Book Review & Lessons from Lives of the Stoics by Ryan Holiday & Stephen Hanselman
- Shaad Mulla
- Oct 17, 2020
- 8 min read
Updated: Feb 18

It was 49AD. One of the biggest philosophical experiments in the history of humanity was taking place.
Seneca The Stoic was teaching virtue to the soon to be future emperor of Rome, Nero.
Nero who had the attention span of a modern-day TikTok obsessed teenager had to listen to something deep and profound.
Nero who was the equivalent to today’s spoilt rich kid was learning the art of temperance.
Did it work? Did Nero go on to rule with courage, wisdom, justice, and temperance and follow the 4 virtues of Stoicism?
Was Seneca able to prevent him from turning like other emperors before him i.e. tyrant, slaves of passion, egoistic?
Well, you’ll have to read the book Lives of the Stoics by Ryan Holiday & Stephen Hanselman to find out.
An experiment in Roman Times
Today the world's obsessed with startups. Many startups are experimenting to see what works and what doesn’t. What works best will likely be here for 100s of years.
In a similar way, 2000 years ago the world was obsessed with philosophy.
Different philosophies like the startups of today were cropping up in different parts of Europe and Asia.
Experimentation was going on like crazy. The philosophical experiments aimed at living a good life. These experiments were being carried out both on an individual level as well as on a social & political level.
One such philosophy that was cropping up and becoming well known was Stoicism. Started by Zeno in Greece it, later on, spread to the Roman empire.
The book goes on in-depth on how 26 Stoics applied the philosophy to their life. And also applied it to educate some of the most tyrannical emperors on the planet.
It is this friction, between the ones who were slaves to their passion and the ones who were resisting it (stoics) that the book is able to highlight in the best way.
In the entire book, you will see how Stoicism loses miserably to the tyrants. It's like watching the Semifinals of the 2014 FIFA Football world cup between Germany and Brazil where German crushed Brazil 7-1.
But on a deeper level, Stoicism wins hands down. It wins because winning was not about standards such as (fame, money or power). The win was towards the 4 virtues courage, temperance, justice and wisdom that the Stoics compared themselves to. These virtues that the Stoics worked upon helped bring the world closer. It helped prevent the world from falling apart.
Even though the Stoics are long gone, Stoicism is still winning and continues to do so by inspiring us to follow the 4 virtues even today.
Why Stoicism has resurfaced today & why you should read the book
Owing to the huge changes taking place in the world today, Stoicism is making a comeback. Its need has been called on for once again.
There is a great similarity between what was happening then in Greek and Roman times and what's happening today.
When you read the book and see the push and pull between the stoics and the greedy emperors it rings a shocking similarity to today.
The Ceasars and Commodus of yesterday have been replaced by the Hitlers, Lenins, Maos, Putins, and Jinping of today.
As history is rich with Stoics being able to stand against these Dividers in Chiefs, we need them even more. The world needs more Senecas, Marcus Aurelius, Catos, Porcias...
The Stoics
The book goes into detail, 20 to 30 pages each describing the life and covering the essence of the following 26 Stoics:
Zeno the Prophet, Cleanthes the Apostle, Aristo the Challenger, Chrysippus the Fighter, Zeno the Maintainer, Diogenes the Diplomat, Antipater the Ethicist, Panaetius the Connector, Publius Rutilius Rufus the Last Honest Man, Posidonius the Genius, Diotimus the Vicious, Cicero the Fellow Traveler, Cato the Younger, Rome’s Iron Man, Porcia Cato the Iron Woman, Athenodorus Cananites the Kingmaker, Arius Didymus the Kingmaker II, Agrippinus the Different, Seneca the Striver, Cornutus the Common, Gaius Rubellius Plautus the Man Who Would Not Be King, Thrasea the Fearless, Helvidius Priscus the Senator, Musonius Rufus the Unbreakable, Epictetus the Free Man, Junius Rusticus the Dutiful, Marcus Aurelius the Philosopher King
Even though Ryan has named only 26, and told their story, there must have been tens of thousands who were lesser-known. Many who practiced it in their day to day life, applying it in their business, family life and relationships.
The Story in Short
The simple thread that connects the 26 Stoics goes like this.
Once upon a time, Zeno loses his wealth in one go and decides to dedicate the rest of his life to philosophy. He discovers Stoicism. He starts teaching his early students at a place named Stoa Poikile in Greece.
Later, students in succession like Cleanthes, Aristo, Chrysippus, Zeno of Tarsus successively take the task of making Stoicism well known in entire Greece.
As years pass the power shifts from Greece to Rome. When Greece sends Diogenes to Rome, this marks the official entry of Stoicism right at the center of Roman politics.
Rome is where the real drama starts and thus follows the biggest experiment in philosophical history. i.e The application of Stoicism to help rule an empire. The successive remaining Stoics from Cato to Seneca to Helvidus all put this grand experiment to test.
The dream of finally a Stoic philosopher ruling the empire comes true when Marcus Aurelius becomes the ruler. This is the final biggest dent that Stoicism makes in history. The stark contrast between Marcus and other slaves to their desires obsessed rulers before and after him becomes a living breathing example of the true powers of Stoicism.
Though I have wondered why after Marcus' rule Stoicism runs out of favor and disappears.
What Happens when an Honest Man Enters corrupt Roman Politics
If you take Jim Gordon, the incorruptible and fighter of justice from Gotham city, and put him into politics you get Rufus.
Publius Rutilius Rufus is the guy who never compromises, never bends and that is why he is known as the Last Honest Man!
His story can be seen as how sticking to an idealism like 'honesty' can get in your way of career growth. But then there are enough examples in the book where Stoics took a shortcut or overlooked or compromised on their virtues and it didn’t land them anywhere, sometimes it left them worse.
We need more humans like Rufus today if we want to fight and win the rampant corruption existing in the world.
Lady Stoic
The role of women has always been sidelined by history. In most of history, it’s as if women were non-existent. Their role and influence in men’s life are "shown" as close to non-existent. I can only imagine Ryan & Stephen trying their best to read through history books to find a written story talking about women. Must be close to finding a diamond in the rough.
In the book, they put out the story of Porcia, the woman who was right at the center of the Stoic movement. The woman who saw her parents die for Stoicism. The woman who supported her husband like a true Stoic and helped him bring about one of the biggest assassinations in history.
This story itself gives us a glimpse into how many women during those times contributed and supported and put up with all that came to them with a Stoic Iron will!
Stoic Slave

