How to Pick Your Next Book

Books are like breakfast cereal. The more choices you have, the harder it is to pick one.

Why do some books go in one ear and out the other? Why is it so hard to make a choice when the choices are endless? What defines “good”?

After 10 years and reading over 700 books, I have an answer (not the answer). My system made me much more comfortable choosing new books to read and understanding the context of each of those books. Books need to be read in a rough order so they can be fully understood and integrated into your personality.

My order isn’t what you’d expect. It’s certainly not what you learned in school, and it contains a lot of “low” art. I’ll explain why that’s bullshit. This is the truest order of reading books to create a good life that I can currently muster. Obviously, it’s incomplete, but it’s the best I can do.
It’s also not a reading list. I will make a lot of specific recommendations, but I believe that the category works. You may read Campbell — I may read Jung — but I think we will mostly come to the same conclusions.

The deep, unconscious motivation for reading needs to be straightened out. When you sit down to read, you need to know the force keeping your eyes on the page. If it is to “seem” well-read, it won’t last. It took most of my 20s to start getting my relationship to reading sorted out. Hopefully, you can skip some of that. At the core, it’s about habits, and plenty of people have written about forming good habits. Get the motivations and the queues right; the rest is automatic.

Let’s dive into the proper order, and I will explain my theories as we go. Depending on where you are on your reading journey, this can be started at the beginning or the middle. It also can, and will, repeat many times over a lifetime.

OK, so you’re completely at a loss as to what to read first out of the endless array of books. Here’s a good place to start:

#1. Fiction (Beginning with True Interest)

Forget what you’re supposed to read. Seriously, just drop it and pick stories that you are drawn to. Movies, short stories, TV, and graphic novels are all valid forms of fiction. All that matters is that you pay attention to how it makes you feel.

In school, we are forced to take tests on books we didn’t read to pass a test and prove that we’re “educated.” It’s entirely backward. I promise that if you allow yourself to follow your Harry Potter obsession to its very core, you will eventually find yourself reading Dostoyevsky (just don’t count on it).

Or, you’ll read trash for the rest of your life — more power to you. Maybe you’re a busy-as-hell CEO doing a lot of good. Don’t let anyone shame you for your choice in literature. I have to say, though — if you truly indulge in the books you really like — and they happen to be shallow, you will eventually get bored with them and ready to move on. Let it happen naturally.

Lots of books that people think are “shallow” only seem shallow on the surface. Look into the archetypes of Harry Potter, for example. J.K. Rowling got it exactly right. Why would we assume it’s an accident that she can fill a stadium to listen to her read a children’s book?

And that brings us to the importance of true interest. Your interest knows a lot more than you in a lot of ways. For example: Have you ever watched children play? They play house, or they play explorers. They give each person roles: “You be the daddy,” or “You be the bad guy.” What are they doing? They are acting out how to behave in the world long before they could explain it out loud.

That doesn’t stop when you get to be an adult. You only lose the will to play if you fear that you’ll do something wrong and embarrass yourself. Still, your interest is to teach you things about yourself that you can’t explain with words.

That’s why fiction is so important. It’s the adult playground. It’s the place where you can explore what sort of person you want to be long before you could articulate it. If you shame yourself out of the fiction you are truly interested in; you miss the only opportunity to grow.

So, if you truly have no idea what you want to read next — pick up a story, no matter how “childish” that calls to you. Don’t read books that you think you should. Find the place in your heart that yearns for an adventure with Dragons or a steamy romance, and follow that to the very bottom.

If you can’t think of a book like this, go to the bookstore. When you walk the aisles, watch for a book to “shine forth” (This actually works). Pick that one. Don’t binge it shamefully; That prevents you from growing. Read it mindfully and proudly.

Here are some of my favorites:

  • Harry Potter series (obviously)
  • The Kingkiller Chronicle by Patrick Rothfuss
  • Island by Aldous Huxley
  • The Alchemist by Paulo Coelho
  • The Hitchhiker’s Guide to the Galaxy by Douglas Adams

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#2. Self-Help (Get Your Life in Order First)

Why do people shit on self-help? Because they are afraid to admit that they might not already be perfect.

I love people who love self-help. It says that they don’t care if people see them reading books about getting better. They aren’t afraid to admit that they could improve themselves.

Does some self-help seem obvious and trite to you? Don’t read those books. But don’t forget — that book might save someone else’s life (maybe even you in the future). Besides, it’s nice that self-help is unpretentious and easy to read. I see that as a bonus.

No matter where you are in your life, there is a self-help book that can help you. They usually aren’t great literature, but that’s not what they are trying to be. They are brass tacks. They want to tell you how to do the exact, practical thing you are trying to do.

The reason they come after fiction is that it’s the order people learn naturally. As I said, humans act out what they believe long before they can articulate it. Reading fiction is about acting out values. Self-help is about articulating them.

