Meet Ryan Holiday: The marketer who became the modern godfather of Stoicism

Stoicism has been experiencing a revival in recent times, with American marketer Ryan Holiday serving as the unlikely modern godfather of the ancient philosophy. Ahead of a lecture in Dublin, he meets Aoife Barry

Ryan Holiday writes about ways that Stoicism can help us deal with life’s trials

The ancient Stoic philosophers don’t know it, but their chief marketing officer is an American named Ryan Holiday. 

He’s the self-created founder of the modern Stoicism movement, distilling the philosophies of figures such as Marcus Aurelius and Epictetus for people in need of guidance in the 2020s.

If you thought that there would be a small readership for the philosophical musings of long-dead men, you’d be wrong — Holiday’s written multiple bestselling books and created an entire brand around the Stoics.

When he speaks to the Irish Examiner, the 37-year-old is preparing to head to Ireland for a live show — The Stoic Life — at Dublin’s Convention Centre on November 15, having just returned home to Austin, Texas, after a tour in Australia.

Tanned and smiling, Holiday is a relaxed interviewee. His marketing background also ensures he brings the chat back around to the topic of Stoicism if we drift off it. But more about his previous — and controversial — career choice later.

The Irish event is part of Holiday’s first world tour.

“Normally I talk at conferences, or to companies or sports teams. I would say most of my audiences are not there voluntarily, like their boss made them come, right?” he says with a laugh.

“So it’s very fun and overwhelming in Australia, to be like, ‘Oh, these are 2,000 people who are fascinated by ancient philosophy.’”

Holiday’s surprise underplays his success. He’s sold more than 2m copies of his books about Stoicism, his first being The Obstacle is the Way: The Timeless Art of Turning Trials into Triumph. 

In it, he shares the stories of how people like Ulysses S Grant and Rubin ‘Hurricane’ Carter dealt with obstacles by turning them into opportunities. 

For Carter, the challenge was being wrongly accused of a triple homicide; for Grant, it was the trials of the American Civil War.

It seems the teachings of the Stoics can truly be applied to all types of problems, though most of Holiday’s readers are likely dealing with issues around family, work, and living productively in today’s busy modern world.

Ryan Holiday's collected works to date.

The Obstacle is the Way was followed by Ego is the Enemy; The Daily Stoic; The Daily Stoic Journal; Stillness is the Key; Lives of the Stoics; Courage is Calling; Discipline is Destiny; The Boy Who Would be King; The Girl Who Would Be Free and Right Thing, Right Now.

Yet it “sort of blows my mind”, says Holiday, to realise that the work he’s put into showing these ancient ideas are relevant in today’s world has paid off. 

Still, he knows that some people will have preconceived notions about Stoicism.

“I think people think Stoicism is the absence of emotion, but I think it’s closer to smiling through adversity and the ups and downs of life. There’s actually a cheerfulness to Stoicism,” he says. 

“One of the things I’ve been saying on stage is that Marcus Aurelius’s life was incredibly dark. He lost multiple children. He lived through a plague. He lived through war. So one read is that it’s a little depressing when you read the Stoics, but the other read is [the fact] they kept going was an act of immense hope and optimism and determination.”

SIMILAR TRIALS

Marcus Aurelius was a Roman emperor imbued with incredible power. 

But with power comes difficulties, and so he would write privately to himself about his struggles in life and how to deal with them. 

These were later published under the title Meditations, and encountering this book aged 19 kicked off Holiday’s interest in Stoicism. He maintains that the Stoics’ lives 2,000 years ago contained similar trials to what we experience today.

“There’s this passage in Meditations where Marcus Aurelius is complaining about this person that he’s sitting next to that smells, and he’s like, ‘Should I say something? Do I just have to endure it?’ It’s like you’re sitting next to someone on a plane and they’re taking your armrest, what are you supposed to do?” says Holiday. 

“The Stoics existed in a world that had the same kind of people and the same kind of problems that we have now, and that’s what’s made their insights about that survive for so long.”

Holiday has built a career on sharing the work of the Stoics, but calls his popularity “surreal”. Have the Stoics helped him deal with success?

“Seneca was a famous playwright. Marcus Aurelius would have been mobbed by crowds everywhere. And they talk about how it sounds ungrateful to call it ‘meaningless’, but they’re just saying that [fame and success] doesn’t say anything about you as a person, just as your work not being appreciated in the moment doesn’t say anything about you as a person,” he says. 

“And the idea in Stoicism was that you should be able to accept it without arrogance and to let go with indifference.”

A striking feature of contemporary Stoicism is how masculine it appears to be. The main thought leaders in this space are male and, anecdotally at least, it attracts many male followers. 

It’s tempting to think that it’s self-help repackaged for men, but Holiday maintains that his work attracts a gender-balanced audience.

“Going back to the very beginning of Stoicism, there was this question of whether women should be taught philosophy. And Musonius Rufus, one of the great Stoic teachers, was like, ‘Absolutely, there’s nothing gendered about any of this. Virtue is virtue, and it doesn’t know sex,’” says Holiday.

