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10 Best Ryan Holiday Books You Have To Read

This collection of the best Ryan Holiday books to read is perfect if you’re looking for an introduction to stoicism or you want to read about media manipulation.

You might be familiar with books like The Obstacle Is The Way and Stillness Is The Key. These books focus on the philosophy of stoicism and are what made Holiday famous.

But there are plenty of other books by Ryan Holiday that you might not be aware of. His first one, Trust Me, I’m Lying, and Conspiracy, which is one of my favourite books of his.

They’re great to read if you want to learn more about philosophy, particularly stoicism, as well as media manipulation, which is what some of Holiday’s earlier books focus on.

Whichever one of Ryan Holiday’s books you read, you’re sure to learn a lot and pick up some valuable lessons in the process!

Best Ryan Holiday Books

five books by ryan holiday
Some of the Ryan Holiday books I’ve read


Conspiracy: A True Story of Power, Sex, and a Billionaire’s Secret Plot to Destroy a Media Empire
  • Holiday, Ryan (Author)
  • English (Publication Language)
  • 336 Pages – 03/28/2019 (Publication Date) – Profile Books (Publisher)

Conspiracy is the best Ryan Holiday book that I’ve read. It’s different from his others in that it doesn’t focus on philosophy or his working life.

It looks at the downfall of the website Gawker, which was infamous for posting brutal articles on several celebrities and outing the tech billionaire Peter Thiel as gay.

It’s this last point that is the subject of the book as Thiel’s resentment leads him to put together a conspiracy to bring down the website. How this came about is incredible and had me glued page after page.

Conspiracy is a fascinating read, and just downright bonkers at times. It’s a good insight into billionaires’ minds and their influence over society without us even realising it.

The Obstacle Is The Way

Obstacle Is The Way
  • Holiday, Ryan (Author)
  • English (Publication Language)
  • 201 Pages – 06/04/2015 (Publication Date) – Profile Books Ltd (Publisher)

The Obstacle Is The Way is probably the most well-known of Ryan Holiday’s books. It’s the one that thrust him into the limelight.

The book is, as the name suggests, about overcoming obstacles and looks at how we can overcome them, learn from them, and even thrive from them.

Holiday uses a variety of examples to explain his points, and several stories to highlight how famous and historical figures were able to overcome adversity in their lives.

The Obstacle Is The Way is a good book to read if you’re looking for a self-help book that can help with your mental health and daily life. You’ll be inspired to become a better version of yourself after reading it!

Ego Is The Enemy

Ego is the Enemy: The Fight to Master Our Greatest Opponent
  • Holiday, Ryan (Author)
  • English (Publication Language)
  • 08/03/2017 (Publication Date) – Profile Books Ltd (Publisher)

Ego Is The Enemy looks at how ego affects our lives and the negative effects of letting it run wild.

Everyone has an ego but some of us have more ego than others. The downsides of this are made apparent in the book as Holiday uses a variety of figures to highlight how too much ego is a bad thing.

I felt Ego Is The Enemy wasn’t as good as some of his other books but there are still a lot of useful lessons you can learn from the book.

If you want a corrective or feel like you need humbling, then this book is perfect and will certainly do that!

Stillness Is The Key

Stillness is the Key: An Ancient Strategy for Modern Life
  • Holiday, Ryan (Author)
  • English (Publication Language)
  • 288 Pages – 10/08/2020 (Publication Date) – Profile Books (Publisher)

Stillness Is The Key is one of the best Ryan Holiday books and is another that looks at an aspect of Stoicism.

It concerns how we can find peace and tranquillity in the modern world and how stoics have achieved this in the past and present.

Given the ever-more hectic nature of the world we live in, this is a good book to read if you want some inspiration on how to slow down a little.

I liked Stillness Is The Key and learned a lot from reading.

This is a book where the examples Holiday highlights come in handy as you can see how figures with a lot on their plate were able to relax and not let the chaos around them consume them.

Courage Is Calling

Courage Is Calling
  • English (Publication Language)
  • 304 Pages – 09/08/2022 (Publication Date) – Profile Books (Publisher)

Courage Is Calling is the first in a series of books where Holiday looks at the four stoic virtues, courage, discipline, temperance, and wisdom, in detail.

If you’ve read any of his other books on stoicism then you’ll be familiar with the format. Holiday uses stories from the past and famous figures familiar to use to highlight the importance of courage.

While you get a lot from these books on the importance of the virtues, one of the things I like about them is that you learn about new figures or some historical event you weren’t aware of.

This is what makes Courage Is Calling such a good book. Not only do you get a lesson on the virtues of courage, but you get a history lesson of sorts too!

Discipline Is Destiny

Discipline Is Destiny: The Power of Self-Control (The Stoic Virtues Series)
  • Hardcover Book
  • Holiday, Ryan (Author)
  • English (Publication Language)
  • 352 Pages – 09/27/2022 (Publication Date) – Portfolio (Publisher)

Discipline Is Destiny is the second of Ryan Holiday’s books that looks at the four stoic virtues, with this one focusing on, as you may have guessed from the title, discipline.

