popular?
hat is it that made the former PR man turned lay philosopher Ryan Holiday a giant of the bestseller lists? That his writing on stoic philosophy is beloved by everyone from professional athletes, politicians and tech CEOs will have helped. Investor-entrepreneur Tim Ferriss calls stoicism the “ideal operating system”, whileElizabeth Holmes constantly cited Marcus Aurelius’s Meditations, before her imprisonment.
When The Obstacle Is the Way came out, “it sold maybe 3,000 copies in its first week”, says Holiday. “It did not exceed anyone’s expectations ... It wasn’t until a year or so later that the sales really started to take off, when it began to make its way through professional sports.” Whole teams – Miami Heat , Seattle Seahawks – adopted his books as bibles, “and I found this to be true in every country, in sports that I honestly didn’t even know existed”.
Anyway, back to our era: “When the old understanding of the universe had not given way to the Christian understanding, where was a person to turn for meaning and purpose and structure? A way of living? Stoic philosophy, and indeed all the schools of ancient philosophy, cynicism and Epicureanism, this was a heyday of philosophy as a sort of civic religion.”
It was around the time he was at American Apparel, in his early-to-mid 20s, that Holiday started writing The Obstacle Is the Way, and even though I read the edition that he’s recently revised, it still reads like a young man enamoured of the Great Man theory of history. It’s a compendium of people who don’t listen to experts and, as a result, win big. When the markets are telling you one thing, do the opposite; when doctors tell you you’ll never walk again, just keep on trying to walk.
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