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!
Table of Contents
All Ryan Holiday Books in Order
If you want to take a look at Ryan’s full bibliography before you see what I consider to be his best books, the following list has all of the books he’s published.
- Trust Me, I’m Lying (2012) Buy on Amazon
- Growth Hacker Marketing (2013) Buy on Amazon
- The Obstacle Is the Way (2014) Buy on Amazon
- Ego Is the Enemy (2016) Buy on Amazon
- The Daily Stoic (2016) Buy on Amazon
- Perennial Seller (2017) Buy on Amazon
- The Daily Stoic Journal (2017) Buy on Amazon
- Conspiracy (2018) Buy on Amazon
- Stillness Is the Key (2019) Buy on Amazon
- Lives of the Stoics (2020) Buy on Amazon
- Courage Is Calling (2021) Buy on Amazon
- The Boy Who Would Be King (2021) Buy on Amazon
- The Girl Who Would Be Free (2022) Buy on Amazon
- Discipline Is Destiny (2022) Buy on Amazon
- The Daily Dad (2023) Buy on Amazon
- Right Thing, Right Now (2024) Buy on Amazon
Best Ryan Holiday Books
Conspiracy
- Conspiracy theories are legion
- Conspiracies are rare
- And of the few that do exist, fewer are ever discovered, let alone explained
- This story is the exception
- In 2016, media giant Gawker was forced to declare bankruptcy after a $140 million dollar judgment in court over an illegally recorded sex tape of Hulk Hogan
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
- Libro usado en buenas condiciones, por su antiguedad podria contener señales normales de uso
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
- As in ‘The Obstacle is the Way’, Ryan Holiday delivers practical and inspiring philosophy, this time exploring a powerful concept that runs back centuries, across borders and schools of thought: ego
- Ego is our biggest enemy
- Early in our careers, it can prevent us from learning and developing our talents
- When we taste success, ego can blind us to our own faults, alienate us from others and lead to our downfall
- In failure, ego is devastating and makes recovery all the more difficult
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
- Throughout history, there has been one quality that great leaders, makers, artists and fighters have shared
- The Zen Buddhists described it as inner peace, the Stoics called it ataraxia and Ryan Holiday calls it stillness: the ability to be steady, focused and calm in a constantly busy world
- Drawing on a wide range of history’s greatest thinkers, Holiday shows us how crucial stillness is, and how it can be cultivated in our own lives today
- Just as Winston Churchill, Oprah Winfrey and baseball player Sadaharu Oh have done, we can all benefit from stillness to feed into our greater ambitions – whether building a business or simply finding happiness, peace and self-direction
- Stillness is the key to the self-mastery, discipline and focus necessary to succeed in this competitive, noisy world
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
- INSTANT NEW YORK TIMES BESTSELLER’An urgent call to arms for each and all of us
- ‘ Matthew McConaughey’Ryan Holiday is a genius
- ‘ Chris Evans’A clear and inspiring guide for how to develop this highest of human virtues
- ‘ – Robert GreeneAn inspiring anthem to the power, promise, and challenges of courage, the first in a series examining the timeless Stoic virtues from #1 New York Times bestselling author Ryan HolidayFortune favours the bold
- All great leaders of history have known this, and were successful because of the risks they dared to take
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 us 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
- The instant New York Times, Wall Street Journal, and USA Today Bestseller!In his New York Times bestselling book Courage is Calling, author Ryan Holiday made the Stoic case for a bold and brave life
- In this much-anticipated second book of his Stoic Virtue series, Holiday celebrates the awesome power of self-discipline and those who have seized it
- To master anything, one must first master themselves–one’s emotions, one’s thoughts, one’s actions
- Eisenhower famously said that freedom is really the opportunity to practice self-discipline
- Cicero called the virtue of temperance the polish of life
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
- THE INSTANT NEW YORK TIMES BESTSELLER’In story after page-turning story, Lives of the Stoics brings ancient philosophers to life
- ‘ – David Epstein, bestselling author of Range’Wonderful’ – Chris Bosh, two-time NBA ChampionFor millennia, Stoicism has been the ancient philosophy that attracts those who seek greatness, from athletes to politicians and everyone in between
- And no wonder: its embrace of self-mastery, virtue and indifference to that which we cannot control has much to offer those grappling with today’s chaotic world
- But who were the Stoics? In this book, Ryan Holiday and Stephen Hanselman offer a fresh approach to understanding Stoicism through the lives of the people who practiced it – from Cicero to Zeno, Cato to Seneca, Diogenes to Marcus Aurelius
- Through short biographies of all the famous, and lesser-known, Stoics, this book will show what it means to live stoically, and reveal the lessons to be learned from their struggles and successes
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 for others. Marcus Aurelius has his 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
- ‘No role is so well suited to philosophy as the one you happen to be in right now
- ‘ – Marcus AureliusThe Stoics’ unique blend of practicality and wisdom has been inspiring the most successful among us for centuries, from Roman Emperors to Barack Obama, and most recently via Ryan Holiday’s bestselling The Obstacle is the Way
- If that book introduced readers to the idea that what is in the way is the way, The Daily Stoic widens our view on the Stoic philosophy and shows that it can be applied to any problem
- From how to manage failure to getting what you want, the ideas of Seneca, Epictetus, Marcus Aurelius and others continue to be vitally relevant to today’s doers and thinkers
- Here, in bold new translations of the ancient classics, language is stripped down to reveal powerful aphorisms that cut straight to the heart of our day-to-day challenges
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
- The cult classic that predicted the rise of fake news—revised and updated for the post-Trump, post-Gawker age
- Hailed as “astonishing and disturbing” by the Financial Times and “essential reading” by TechCrunch at its original publication, former American Apparel marketing director Ryan Holiday’s first book sounded a prescient alarm about the dangers of fake news
- It’s all the more relevant today
- Trust Me, I’m Lying was the first book to blow the lid off the speed and force at which rumors travel online—and get “traded up” the media ecosystem until they become real headlines and generate real responses in the real world
- The culprit? Marketers and professional media manipulators, encouraged by the toxic economics of the news business
Trust Me, I’m Lying is Ryan Holiday’s first book and is an exposé of his time working as a media strategist for Tucker Max and Robert Greene, 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
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.
- A primer on the future of PR, marketing and advertising — now revised and updated with new case studies”Forget everything you thought you knew about marketing and read this book
- And then make everyone you work with read it, too
- ” —Jason Harris, CEO of MekanismMegabrands like Dropbox, Instagram, Snapchat, and Airbnb were barely a blip on the radar years ago, but now they’re worth billions—with hardly a dime spent on traditional marketing
- No press releases, no TV commercials, no billboards
- Instead, they relied on growth hacking to reach users and build their businesses
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.
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’s 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.