Ryan Holiday Books: How His 11 Books Helped Stoicism Grow

Updated September 8, 2023

If you've recently become aware of Stoicism and its potential to improve your life, you probably have Ryan Holiday to thank. In this article, we're going to take a closer look at the eleven Ryan Holiday books that have helped to grow awareness of the philosophy in the modern day.

While there are some who criticize Holiday for turning the wisdom of the ancient Stoics into "lifehacks," the truth is that many fewer people would probably even know about the philosophy without his efforts.

Let's take a closer look at the books that Ryan Holiday has written that have furthered the cause of achieving tranquility, balance, and "good spirit" in our individual lives through the Stoic virtues.

Who Is Ryan Holiday?

Ryan Holiday is famous for being the best-known proponent of Stoicism in the modern day. A writer and media strategist, as a younger man, he had a successful marketing career at American Apparel before founding his own creative agency. He's written books on both marketing and Stoicism, which have been translated into thirty languages and have sold millions of copies.

With a massive email list (hundreds of thousands of people are subscribed) where he sends out insights, thoughts, and ideas about Stoicism and how it can be applied to 21st-century life, he's managed to become the guy that everyone associates with Stoicism.

  • Since he has risen in prominence as the man who spreads the word about Stoicism, he's also opened a book shop outside of Austin, named the Painted Porch Bookshop after the painted stoa from which Stoicism gets its name.

Holiday came across Stoicism when he was in college and has been credited by The New York Times as one of the reasons that Stoicism has become increasingly popular. His ability to make the ancient wisdom of Stoicism accessible to modern Stoicism has particularly hit home with Silicon Valley entrepreneurs, but people from all walks of life have benefited from his work.

A List of Ryan Holiday Books About Stoicism

Holiday has written an impressive number of books, considering that his first one was only published a bit over a decade ago. While a handful of his books focus on marketing, including the first book he wrote and published, it is really in the world of Stoicism where he has caught the world's eye.

Let's take a look at the eleven books Holiday has written about Stoicism over the years.

1. The Obstacle Is the Way: The Timeless Art of Turning Trials into Triumph

With more than 25,000 reviews on Amazon, more than 74,000 ratings on Goodreads, and more than two million copies sold, The Obstacle Is the Way has certainly done its part in spreading the word about Stoicism.

marcus aurelius ryan holiday books

"The mind adapts and converts to its own purposes the obstacle to our acting. The impediment to action advances action. What stands in the way becomes the way."

- Marcus Aurelius

Published in 2014, this book has been spoken of highly by everyone from Arnold Schwarzenegger to LL Cool J. Focusing on the idea that we can turn the obstacles we face into opportunities to improve ourselves, The Obstacle is the Way takes a look at some of the most successful people in history have used the principles of Stoicism to triumph despite seemingly impossible situations.

2. Ego Is the Enemy

Ego is the Enemy was instantaneously a best seller over at the Wall Street Journal and USA Today.

marcus aurelius ryan holiday books

“Remember: Matter. How tiny your share of it. Time. How brief and fleeting your allotment of it. Fate. How small a role you play in it.”

- Marcus Aurelius

The central theme of the book is that the most common enemy we all share doesn't lie outside ourselves in external events. Instead, it's inside us: our ego.

  • We fail to cultivate our talent and have the humility to learn when we are young.
  • We refuse to see our own faults and are ultimately held back by our ego.

Covering the gamut from history to philosophy to literature, Holiday shows us how some of the most significant figures in history overcame their own egos and achieved the highest levels of success and power.

3. The Daily Stoic: 366 Meditations on Wisdom, Perseverance, and the Art of Living

One of the things that Holiday drives home about Stoicism is the fact that it's supposed to be integrated into our daily lives. This isn't a philosophy that we simply think about in an abstract way or use to make ourselves seem smart and interesting at parties.

epictetus ryan holiday books

“If a person gave away your body to some passerby, you’d be furious. Yet you hand over your mind to anyone who comes along, so they may abuse you, leaving it disturbed and troubled—have you no shame in that?”

- Epictetus

In his bestselling book The Daily Stoic, Holiday gives adherents to Stoicism a way to really make sure Stoic thought is a part of their everyday life.

Stoicism isn't just something you learn about in school and then forget about as life sinks in. The practice of being a Stoic takes place in the small moments and the big moments, the quiet experiences of meditation and the explosion minutes of chaos.

This is a great way for people to plant the seeds of Stoicism in their minds as they go about their lives. With 366 days of exercises and insights, readers can enjoy historical anecdotes, inspirational and powerful quotations, fascinating commentary, and much more.