I read Harry Potter as a boy. At that age, I just loved it — I had no idea why. Later in life, I read a bunch of philosophy, mythology, and self-help. With the new context, Harry Potter suddenly took on a whole new meaning. While other fiction books I loved as a kid fell away, Harry Potter stayed because it got all the deeper elements exactly right.

Right, so, self-help can enrich fiction and vice versa — but that’s not the only reason self-help is high on this list. If you are struggling to pay your bills and maintain professional and personal relationships, you won’t have the luxury of reading. You’ll be too busy trying to survive.

If you get caught in that trap, it’s hard to get out. Reading is essential to life-long success. If you’re too busy to read, you’re never going to learn new ways to exit the struggle. Chaos piles up, and life gets out of hand. It happens to a lot of people.

If you feel the chaos of life piling up on you, the last thing you need is some snob telling you to read Neitzche. You need to read Tony Robbins. You need to get out of the hole so that you have the damn luxury of reading Neitzche someday.

Here are three vital things to read about if you haven’t already mastered them:

  • Money
  • Relationships
  • Health

Here are some of the most life-changing books I’ve come across:

  • 12 Rules for Life by Jordan Peterson
  • Unshakeable by Tony Robbins
  • Atomic Habits by James Clear
  • The Power of Now by Eckart Tolle
  • 7 Habit of Highly Effective People by Stephen R. Covey

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#3. Mythology (Learn to See What Matters)

About a year ago, Carl Jung turned my world inside out. He helped me see that the world is not only composed of matter but also what matters. In case you didn’t know, this is the primary struggle of modern people. What is the meaning if everything is measured?

Modern thinking has tricked us into thinking that life is subject and object, and they are perfectly separable. Think again, Jung says! You don’t see a chair; you see a sitting-down place. The chair doesn’t exist without your butt to sit in it!

I could go on and on about this topic (my friends will tell you with a deep sigh). The point is: Science is for measurement, stories are for values. As the great Scottish philosopher David Hume said:

“You Can’t Derive An Ought From An Is.”

Science can tell us what there is (roughly), but it can’t tell us what to do. See? This observation really blew my mind — sorry if I stress an obvious point.

Stories are just as important as science. The story of your life matters. What you value matters. What you value determines what you can see. To change your story is to change your life.
Good and bad isn’t something that exists out there. As great Russian writer Alexander Solzhenitsyn put it:

“The Line Dividing Good And Evil Cuts Through The Heart Of Every Human Being.”

That’s why your eyes are so glued to the TV while watching your favorite hero. You’re trying to understand the good and evil in your own heart. You’re trying to understand yourself.
Becoming aware of this process completely changed my life. It started simple, and I never felt like rushing my understanding. In the end, it’s as simple as understanding how to tell a story. Anything more is just gravy.

Even if you’re not a writer, it’s important to understand how stories work. They make human life possible.

Here are my favorites, from easy to difficult:

  • Save the Cat! by Blake Snyder
  • On Writing by Stephen King
  • Hero with a Thousand Faces by Joseph Campbell
  • Modern Man in Search of Meaning by Carl Jung
  • Maps of Meaning by Jordan Peterson
  • The Origins and History of Consciousness by Erich Neumann

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#4. Pop-Science (Get Your Facts Straight)

“If You Go To Thinking Take Your Heart With You. If You Go To Love, Take Your Head With You. Love Is Empty Without Thinking, Thinking Hollow Without Love.”

Another quote by Carl Jung. Before I read him, I was too much thinking and too little heart. Stories are heart, science is thinking. With all my facts in a neat row and no love, I was hollow.
That’s why mythology was so important to me about a year ago. I discovered a meaning in life that didn’t ask me to believe in wishful thinking (which some overly optimistic self-help writers tend to sell). I needed a more robust version of meaning for the modern mind that wasn’t based on ignoring science. That’s what thinkers like Jung gave me.

I say pop-science because science needs a good storyteller to make it relevant to our lives. Otherwise, it is a phonebook. As Jung would claim, no information is meaning-neutral (despite what some egg-heads might have you believe). Unless you’re a scientist, it’s OK if you don’t wanna read scientific journals.

There are many great scientific storytellers out there. They were my first love, so to speak. When I was a kid, I read Hawking, Dawkins, and Sagan. What makes them great was not only the science but the way they mixed in storytelling. I was obsessed with rationality. I only learned later that it was just a story; A good one, but not the only one.

Read the great science storytellers of our age so that you don’t fall for pseudoscience. Learn to think critically as well as with passion and meaning. You can’t lean too far one way or the other. Strike a balance that makes you comfortable.

While this isn’t an urgent category, it’s important if you want to be a respected and trusted person. Without an ability to see fact from fiction, you are vulnerable to believe things that certain string-pullers would like you to believe. Myths show us what we stand for; facts prevent us from falling for anything.

Do you always avoid science? Dip your toe in the pool. There is more fun here than you think. Here are my favorites:

  • A Brief History of Time by Stephen Hawking
  • The Selfish Gene by Richard Dawkins
  • How to Change Your Mind by Michael Pollen
  • Why We Sleep by Matthew Walker
  • Flow by Mihaly Csikszentmihalyi

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#5. History (Know Where You Come From)

I struggle the most to read history. The way it was taught in school made it seem like memorizing dates and battles for tests.

