Hi all, I’m back today, easing into a writing rhythm again with a shorter one.
Below, I’ll share an announcement, pass along a few updates from my time off, and dig into some of my recent reading, along with a question it left me with.
My First Book Event
My first official book event for The Stoic Systems Thinker is this Thursday, September 10, at 6:30 pm in Ann Arbor, Michigan.
It’s at Booksweet, an outstanding independently owned bookstore near the University of Michigan. I plan to talk about the book, read a brief excerpt from one of my favorite chapters, and then open it up for Q&A. I’ll sign books while I’m there. And refreshments will be served.
If you’re close to Ann Arbor and want to learn more about the book (and support a great bookstore while you’re at it), please come on by.
August Updates
August was nice. I enjoyed two weeks of lake vacations with my wife and two daughters: the first on Lake Michigan in Grand Haven with my wife’s family and the second on Walloon Lake in northern Michigan with two other families we know. Both trips were relaxing and exactly what I needed after the several-month sprint of the book launch.
While I was off, two podcasts I recorded dropped.
The first was a conversation with Erick Cloward of the Stoic Coffee Podcast.
It’s always great to hop on a call with a complete stranger and hit it off. Erick also came from technology and found Stoicism later in life. We reflected on that shared path over a wide-ranging 75-minute conversation. I came out energized and happy to have made a new friend.
The second was my fourth appearance on The Poker Zoo.
The Poker Zoo is hosted by Chris, an old poker friend who goes by Persuadeo. We talked about poker, the book, and my last essay, We Live in a Sample Size of One. In particular, we discussed how these ideas — Stoicism and systems thinking — apply to both poker and life.
It’s been a while since I’ve been back to Vegas and seen Chris in person, but it’s always nice to catch up, even through a video call. It left me with an itch I haven’t scratched yet: getting back to the tables sometime soon.
Now on to today’s essay.
Starting the Distillation Process
It took me a long time to find my groove as a writer. The turning point (for me, at least) was recognizing that my best writing comes from reflecting on what I’ve read, connecting those ideas across multiple works, and layering on my own experiences. Some creatively inclined writers can conjure entire worlds in their heads.1 I’m not built that way. Where I do my best work is exploring a topic systematically, breaking it down, and connecting the dots.
That means my writing system runs on inputs. I have to read and digest what others have written before I can produce anything worth reading myself. The reading is fairly constant. I generally read about 75 books a year, and this year will likely land in that neighborhood.
When I read, I mark up my books: underlines, stars, notes in the margins. That practice alone has helped me understand and retain much more of what I read. But it’s only half the process. I also return to those marks and highlights to transcribe them into a secondary note system2 — a commonplace book of whatever resonated with me.
I’ve written about this before, so I won’t repeat the why. Just know that transcribing solidifies a book’s key ideas in my mind. It’s a zoom-out and a zoom-in at once: I see the book’s overall arc while revisiting the specific lines I highlighted, page by page. I’ve also found that some distance from the first read sharpens my understanding. Two to three months seems to be the sweet spot.
I fell behind over the past four or five months, and my “to transcribe” pile grew to double digits by August. But over this long Labor Day weekend, I knocked out nine of them. One was Jim Collins’s What to Make of a Life, which I read back in June. Three months later, right in that sweet spot, the ideas came flooding back. I’ll wrap up today with a few, along with some brief commentary.
What to Make of a Life
Jim Collins has a gift for taking a big idea, exploring every corner of it, and laying it out in plain language.
He studied people who had found their “one big thing” and saw three patterns in every case:
Discovering and deploying their encodings — Collins’s term for the innate wiring that decides what work fits us. They found what they were meant to do and leaned into it.
Flipping the arrow of money. They stopped making decisions because of money and let the money follow the work.
Focusing the inner fire. They found what drove them and shut out everything else.
Start with encodings. Collins believes they lie within us and are awakened over the course of life. They exist whether or not we know about them, and we may never find all of them.3 He likens them to stars.