It’s one thing to talk about freedom when you are born free and something other to talk about it when you were once a slave. We who are born free have to practice the art of letting go and force ourselves to see our limited control in this world. Force ourselves to see where we have real freedom and where we don't.
Slaves do not have a choice. They are born in a world where they can literally first-hand experience the limit of human control. They know exactly where freedom and control ends. In those regards, I wonder if they are freer?
One such slave was Epictetus.
Thanks to his slave owner who played a role in Emperor Nero’s life, Epictetus watched in silence how “free men” with the illusion of control screwed up everything!
If Frederick Douglass the American slave taught us that freedom is about becoming free of the ultimate fear which is of death, Epictetus teaches that that true freedom is realizing what part of our life we have control over and where we are truly free!
The Stoic that wasn’t!

Cicero is an amazing example of a guy who lacked skin in the game with respect to Stoicism.
Even though he wrote a lot and hung out with many Stoics of his day he never applied the philosophy to reality. There are many instances and examples in the book where his actions are well governed by fame and desire for higher rank in office.
There is one instance where he is mistrusted to the point where Brutus never tells him his secret intention of killing the emperor. And Cicero after the murder doesn’t shy away from taking the credit even though he had no idea and wasn’t involved in the plot to kill the emperor.
What's missing in the book?
There are instances where for example Thrasea is in conversation whit his friends on the topic of the immortality of the soul. This happens just before he receives the news of being found guilty and sentenced to death.
Such instances show that there were many other thought processes and philosophical ideas that the Stoics were involved in contemplating and believing. These thoughts even though seen with suspicion and disbelief today surely helped the Stoics with practicing their philosophy. It’s also likely that many of these thoughts were lost as history has a point of nitpicking from the past.
It would have been amazing if these ideas too were talked about and what role they played in Stoicism.
Another thing missing is what happened to Stoicism after Marcus Aurelius? Marcus's reign as a Stoic emperor was the peak of Stoicism. What happened to Stoicism, what prompted its decline hasn't been said in the book.
Summary
To Summarise this is by far the best book I have read on Stoicism. To learn about principles is one thing. To actually see the creators and promoters struggle in applying their principles i.e. walk the talk is another.
You will end up learning about Stoic philosophy in a completely different way.
Seven Quotes from my notes!
> Learn. Apply. Learn. Apply. Learn. Apply. This is the Stoic way.
> If you want the job done right, there’s no one better to do it than a Stoic. If you want someone to aid you in your crimes and corruption, there’s nobody worse.
> The study of science can sometimes lead a person to atheism, but in Posidonius’s case, his experiments with the tides and his observations of the stars had given him a strong sense of a creator—that there was a providential fate governing the universe.
> To Musonius, the sign of a successful philosopher was not the loud cheering of supporters. It was silence. Because it meant the audience was actually thinking—it meant they were wrestling with the difficult ideas that the speaker was getting across.
> “If one accomplishes some good though with toil, the toil passes, but the good remains, If one does something dishonorable with pleasure, the pleasure passes, but the dishonor remains.” - Musonius Rufus
> “For no man is a slave who is free in his will,” - Epictetus
> Marcus didn’t weep because he was weak. He didn’t weep because he was un-Stoic. He cried because he was human. Because these very painful experiences made him sad. “Neither philosophy nor empire,” Antoninus said sympathetically as he let his son sob, “takes away natural feeling.”
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