The man who took stoic wisdom from Ancient Greece and transformed it into a modern self-help empire

Ryan Holiday’s books have sold millions of copies, he explains how a two thousand year old philosophy can help people with contemporary life

Anyone with Holiday as their surname is bound to have a sunny disposition, is what I told myself ahead of interviewing Ryan Holiday, the author credited with popularising Stoicism, the ancient philosophy adopted by Roman Emperors and slaves alike.
His books, of which there are 12, have sold over five million copies in 40 languages worldwide. His most recent, Right Thing, Right Now, is pitch perfect for navigating one of the most un-virtuous times in living memory. The New York Times called Holiday “a self-help sage, who is now sought-after guru to NFL coaches, Olympians, hip-hop stars and Silicon Valley entrepreneurs”. Alongside his writing, Holiday owns an independent book store in Bastrop Texas where he lives on a 40-acre ranch with his wife and two sons.
A wizard at seizing the zeitgeist, Holiday has turned a dusty 2000-year-old philosophy into a viral entity. His brand, The Daily Stoic, which has a newsletter, podcast, YouTube channel and Instagram account with 3.3 million followers, is littered with pithy Stoic tips for getting good at life.
That is an amorphous amount of success for someone under the age of 40 (Holiday turned 37 in June). But then Holiday peaked early. “I found Stoicism at 19. I read Marcus Aurelius’ Meditations in my college apartment, and I just remember thinking: where has this been my whole life? This is all the stuff that I wish I’d been taught in school about how to be a responsible, mature, resilient human being,” says Holiday, who admits that Stoic philosophy, though refreshingly practical, is a lifelong practice.
He explains: “At first, you’re like. Oh yeah, this is definitely the way to be. And then there’s another part of you that realises. Oh, this is going to be a lot of work… I wouldn’t say I’m good at any of these Stoic ideas. But, after many years of work, I’m a lot better.”
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Somewhat antithetical to his current role as a modern Stoic interpreter, in the 2010s Holiday was a marketing strategist navigating the fall out of American Apparel, the fashion retailer that was mired in controversy before its eventual demise. “I was trying to be as Stoic as I could inside a very insane company in a very insane period,” he says, adding that “ultimately, I asked myself: is this what you want to do with your life? Help people sell T-shirts and stuff? Probably not.” And so, in 2014 he threw a curveball by pitching a book about Stoic philosophy. “My publisher said: ‘that’s not going to work’. And I didn’t think it would either. This idea that a book about an obscure school of ancient philosophy would sell millions of copies was ridiculous,” he reflects.
The tome that changed his trajectory from marketing savant to the Stoic sophist that he’s known as today is The Obstacle is The Way: The Timeless Art of Turning Trials into Triumphs. His following books inspect Stoic workarounds on ego, discipline, courage and creating stillness. Contrary to the wellness tropes that count on wealth or privilege to adopt its teachings, Stoicism is egalitarian at its heart.
“I’m sure there’s something transformative and eye opening about a 10-day meditation retreat. But, who has time? And how does that translate to this crazy world we all live in, where we have jobs and kids and responsibilities?” says Holiday.
“There’s something about Stoicism being a Western philosophy that is uniquely suited to life in the West,” he says, citing Zeno of Citium, the founder of Stoicism. “He was a merchant who lost everything in a shipwreck, and so at the beginning of Stoicism, you have a person with a job that still exists today, dealing with something that still happens, which is, you go belly up, and then you’ve got to figure it out. There’s something timeless and practical and real about Stoic philosophy that translates well for this moment in time, but also all moments in time.”
As for Holiday’s disposition, he comes across as grounded, warm and self-deprecating; someone you’d trust with your innermost secrets. But, then again, his first, less talked about, book is a marketing bible titled: Trust Me I’m Lying: Confessions of a Media Manipulator…
“One of my favourite quotes from the Stoics is that you should always be asking yourself: is this thing I’m about to do essential? Because most of what we do, Marcus Aurelius says, is not essential, and when we eliminate the inessential, we get the double benefit of doing the essential things better.” 
At the heart of it, he says, is elimination, starting by limiting your inputs. “I used to be an ‘inbox zero’ person. Now I embrace [the unopened emails]. If I didn’t ask for it, I don’t have to process it,” says Holiday of purposefully practising essentiality.
“There’s something really hard about acceptance because if you’re accomplished or driven, you don’t get to where you are by accepting things. The whole game is: don’t accept the odds, make it happen anyway.” But, says Holiday, acceptance is the first step in solving a problem that is made easier by practising neutrality. 
“There’s a line in Marcus Aurelius’ Meditations in which he says: ‘You always have the power to have no opinion’. To come at things from a place of non-judgement is magical. Difficult but magical.” The point, suggests Holiday, is that living in a state of resistance to a situation, however bad, is futile and stress inducing. “The faster you can get to acceptance, the faster you can get to a solution or the learning of the lesson,” he says.
“I think about this a lot. I’ve written quite a few books in a relatively short amount of time, and I’ve given a lot of talks. But ultimately if you like what you do, you’ll probably want to do it for a long time and so it’s better to settle in for a longer trajectory. So [ask yourself] are you operating at a pace that can allow you to do that? Or are you going to put yourself into an early grave?” The key, says Holiday, is to avoid comparison. 
“Measuring yourself against other people is a timeless, toxic thing. There’s a story about Julius Caesar as a young man coming across a statue of Alexander the Great and breaking down into tears because they were the same age, and by that age, Alexander the Great had conquered the entire world,” he says, adding that if you focus solely on your own path, you will be happier. “It’s a bad habit to pace yourself against other people because you can only control the race you’re running.”
“Stoicism at its core asks: what is in your control and what’s not in your control? Most of the things we’re anxious about is just us emoting about things that are not in our control,” says Holiday. “Seneca’s line is that he who suffers before it is necessary, suffers more than necessary. And therefore he recommends being mindful of when you are catastrophising about some future event that hasn’t yet happened.”
“To me, the Stoic practice of Memento Mori – of meditating on your mortality – is so important because it puts everything in perspective. Why are you putting this off till tomorrow? You don’t know that you have tomorrow,” says Holiday. 
“Seneca says the one thing all fools have in common is that they’re getting ready to start.” A common example of this, says Holiday, is New Year’s resolutions. “Why put things off until January when there’s still three months left in the year. If it’s not good for you [in January], it’s not good for you in November.”
The roots of prohibition, Holiday reminds, began with moderation. “It’s not so popular these days because in the early 1900s we had the temperance movement which led to the banning of alcohol. But the idea of temperance or balance of maintaining the right amount, is such an underrated concept,” he says, adding: “We’re so all or nothing, or we take things to extremes but moderation is such an underrated virtue.”
“I think about Justice as a virtue that we give rather than get. So instead of thinking of standards that everyone should operate by, it’s really important that we think about the standards we’re going to set for ourselves, and just try to live up to them. Otherwise you’re just winging it all the time and then you wonder, why when big, vexing decisions come up, you don’t make the right call,” he says. 
“It’s because you don’t have practice. If you do it in a thousand small ways, when some big career altering, life changing moment comes along, you’ve built the muscle and the habit to do that hard right thing.”
Holiday will be speaking live at the Troxy in London on Nov 12. Get your tickets here.
The new and updated 10th anniversary edition of The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumphs by Ryan Holiday is out now (Profile, £16.99).
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