I have more than 2,000 journal entries. Spread across roughly fifteen years, they add up to something close to 12,000 pages in Word documents — some professional, some personal, some just to-do lists, some gratitude lists, some meaningless, some powerful. I don't say that to impress anyone. I say it because I find it genuinely surprising when I think about it. I didn't set out to write 12,000 pages. I just kept showing up.
The question I've been asked — and have asked myself — is where that habit came from. The honest answer is that I'm not entirely sure. But the more I think about it, the more convinced I am that it was never really separate from reading. They were always the same thing, wearing different clothes.
If you haven't read it yet, the origin story behind this site — and why I've always treated reading as an investment — is in Why I'll Never Read 200 Books in a Year.
I've lived in my head for most of my life. I'm an introvert by nature — not the kind who can't function in social situations, but the kind who plays the role of extrovert when the job requires it and then needs to go somewhere quiet to recover. Reading was always the natural expression of that. It was a way of being inside something without having to perform. You could take in ideas, sit with them, turn them over, without anyone watching.
Journalling, I think, was always the other half of that same impulse — the output to reading's input. But for a long time I didn't know how to do it. I wasn't interested in a "dear diary" approach. I wasn't trying to document feelings for their own sake. I just had this vague sense that some things were worth capturing, and no clear method for doing it.
The first time I actually tried was in 2008, when I moved to Augusta, Georgia to work for the Lynx. It was a significant move — a new city, a new chapter, the first time something felt like it might be the beginning of a real career rather than just a job. I felt that it needed to be documented, even if I didn't fully understand why. I started writing. I wasn't very good at it. I have maybe twenty entries from that period.
Then Augusta folded. I moved to South Carolina, then to Manchester, and the journals went quiet for a couple of years.
What changed things was meeting Charlie Chislaughi.
Charlie is a sales trainer — one of the best I've ever encountered. We brought him in at Manchester, and later at NASCAR, and every time we worked together he had this habit of pushing me to write things down. Not just notes from the session. Everything. He was fascinated by the approach we were taking to the business, and he kept telling me that what we were building was worth documenting — that it could eventually become something more formal, an academic text. He became a mentor and a friend, and his encouragement planted something that took a few more years to fully take root.
By the time I was at Salem, the entries were more regular. By Manchester and NASCAR, they had become something close to a practice. Not every day — I've never been a daily journalist — but consistent enough that the pages started to accumulate in a way I could feel.
The real acceleration came when I found the Stoics.
I don't remember the exact sequence, but somewhere in the middle of my NASCAR years I started reading Ryan Holiday — The Obstacle Is the Way first, then The Daily Stoic. I'd read widely for years, but something about Stoicism landed differently. It wasn't just philosophy as an intellectual exercise. It was philosophy as a daily practice. The Stoics — Marcus Aurelius especially — didn't just think about how to live. They wrote about it, privately, repeatedly, as a discipline. Meditations wasn't a book Marcus Aurelius intended for publication. It was a journal. Notes to himself. A man in one of the most powerful positions in the ancient world, writing in the dark, trying to hold himself to account.
That reframing changed something for me. The journal stopped being a record and started being a practice. I wasn't documenting what had happened. I was working something out. Processing decisions, testing ideas, holding my own thinking up to the light. The entries got longer, more frequent, more honest. The 200-plus entries per year that I've maintained consistently since then didn't start because I set a target. They started because the habit had finally found its purpose.
Looking back, I think the childhood version of me understood this connection intuitively, even without the language for it.
Reading the encyclopedias cover to cover wasn't just about accumulating facts. It was about the feeling of having something inside you that wasn't there before — a framework, a reference point, a new way of seeing something. Journalling, at its best, does the same thing in reverse. You take what's inside — the half-formed thought, the unresolved tension, the thing you've been carrying around — and you put it outside yourself, where you can actually look at it.
They're both, at their core, about the same thing: trying to understand. Reading is how I take the world in. Writing is how I make sense of what I've taken in. One without the other has always felt incomplete.
I don't know yet what the journals will become. Charlie's idea — that they might eventually form the foundation of something more formal — has stayed with me. There are fifteen years of observations about leadership, sales, culture, sport, and life in those pages. Some of it is probably not worth revisiting. Some of it, I suspect, is better than I realise.
What I do know is that the habit started because of reading, and the reading has been better because of the habit. They've been feeding each other for a long time now, and I don't expect that to change.
Marcus Aurelius wrote his Meditations to no one in particular. He was just a man trying to think clearly in a complicated world. That seems like enough of a reason.
— Ryan