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)


When the Less Efficient Method Gets the Job Done Faster

I’ve been rethinking how I read books. My previous method was to buy books, read them one at a time until I finished or decided they weren’t worth my time, and moved to the next one. I’d postpone buying books until I’d finished (or nearly finished) my current batch.

My focus was on quality. Some books are tough reads, but still worthwhile. This method encourages dedication.

But, of course, it naturally leads to a problem. Sometimes I’d recognize that a book is worth reading, but I wouldn’t feel like reading it right now. Perhaps it was too difficult or dry to read casually. My response was to not read anything at all.

Now I’m trying a new strategy: never be afraid to start, stop or buy books. Have as many open book threads as I like. I won’t guilt myself for not finishing an “important” book. I won’t feel bad about buying new books when I have unread books at home.

This does reduce quality. With no commitment device, I’m reducing the chances of getting through some of those denser books I think I probably should read. But it increases smoothness. By lowering the friction between me picking up a book, I’m hoping this new approach will result in more books read and less time browsing online.

Quality or Smoothness?

This is a tradeoff you can see in many areas of life: quality or smoothness.

It’s the difference between showing up to the gym, doing a workout that isn’t optimized for fitness and doesn’t push you very much, versus the intense workout you really should be doing. If the choice is between the two workouts, the intense one will benefit you more.

But that’s rarely the decision. The decision isn’t between the efficient method and the inefficient one. It’s between the inefficient one and nothing.

Learning is another example. I hesitate to recommend some of the tactics I suggest for students to adults learning for pleasure. Why? Because although the studying tactics work well, they also increase intensity. That’s fine if you’re a committed student and need to pass your exam anyways. Why not do it in less time?

Someone learning for pleasure faces a different tradeoff, however. The more intense method may increase friction. That increased friction is going to result in less time spent learning. Even if they are learning 50% faster with each hour spent, the increase in friction might mean they cut their studying time in half, resulting in less being learned, in total.

Optimizing for Smoothness

Look for areas of your life you frequently neglect. These are areas you’re implicitly making a choice between doing an easy thing and doing nothing. For that, I see three options:

  1. Increase your motivation and do the hard thing.
  2. Keep your motivation constant and make it easier to do.
  3. Do nothing.

Sometimes the first choice will be the right one. But it can’t be the right choice at all times and all circumstances. It’s not usually possible to raise your motivation for doing everything permanently. So increasing your intensity for one area of life, generally means becoming a little more dependent on your habits in other areas.

Smoothness is particularly valuable for the many things you feel guilty about not doing, but have no immediate consequences for avoiding. Exercising, reading books, investing, learning and charity are all things that can go slack for months or years before having major consequences.

How to Reduce Friction

There are many ways to reduce friction, but the problem becomes a lot easier once you recognize that reducing friction is often also an admission to reduce quality. If you can be okay with that decision, it becomes a lot easier to find ways to make an area of your life smoother.

Take my own reading experience, as an example. I had a hard time starting or buying new books when I knew that some of my books were unread or unfinished. To me, it felt like laziness having half a dozen books in various states of completion.

But once I realized that the lazier method was probable more effective in the long-run, I accepted it. Now I have more unfinished books, but I also spend more time reading.

Here’s a few concrete ways you can reduce friction:

1. Lower the minimum time required.

Do you believe that there’s no point exercising if you can’t exercise for at least 30 minutes? That may sound silly, as articulated, but there would be a lot of people who wouldn’t bother doing pushups or situps because it wasn’t a “full” workout.

2. Lower your expectations for the task.

Don’t expect to write a masterpiece every time you decide to write. Writing garbage is fine too. Writing garbage can be uncomfortable if it feels like a tradeoff between garbage and good work. In some situations it is, and you need to push yourself to a higher standard. But more often the tradeoff is between writing garbage and writing nothing.

3. Lower barriers to entry.

Buy too many books. The worst thing that can happen isn’t having too many unread books, but not having a book that interests you when you want to read. If buying too many books is a luxury you can’t afford, borrow too many from the library instead.

What are some things you currently don’t do, but should? Could doing a watered-down version of those same tasks, even if the output is worse, be better than what you’re currently doing? Share your thoughts in the comments.