Lives of the Stoics by Ryan Holiday & Stephen Hanselman: Summary & Notes

Front cover of Lives of the Stoics by Ryan Holiday and Stephen Hanselman.

In short

Lives of the Stoics is a collection of short biographies of the most famous Greek and Roman stoics (or students of Stoicism, like Cicero). The book can be best described as a moral biography in the style of Plutarch: it’s not so much about the actual details of the lives, but about the moral lessons we can take from them. Although in some ways the Lives of the Stoics is a bit speculative – there simply aren’t that many detailed historical sources – it is nonetheless an interesting read if you’re into Stoicism, or the application of philosophy in practice.

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Book Summary & Notes

All text between quotation marks is taken directly from the book.

“The only reason to study philosophy is to become a better person. Anything else, as Nietzsche said, is merely a “critique of words by means of other words.” Stoicism is the perfect example of this: highly practical and concerned with how to live in real life.

What was important in Stoicism is the question of how to live, which choices to make or principles to follow. It’s not about words, but about actions. The Stoic four virtues reflect this – they are simple and applicable in daily life: courage, temperance, justice and wisdom.

“It should not surprise us then that we can learn just as much from the Stoics’ lived experiences (their works) as we can from their philosophical writings (their words).” That is exactly the idea of the book: to look at the lives, and deaths, of the Stoics and take learning from that.

Zeno – The founder of Stoicism

He started his life as a merchant, but after a shipwreck ended up in Athens were he sought out a bookshop. “Zeno was hearing Socrates’s teaching as they had been conducted in those very streets just a few generations before. The passage that struck him most was “The Choice of Hercules,” itself a story of a hero at a crossroads. In this myth, Hercules is forced to choose between two maidens, one representing virtue and the other vice – one a life of virtuous hard work, the other of laziness. “You must,” Zeno would have heard the character Virtue say, “accustom your body to be the servant of your mind, and train it with toil and sweat.” And then he heard Vice offer a very different choice. “Wait a minute!” she cries. “Don’t you see what a long and hard road to the joy she describes? Come the easy way with me!”
Two roads diverge in the wood, or, rather, in a bookstore in Athens. The Stoic chooses the hard one.”

Even though he had a background as a rich merchant, this did not impact the levels of discomfort he was willing to endure. He showed that money mattered little, and apparently his temperateness was known throughout Athens – even becoming a proverb in the form of “He is more temperate than Zeno the philosopher.”


In order to support himself he worked manual labor jobs – earning the nickname “water-boy” because he carried jugs of water at night. He even kept this up after he became a philosopher of name – studying during the day, working at night.

This also lead to an interesting anecdote:

“When suspicious citizens of Athens thought the middle-aged Cleanthes looked in too fine a condition to be burning the candle at both ends, they hauled him before the court to give an account of how he made a living. Quite readily, he brought forth a gardener for whom he drew water and a woman whose grain he crushed to testify in his defense. Not only would the resourceful Cleanthes be acquitted, but he would also be awarded a hundred drachmas – many times what he had in his pocket on coming to Athens.
The large settlement was a message from the city elders: We could use more folks like this. Centuries later, we still don’t have enough people like him.”

“Kierkegaard would later make the distinction between a genius and an apostle. The genius brings new light and work into the world. The genius is the prophet. The creator. The apostle comes next – a mere man (or woman) who communicates and spreads this message. Given Cleanthes’s dedication to Zeno, it seems likely that the two were never contemporaries or peers, but always master and student. Zeno, the prophet. Cleanthes, the apostle of Stoicism.”

“Fate guides the man who’s willing, drags the unwilling.” – Cleanthes

“Cleanthes loved the challenge of poetry, believing that the “fettering rules” of the medium allowed him to reach people in a deep and moving way. He offered the analogy of the way that a trumpet focuses our breath into a brilliant sound. This too would be a metaphorical insight that remains central to Stoicism: that obstacles and limitations – if responded to properly – create opportunities for beauty and excellence.”


Aristo focused on high-level principles that could be internalized by any student. Virtue was the highest good, and anything that tried to add or limit or explain that only led to confusion. Zeno was against this: he thought that not everything could be defined easily, and that there were always gray areas between vice and virtue (like money, or health). These Zeno called “preferred indifference”, they don’t a moral difference, but it’s nicer to be healthy than not.


Chrysippus was the competitive defender of Stoicism. He studied the rival philosophical school, not just to learn from them, but also to understand the arguments and weak points of them. Similarly, he did this for his own Stoic believes: to see where they had to be improved.

“In fact, he was so fond of quoting other writers that their voices sometimes overshadowed his own in some of his writings. Critics of his books called these quotations “extraneous,” but a better reading is that Chrysippus truly loved sharing and sampling from the great thinkers and playwrights of history, and he would become notorious as a result for his diligent citation of them and other sources whenever they supported his points.”

