The Best Books I’ve Ever Read Categorized By What They’ve Taught Me
As a general principle, if I have to do something, I don’t want to do it. I have a strong internal beat to have the freedom to choose for myself. So, naturally I was never a big reader in school. In fact, I hated reading. It was a chore, I had to read books I wasn’t interested in and on and on.
I discovered this principle after college when, strangely, I started to love reading. It was for the pure joy of discovery or learning something new that I chose to learn. Since then, I’ve read hundreds of books that have shaped how I look at the world, so I’m sharing them here with anyone who is interested. Many of these books appear on the list in multiple sections.
Books That Have Had The Biggest Impact On Me
This book came for me at a truly pivotal time in my life, and in some ways I think it saved my life. The gist is this book, and particularly the chapter titled “Investment In Loss” let me view the world as non-linear, and gave me the permission to take a step backward in order to make a bigger leap forward.
It’s funny, I read Principles before it was a book. Ray Dalio put Principles out as a PDF and I devoured it back in 2007 or so. The Idea of systematizing operating principles into a manual for my life was very interesting at the time. Since then, I’ve re-read Principles in book for as soon as it came out, and I use Dalio’s app to help me systematize my own principles and use ones that he has already formed.
This 1000+ page turner is easily my favorite work of fiction. In Greek mythology, Atlas holds up the world on his shoulders. This book dives into the question of “what if Atlas shrugged, and didn’t want to hold it up anymore?” The fact is that entrepreneurs and risk takers hold the world up and create more opportunities for others. What happens if we dis-incentivize people from taking the risks to build massive companies and create wealth? It’s a philosophical treatise cloaked in a riveting novel with a strong female hero, that will make you question the philosophical underpinnings of where our world is headed.
Nassim Taleb is easily one of my favorite authors and thought provokers. He’s a philosopher and a risk taker - and that qualifies him to have a rather abrupt and brash view on just about everything. All his books are great, but this one rests on one simple axiom - that the most powerful incentive to good decisions, alignment and avoidance of fraud is to have skin in the game. I share Taleb’s distaste for bureaucrats and media personalities that promote expertise in some subject but have no stake in the subject’s outcome. “Intellect without balls is like a racecar without tires.”
Every parent with pre-teen or teenage kids should read this. It’s masterful at bringing together 6 forces that are making our kids more fragile and less resilient. The #1 takeaway is that prolific social media use in kids is directly tied to higher suicide rates - these rates are off the chart.
The book delves into what’s happening on college campuses with cancel culture and safe spaces also. The book is right down the middle in terms of political slant, and did a great job of opening my eyes to a number of issues that I need to head off to raise my 3 boys to happy, healthy adults.
On Mental Models and Decision Making
On Shaping My General Philosophy
On Self Improvement
On Dealing with Work, Focus and Multi-potentialism
On Technology and the Future
On Risk and Investing
Disclosure: I only recommend products I would use myself and all opinions expressed here are my own. This post may contain affiliate links that at no additional cost to you, I may earn a small commission.