Are There Books You Should Reread Every Year?

I have friends who have books they read every year. Rereading the same book repeatedly seems to offer them new insights on each passing.

Stephen Marche claims to have read Hamlet over 100 times. According to him, this extreme rereading, “provides the physical activity of reading without the mental acuity usually required.” This allows him to appreciate the text in a completely different way.

I’m fascinated by rereading, although I’m afraid I’ve done very little of it. I’ve read hundreds of books which sit on my bookshelf, barely remembered.

From an information standpoint, rereading seems absurdly wasteful. It must be the case that you get the most information from a book on its first pass through. Subsequent readings may catch some missed information, but surely less than the first. In a world of nearly-infinite books, why spend countless hours revisiting old ones?

Rereading as Structured Thinking

But behind that reasoning, there’s an assumption. Namely, that the main value of a book is the information it provides.

Rereading may be horribly inefficient from the process of gathering information, but perhaps its virtues lie in structuring your ability to think about a topic better. Knowing the exact content of a text means you need far fewer mental faculties to read it. The ease of reading opens up more mental space for contemplation.

Structured thinking is actually quite difficult to do. The mind wanders and flits about to different daydreams and emotions. It can be difficult to sustain contemplation of an important topic for the time required to develop an insight about it.

Writing helps structure thinking. Long before I wrote a blog, I kept a journal. Not a log of daily events, but a canvas to sketch out my thinking. Many problems which were fuzzy in my head became clear once I wrote them down.

But most writing is unguided. It helps organize thoughts, but it doesn’t give a template for having them. I’ve started journal entries with the intention to write about one topic and ended up moving to another. Writing constrains some aspects of the thinking process, freeing mental resources for others, but it does so in a particular way. Sometimes you need a different type of structuring to get the kind of thinking you desire.

Cued Thoughts and Rereading

Rereading has some virtues in that, once read, the material becomes a lot easier. However, the act of reading still primes your mind to think on tangents roughly related to the source material. Ritual re-reading, therefore, acts as a guide to your thinking patterns, pushing you along familiar grooves, but giving you the freedom to discover new ideas within the same topic.

I’ve only reread a handful of books, so in this practice I’m a novice. But for the few books I have reread (such as The Count of Monte Cristo), I found the predictability of the story allowed me to focus on other things on subsequent visits.

Rereading to Cultivate Mental Habits

Although I’ve reread few books, I’ve relistened to many audio books multiple times. Years ago, I remember putting the same CDs of a Zig Ziglar or Brian Tracy book into a walkman every time I went for a morning jog. I heard the same tapes dozens of times.

The value here wasn’t so much informational. With all due respect to Ziglar and Tracy, much of their writing struck me as common sense. Given the abundance of story telling, and easy explanations, it certainly wasn’t so dense that I couldn’t get the main points from one or two listenings.

Instead, the value was to cultivate a way of thinking. I was new to setting goals, being organized and productive, trying to start a business. These were domains where I hadn’t cultivated strong mental habits, so simply hearing ideas once or twice wasn’t enough.

Now I wonder whether I should be repeating the same process with new mental habits. Should I be cultivating discipline by rereading the Bhagavad Gita, or combating my perfectionism by rereading the Dao De Jing?

What do you think? Are there any books you’ve read multiple times? Are there books you’d recommend others read repeatedly? Share your thoughts in the comments. (HT to Tyler Cowen for inspiring this post)