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

 

The Art of Learning

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.

Principles

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.

 

 

Atlas Shrugged

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.

 

Skin in the Game

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.”

The Coddling Of The American Mind

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

Principles

Thinking In Bets

Superforecasting

Essentialism

Decisive

Great Mental Models

The Almanack of Naval Ravikant

 

On Shaping My General Philosophy

The Almanack of Naval Ravikant

Principles

Atlas Shrugged

Man’s Search for Meaning

Self Reliance - Emerson

Meditations

The Daily Stoic

Zen and the Art of Motorcycle Maintenance

The 4 Hour Workweek

 

On Self Improvement

The Art of Learning

The Art of Virtue

7 Habits of Highly Effective People

Seeking Wisdom: From Darwin to Munger

Great Mental Models

Tools of Titans

Mastery

Smarter Faster Better

Atomic Habits

On Dealing with Work, Focus and Multi-potentialism

Deep Work

So Good They Can’t Ignore You

Range

Choose Yourself

ReWork

Peak

The Obstacle is the Way

Designing Your Life

On Technology and the Future

Inevitable

Abundance

Bold

 

On Entrepreneurship

The Third Wave

Creative Confidence

Stealing Fire

Zero To One

The Startup Owner’s Manual

Remote

 

On Risk and Investing

Antifragile

Skin in the Game

Thinking in Bets

The Psychology of Money

Reminisces of a Stock Operator

Market Wizards

Security Analysis

Trading Risk

On Business

Trillion Dollar Coach

Extreme Ownership

Managing Oneself

The Science of Success

The Snowball

Biographies

Finding My Virginity

Einstein

Elon Musk

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.