Here's What I Noticed About Ryan Holiday's Favorite Books

When it comes to promoting reading as a path to success, few people today top Ryan Holiday.

Ryan, a voracious reader himself, is now an accomplished author, having written a number of bestsellers like Perrenial Seller, Trust Me I’m Lying, and The Ego is the Enemy (among others).

He’s also famous for his notecard system which he learned during his time as a research assistant with Robert Greene.

But why I’m really into Ryan is because he reads a ton of books.

I subscribe to his monthly newsletter, which frankly, inspired me to write my own (you can sign up on the site).

Like the true nerd that I am, when I see Ryan Holiday’s favorite books pop up in my inbox every month, I practically break my finger rushing to click the email open.

ryan holiday reading list

Then I read that post with my Goodreads or Amazon wish list open and start adding.

I also pay attention when he posts book recommendations on Twitter or writes any number of articles about the books he’s loved.

One thing I’ve noticed over the years, having read many of these lists, is he has a core list of books he recommends over and over.

That’s not to say it’s list is boring because it’s the same stuff. In fact, I think he does a great job of switching things up, it’s very rare on any list I read that I don’t find a handful of books that strike my fancy.

What I like though, is that he seems to have a group of books that deeply matter. This is the core of many of his articles.

From there, lots of the books he recommends are offshoots of these core books. They might be on the same topic (Stoicism) but sometimes could also follow a type of person (powerful or courageous).

For example, in a post about Meditations, he says this about Gregory Hays’ introduction:

Hays’s introduction also lists Alexander Pope, Goethe and William Alexander Percy as students and fans of Marcus Aurelius. Reading works by all of these individuals—especially Percy (and his adopted son, Walker Percy)—sent me down a rabbit hole that would be one of the most enjoyable of my reading life.

As someone who tends to read books along a path, I find this interesting.

When I look back over the books I’ve read from month to month (check out my monthly reads) more often than not there’s a pattern to them.

This summer, I was all about the Ancient Greeks, the last few months, I’ve been digging into fantasy. I’ve gone on binges from World War II to Mount Everest to Mormons.

I never start out intending to do it on purpose. I find something that strikes me on some page or footnote and that sends me off on to the next.

In Ryan’s recommendations, I almost always notice a thread of the Stoics throughout. Of course, it’s obvious when talking about Seneca or Marcus Aurelius. But you can see it as well in Rockefeller and Graham, and the other non-fiction choices as well.

As he says in his 100 things post about the disciplines of Stoicism:

When I get asked to explain the three disciplines, this is usually my short answer: See things for what they are. Do what we can. Endure and bear what we must.

You’ll likely find that the people who have managed to follow those three disciplines (both knowingly and unknowingly) attract his attention.

Ryan’s Reads


To highlight what I mean in real life, I decided to share some of Ryan’s favorite reads. With each, I’ll include a passage where he speaks about his feelings on the book.

I got all of these from various posts throughout the years, I’ll link to each post. And I’ll also highlight the section of his blurb that, I think at least, ties that thread back to the Stoics.

It’s certainly not an earth shattering discovery, but something that popped out to me as I read through a lot of these.

Meditations by Marcus Aurelius

This is the cover of the Hays version.

Ryan is a huge fan of the Stoics. I actually credit him with getting me into them too. Once I kept seeing these guys on lists I wanted to dig deeper.

Ryan loves this book.

No, like looooooooooooves this book. He loves it so much he’s read it 100 times. Yup.

Then he wrote a post about 100 things he’s learned from those 100 reads.

Here’s what he says:

In Book Five, I learned what philosophy really was. It’s not an “instructor,” as Marcus put it. It’s not the courses I was taking in school. It is medicine. It’s “a soothing ointment, a warm lotion.” It’s designed to help us deal with the difficulties of life—to heal, as Epicurus said, the suffering of man.

I’ve picked this one up, the Hays translation that Ryan recommends, and will be reading it in the coming months. (I feel another burst of obsession on the Ancient Greeks and Roman’s coming my way).

