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Author Ryan Holiday, once a controversial publicist, now teaches stoicism to figures like Arnold Schwarzenegger and Tom Brady. He shares lessons on comfort, discipline, meaning and AI.
Author Ryan Holiday has become the modern poster boy for stoicism, the ancient philosophy that holds we always control how we respond even when we cannot control what happens to us.
The 39-year-old university dropout once played the role of the villain, handling public relations for American Apparel when its founder was accused of rape. He then drew negative media attention for his first book about duping the media. What he did next earned him his fan base: he turned to writing about the philosophy that transformed his own approach to life.
From Controversy to Stoic Principles
His subsequent books, including The Obstacle Is the Way and Ego Is the Enemy, inspired everyone from Arnold Schwarzenegger to Tom Brady to Rory McIlroy, who credited stoicism with helping him maintain his consistently high ranking on the PGA Tour. Holiday was the keynote speaker at the US Naval Academy for four years in a row until the academy cancelled him.
He had refused a directive not to mention the removal of the supposedly controversial book I Know Why the Caged Bird Sings. He wrote in an op-ed that he could not, in good conscience, lecture future leaders and warriors on the virtue of courage and doing the right thing, and then fold when asked not to mention such an egregious and fundamentally anti-wisdom course of action.
He is now 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. On comfort, Holiday said people want life to be nice and easy and reassuring.
Some people live a life of comfort where everything is delivered and the temperature is always perfect inside the house, and they choose how things go. Others set up a whole information system that only tells them what they want to hear, never forcing them to think differently or accept things they do not like. One basic stoic idea is that anything unexpected lands heaviest. The stoics would say fortune reminds you who is really in charge.
Discipline as a Stoic Virtue
If you want things to be a certain way and expect them to be that way, it is really hard when they are not. So the stoics contemplated all possibilities and deliberately exposed themselves to those things so that if they did happen, they were not unfamiliar with them. On discipline, Holiday said the stoics believed discipline is a virtue. Seneca says you treat the body rigorously so it is not disobedient to the mind.
But their rendering of discipline was inseparable from temperance or moderation. They believed all virtues were a midpoint between vices. On one end of the spectrum is cowardice, on the other is recklessness, and courage is in the middle. Too much comfort or too much exertion are both extremes and not super productive.
Holiday loves endurance sports, but if he is injured or sick, it requires discipline not to do it. For some people, discipline means getting off the couch and stopping lying around. For others, it means you need to rest. It is knowing where your capacity is and then trying to stay at a threshold right below that, not so far down that you are unfulfilled.
Finding Meaning Through Service
If stoicism is self-flagellation for you, Holiday thinks you are doing it wrong. On meaning, Holiday said you have to have some kind of meaning or purpose, otherwise it just becomes about money, fame or the endless rush of conflict on the internet. None of that is good for society or good for the soul. Stoicism is about 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 is a great stoic named Agrippinus, who lived in the time of Nero, a pretty conformist time when the emperor of Rome was so fragile that he banished talented poets because they made him look bad. Agrippinus was asked why he did not try to blend in. He said society is like a garment.
Some people are the white threads. He was like the red thread that makes the rest of it look good. He wanted to be the stripe, and there is a moral courage in deciding to be whatever you are uniquely positioned to be. Holiday also cited the Meditations of Marcus Aurelius, which asks: A better wrestler?
But not a better citizen, a better person, a better resource in tight places, a better forgiver of faults. Holiday thinks Marcus Aurelius is saying how selfish a lot of our hobbies tend to be. Many New Year resolutions are I want to get a six-pack or I want to quit smoking. Less often is the resolution I want to be more generous in 2027 or I want to volunteer.
Stoicism in the Age of AI
Stoicism can make us better, stronger and faster in a lot of domains, but it should challenge us at our ethical and moral centre as well. It begs the question: what are you going to spend your one life doing? On AI and change, Holiday said the one constant in history has been change, and it is 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 you are trying to preserve, or worry is threatened, was itself at one point a threatening change looming on the horizon. That is not to minimise what AI represents, because Holiday thinks it is existential in many ways. But it is fascinating to read about the second half of the 20th century, and it is easy to forget that the threat of nuclear annihilation was looming.
The stoics 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 is all there is. We decide what line of work we go into, how we run our companies, how we vote, how we participate locally in our community and how we raise our children. There is a line from Marcus Aurelius where he says: Frightened of change? But what can exist without it?
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theage:This story was compiled and edited by the HeadTopics newsroom and HT AI from the reports above.
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