“It’s not that Chrysippus forsook all pleasures and money; it’s that he was suspicious of wanting, lusting for anything. A wise man can make use of whatever comes his way, he said, but is in want of nothing. “On the other hand,” he said, “nothing is needed by the fool for he does not understand how to use anything but he is in want of everything.”
There is no better definition of a Stoic: to have but not want, to enjoy without needing.”


“Antipater was the major force in moving the Stoics in this commonsense direction. He loosened the absolutism of being either all virtuous or vicious. He stopped minimizing the “indifferent” things of daily live – whom we marry, how we dress, what we eat – and brought ethics to the forefront of the philosopher’s concern, so that philosophy could be a productive life practice. A guide to living. An operating system.”


“The previous Stoics had sometimes actively flouted social convention, but Panaetius saw each human being as having a unique prosopon, Greek for “character” or “role,” that must be fulfilled with honor and courage and commitment, however humble or impressive.

Panaetius argues that if we are to live an ethical life and choose appropriate actions, we must find a way to balance:

1) the roles and duties common to us all as human beings;
2) the roles and duties unique to our individual daimon, or personal genius/calling;
3) the roles and duties assigned to us by the chance of our social station (family and profession);
4) the roles and duties that arise from decisions and commitments we have made.”

“Panaetius believed that each person had an inborn desire for leadership, and that we are obligated to fulfill this potential in our own unique way. We may not all be able to be Scipio on the battlefield, or even Panaetius with an elite education and diplomatic connections, but we can serve the public good in many other ways with equal courage.”

Publius Rutilius Rufus

“The Roman Republic’s institutions had been greatly weakened and all that remained was valiant resistance from great and honorable men. How much longer could they hold back the tides? How much longer could they preserve the ethics and political institutions that Greece had brought to Rome?

With Julius Caesar coming, the answer, sadly, was not much longer.

But for a time, Rutilius Rufus had let his light shine. He had been a force for good in the world and had suffered for it. But never, it seems, did he question whether it was worth it. Nor did he harbor any bitterness about his fate. He had looked at himself and the corruption around him and decided that no matter what other people said or did, his job was to be good.”


“Perhaps these are the ideal conditions in which Stoicism emerges: a homeland lacking strong leadership and buffeted by powerful outside forces; a ringside seat to the perils of excess and greed. It was all an early lesson that in an unpredictable world, the only thing we can really manage is ourselves – and that the space between our ears is the only territory we can conquer in any kind of certain and enduring way.”


“If you have a garden and a library,” Cicero would write in a letter to a friend as they discussed Chrysippus and Diodotus, “you have everything you need.” Clearly there was a part of him that didn’t fully believe that, that could not be content with the simple or reflective life. Like many people, he seemed to believe that he needed wealth and fame too. Like many of us who crave those same things, he did not realize what they would cost him until he got them…and by then it was too late.)”

Cicero was a “fair-weather” philosopher or Stoic, in that he admired the Stoic virtues and people like Cato, who were willing to give their life to stand up for their principles, but he himself wasn’t willing to commit to this. When Caesar took power he censored himself, and didn’t stood up for his own principles. “Both Cato and Cicero cared about what was right – but Cicero cared about himself a little bit more. Cato believed in courage. Cicero believed in not getting killed.”

“Cicero had long talked a big game. He had written about duty; he had admired the great men of history. He had accomplished so much in his life. He had accumulated mansions and honors. He had been to all the right schools. He had held all the right jobs. He had made his name so famous that no one would ever care about his lowly origins again. He was not just a new man, he was, for a period, the man.
But he had compromised much to get there. He had ignored the sterner parts of Stoicism – the parts about self-discipline and moderation […], the duties and the obligations. He had ignored his conscience, in defiance of the oracle, to seek out the cheers of the crowd. If he had followed Posidonius and Zeno better, his life might not have turned out differently, but he would have been steadier. He would have been stronger.
Now, when it counted, there was nothing in him, nothing in his fair-weather personal philosophy that could have helped him stand up in this moment where cruel fate was bearing down on him. He could not rely on the inner citadel that countless Stoics had when they faced death, because he had not built it when he had the chances.”


“Most strong-willed leaders have a temper. It’s the truly great ones who manage to conquer it with the same courage and control with which they deal with all of life’s obstacles.”

“We naturally care what other people think of us; we don’t want to seem too different, so we acquire the same tastes as everyone else. We accept what the crowd does so the crowd will accept us. But in doing this, we weaken ourselves. We compromise, often without knowing it; we allow ourselves to be bought – without even the benefit of getting paid for it.”


“Individuality and autonomy, these are things many people pay lip service to – in fact, it’s almost become a new form of conformity. We talk about being our unique selves, about letting our colors shine, but deep down we know this is just talk. Under pressure, when it really counts, we want the same things as everyone else. We do the same things as everyone else.”


