What order should you read Ryan Holiday books? & Which Are the Best?

If you're reading this, then it is likely that you've come across Ryan Holiday on somebody's podcast, or come across him somewhere on the internet. He has been around for years (a student of Robert Greene) but it seems that his message and philosophy are coming back into the forefront of people's minds. As we lose our way as a society, we're looking for some kind of wisdom to guide us through the storm.

Well, we have been reading Ryan Holidays many books for years, and started our journey with him when he published 'Trust Me, I am lying" all the way back in 2012. But since then, he has moved away from marketing and written several best-selling books that are underrated as some of the most influential books of our time.

So, if you're here then we are going to help you figure out what order should you read Ryan Holiday books and which of them are the best?

Lets go.

Which Ryan Holiday should I read first?

Well, Ryan Holiday writes about several different topics, so whichever is most interesting to you (and why you wanted to read his books in the first place) should be where you head first. His books are in three categories: Marketing, self-help and Stoic Philosophy.

Holiday started his authorship writing about marketing, so if you're interested in marketing then you should read Trust Me, I'm Lying and Growth Hacker before reading anything else.

If you've come across Holiday for his self-help books, then the best book to start with is The Obstacle is the Way. It is not only his most popular and best selling book, but is considered as the best by many. Then you should read Ego is the Enemy next Stillness is Key, The Daily Dad and Courage is Calling.

As you may also know, Holiday is one of the most important modern stoic philosophers of our time, and he has written at length about the stoics and their lives. The two books to read here are The Daily Stoic (you should get this book regardless of which other Holiday book you buy) and The Lives of the Stoics). 

Below we are going to give you a run-down on which books we think are Ryan Holiday's best, and we are going to tell you why.

All of which you can buy here:


Which Ryan Holiday Books are the Best?

  1. The Obstacle is the way (2014)
  2. Stillness is Key (2019)
  3. The Daily Stoic (2016)
  4. Ego is the Enemy (2016)
  5. Lives of the Stoics (2020)

The Obstacle is the Way (2014)

The best Ryan Holiday book to start with is The Obstacle is the Way. It was published in 2014 and laid out three stages of building a mindset that will enable you to overcome almost any challenge.

The reason it is the best Ryan Holiday book to start with is that it sets out Holiday's way of thinking, and acquaints you with his writing style. It is by far the most accessible of his books and many of the lessons can be applied almost immediately into your life.

It is a fantastic book, and not only is one of Ryan Holiday's Best, but the best way to start reading his books.

The Obstacle is the Way

The Daily Stoic (2016)

Ok, so now you understand a little bit about the mindset and stoic philosophy from The Obstacle is the Way, but maybe you need a little bit of guidance every day. Well, then the book to buy next is "The Daily Stoic"

The principle that created this book is very similar to why many people read their horoscopes in the morning before starting the day. The book has a stoic meditation for every single day of the year. So, every morning you may open the book, read a passage from one of the great stoic thinkers from history, and an interpretation from Holiday.

The book is a really really good way to be mindful and build your own version of stoic philosophy into your life.


The daily stoic

Stillness is Key (2019)

The world around us is chaos. And to survive it, we must find a way to create inner stillness. A clarity of mind that enables us to remove the clutter and focus on what is truly important.

The book goes deeper into strategies for creating a space for your mind and keeping a clear head. It's an extension from part one of The Obstacle is the Way.

Ryan Holiday is a marketing genius, and my copy has been printed and covered with a textured matt black. I know for a fact that he has thought about how the book should feel in your hand, and how it should promote tranquility.

The pages and messages in the book can be read at any time and



stillness is key

Ego is the Enemy (2016)

In your life, it is likely that your ego is ultimately causing you harm. You are likely to be your own worst enemy.

The book is set out in a very similar way to The Obstacle is the Way and works through three stages of dismantling your ego and starting to live a life unshackled by your pride, expectations of life and therefore, anxieties and neurosis.

The book is still fantastic, but you really do need to read it after understanding a little more stoic philosophy and understanding many of Holiday's key messages.

The book doesn't focus as much on the stoic writers, but the themes and ideas running through the book are certainly stoic.


ego is the enemy

Lives of the Stoics

This is not one of the best of Ryan Holiday's books, and it is a little dry at times. Not down to the writing but really the subject matter.

The book details the lives of writers, philosophers, emperors and royalty and looks at their way of life, lessons from their lives and writings across generations of human existence. Personally, I found it fascinating and I really enjoyed fleshing out the people I have read in other Holiday books, but I can see why many would give up. My husband being one of them.

While this book firmly sits within the 'Stoic philosophy' section of Holiday's books, you can certainly draw out threads that may help your own life, or allow you to place many of Holiday's thinking in history. It is a great one if you're really into philosophy.


lives of the stoics

Final Thoughts

Hopefully, you've found this post useful and you've found the book you want to start with. Ryan Holiday is a fantastic author and each of his books are thoughtfully put together and enjoyable in its own way.

If you agree or disagree with our assessment of the best Ryan Holiday books then feel free to leave a comment below. Also, let us know what you think of his books too.


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