Get it: Goodreads | Amazon

Titan: The Life of John D. Rockefeller Sr. by Ron Chernow


I tend to (avoid?) let’s go with ignore most biographies. I’m not exactly sure exactly why. Part of it could be the length of many just put me off. Is 1,000 pages on someone that interesting?

When I do go with bios, I tend to lean on Paul Johnson and his catalog, I can bang it out and get the salient points relatively quickly.

And yet, I know there are some people that this won’t do justice. You have to go all in. This book is one of them.

I found this book on at least three lists put out by Ryan, so you know it has to be the real deal.

Ryan says:

I think it says something about the quality of the writing and the empathic understanding of the writer that the main lessons you would take away from someone like Rockefeller would not be business, but life lessons. In fact, when I went back through and took notes on this book, I filled out more cards for Stoicism than I did for Strategy, Business or Money.

I’ve seen Titan recommended by a number of big readers I respect, so it might just be in my future.

Get it: Goodreads | Amazon

Personal History by Katharine Graham

personal history

Remember when I said I don’t read biographies?

Well, I lied. I read this one.

And, it’s a favorite of mine as well. So, I was happy to see it make a few lists. I knew nothing about Katharine Graham before I picked up this book, but once I finished I was so impressed and inspired by a woman who had gone through so much and yet persisted, coming out stronger in the end.

She’s become one of the people I’ve really looked up to in life, especially as a woman.

Ryan says:

After the tragic suicide of her husband, who ran the The Washington Post and which they both ownedKatharine Graham, at age 46 and a mother of three, with no work experience to speak of, found herself overseeing the Post through its most tumultuous and difficult years (think Watergate and the Pentagon papers). Eventually, she became one of the best CEOs of the 20th century, period. She pulled through and endured with a strong sense of purpose, fortitude, and strength that we can all learn from.

Dig into this before the new movie The Post comes out. Graham is played by Meryl Streep and from the looks of it, you’ll learn a lot about her backstory.

Get it: Goodreads | Amazon

The Subtle Art of Not Giving a F*ck: A Counterintuitive Approach to Living a Good Life by Mark Manson

mark manson

Full disclosure: I’m also a big Mark Manson fangirl. I love his blog and so when I saw this book come out, I snapped it up and read it in about 2 days.

It’s one I’m actually planning on re-reading because there were so many ‘oh shit’ moments I had while reading, I’m convinced I missed a few of them.

I’d recommend this book to anyone.

Here’s what Ryan said:

To me, practical philosophy has always been the art knowing what to—and what not to—give a fuck about. That’s what Mark’s book is about. It’s not about apathy. It’s about cultivating indifference to things that don’t matter.

This is one lesson that’s really important to take away. And something that I’ve learned from my minor reading of the Stoics thus far, learning how to not get caught up in the things that don’t matter.

Get it: Goodreads | Amazon

The 48 Laws of Power by Robert Greene

laws of power

A few years ago, I think everyone I knew was reading this book. I had it in paperback before Kindle and it was quite the tome to carry around (which I used to do on the New York City subway).

Look at me, all intellectual and stuff.

Ryan is big on Robert Greene, mostly because he was an assistant to him. So you can also get really meta and see the thread between the two and their approach as well.

Ryan says:

It is impossible to describe this book and do it justice. But if you plan on living life on your terms, climbing as high as you’d like to go, and avoid being controlled by others, then you need to read this book. Robert is an amazing researcher and storyteller — he has a profound ability to explain timeless truths through story and example.

You can learn a lot of lessons from this, there are many small actions you can take to reclaim and exert your own power with going to war or engaging in battles. I found I enjoyed it more broken into laws versus consuming it all at once.

Get it: Goodreads | Amazon

Final Thoughts

These five books pop up over and over again on Ryan’s lists. I’ve read three and have bought another, so clearly they jumped out at me too.

This exercise was interesting because it made me want to take a closer look at what I read too. Do I choose books because of one reason (that actually means nothing) or is there a deeper thread I’m looking for in my choices too?

It’s something I want to consider more as I move forward.