The Reading Behind the Writing

I get asked one question more than any other: how did I decide what to write about?

I think many of us have an image of a writer sitting in a library or cabin somewhere, conjuring inspiration out of thin air. While some are probably gifted enough to work that way, I am not one of them. Most of what makes it into my finished work started in someone else’s book.

But before I get into that, I’d like to start with a thank you. The Stoic Systems Thinker has been out in the world for a few weeks now, in ebook, paperback, and hardcover. The support and the early praise have meant more than I can fit in a newsletter.

A few of the first reviews are in from early readers:

It’s a vulnerable feeling to put my work out there. And humbling to know that others have read it and shared such kind thoughts. If it lands with you, please let me know and share it with others.

A few months ago, I wrote about my Zettelkasten system. It walked through how what I read moves through my digital knowledge system and into my writing.

Despite the wealth of knowledge at my disposal, I don’t quote most of my source material directly. Almost every chapter is downstream of something I read, underlined, and argued with in the margins, then connected to something else I’d read years earlier.

After I’ve read something and captured my notes, my thoughts can sit for months or even years before surfacing again. My reading leads to my writing, and my writing is what eventually becomes the raw material for a book. So the way I figure it, my job as a writer is to read widely enough so that those connections have a chance to collide.

Let me show you what I mean. Here’s a short passage from the second interlude of my book:

The passage reads like a single idea when it’s actually a collision of several.

The part about variance and expected value came from years of reading the work of authors like Leonard Mlodinow and Nassim Taleb, and from sitting at poker tables losing money despite playing well (and winning money despite making mistakes). The turn at the end, the part meant to steady you when the odds don’t break your way, came from my reading of the Stoics — Marcus Aurelius, Seneca, and Epictetus. I didn’t come up with these ideas myself. My contribution was noting that they belonged in the same paragraph.

That’s the whole system. And it only works if I keep feeding it new material.

So, in the spirit of feeding the system, here are seven of my favorite books from the first half of 2026. This is a midyear check-in, not the full year-end accounting I usually do (you can check out my lists of favorite books from 2025 and 2024), so I’ll keep each book to a paragraph on what stuck with me most.

Since I just credited Mlodinow, I’ll start here. His book is a tour of how thoroughly randomness runs our lives and how badly our minds handle it. We judge people by their results and expect events to happen for clean, understandable reasons, even though we only assemble those tidy stories in hindsight. I underlined so many passages in this book. One of my favorites was pure Stoicism. At the end of the book, Mlodinow reflected on his lessons learned: “We ought to identify and appreciate the good luck that we have and recognize the random events that contribute to our success. It has taught me, too, to accept the chance events that may cause us grief. Most of all, it has taught me to appreciate the absence of bad luck, the absence of events that might have brought us down, and the absence of the disease, famine, and accident that have not or have not yet befallen us.” His chapter on Zeno’s paradox also sent me straight back to the fractal rabbit hole I fell into while writing about The Coastline of Knowledge. The closer you look, the more there is to see.

Shahade is best known as a chess champion, but I first came to know her through the poker world, where she’s every bit as accomplished. This is a wonderful book about decision-making. She wraps the concepts in games, then extends them into how we think and live. Since I just spent the last 18 months writing my book on a similar topic, I found myself smiling at research I’d already dug into in my own writing and scribbling notes on ideas that were new to me. The idea I keep returning to is her stance on results. Shahade’s advice: “Detach yourself from results by going out of your way to praise well-played failures while critiquing sloppy success.” In doing so, we should judge ourselves only on the part we control — our processes. She also offers the best career advice I’ve read in a while. Pick two things you’re very good at but not elite at, and you can become exceptional at their intersection. That’s more or less the whole story of my career.

I’ll admit a bias here: Epstein is the writer I want to be when I grow up. He takes ideas that sound simple, dives into the underlying science, and somehow makes the whole thing feel like a conversation rather than a lecture. I first read Range a few years ago and devoured it in two days. When I saw that Epstein had released this one, I immediately placed a preorder. Inside the Box is about constraints. His case is that boundaries, rules, and limits are what unleash creative work rather than smother it. After twenty-some years of watching teams flounder in open-ended ambiguity and come alive once someone drew a few hard lines, I felt that argument in my bones. And staying true to my first experience with one of his books, I read it in three days on vacation in Maine last weekend.

