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