50 Books That Stayed With Me: 1 of 50

1 out of 50

Hi,
Hope you're doing well and staying safe.

I’ve been thinking about adding a little shape to this very random blog, and what better way than to start a series about books that stuck with me? Not because they were flawless or popular — but because they lingered. Some shifted my thinking. Some just made me feel seen. Others were simply fun as hell to read.

These aren’t reviews. They’re reflections. Sometimes I’ll rope in a friend. Sometimes it’ll just be me. Let’s see how it goes.

Here’s 1 out of 50.

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1 out of 50: Fooled by randomness by Nassim Taleb

Some books don’t change your life so much as they quietly rearrange your assumptions. You go in thinking you know how things work — success, luck, skill, risk — and you come out realizing you’ve been standing on thinner ice than you thought.

Fooled by Randomness was one of those for me. Taleb can be a bit much for many, but he is full of wisdom. Beneath all the edge is a deeply clarifying idea: that we are far more at the mercy of chance than we’d like to believe, and that we often reshape randomness into reason to make ourselves feel in control.

The book sits at this interesting intersection of probability, psychology, and finance — but at its heart, it’s about storytelling. The quiet, constant narratives we build to explain why things happen. Taleb argues that often, a lot of what we call skill, especially in high-stakes fields like investing or entrepreneurship, can be luck, but we wrap it in neat explanations after the fact. That’s hindsight bias: the tendency to treat outcomes as obvious in retrospect, even when they weren’t.

Then there’s survivorship bias, which hit harder the more I sat with it. We hear from the winners, the trader who timed the market, the founder who made it big, and we turn their paths into models for success. But we ignore the ones who took the same risks, made the same bets, and vanished. Not because they were wrong, but because randomness didn’t choose them.

One idea I keep coming back to is Taleb’s thought experiment of alternative histories. If you lived your life 1,000 times, how many different versions of you would exist? Some careers — say, dentistry — have narrow variance: you’d likely earn a similar income and live a broadly similar life across all timelines. But others — trading, art, startups — are wildly volatile. In those cases, a single stroke of timing or luck could shift everything. That’s what makes them more random, and also more seductive.

And that’s where the real insight lies: just because something worked doesn’t mean it was a good decision — and just because it failed doesn’t mean it was a bad one. In careers significantly influenced by luck, it’s even more important to focus on the process itself, not the outcome. Taleb emphasizes this over and over, and it’s an idea that has been echoed in various philosophies, including the Bhagavad Gita.

“Heroes are heroes because they are heroic in behavior, not because they won or lost.” -
Nassim Taleb

Taleb isn’t warm. He’s abrasive, almost gleeful in his criticism of economists, analysts, journalists, anyone who claims to see order in chaos. But behind the provocation is a quiet ask: be humble. Especially about things that worked out.

After reading it, I found myself noticing randomness everywhere, in markets, in sports , in who gets praised and who gets forgotten. And maybe most of all, in how we assign meaning to things just to feel more in control.

Fooled by Randomness is about living in a world with uncertainty. Its brilliant. I highly recommend it.

Thank you for reading. Stay safe.