The Stoic Systems Thinker is live on Amazon today.

That feels so good to type. Since first sharing this project last August, I’ve been anxiously waiting for this day. I’m not sure I ever fully believed it would come. But here we are.

Eighteen months ago, I wrote a note to myself: I should write a book about thinking.

I write many notes to myself. Some of them grow legs. Most don’t turn into much of anything. Why would this one be any different?

But for several months, this particular thought kept rattling around in my head. I thought about it off and on throughout the holidays in 2024 and into the beginning of 2025. It stayed there until I finally connected with the Manuscripts team later that spring to figure out how to get this done.

I knew it would be a challenge. Even so, I underestimated how much actual work it would take. I spent months outlining, writing, editing, rewriting, selling, and writing some more. Long nights. Weekends. It was a challenging stretch.

But that’s all behind me, so I’ll say it again. We’re here.

I’d like to thank you — the readers of this newsletter — for taking the time to read my work. Whether you’ve been with me since I started my poker blog in 2020 or you signed up last week. Whether you’re reading this in your email inbox or on my website. I appreciate you. Every essay I’ve written — and every note you sent back with ideas, comments, and feedback — shaped what this book became.

If you read through my backlog of essays, you’ll find the same theme in all of them: a systems-thinking lens with a Stoic foundation, applied to life and the messy business of figuring out what to do next.

And today, I get to share my attempt at pulling that together into a book.

The world’s complexity is increasing at a dizzying rate. Our thinking habits haven’t kept up.

I picture this divergence as two curves: one rising exponentially, the other plateauing and beginning to fall.

I call the space between these curves the thinking gap. And I think it’s one of the most important challenges we face as a society today.

The good news is that we have agency over one of those curves. We can reverse that downward trend in our thinking ability. And like any other skill, the best way to get better at thinking is to practice it. This is called metacognition, or thinking about thinking.

The Stoic Systems Thinker is my attempt at translating these ideas into a practical operating system to help us manage our lives. The book connects two overlapping traditions: systems thinking and Stoicism. Despite originating two thousand years apart, they complement one another and can form the foundation of an operating system for life.

Systems thinking gives us the structural vocabulary to understand the world — feedback loops, stocks and flows, leverage points, and emergence. Stoicism gives us the personal discipline to use that vocabulary well — the dichotomy of control, premeditatio malorum, amor fati, and the inner citadel. Neither is enough on its own. But together, they form a structure for handling life and what it throws at you.

I’m not a philosopher or a systems theorist — though I do draw on the wisdom of many in the book who are. Rather, I’m a practitioner who has studied and applied these ideas through ups and downs. I’ve held impressive job titles and been pushed aside at companies. I’ve run up and lost poker bankrolls. I started a profitable business and watched it fade away. I optimized the wrong things for a decade.

But eventually I learned to ask better questions — ones that helped me see how things connect, and let go of what I can’t control.

This book is the one I wish I had ten years ago.

I’ve shared excerpts from the manuscript as I’ve developed it this past year. But this is the first time I’m pulling from the final product.

Below is the introduction to Chapter 13, titled “Knowing What to Do Next.” This chapter’s seeds grew from my Priority Stacks essay last year. It sits within Part III of the book, where I explore how to apply some of these ideas to the most important system of all: our own lives.

Over the past few years, one question I keep returning to is: How do you align what you do with the energy you actually have, rather than the energy you wish you had? The chapter is my ongoing work toward finding an answer.

Here’s how it opens.

It is not that we have a short time to live, but that we waste a lot of it.
-Seneca

I’m staring at my task list on a Tuesday afternoon. It contains twenty-seven items, ranging from “compile research on cognitive biases” to “identify birthday gift for my wife” to “prepare for my afternoon meeting.” 

My energy is a sluggish 3 out of 10. I have exactly ninety minutes before my next meeting, a window that should be sufficient to make real progress on something. Yet I’m frozen. The cursor blinks at me, a steady, mocking metronome marking the seconds I’m wasting.

In the past, I would have scanned the list for something marked “High Priority.” I’d try to force myself through it, likely producing mediocre work while battling the distraction of twenty-six other items screaming for my attention. Or perhaps worse, I’d spend twenty minutes paralyzed by indecision, toggling between tabs. Ultimately, I’d check email and call it productivity.

This paralysis is a symptom of what author Chris Guillebeau calls “Time Anxiety”—the pervasive, nagging feeling that it’s too late to do what needs to be done, or that we lack the time to do it all. We look at our task list and see proof of our inadequacy rather than a plan for the day.

Seneca anticipated this modern malaise two thousand years ago. I once interpreted these words as an admonishment against idleness—a command to cease any activity that didn’t produce a tangible result. “Not wasting time” meant I needed to be constantly in motion.

I see it differently now. We don’t waste time by doing nothing. We waste it by doing the wrong things at the wrong moments. Our finite resources are squandered when we force high-leverage work without the energy for it.

In the last chapter, we built a system to capture and organize the knowledge that feeds our plans. But knowing what you know isn’t enough. You also need to know when to act on it—and that depends on a resource no knowledge system can manage for you: your energy.

We often believe that if we can just rank our tasks properly, execution will naturally follow. This assumption relies on a mental model of humans as machines: static entities with constant, predictable output. But machines don’t feel creative in the morning. They don’t face an afternoon slump. They simply process inputs until the job is done.

You are not a machine. You’re a biological system with fluctuating resources.

When we ignore these fluctuations, deciding what to do becomes overwhelming. We focus on optimizing the task list, yet overlook the state of the person executing it.

The complex system of our daily lives demands a different question. Not “What is the most important thing to do?” but “What is the best thing to do right now?”

We’ve historically approached prioritization with the mindset of an engineer. Yet, doing the work more closely resembles surfing.

Continued within the book…

You can read the book today!

The Stoic Systems Thinker is available as an ebook, paperback, and hardcover.

Here’s the direct link, in whatever format you prefer:

If you’d rather read a bit more before deciding, I’ve put together a downloadable PDF of the full Chapter 13.

To accompany the chapter, I’ve included three practical worksheets you can use to implement the Priority Stacks framework I outline in the text.

The link is below.

I’m incredibly proud of my work — and also admittedly biased. Thankfully, others have weighed in, too.

Once again, you can order the book here:

If you read the book and find it resonates with you, please consider leaving a review on Amazon.

Early reviews are what fuel a book’s launch trajectory. More positive reviews tell Amazon’s algorithm the book is worth surfacing to other readers, which decides how many people who would have benefited ever find it. And reviews tell the next person who lands on the book’s page whether it’s worth their time. Both of those are out of my hands once the book is out. But they’re in yours.

You don’t need to write a long review. A few honest sentences about what landed for you are plenty. It’s one of the most impactful things you can do to help an author.

Thanks for making it this far. I appreciate your support. And if you grab a copy, I hope you like it.

Back in your inbox in a couple of weeks with another essay.

All the best,
Michael