2 books that plague me

Antifragile  – Nassim Nicholas Taleb 

In 2021 I wrote “Incerto” as one of my favorite books but Incerto is actually a collection of 5 books, and I recommend all of them, but the core idea in the series is what the author calls Antifragility - things that improve through disorder.

Over the past few years I have modeled my entire life around the principles in this book and I now expect to take them to my grave. My appreciation for this work has grown over time, and

The philosophical lesson of the book is to live and invest in a way that when pain comes to you, you don’t just endure, you get stronger. I've done a pretty decent job of living that way, but now as I get a better understanding of myself and how I want to invest going forward I plan to model my financial plan around this idea as well.

Specifically the barbell strategy, where one puts ~90% of their investments in bulletproof low-risk assets that produce just enough income to live off, which usually means living very light, and then taking that last 10% and essentially betting big against the market and losing money month over month and year over year until some big unexpected shock occurs and the gains from that event should make the investor wildly long term profitable. When I read about this years ago it was so engaging but I didn't really understand how to do it, now that I have a deeper understanding of markets, it's become even more appealing than before.

The point is, this series not only taught me so much about how to live and invest but the quotes from it are phrases I still rattle off on a daily basis. When a book festers in my mind like this for half a decade without calming, I can't help but acknowledge it's trying to tell me something I need to listen to.

Infinite Jest  – David Foster Wallace

Trying to describe Infinite Jest is extremely difficult. The book is ~1100 pages, it’s nearly plotless, and it’s written in a way that is intentionally difficult to read. 

However, it taught my perhaps one of the most important lessons I’ve learned in life, that everyone worships something. 

What you choose to worship is maybe the most important decision of your life, and making the wrong decision can potentially destroy your life 

IJ is a long bleak road filled with dark humor, suicide, drug addiction, and crippling loneliness. It’s written in 1996 as a prediction of American culture ~25 years in the future, basically our current culture, and it’s spot on.

I've read this book twice now (2019, 2021) and plan to read it again in 2024. There is nothing else like it