📖 6 Reading Rules I'm Stealing from Ryan Holiday

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💡 The Big Idea: Reflections on a Bestselling Author’s Rules for Reading in 2026.

Ryan Holiday is kind of a reading/writing hero of mine.

I’ve long been fascinated by his note-card based writing process, and I have a dream to someday run a bookstore like he does with The Painted Porch.

Basically, I want to be like Ryan when I grow up (minus the stoicism).

Recently, he published his 31 reading Rules for 2026. While I generally agree with just about all of them, in this newsletter, I want to share and expound a little more on some of my favorites.

Always Carry a Book

Phone, wallet, keys (as Adam Sandler says) and book… I’ve read at the Grammys, before surgery, on planes, beaches, in cars, lines, helicopters, at the White House, at the DMV, backstage before talks, while waiting for a table at a restaurant, in waiting rooms, and on and on. Use every pocket of time you get. - Ryan Holiday

This is why I always read physical books.

When I was reading digital books, I always had them with me but I never read them. I opened my phone and always ended up somewhere else instead.

But when I started carrying a physical book with me everywhere, the analog cue was enough for me to read a few pages here and there instead of checking the feeds.

The result has been a reading habit that has stuck, and has completely changed my life.

Argue with the Author

If you’re not finding something to note or mark up…it says something about what you’re reading. Reading is a conversation. Great readers underline and make notes in the margins. They ask questions. They put the author on trial. They talk back. They put books through the wringer. - Ryan Holiday

One of the most impactful book I ever read was How to Read a Book by Mortimer Adler where he teaches 4 levels of reading for working a book:

Level 1: Elementary Reading - where you ask “what does this sentence say?”
Level 2: Inspectional Reading - where you figure out “what is this book about?”
Level 3: Analytical Reading - where you ask clarifying questions about what the author is saying.
Level 4: Syntopical Reading - where compare the book in relation to other books that you’ve read.

I actually hated the book at the time, but the perspective of understanding the author’s arguments and responding to them has been life-changing. Nothing has had a bigger impact on how much benefit I get out of the books that I read.

Do Something With What You Read

When great readers read, they ask themselves a simple question: What do I plan to do with this information? - Ryan Holiday

There are three different levels of knowledge:

Information - where you have something and can dig it up if you need it.
Revelation - where you are know something not just where to find it, but the actual content itself.
Application - where you do something with what you know that create real-world impact.

Bottom line: If you don’t actually do anything with what you read, you’re not really getting everything that you can out of the book.

You don’t need to do everything the author tells you to do. But you do need to something if you want it to stick.

Pick Books That Challenge Your Biases

If you only find yourself underlining and agreeing with the authors you read, you are not reading diversely or critically enough. You should be arguing with the authors you read. You should know enough about the topic to spot when they are wrong too. - Ryan Holiday

One of the most influential books I’ve ever read is Liminal Thinking by Dave Gray, where he explains how we tend to surround ourselves with people who re-enforce our “bubble of belief.” He even compares The Internet to a grocery store for facts where you can find anything you want to support the beliefs you want to hold.

The bottom line? There’s a whole lot we don’t know. And if we really want to grow, we should be picking things to read that we should be looking for things that challenge our firmly-held beliefs, not reinforce them.

Read What Your Heroes are Reading

“What’s a book that changed your life?” is a question that will change your life._ Ask people you admire for book recommendations. Emerson’s line was, “If we encounter a man of rare intellect, we should ask him what books he reads. - Ryan Holiday

I have rule: whenever someone I look up to recommends a book, I open up the Amazon app and buy it immediately. That way, I always have something pre-vetted laying around to read after I finish the book I’m currently on.

Many of the best books I've ever read have come from this approach. It's a much better way to build a reading list than relying on the bestsellers list.

Just Buy the Book

If you see a book you want, buy it. Don’t worry about the price. Reading is not a luxury. It’s not something you splurge on. It’s a necessity. Even if all you get is one life-changing idea from a book, that’s still a pretty good ROI. - Ryan Holiday

Even if you buy 2-3 books per month, it’s still not a significant financial investment. The return you’ll get from the wisdom you gain will far outweigh the cost.

And if you’re not in a position to spend anything on books, start where I did: place a reserve on the book at your local library. Just start building your backlog of books to read, and make this the year you up your reading game.

— Mike

Practical PKM