“I’ve always tried to think about it that way, that it’s for human beings, not for men or women. And I would say probably 50% of my audience is women, which I really like and appreciate. I think this theory of the big Stoic man who has no emotion is not helpful and not representative.”

But Holiday, a father of two young boys, is well aware of the challenges for men in American society in particular. 

“I do fear that there’s not a lot of good guidance for men out there, and I think Stoicism is great for that. I try to be really cognisant, though, of not [just] telling men what they want to hear.”

He rejects toxic Stoicism, “this idea of ignore your emotions, stuff it all down, don’t care what other people think”.

Ryan Holiday: "The ancient world was broken and messed up and filled with demagogues and tyrants also, and so I think every citizen and person has an obligation to try to put things on the right path and put them in the right direction."

IT HAPPENED TO ME

Those who associate Holiday solely with Stoicism might be surprised to hear that his very first book was about the absolute opposite of it. Trust Me, I’m Lying: Confessions of a Media Manipulator was a 2012 exposé of Holiday’s career as a media strategist. 

It detailed very un-Stoic behaviour, like stunts he pulled while working on controversial publicity campaigns. (In one instance, he spray-painted billboards for a film by his client Tucker Max, and then contacted blogs posing as a stranger who spotted the defacement.) 

How does he feel about the version of him now compared to the version of him back then?

“I wrote Trust Me, I’m Lying because I didn’t want to be in that world any more, and I didn’t want to be that person,” he says. Both the book and Holiday were criticised, but he says it was better to write about what he did than ignore it.

“The best way to profit from it would have been to keep it private. I was trying, in my own way, to expose what I thought was broken in the media system and I wish we had addressed some of those things sooner, and maybe we would have very different politics in America than we do right now.” He fears that the news landscape is “probably worse” now than back in the 2000s.

But does he feel hopeful about Vice President Kamala Harris’s run for the role of US president? His answer is, well, stoical. “I think a Stoic would be reluctant to be hopeful, because that sets you up for disappointment. Obviously I want the scourge of Trump to go away, and there’s no one who less embodies these ideas of Stoicism than ‘the Cheeto man’, as my children call him,” says Holiday.

Ryan Holiday: “Normally I talk at conferences, or to companies or sports teams. I would say most of my audiences are not there voluntarily, like their boss made them come, right?” he says with a laugh.

“The ancient world was broken and messed up and filled with demagogues and tyrants also, and so I think every citizen and person has an obligation to try to put things on the right path and put them in the right direction. And then also, Stoicism is there to help you navigate situations like this and not be broken by them — and, most importantly, not be corrupted by them.”

Because Holiday is writing about ways that Stoicism can help us deal with life’s trials, does he feel pressure to be a perfect example of the philosophy?

“It’s a strange thing, because I’ve become this representative of a thing that I did not invent,” he acknowledges. 

“Stoicism is a philosophy that I use in my life, and I aspire to. The way that people think about me because of Stoicism is how I think about the Stoics. I have this weird relationship with it, in that when somebody tells me all the ways that my books have changed their life, I go, ‘I agree — it happened to me also.’”

A GOOD STEWARD

By this, he means that the ideas within his books came from the Stoics, and these ideas helped him too.

“I feel a lot of responsibility. I have a little note card here next to my desk, and it just says, ‘Are you being a good steward of Stoicism?’” he says. “Because I’ve been incredibly lucky that I am associated with, and I get to talk about, this thing that’s not mine, I feel like I have to do a good job representing it as a person, and being true to it as a writer.”

For example, he is trying to ensure he includes the element of social justice when he writes and talks about Stoicism.

“There’s a version of Stoicism where you just don’t talk about that, because it’s not what people want to hear about on Instagram,” he says. 

“But I feel if I have the audience, that’s precisely who I have to talk about these ideas to, because that’s the responsibility that comes with the privileges of the success I’ve had.”

The journey to Stoicism began with Holiday wanting to be more productive and resilient. He liked the masculine side of it too, he says. 

But he has learned that the more you read the work of the Stoics, the more you see what Stoicism asks of you. “It would be easier, from a creative standpoint and a business standpoint, to just talk about the stuff that we all agree on, but that would be to eliminate or
obscure some of the most essential parts of Stoicism. It’s courage, discipline, justice and wisdom — they’re four equal [Stoic] virtues, and I feel obligated to talk about all of them.”

Ultimately, Holiday sees his work as a form of paying forward what Stoicism has given him. 

“Sometimes people will say, ‘Oh, you’re just a populariser,’” he says. “And I go, ‘That sounds like an awesome compliment, thank you.’ That’s what I’m trying to do. I’m trying to popularise these wonderful, life-changing ideas we have from antiquity.”

• Ryan Holiday Live in Dublin: The Stoic Life takes place at the Convention Centre on November 15. Tickets from €55.83 at eventbrite. His podcast, The Daily Stoic, is available wherever you get your podcasts.