That’s a shame because I finally realize that we are a historical animal. Reaching about history is reading about yourself. Without knowing about what happened in the 20th century, for example, we might be doomed to repeat the mistakes. That would be a disaster.

In recent years, I have been slowly engaging more and more with history. I’m sure many people could give you much better recommendations — but I can give you the point of view of a convert.
Not interested in history? That’s OK — stay higher on this list. Read long enough, and I promise you’ll come around. Nothing beats the feeling of realizing that someone 2,000 years old was going through the same things are you are.

Here are my favorites:

  • Meditations by Marcus Aurelius
  • Einstein by Walter Isaacson
  • Sapiens by Yuval Noah Hariri
  • Man’s Search for Meaning by Victor Frankl
  • Walden by Henry David Thoreau
  • Benjamin Franklin by Walter Isaacson

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#6. Philosophy (Tie it All Together)

In a lot of ways, I lived this list backward. I suppose that makes me a cautionary tale.
I studied philosophy in college. While I am very thankful that I did, I think a lot of what I learned fell on deaf ears. Only now do I even begin to understand Neitzche, for example. And only barely. I had no business reading him at 21 when I was mostly just trying to get laid.
That being said, philosophy is the ultimate self-help. It’s not as concrete and actionable as “self-help,” but it has the same aim. How does one live? If you want to know deeper truths to help you live a better life, read philosophy.

Philosophy is the highest level of abstraction. It’s thinking about thinking about thinking. It hurts the brain. I have a secret for you…a lot of it is nonsense.

When it’s not, it will knock your socks off. But when it is, it will make you read the same sentence 40 times and get no closer to understanding it. For a lot of the greats, I recommend reading secondary materials. Most of this stuff can be summarized. Only if you are a wild man on a mission should you dive into the source material!

That being said, I love philosophy, and I love philosophizing. It’s a hobby for me — like knitting. It doesn’t have to be a hobby for you.

There are a lot of great YouTube videos about philosophy. I recommend watching a lot of them before picking up any philosophical text. There is no rush, and there is no test. This should be fun. If it’s not, quit.

That being said, nothing will change your world like reading philosophy. Like Plato’s cave, you’ll see the world for the first time, and it will be marvelous. This can happen over and over. It’s truly something.

Here’s a shortlist, starting easy:

  • Daily Stoic by Ryan Holiday (concrete and actionable)
  • Zen and the Art of Motorcycle Maintenance by Robert Pirsig (Fiction, stunning writing)
  • The Apology by Plato (where we started in the West)
  • Beyond Good and Evil by Fridrich Nietzche (where we ended up)

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#7. Political (If Ever)

I feel intensely bored by politics.

For the most part, I think you can leave the political chatter to the heads on TV. Without deeper understanding gained from the above categories, political talk is powerless and toothless. With a deeper understanding, you see that it’s best to try not to engage on this level, ever.

People usually start with politics because they want to feel like they are doing something important. I’m here to tell you; nothing is more pressing or important than getting yourself in order. Without that inner work, any political change you make is likely to make things worse.

Politics is nothing more than recent history without any perspective or wisdom. Without a little time and distance, you can’t really see the forest for the trees. After a while of tree-gazing, you lose the ability to perceive forests at all.

Occasionally, politics pokes its ugly head into our lives, whether we like it or not. That’s to be expected and dealt with. Treat politics like fighting and reading like karate. A great karate master never goes out looking for a fight — but he will whip your ass if you start one.

Yes, vote. Make sure you engage with your community. But unless you’re passionate about something, there is no reason to be “informed.” Truly informed people know Plato as well as Twitter.

That being said, I have a few books that shaped my point of view:

  • Capital in the Twenty-First Century by Thomas Piketty
  • Basic Economics by Thomas Sowell
  • The Gulag Archipelago by Alexander Solzhenitsyn
  • Brave New World by Aldous Huxley
  • The Federalist Papers by Hamilton, Madison, Jay

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If you read these, you avoid the “he said, she said,” of most political writing. Here’s my basic takeaway (OPINION INCOMING):

The right wants stability. The left warns that stability makes power accumulate into fewer and fewer hands. Both are right. We have to talk to stay in balance. If you’re right or left is mostly due to your personality. The best political action you can make is to learn to talk to people unlike you. I’m a writer, and I live in LA. Of course, I lean left. But my parents are hard-working people from Louisiana. I have learned to speak with them. That feels important.

Reading great books starts with the reader. All books are about you if you’re reading them.

Read to have a good life, not to seem smart. Get smart as a byproduct.

Start easy, keep it fun, and never let it become homework. School is over, and you never have to do homework again.

Read the great books when they call to you. Let books change you from the inside out.

After over 700 books, I believe that nothing is more important.



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