“I don’t want to read all the books; I just want to read the best 100 over and over again.” - Naval Ravikant
Note: Video version coming soon! Check back here on Substack or Subscribe On YouTube to catch it when it drops.
No matter how good the book, you won’t retain everything you read, especially if you’re listening to the audiobook while doing dishes. Whenever I re-read a book, I always find something new. Sometimes the first read gives you the birds-eye view, and the following reads give you the golden nuggets.
That’s why I keep a short list of books I come back to every year. These four in particular have changed how I think, live, and work. They’ve earned a permanent place in my mental operating system, and they get better every time. Links to purchase are at the bottom of the article.
Here they are, in no particular order.
1. Antifragile by Nassim Nicholas Taleb
This one cracked my brain open the first time I read it. It’s the most intellectually demanding book on the list—and the one that’s had the most profound impact on how I see the world. Taleb coins the term antifragile to describe things that grow stronger from chaos and disorder. Not just robust, but improved by stress over time.
Antifragile will rewire your understanding of how systems—biological, financial, personal—actually work.
One of the quotes that stuck with me:
“Wind extinguishes a candle and energizes fire. Likewise with randomness, uncertainty, and chaos: you want to be the fire and wish for the wind.”
Taleb’s central idea is that there’s a category beyond resilience, antifragility. Where most things break under stress, antifragile systems actually improve when exposed to volatility. Muscles. Markets. Startups. Even people. And once you see it, you can’t unsee it. Think of the Hydra, the multi headed beast from greek mythology: cut one head off, two more grow back. Thats antifragile.
I re-read this book because I retain 5% more with each read. It shapes how I see the world. The more I absorb Taleb’s thinking, the more I recognize patterns in culture, in nature, and in human behavior. In a world obsessed with control and short term thinking, Antifragile gives me a different target: to become someone who gets stronger when life gets messy, to not over-optimize, and to increase my surface area for luck.
Simply put, it's your smartest friend's favorite book.
2. The Defining Decade by Meg Jay
This book is a cold splash of water, in a good way. It’s written for people in their twenties, a stage of life most of us are living very differently than our parents did. Meg Jay makes the case that your twenties are the most foundational, high-leverage years of your adult life, and treating them like a warm-up lap can cost you more than you realize. The decisions—or non-decisions—you make in that window have high consequences across the rest of your life.
“We think that by avoiding decisions now, we keep all of our options open for later. But not making choices is a choice all the same.”
Every time I re-read this book, I catch myself re-evaluating: Am I drifting? Am I postponing hard decisions under the illusion that I have more time?
“Thirty is not the new twenty. Claim your adulthood. Get some skin in the game.”
What makes this book awesome is how practical it is. It’s not about hustle or “growing up.” Rather, it should prevent you from going on autopilot, when many of our peers are. Saying yes to the things that build identity capital and shape your future self. I read it after my birthday every year, and use it as a temperature check to make sure I’m focused on the right things, and not neglecting stuff that’s going to bite me in the ass later.
And honestly, that’s the hardest part with books in general. It’s not reading them, but remembering them. Implementing them.
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3. The Almanac of Naval Ravikant by Eric Jorgenson
This book is like a concentrated dose of wisdom. It’s a distilled philosophy. Naval Ravikant is one of the greatest thinkers I’ve come across, and this book captures his philosophy in a way that feels timeless. Every time I read it, I find something I swear wasn’t there the year before.
“Desire is a contract you make with yourself to be unhappy until you get what you want.”
That quote alone should change your life. Naval has a way of reframing things you thought you understood—like how happiness isn’t something you chase, and how wealth isn’t just about money, it’s something you train for. His ideas are simple, but not easy. They require thought, patience, and unlearning.
“The three big ones in life are wealth, health, and happiness. We pursue them in that order, but their importance is in the reverse order.”
What I love about this book is that it’s not trying to sell you anything. In fact, Naval doesn’t make a penny from it! Plus, he didn’t even write it.
The books is broken into three parts: Wealth, Health, and Happiness. Reading it every year helps to ground me, and ensure I’m spending time on the right things. It helps me zoom out, reconnect with what matters, and make better decisions—both big and small. Even when I don’t need a full re-read, I’ll revisit individual chapters often.
4. The 4-Hour Workweek by Tim Ferriss
A classic—and maybe a cliché—but for good reason!
I think people misunderstand what this book is really about. It’s not about working four hours a week. It’s about designing a life that’s aligned with what actually excites you.
“People don’t want to be millionaires—they want to experience what they believe only millions can buy.”
Tim Ferriss doesn’t just challenge the 9-to-5 grind; he gives you a playbook for escaping it. And even if you don’t want to move to Thailand or automate a drop-shipping business, the core message still hits: your time is your most valuable asset, and the way we’ve been taught to trade it is broken!
“Focus on being productive instead of busy.”
This book is jam-packed with practical instructions for launching and running a business. I don’t care what anyone says, it is an absolute gold mine. And if you’re already a seasoned entrepreneur, this book is a recalibration tool. It’s one I’ll probably revisit every year, for the rest of my professional life. If you like the 80/20 principle, you will appreciate this book.
Forget business, this is a guidebook for how to be effective at anything.
So yeah—those are the four I keep coming back to. What are yours? Drop a comment.
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The Books
Antifragile by Nassim Nicholas Taleb
The Defining Decade by Meg Jay
The Almanac of Naval Ravikant by Eric Jorgenson
The 4-Hour Workweek by Tim Ferriss
Here's the video!
https://youtu.be/38Qx0eSbdh8