How to Pick Which Books to Read

I often get asked what my favorite books are. I struggle to answer this question because, implicitly, the person is conflating two different questions:

1. What are your favorite books?
2. What books should I read?

Most of my favorite books aren’t personal development books. The best books I’ve read probably aren’t going to be all that great for someone who’s in the market for inspiring/useful life advice.

The correct, although less satisfying, answer is that the best book is the one that teaches you something important you didn’t already know. Given what people know is different, a book might be life-changing for you and boring pablum for somebody else.

The Hierarchy of Books

Therefore, instead of trying to offer a suggestion for what are the “best” books, I think the right way to read books is to think of them like an inverted pyramid.

At the bottom, are the best books which provide an entry point to a topic. These books are good ones to start with if you haven’t read very much, or at least haven’t read much on that topic.

As you go up the layers, the books become increasingly smarter and more nuanced, but paradoxically, less helpful. They’re less helpful because they’re providing increasingly sophisticated distinctions. They dig deeper to build more fundamental pictures of the world and fill in more esoteric details, rather than offer straightforward answers to basic questions.

The thing is, if you’ve read enough books at a lower layer, the upper layers are actually really good! They answer deeper questions more thoughtfully than lower layers.

The problem is that, from the vantage point of anyone within the pyramid, books at levels lower than your own are at best gross simplifications and, at worst, outright false. The assumptions they make and details they gloss over are just too large for them to be taken seriously.

Books at levels higher than your own feel pedantic. Arguments over minutea, definitions and esoterica that nobody in the real world actually cares about. You want a yes-or-no answer, and instead they spend hundreds of pages to say, “Maybe?”

Ascending the Hierarchy

The goal of any lifelong learning effort, in my opinion, is that you start with the lower levels and proceed up to higher ones. 

A mistaken impression of how knowledge works is that the process of learning, or ascending the hierarchy of books, is strictly additive. That is to say, you get the same picture you had before, just at a higher resolution.

Knowledge just doesn’t work that way. As you climb the hierarchy, you get more detail and nuance to your existing picture, yes. But you also start to realize how many assumptions, approximations and mistaken concepts were underpinning that original picture.

Learning isn’t just about fleshing out, but also reorganizing the fundamental substructure of what you’ve learned.

Quick example: When I was young I read Rich Dad, Poor Dad and thought it was a great book. It taught, I thought, about the importance of saving and investing to build wealth. Later, I found critiques that attack the books pro-real-estate, active-management investing philosophy which probably aren’t best for the average investor. 

Question: Is Rich Dad, Poor Dad a good book? I still think, for the person who doesn’t yet have the concept of investing deeply understood, it’s a decent one. For the person who has these concepts mastered, however, the more specific advice is probably wrong enough to be harmful.

I don’t think there’s an absolute answer to the question of whether a book is good or not, independent of where you are in the hierarchy.

What is the Hierarchy?

The exact books in each layer of the hierarchy is going to differ, depending on the topic and background of the person reading it.

My rough guide, however, in order from easiest to hardest, would be:

1. Popular beginner books. These books assume no prior knowledge and are maximally lucid and entertaining. They are probably full of hidden assumptions and flaws, but they communicate their essential idea well. These may be written by an expert, but they are also sometimes written by people known for communicating well rather than being especially knowledgeable about a topic. (e.g. Most self-help books, mass media coverage of a topic, etc.)
2. Specialist books, written for a mass audience. These books likely assume general background knowledge, but no knowledge of the subject the author is going to introduce. These are usually written by experts, or with the help of experts. (e.g. journalist-expert-combo bestsellers, mass market “idea” books, etc.)
3. Specialist books, written for specialists. These aren’t meant for mass consumption. You need to understand the field and have signficant background knowledge to make sense of them. Yet, the discussions are aimed at nuance since that shared background means you can get straight at the important unresolved questions rather than get everyone else caught up first. (e.g. academic monographs, review papers, textbooks, etc.)
4. Primary research, journal articles, expert commentary. This is the final level. Now, not only do you need to have considerable background knowledge to understand the discussion, you often need to be sufficiently engaged in the community discussing it to know what facts, theories and ideas are even being referenced. (e.g. individual journal articles, blog articles aimed at other academics/theorists, etc.)

There’s no shame in starting lower in the hierarchy. Those books are probably going to be the most useful to you and serve as a good stepping stone to later books.

Unlearning false, simplistic ideas from earlier layers is always going to be present. Ideally, the best books from the earlier layers require the least unlearning, but sometimes a book which is super compelling (and thus easy/fun to read) may be worth some extra unlearning later if it encourages you to read more about the topic at all.

There are, of course, books at a lower level which are so profoundly false and misleading that you’re better off having read nothing at all. These should be avoided, although it’s often hard to know which are which until you get further up. (Expert reviews can help, but as has been mentioned, those higher up on the hierarchy often have a harder time separating a flawed-but-acceptable starting point with one which is unacceptably inaccurate.)

Most importantly, however, it is to expect that anything you learned at the lower level might get replaced/adjusted at a higher level as you learn more. If you go into any learning activity with the expectation that knowledge is tentative, then you’ll be better equipped to deal with the changes which occur when you get to a higher level.

As books get higher up the hierarchy, perspectives and theories multiply, and it also becomes harder and harder to say what the “right” viewpoint is. Things which seemed straightforward at the first level become unexpectedly contentious once you dig into deeper books.

Which Books Should You Read?

I hope, by now, you can see that this question is misguided. It’s wrong because there often is no “best” book, but many different ones, depending on where you are in the hierarchy.

It’s also wrong because the correct approach isn’t to read the “best” books, but to read a lot of books. The weaknesses that result from reading bad books are overwhelmingly corrected by reading lots of them.

Instead of asking which books you should read, therefore, you should just start buying and reading lots of books. Most won’t be lifechanging. But occasionally you’ll read enough to push up the hierarchy and, when you look down, you’ll see how much you’ve learned.