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.
asserted
man → waste → time
Holiday knows a thing or two about that.
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Holiday → know → 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.
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old → become → villain
A university dropout, he handled public relations for American Apparel when its founder was accused of rape.
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founder → handle → 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.
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I → become → 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.
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that → do → 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.
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Stillness → include → 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.
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him → inspire → Tour
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.
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which → cancel → oppression
(Hitler’s Mein Kampf was not removed from the library.)
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Kampf → remove → 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.
uncertain
he → lecture → 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”.
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he → tour → distraction
He spoke to this masthead while driving his two sons home from school in Austin, Texas, about comfort, discipline, meaning, AI and change.
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He → speak → comfort
Below are Holiday’s thoughts, edited for length and clarity.
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thoughts → edit → length
Ryan Holiday on discomfort: ‘Anything unexpected lands heaviest’
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Anything → land → discomfort
“We don’t want things in life to be hard or challenging.
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things → want → life
We want them to be nice and easy and reassuring.
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them → want → ?
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.
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things → be → house
And there are people who have set up a whole information system that only tells them what they want to hear.
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they → be → what
It never forces them to think differently or accept things they don’t like.
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they → force → things
One of the basic stoic ideas is that anything unexpected lands heaviest.
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anything → land → ideas
But then you’re really rattled and have difficulty dealing with it when that’s not the case.
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that → ’re → it
The stoics would say that fortune reminds you who’s really in charge.
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who → say → charge
One of the basic stoic ideas is that anything unexpected lands heaviest.
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anything → land → ideas
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.
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they → want → ?
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.
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they → do → 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.
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rendering → believe → temperance
So, they believed that all the virtues were a midpoint between vices.
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virtues → believe → vices
I love endurance sports, but if I’ve injured myself or if I’m sick, it requires discipline to not do it.
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it → love → 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’.
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you → get → people
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.
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you → know → that
If, for you, stoicism is self-flagellation, I think you’re doing it wrong.
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you → think → it
On meaning: ‘We were made to contribute’
“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.
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none → make → soul
Stoicism is about sort of being of service and making a difference.
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Stoicism → make → difference
We were made to contribute to what they would call the common good.
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they → make → what
And some of that has to be about fulfilling your individual potential.
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some → have → 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.
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him → ’ → poets
Agrippinus was asked, ‘Why don’t you try to blend in?’ and he says, ‘Society is like a garment.
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Society → ask → garment
I am like the red thread that makes the rest of it look good’.
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rest → make → it
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.
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you → want → that
…and 22 more, not listed.
The Aporia