As a teacher to Nero, Seneca tried to teach him to be good (or at least better), but he made little progress. But still Seneca kept trying and kept showing up to work. “As he would later write, the difference between the Stoics and the Epicureans was that the Stoics felt that politics was a duty. “The two sects, the Epicureans and the Stoics, are at variance, as in most things,” Seneca wrote. “Epicurus says: ‘The wise man will not engage in public affairs except in an emergency.’ Zeno says: ‘He will engage in public affairs unless something prevents him.’”

Gaius Rubellius Plautus

“That is our deepest fear anyway: that the people we loathe are actually better than us, and that we loathe them not because they are inferior but because they have something we lack.”

Musonius Rufus

“Suffer and endure toward virtue – that’s the core of Musonius’s teachings. As he said, “And yet would not anyone admit how much better it is, instead of exerting oneself to win someone else’s wife, to exert oneself to discipline one’s desires; instead of enduring hardships for the sake of money, to train oneself to want little; instead of giving oneself trouble about getting notoriety, to give oneself trouble how not to thirst for notoriety; instead of trying to find a way to injure an envied person, to inquire how not to envy anyone; and instead of slaving, as sycophant do, to win false friends, to undergo suffering in order to possess true friends?”


Epictetus famous dichotomy of control states that there are things that are up to us, and things that are not up to us. The key is to focus on the things we can control and that are thus completely up to us. “Our attitudes. Our emotions. Our wants. Our desires. Our opinions about what has happened to us. Epictetus believed that as powerless as humans were over their external conditions, they always retained the ability to choose how they responded.”

“Every situation has two handles,” Epictetus taught. One of these handles was weak and one of them was strong. No matter our condition, no matter how undesirable the situation, we retain the ability to choose which one we will grab. Are we going to choose to see that our brother is a selfish jerk? Or are we going to remember that we share the same mother, that he’s not this way on purpose, that we love him, that we have our own bad impulses too?
This decision – which handle we grab, day in and day out, with anyone and everyone we deal with – determines what kind of life we have. And what kind of person we will be.”

“It was from Aulus Gellius that one of Epictetus’s most famous sayings is preserved:
[Epictetus] used to say that there were two faults which were by far the worst and most disgusting of all, lack of endurance and lack of self-restraint, when we cannot put up with or bear the wrongs which we ought to endure, or cannot restrain ourselves from actions or pleasures from which we ought to refrain. “Therefore,” he said, “if anyone would take these two words to heart and use them for his own guidance and regulation, he will be almost without sin and will lead a very peaceful life. These two words,” he said, “are persist and resist.”

Junius Rusticus

“It’s an example that should challenge every talented and brilliant person: You owe it to yourself and to to the world to actively engage with the brief moment you have on this planet. You cannot retreat exclusively into idea. You must contribute.”

Marcus Aurelius

“Since Plato, it had been the dream of wise men that one day there might be such a thing as a philosopher kind. Although the Stoics had been close to power for centuries, none of them had come close to wielding supreme command themselves. Time and time again they had hoped the new emperor would be better, that this one would listen, that this one would put the people before his own needs. Each one would prove, sadly, that absolute power corrupts absolutely.”

“His dictum in life and in leadership was simple and straightforward: “Do the right thing. The rest doesn’t matter.” No better expression or embodiment of Stoicism is found in his line (and his living of that line) than: “Waste no more time talking about what a good man is like. Be one.”

Marcus Aurelius was by no means perfect – he prosecuted the Christians and viewed a large part of the world as barbarians. But “it’s unfair to compare Marcus only to his own writings, or to the impossibly high standards of his philosophy. Instead, he should also be looked at in the company of the other men (and women) who held supreme power, which Dio Cassius did well when he observed that “he ruled better than any others who had ever been in any position of power.”


“There is no role so well suited to philosophy as the one you happen to be in right now,” Marcus Aurelius would write. He probably meant the role of emperor, but the meaning can easily be extended: The role of parent. The role of spouse. The role of a person waiting in line. The role of a person who had just been given bad news. The role of a person who is rich. The role of a person sent into exile or delivered into bankruptcy. The role of a person who finds themselves enslaved, literally or otherwise.
All this was philosophy. All of this was what made someone a Stoic.

“Did many of the Stoics fall short? Absolutely. They were tempted by wealth and made embarrassing compromises as the groped for fame. They lost their temper. They lied. They eliminated rivals…or looked the other way while someone else did. They were silent when they should have spoken up. They enforced laws that they ought to have questioned. They were not always happy; they did not always bear adversity with the dignity one would expect.
No one in this book managed, in every minute of their life, to live up to those lofty virtues of courage and justice and moderation and wisdom. Yet in their unique struggles and triumphs, they each managed to teach us something, proving, intentionally or not, why the principles they purported to believe were superior to the choices they actually made.
Most of all, the Stoics taught us by the fact that they tried. What matters is what we can learn from their successes and their failures in this lifelong pursuit.”

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