4. The Daily Stoic Journal: 366 Days of Writing and Reflection on the Art of Living

Some of the most impressive characters in history have kept journals, including the Roman Emperor and Stoic Marcus Aurelius. Not all journaling is created equal, though-- there's a big difference between writing jotting down the office gossip of the day and thoroughly examining one's actions based on their virtuousness.

epictetus ryan holiday books

"Keep this thought at the ready at daybreak, and through the day and night-- there is only one path to happiness, and that is in giving up all outside of your sphere of choice, regarding nothing else as your possession, surrendering all else to God and Fortune."

- Epictetus

I've written a guide for how to journal that you can check out, and you certainly don't have to buy a special $30 book to benefit from it. However, those who are looking for a bit of structure in their Stoic journaling might enjoy checking out Holiday's Daily Stoic Journal.

“Stoicism is designed to be medicine for the soul.”

- Ryan Holiday

This is a book that gives you space to take notes both in the morning and the evening. Furthermore, you'll find advice along the way to help you integrate the wisdom of Stoicism into your actual life.

5. Stillness Is the Key

The third part of the trilogy, along with The Obstacle Is the Way and Ego is the Enemy, Stillness Is the Key, is a book that focuses on one Stoic concept through the lens of great historical and contemporary figures.

“Most of us would be seized with fear if our bodies went numb, and would do everything possible to avoid it, yet we take no interest at all in the numbing of our souls."

- Epictetus

In this book, he argues that all great leaders, artists, thinkers, visionaries, and athletes share the quality of knowing how to avoid distraction and tap into valuable insights. He calls this phenomenon stillness-- essentially, this is about the ability to maintain tranquility and steadiness despite the dizzying spinning of the outside world.

6. Lives of the Stoics: The Art of Living from Zeno to Marcus Aurelius: Lessons on the Art of Living

If you've been searching for a way to learn more about the great Stoic philosophers without digging into dense academic texts, you might want to check out Lives of the Stoics.

“When the student is ready, the old Zen saying goes, the teacher appears.”

- Ryan Holiday

Written for laymen and easy to read, Holiday takes this opportunity to dive into who each of the best-known Stoic philosophers were and how the philosophy directed their actions and lives. Through the lens of everyone from Epictetus to Marcus Aurelius, the intent is to help individuals understand how to really apply Stoic philosophy to their own lives.

7. The Daily Dad: 366 Meditations on Parenting, Love, and Raising Great Kids

If you loved The Daily Stoic and are working to incorporate Stoicism into your life as a parent, you'll certainly be interested to learn about The Daily Dad.

marcus aurelius ryan holiday books

“Life is short. Do not forget about the most important things in our life, living for other people and doing good for them.”

- Marcus Aurelius

Recently released in May 2023, this is another dose of 366 meditations that you can access one at a time, each day. Providing meditations on parenting that won't overwhelm you or feel like too much of a time commitment, you'll find more great stories about the lessons from the lives of legends.

8. Courage Is Calling: Fortune Favors the Brave

Making up half of the "Stoic Virtues Series" along with Discipline is Destiny, Courage Is Calling discusses one of the most universal concepts that we deal with as humans: fear.

"Don’t worry about whether things will be hard. Because they will be. Instead, focus on the fact that these things will help you. This is why you needn’t fear them."

- Ryan Holiday

Taking a closer look at all of the most prominent elements of fear, Courage Is Calling is a book that will help you think about how fear impacts your life while also giving you practical advice regarding how to conquer your fear. Furthermore, you'll find in these pages examples of how you can practice being brave and exhibiting courage as you go through your life.

9. Discipline Is Destiny: The Power of Self-Control

While Courage Is Calling centers on the need to overcome fear in order to be the best possible version of yourself, Discipline Is Destiny highlights the importance of self-control while pursuing a bold and brave life.

"When force of circumstance upsets your equanimity lose no time in recovering your self-control, and do not remain out of tune longer than you can help. Habitual recurrence to the harmony will increase your mastery of it."

- Marcus Aurelius

In this book, he puts forward the Stoic idea that we must master ourselves before we can master anything. We have to have the self-awareness to understand our own thoughts, emotions, and actions, and exert control over them.

“In a world of distraction, focusing is a superpower.”

- Ryan Holiday

Again, using stories from impressive historical characters such as Queen Elizabeth II, Lou Gehrig, and, of course, Marcus Aurelius, this is a book that can help you understand just how important it is to not fall prey to the dangers of hedonism and extravagance. Beyond that, though, he paints a picture of just how powerful balance and self-discipline can be in one's life.

