The Great Books Project

Join me for this 5-year journey

The School of Athens by Raphael

The first book I can think of that changed my life was “Atlas Shrugged” by Ayn Rand. I read it Sophomore year of high school. 

I know, I know. But for all Atlas Shrugged’s faults, it inspired an interest in philosophy for me from a young age. It made me want to seek out ideas I didn’t necessarily agree with to see if there might be some sense in them.

The next book that I can think of that changed my life was “The 4-Hour Body” by Tim Ferriss. It transformed my mental image of my body from something I was stuck with to something I could change and improve.

I was always a kinda pudgy, out-of-shape, unfit kid who avoided sports. But 4HB inspired me to try actually messing around with what I could do with my body and made me significantly healthier and more fit in the process. It also kicked off a now decade-plus exercise habit, leading to fun things at various times like running a marathon, deadlifting 400+ pounds, and running half a dozen spartan races with friends. 

Other books throughout the years kept changing my life in new and exciting ways, usually by changing the way I thought in some meaningful aspect. “Antifragile,” “Letters from a Stoic,” “Finite and Infinite Games,” “Infinite Jest,” “The Denial of Death,” “Words that Work,” “Seeing Like a State,” every now and then I’d pick up a book and come out the other side a different person. 

And then… it stopped happening as much. The more you read, the less likely it seems that any additional book will impact you in some meaningful way. Not because you know everything, but because there are so few truly great books. And because so many books are poorly repackaged rehashes of earlier ideas. Or stretched blog posts.

So I got bored of reading. I fell off my habit for much of 2020 and 2021, and I honestly don’t think I’ve read a “life-changing book” in the last two or three years. 

It makes me exceptionally sad to write that sentence. Like I lost a friend. But obviously, there are still great books out there I just haven’t found yet, so I need a better process for finding them. 

In high school and college, we all have to suffer through forced readings of books we’re told are great but typically bore us to no end. Shakespeare, The Odyssey, The Inferno, The Prince. Maybe you liked one or two of the books that were shoved down your throat, but you more likely skimmed them and then read the spark notes like the rest of us. 

And I think that’s the right reaction at that stage of life. Trying to force a kid to like these books is idiotic. They need to develop a love of reading first, and that doesn’t come from trying to parse old English puns. It probably comes from easier books that give you quick wins and that open your eyes to some new way of seeing. And once those easier books start to run dry and stop impressing you, then you turn to the older and harder stuff. 

This brings us to the Great Books Project. I found Tommy Collison’s list of Great Books a couple years ago and was seriously inspired by it. What a fantastic idea for a project. Try to get through the classic great works over a few years and see what you learn from them. 

I didn’t do anything with his list when I found it, but when I realized I was getting bored with reading, I decided it was time to revisit it and put together a Great Books plan of my own. I pulled most of the books from Tommy’s list as well as the Ten Year Reading Plan, and started working through it last month.

The first big change I made from Tommy’s and other plans is I’m going to try to read all the great works in their rough chronological order, instead of grouping them by theme.

I think there’s a special beauty to this, because I’ll see what themes emerged in different time periods, and I’ll almost always know any older works being referenced in newer ones. It’s already been interesting to see the parallels between characters in Gilgamesh, the Iliad, the Odyssey, and Genesis, and I suspect many more of these common themes will emerge in similarly-timed works throughout the centuries. 

Another stance I’m taking is that I’m not going to try to go super deep on any of the books unless I really want to. I’m not going to force myself to fully understand parts that bore or disinterest me, nor am I going to try to go through multiple translations or interpretations to fully sus things out. 

Isn’t that a waste? I don’t think so. A book is like a trip. If you obsess over getting everything out of it in one go, you won’t get to fully enjoy it or take in what stands out to you. And if it ends up being good, you can always go back to it again in the future. The best books are worth re-reading like the best cities are worth revisiting, and most of what makes a book “the best” is how it resonates with you personally. 

Also, for my last controversial take, I’m not going to agonize over what translation I choose for things. I’ll probably bias toward whatever has the highest reviews on Amazon. Again, if I like the book, I can read another translation and cross-reference later. I can probably read the book during the time some people obsess over which translation to pick. 

So since I’m giving myself these permissions, I’m targeting a breakneck pace of 1 book per week. That’s a little insane, so I’ll have to see if I need to adjust it as I go, but even at that pace, this is looking like a 5-year project. 

5 years isn’t so long though. There’s a little story I like where a kid says to his mom “I don’t want to be a doctor! I have to go through 8 years of medical school!” and the mom says “you’re going to go through 8 years of life anyway, you may as well be a doctor at the end of it!” 

As I go I’ll share what I’m learning from each book here. So far people don’t seem to like those articles quite as much as the normal ones, but they’re fun for me so I hope you’ll tolerate them. I’ll keep playing with the structure, too, to see what makes them the most interesting. 

But anyway I know you want the list, so here it is. Feel free to make a copy if you decide to follow this journey with me. 

My continually updating great books spreadsheet is here. Make sure you subscribe to this newsletter too so you get the updates!

Neil and Adil are doing this with me too, and it will be our new focus on Made You Think. So if you prefer audio discussions of books, make sure you subscribe there. 

Finally, if you have any other books you think I should add I’d love to hear them in the comments. I think it’s particularly light on African and Asian literature. Please do not recommend something from the last 100 years unless it is TRULY excellent. 

Happy reading!