A Reading Strategy

I started this year unhappy with my reading habits - they were sporadic, haphazard and focused on filling time. These aren’t necessarily bad things, but I did feel stupid when I’d forgotten some key insights from a book I read less than a month prior. I started using Readwise and their Reader in January of this year, and after 10 months, my reading is in a much better place. I’m able to consistently dedicate time to reading, I read a good mix of fiction and non-fiction, and am able to recollect and resurface interesting bits from my reading to jog my memory.

Still, things could be a lot better. The highlights I get from Readwise are a smattering of 10 things everyday spread across readings I’ve done through the months. This, I imagine, is a problem that’s only exarcebated the more I read. Reading Boretti’s excellent article on effective spaced repitition made me realize that my flashcards sucked, and I was using Readwise as a crutch to postpone understanding. Finally, Readwise itself is quite annoying to use when I read a physical book (which is generally better for retention) since importing the highlights from a page is clunky at best - involving an elaborate photo taking procedure mixed with some awful highlighting software.

The haphazardness of my reading has also not gone away - my sources of articles are a few common newsletters (Stratechery, Commoncog, Money Stuff) and random technical writeups I find interesting on HackerNews. I also read to learn how to write - and I need tools that force me to rewrite things I’ve read especially in knowledge based areas like history.

Reflecting on what I want to get out of my reading, I realized that learning is an important component for me. I shy away from depth and complexity, because it’s difficult, but I also derive large amounts of joy from understanding something deeply when I do put in the time. So I’ve decided to adopt a new reading philosophy with a few tenets.

The source of this philosophy is primarily derived from writings by Cedric Chin. Cedric talks of asking “intersting questions”, and directing your reading towards answering those questions. At the same time, I do not want to suck the serendipity of finding a new book and make my reading completely prescriptive.

With that in mind, here are my current tenets:

• This only applies to non-fiction books, biographies included. Fiction and human-interest stories can be read more freely, and are useful to read in low-energy states. Fiction should be preferred to technical articles as a filler.
• If you see non-fiction on a subject you want to read, first write down what you want to answer from the book/ article. Then look up the best resource to learn about that quickly - prefer non-fiction articles to books for introductions to a subject. This maintains serendipitous discovery while resulting in more structured learning.
• Pre-prescribe curriculums for yourself for reading about a topic. Keep a list of questions along the way and answer them, or expand on them. Some themes are more about doing than reading (most software, expertise reading is very application oriented). Understand what is a stopping point for that theme, and leave questions unanswered at the end. Beware of branch books when devising a curriculum.

These are fairly simple rules, but I anticipate it being quite difficult to adhere to them. Another unadressed component here is flashcards - I don’t believe that creating the flashcard actually gives me as much benefit as using good ones, so I’ll be working on a tool sometime in the near future to automatically extract good flashcards and writing exercises from my reading (including photos).

My current choice of non-fiction is “Thinking in Systems”, so “Systems and Mental Models” felt like a good start to this experiment. A few questions I have in this area:

• What are examples of people who effectively used systems thinking to actually effect change?
• How do I apply mental models in practice?
• What are indicators to know what kinds of systems interventions to make?
• What mental models have been the most effective historically?

My current curriculum for this in order:

• Thinking in Systems (I’m almost done with this)
• Cedric Chin’s Putting Mental Model’s to Practice
• Principles by Ray Dalio
• FS Blog’s list of mental models

Let’s see how it goes!! 🤷