Who knew a history of the notebook could be a page-turner? This was the most pleasant surprise of my year, a perfect companion to Papyrus, which I loved last year. Allen walks through centuries of people thinking on paper and makes the case that the humble notebook has shaped human progress more than we ever credit it. My favorite story is in Chapter 15, where he traces Isaac Newton’s “waste book,” which began life as the commonplace book of a Lincolnshire rector named Barnabas Smith. While Smith had lofty plans when he originally acquired the thousand-page notebook, his ambition fizzled out, and he left most of the pages blank. Newton stumbled across these mostly empty pages while quarantining outside of London during the plague of 1665 and rapidly filled page after page with some of the most groundbreaking mathematical thinking the world had ever seen — the seeds of his famous Principia.

Montaigne has been a bit of an obsession for me this year. I suppose it was somewhat inevitable that I ended up making my way to him — he was steeped in Stoicism and one of the greatest thinkers to ever live. Alongside Zweig’s short, admiring biography, I also read Sarah Bakewell’s How to Live this year. Montaigne’s own Essays are sitting on my “to-read” queue right now, waiting for the two weeks of vacation I’m taking in August. Zweig’s book is about the man who more or less invented the essay by trying to understand himself on paper. Montaigne read history and philosophy to compare his own life against the lives of others, which is the most honest description of why one reads that I’ve ever come across. Two lines have stayed with me. “Books are the best provisions a man can take with him on life’s journey.” And his whole project of guarding the “citadel,” that innermost part of yourself the outside world can’t touch unless you let it. Four hundred years later, I’m trying to do that myself.

I came across Bethan Winn by chance in the thick of my rewrites this year while researching a few thinking-skills topics. I reached out, and she was gracious enough to hop on a video call with an unknown author from the other side of the world (Did I mention that Winn lives in Australia?). After a lovely conversation, Bethan read my manuscript and lent her name to my book as an endorsement. Just an incredibly kind and generous person. With the niceties aside, her book is also excellent! It’s a clear-eyed guide to critical thinking in the age of AI, and it pairs naturally with my argument in Using AI Without Letting It Use You. Winn’s core move is metacognition, thinking about how you think, and her warning is one I’ve taken to heart: every time we hand a cognitive task to AI, we’re making a trade. The questions she keeps returning to are valuable ones like “What can I do that AI can’t?” and “Am I still thinking deeply, or just nodding along to suggestions?” This one is worth reading slowly and keeping handy as a guide.

I’m a sucker for books like this one, and Collins is one of our most thoughtful writers. He has a gift for finding the story inside an idea. This one reminded me of The Second Mountain, another book I hold close and one I cited in the final chapter of my book, “A Life Worth Living.” The spoiler of this book, if you can call it that, is that there’s no single correct way to live a life. What there is, instead, is a set of patterns and hard passages most of us are eventually asked to work through. Beyond the life lessons, it sent me on a week-long rediscovery of the catalogs of Led Zeppelin and The Yardbirds after reading the chapter on Jimmy Page and Robert Plant. (The best part: my two daughters heard it coming from the garage and came out to say, “This music is really good.”) This is a generous, beautifully made book, and it’s the right note to end this list on because it asks the question the whole newsletter circles around: how do we live a meaningful life in the short time we get?

When you look at all seven books, a few core themes appear: chance, constraints, thinking on paper, the self, and how to live. None of these made it into the book I just published, though some of the core ideas within did appear in a different form. But I can already feel pieces of them angling toward whatever comes next.

I didn’t open a single one looking for material. It just found its way into the writing. That’s the mechanism. I read, the ideas sit on the shelf next to one another, and eventually two of them connect in a way that I get to write down.

With that, I have an ask for you. If you’ve read something recently that rearranged how you see things, reply to this email and tell me. I’m always looking for more books to add to my future reading pile.

If you haven’t picked up The Stoic Systems Thinker yet, it’s on Amazon in ebook, paperback, and hardcover. And if you have already read it, an honest review posted on Amazon goes further than you’d think.

Back again in a couple of weeks.

All the best,
Michael