Ready to read some of the works of the great ancient Stoics? Here are our primers on Letters from a Stoic and Meditations.

10. The Boy Who Would Be King: A Fable About Marcus Aurelius

Are there any young Stoics in your life? In early 2021, Ryan Holiday published The Boy Who Would Be King: A Fable About Marcus Aurelius, a short 100-page book for children (and adults) of all ages.

If you're interested in a more narrative peek at the life and lessons of the great Marcus Aurelius, this is a sweet little book. It's also a great way to introduce some of the core ideas of Stoicism to some of the younger souls you know.

11. The Girl Who Would Be Free: A Fable About Epictetus

In the companion to The Boy Who Would Be King, Holiday creates a fable by combining the story of Epictetus, Aurelius, and a number of other historical figures into the character of a young girl. Born into slavery, she manages to overcome her hardships through the power of philosophy. Beyond that, she is able to free herself from her enslavement while also liberating the minds of countless others.

Are you searching for more books to help you improve yourself and learn about Stoicism? Check out our lists of ten books to read to learn about Stoicism, books on overthinking things, and books that will change the way you think.

How Ryan Holiday Influenced the Rise of Modern Stoicism

Though there are certainly some who criticize Ryan Holiday's approach to promoting Stoicism and the ideas he focuses on (perhaps at the expense of others), few can really deny that he has had a huge impact on the growth of philosophy in the modern-day.

He is, one could say, a surprising character to play the role. Not many people would think to utter the words "media manipulator" and "Stoic" in the same sentence, but he gladly calls himself both.

  • It really is incredible in this day and age for anyone to take the ideas of Stoicism and make them not just accessible, but legitimately popular.

Over the last decade or so, more and more people have discovered the potential for this philosophy to really change their lives.

Through his many books, speaking engagements, blog, YouTube channel, and more, Ryan Holiday has been spreading the word about Stoicism to the masses. Beyond that, he does an impressive job finding the essential information in the ancient texts and making it accessible to people from all walks of life. A large community has emerged online surrounding Stoicism, and one can't help but wonder whether there would be such a large following without his efforts.

Criticisms of Ryan Holiday's Interpretation of Stoicism

While there are many followers of Stoicism who have Ryan Holiday to thank for the introduction, there's also a fair share of criticism about him floating around.

One of the major points that people make is that he has diluted this ancient philosophy into "lifehack" type pieces of information. Many have said that philosophy isn't something that should be monetized or marketed in the way that Holiday has with Stoicism.

In response to this type of criticism, Holiday has said the following:

Of all the horrible things to be accused of, making philosophy popular and accessible doesn’t feel like a particularly bad one. Some people want to keep these ideas hopelessly obscure and opaque so they and their university buddies can debate them for a living… and pretend that isn’t ‘monetizing’ philosophy either. They’re just doing it on the taxpayer and student dime.”

Some also argue that he overemphasizes some of the ideas in Stoicism that are applicable to entrepreneurs of Silicon Valley bigwigs. Rather than offering a legitimate picture of the philosophy, these critics accuse him of forcing Stoicism into entrepreneurial and self-help culture.

Stoicism in the Modern Day: Is It Right For You?

Ryan Holiday is a fascinating character who has, perhaps more than anyone else, helped to bring some of the key ideas of Stoicism to the masses. His many books, including The Obstacle, Is the Way, and The Daily Stoic, have turned what was once a philosophy discussed only among academics and the particularly well-read into something that is helping millions of people around the world.

  • While there are many who criticize Holiday's version of Stoicism and have accused him of using Stoicism for the purposes of self-promotion, no one can really deny that he has been instrumental in the growth of the movement.

Whether you've been following Stoicism for years or you are new to the philosophy, it's hard to avoid bumping into the work of Holiday when learning about Stoicism. He's out there spreading the word tirelessly and has been for years. Even if you don't agree with the way he frames Stoicism or the methods he uses to publicize it, his work has created an excellent jumping-off point for the growth of Stoic personalities in our society.

Are you searching for more information about Stoicism, philosophy, and how to live the best possible life? Make sure you check out our Stoic Quotes blog!

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Written by: Sophia Merton
Sophia received her BA from Vassar College and has always maintained a deep interest in the question of how best to live one’s life. She hopes to help others understand how they can apply Stoicism in their day-to-day lives in order to become the person they want to be, embrace the present moment, pursue their purposes, and rid themselves of unnecessary anxiety.

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