The encodings are fixed, just as the stars in the sky are largely fixed. What changes as people move through life is the positioning and size of the frame, and whether a big cluster of encodings sits brightly visible in frame.
That’s a neat illustration of the Perspectives Rule, one of the four DSRP rules I explore in Chapter 2 of my book. A perspective has two parts: a point you look from and a view you see. The stars, our encodings, stay fixed. The frame is the point. Move it, and the view changes.
So how does someone end up out of frame? Collins has a name for it, and it’s a textbook reinforcing feedback loop: the Curse of Competence Doom Loop.
You become reasonably competent at something that doesn’t capture your encodings or ignite the inner fire, but it pays well.
You work hard at it, get better at it, and find some success with it.
That success brings more opportunities to do more of it, at better pay. The experience compounds, and so do the offers.
And one day, you wake up to discover that years or decades have passed. You’re well paid but out of frame. The inner fire is still there, but it's going dormant.
Plenty of executives will recognize themselves here. Many of us know someone who left a job after twenty years to start over. I understand how it happens. When you’re younger and living paycheck to paycheck, the extra money can change your life. But like any reinforcing loop, the pull compounds over time. The longer you ride it, the harder it becomes to hop off.
The way back into frame is simple to describe, though not easy to do.
When you find something you are deeply encoded for and that ignites a raging fire within, the greatest reward for doing your work is the opportunity to continue doing it.
You also have to do the work.
It reminds me of something Austin Kleon has said. To paraphrase: Many people want to be the noun. Far fewer want to do the verb.
Or the line Ryan Holiday shared with me when I met him at his Daily Stoic Live event in Detroit last month: “Many writers like to have written.”
Once you’re back in frame and doing the work, the fire feeds itself. Collins connects this to freedom. Many of us name freedom as the goal and picture it as the absence of obligation. Collins argues otherwise: a good life is built on responsibilities we choose.
The great novelist Toni Morrison said it better than both of us: “Freedom is not having no responsibilities; it’s choosing the ones you want.”
Collins gave me language for something I’ve felt at various points in my career and seen in colleagues. The loop is comfortable right up until you notice it. The question I’ve been sitting with since I transcribed those notes: Where is my frame pointed right now? It’s worth asking about yours, too.
One More Thing
I meant to write a short note. It grew. That’s what happens when you clear out a backlog. The ideas come rushing back.
I have another essay in the works, and I’ll be back on a regular rhythm from here.
If you’re in Ann Arbor, come see me at Booksweet on Thursday.
If you haven’t picked up your copy of my book yet, you can buy it here.
And if someone forwarded this to you, subscribe to my newsletter here.
All the best,
Michael
The Stoic Systems Thinker Is Now Available in Paperback, Hardcover, and Ebook
The Stoic Systems Thinker is my first book, published in June 2026. It combines the emotional resilience of Stoicism with the analytical precision of Systems Thinking to close the gap between how the world works and how we think.
“‘Timely and timeless’ captures this book perfectly.”
Bethan Winn, Author of The Human Edge: Critical Thinking in the Age of AI
1 I’ve been working my way through Stephen King’s catalog these last few years and am currently on Book 6 of The Dark Tower. The vastness of the worlds he builds, and how well he connects them across seven long novels, amazes me.
2 I use a digital system, but I’m conflicted. Digital archives are better for organization, retrieval, and making connections. But I’ve also read enough research on handwriting and retention to take it seriously. The ideal solution may be a tablet that converts handwriting into digital text for easy storage. I might be talking myself into a reMarkable tablet as I write this footnote.
3 It’s almost certain that we don’t know all of our encodings. That’s the beauty of life. There are more things worth exploring than we could get to in a thousand lifetimes. It’s a lesson I wish I'd learned earlier, and one I try to impress upon my daughters: Keep your eyes and your mind open. You never know when you’ll come across something that will interest you and trigger that inner fire.