Ryan Holiday is the modern poster boy for stoicism. Here are his four life lessons

One of Ryan Holiday’s favourite quotes from the stoics is Marcus Aurelius’ line: “Waste no more time arguing what a good man should be. Be one.”

Holiday knows a thing or two about that.

The bestselling author has become – as The New York Times put it – the unlikely poster boy for stoicism, the ancient philosophy that posits that while we don’t always control what happens to us in life, we always control how we respond.

It’s been an unlikely shift because the 39-year-old once played the role of the villain. A university dropout, he handled public relations for American Apparel when its founder was accused of rape. Holiday then became the focus of negative media attention for his first book about duping the media, titled Trust Me, I’m Lying: Confessions of a Media Manipulator.

However, it was what he did next that’s earned him his fan base, as he turned his hand to writing about the philosophy that transformed his own approach to life.

His subsequent books, including The Daily Stoic, The Obstacle Is the Way, Ego Is the Enemy and Stillness Is the Key have sold more than 10 million copies. They have inspired everyone from Arnold Schwarzenegger, to Tom Brady, to Rory McIlroy, who credited it with helping him maintain his consistently high ranking on the PGA Tour.

Today, Holiday’s focus is on being good in action.

He was the keynote speaker to US Naval Academy for four years in a row, until the academy cancelled him for refusing a directive not to mention the removal of “supposedly controversial” books from the Naval Academy library, including books about diversity, equity and inclusion, and Maya Angelou’s autobiography, I Know Why the Caged Bird Sings, which explores themes of resilience in the face of oppression. (Hitler’s Mein Kampf was not removed from the library.)

“I could not, in good conscience, lecture these future leaders and warriors on the virtue of courage and doing the right thing … and fold when asked not to mention such an egregious and fundamentally anti-wisdom course of action,” he wrote in an op-ed for The New York Times in 2025.

This month, Holiday is touring Australia, where he plans to “examine the principles behind steady decision-making, mental resilience and discipline required to remain effective in a world defined by distraction and volatility”.

He spoke to this masthead while driving his two sons home from school in Austin, Texas, about comfort, discipline, meaning, AI and change. Below are Holiday’s thoughts, edited for length and clarity.

“We don’t want things in life to be hard or challenging. We want them to be nice and easy and reassuring.

So, there are some people who are living this life of comfort where everything is delivered, and the temperature is always perfect inside your house, and you get to choose how things go. And there are people who have set up a whole information system that only tells them what they want to hear. It never forces them to think differently or accept things they don’t like.

But then you’re really rattled and have difficulty dealing with it when that’s not the case. The stoics would say that fortune reminds you who’s really in charge.

One of the basic stoic ideas is that anything unexpected lands heaviest.

If you want things to be a certain way, and you expect them to be a certain way, it’s really hard when they’re not that way. So, one thing the stoics did was contemplate all these possibilities, and then try to expose themselves deliberately to those things so that if it did happen, they weren’t unfamiliar with it.”

“The stoics believe that discipline is a virtue – Seneca says you treat the body rigorously, so it’s not disobedient to the mind – but their rendering of the idea of discipline was inseparable from this idea of temperance or moderation.

So, they believed that all the virtues were a midpoint between vices.

On one end of the spectrum is cowardice. On the other end of the spectrum is recklessness, and courage is in the middle: too much comfort or too much exertion are both extremes and not super productive.

I love endurance sports, but if I’ve injured myself or if I’m sick, it requires discipline to not do it. For some people, the discipline is ‘I’ve got to get off the couch and stop lying around’ and then for other people it’s, ‘No, you need to rest’.

It’s knowing where your capacity is and then trying to stay at a threshold right below that, not so far down that you’re unfulfilled. If, for you, stoicism is self-flagellation, I think you’re doing it wrong.”

“You have to have some kind of meaning or purpose to what you’re doing; otherwise, it just becomes about money, or fame, or the endless rush of conflict on the internet and none of that is good for society or good for the soul.

Stoicism is about sort of being of service and making a difference. We were made to contribute to what they would call the common good. And some of that has to be about fulfilling your individual potential.

There’s this great stoic, whose name was Agrippinus, and he lived in the time of Nero – a pretty conformist time – when the emperor of Rome is so fragile that he banishes talented poets because they make him look bad.

Agrippinus was asked, ‘Why don’t you try to blend in?’ and he says, ‘Society is like a garment. Some people are the white threads. I am like the red thread that makes the rest of it look good’. He wanted to be the stripe, and I think that there’s a moral courage in deciding to be whatever it is that you’re uniquely positioned to be.

But, it’s also about leaving this place better than you found it.”

One of my favourite passages in Meditations of Marcus Aurelius goes: “A better wrestler? But not a better citizen, a better person, a better resource in tight places, a better forgiver of faults.”

I think he’s saying how selfish a lot of our hobbies tend to be. A lot of our New Year’s resolutions, are ‘I want to get a six-pack’, ‘I want to quit smoking’. Less often is the resolution ‘I want to be more generous in 2027’ or ‘I want to volunteer’.

Stoicism can make us better, stronger, faster in a lot of domains, but it should be challenging us at our ethical and moral centre as well. It begs the question, ‘what are you going to spend your one life doing?’”

“The one constant in history has been change, and it’s only looking backwards that we see any kind of stability or consistency.

One of the things the stoics point out is how the status quo that you’re trying to preserve or that you worry is threatened was itself, at one point, a threatening change looming on the horizon.

That isn’t to minimise what AI represents because I think this is existential in many ways. But, it’s fascinating to read about the second half of the 20th century, and it’s easy to forget that the threat of nuclear annihilation was looming.

The stoics do talk a lot about how this stuff is outside our control, and we have to focus on what we can do inside this moment. That’s all there is.

Your responsibility is where you can make a positive difference for other people.

We decide what line of work we go into, how we run our companies, how we vote, how we participate locally in our community, how we raise our children.

There’s a line from Marcus Aurelius where he says, ‘Frightened of change? But what can exist without it?’

I do try to remind myself that everything is a product of change. Right now, I’m like every writer going, ‘What’s AI going to do to my industry?’

And then I go, ‘Wait, 20 years ago, when I started writing, all those writers were worried about what the internet was going to do in their industry and I wouldn’t be a writer without that change opening things up’.

That’s what history is; the ceaseless passing of one change or technology into the next, and you have to figure out how to survive and adapt and adjust to it.”

Ryan Holiday’s Australian tour begins in Sydney on Friday, October 16.

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