Why You Should Re-read Books Every Year

several books splayed open overlapping with each other

Join the newsletter

Shoutout to a history teacher

In high school, I took a class called World History (and some dates I don’t remember) with a teacher who was a retired army parachuter. I scoured facebook for his name and unfortunately was unable to find him – though I know we were friends at some point. 

Regardless, here are some more deets on this man:

  1. He ALWAYS wore a combination of brown suit and green tie. He had probably 10 of each, and he would “have fun” with his shirt color each day being either green, brown, or tan/cream colored. 
  2. Retired military parachuter who would rarely discuss and never glamourize his drops during Vietnam wartime
  3. Was adamant that the US school system did not give us enough tools or emphasis on learning international history which ultimately halted our development as global citizens. 
  4. Truly, emphatically, did not give a fuck about seeming cool or relatable to us as teenagers. Was very much “not here to make friends” and instead instill in us a respect for world history and its implications on our present and future. 

One of my favorite things that I learned from him as a person was that he had a handful of books that he read annually and took notes in. Each year, he would use a different color pen (he oscillated between black and blue) and converse with his past self in the margins. 

I didn’t pick up the habit until several years later. Thus far in my quarter century, I have acquired 3 books with which I have done this annual reading: Go Rin No Sho (english: Book of Five Rings) by Miyamoto Musashi, Essentialism by Greg Mckeown, and Dear Senthuran by Akwaeke Emezi. 

My Current Annual Reads

Go Rin No Sho –recommended to me by one of the most evil people I know– I read 2 years in a row and took a lot of beautiful notes because it’s a pdf I used in One Note. It’s a pretty aggressive book because it is the Strategy manifesto of a 16th century Samurai, widely considered to be the best of his time. 

Though I still get the calendar reminder each year, I stopped reading this after 2021 because war and combat strategy was not really how I wanted to model my life. There is a hyper vigilance that his lifestyle required that I don’t have the desire to bring into my cushy world. I do however find valuable insights in the sections about spirit and mutability. 

Essentialism, I read 2017, 2018, and now 2024. I have, however, referenced this concept at least once a quarter for the past 7 years. All of the most useful questions I learned from the book, I have been integrating into my quarterly review rituals. 

It was really fun this year to encounter the 2018 Athena. She was… well steeped in Wharton is what I’ll say. I had some bad, myopic takes- and it’s actually fascinating to so clearly feel my 2018 values through my notes. The passages I underlined, and the conclusions I drew are quite first season Zuko, if you know what I mean. Dogged, isolationist, and kind of sad to witness from a more compassionate lens. 

Dear Senthuran (read 2022-2024) is basically just an anchor that reminds me of my values and the world I want to create. I read through the essays that affirm me in the moments where I feel like I might “die of that specialness” (quote from Audre Lorde). While my margin notes differ, it’s mostly me synthesizing the same idea with different inputs. 

Another interesting aspect of this process is to see how I have opted towards more questions in my notes. Previously, the margins were regurgitations of the writing in my own words or it would be examples that help me understand what I read. But now I have a lot more questions. It feels good to feel like my cognition and media analysis skills are growing. Now I’m at the stage of learning where I think to question the authors rather than consume their ideas wholesale. I appreciate having such a tangible display of that evolution. 

I’m looking for some more literature to fold myself around and add to my list. 

What book have you re-read the most? If you start an annual reading practice, what books will be on your list? 

Join the newsletter