Discipline is an interesting virtue and the stories that Holiday uses to relay its importance are fascinating.

One of the key takeaways from this book is that you don’t have to be super-disciplined, such as waking up at 4 am every day. Instead, being disciplined in small ways, such as forgoing alcohol from time to time can have big effects.

Discipline Is Destiny teaches you that being disciplined isn’t the point, but that being strict with yourself and fair towards others is the path to go down.

Lives of The Stoics

Lives of the Stoics: The Art of Living from Zeno to Marcus Aurelius
  • Holiday, Ryan (Author)
  • English (Publication Language)
  • 352 Pages – 01/06/2022 (Publication Date) – Profile Books (Publisher)

Lives of The Stoics looks at a collection of philosophers from the Stoic school. The figures range from Marcus Aurelius, the Roman Emperor, to Zeno, the founder of Stoicism, and some more obscure figures such as Cleanthes.

26 people are featured in all with the majority being from either ancient Greece or ancient Rome. what we get are mini-biographies of all of these figures who contributed to Stoicism in some way.

For some figures, this is easier than others. Marcus Aurelius, has his own writings, Meditations, to go from, while little is known about some of the figures.

I enjoyed this book as it was an interesting look at a range of people, some I knew about, others I didn’t. If you want an introduction to the philosophy of Stoicism, then Lives of The Stoics is a good place to start!

The Daily Stoic

The Daily Stoic: 366 Meditations on Wisdom, Perseverance, and the Art of Living: Featuring new translations of Seneca, Epictetus, and Marcus Aurelius
  • Ryan Holiday (Author)
  • English (Publication Language)
  • 406 Pages – 11/23/2016 (Publication Date) – Profile Trade (Publisher)

The Daily Stoic is a collection of quotes and passages from several Stoic philosophers and other figures.

This isn’t a conventional book and is instead a kind of devotional book. You read one page each day, and there are different quotes or passages for you to read that serve to inspire you.

You might be familiar with Holiday’s Daily Stoic website, where he has a collection of articles and sends out an email every day highlighting some points of Stoicism.

The Daily Stoic book is essentially this in book form. It’s handy if you want something to look to each day to give you a pep talk and will provide you with lots of wisdom too!

Trust Me, I’m Lying

Trust Me, I’m Lying: Confessions of a Media Manipulator
  • Used Book in Good Condition
  • Holiday, Ryan (Author)
  • English (Publication Language)
  • 352 Pages – 07/02/2013 (Publication Date) – Portfolio (Publisher)

Trust Me, I’m Lying is Ryan Holiday’s first book and is an expose of his time working as a media strategist for Tucker Max and Robert Green among others.

The book was a New York Times bestseller and is an interesting look into the murky world of online journalism.

Trust Me, I’m Lying isn’t like his other books and if you’re used to Holiday’s books on stoicism it will be different from what you’re used to.

However, like Conspiracy, this is a fascinating book and in some ways, Holiday is better when he’s writing about topics such as this than he is with the stoic stuff.

Growth Hacker Marketing

Growth Hacker Marketing: A Primer on the Future of PR, Marketing, and Advertising
  • Holiday, Ryan (Author)
  • English (Publication Language)
  • 176 Pages – 09/30/2014 (Publication Date) – Portfolio (Publisher)

If you want to know what it takes to go viral in the internet age, then Growth Hacker Marketing is a good book to read.

Before he became a guru of stoicism, this was Holiday’s job. He worked for big companies such as American Apparel and used the methods he outlined in the book to great effect.

Growth hacks are what a lot of people turn to when they want to grow their brand or business, but it’s hard to know where to start.

This is where Growth Hacker Marketing comes in and considering it’s written by someone who perfected the art, it’s worth reading if you’re interested in the subject.

All Ryan Holiday Books in Chronological Order

  1. Trust Me, I’m Lying (2012)
  2. Growth Hacker Marketing (2013)
  3. The Obstacle Is the Way (2014)
  4. Ego Is the Enemy (2016)
  5. The Daily Stoic (2016)
  6. Perennial Seller (2017)
  7. The Daily Stoic Journal (2017)
  8. Conspiracy (2018)
  9. Stillness Is the Key (2019)
  10. Lives of the Stoics (2020)
  11. Courage Is Calling (2021)
  12. The Boy Who Would Be King (2021)
  13. The Girl Who Would Be Free (2022)
  14. Discipline Is Destiny (2022)

Looking For More Books To Read?

Best Michael Crichton Books – If you want to read some adventurous novels based around science, then this selection of books by Crichton is perfect!

Best George Orwell Books – Orwell’s books are perfect to read after some of Holiday’s as his novels and other books put some of the lessons in these books into practice.

Best Michio Kaku Books – Some great science-based books that will blow your mind.

Best Michael Lewis Books – Another set of books that ties in well with the concepts in Holiday’s books.

Best Albert Camus Books – Camus’ books focus on the philosophy of absurdism rather than stoicism but if you want a counterpoint to Holiday’s work, they’re a good place to start.