I’ve Been Trying to Explain Zen for Thirty Years. Here’s Why I Finally Stopped.

I’ve Been Trying to Explain Zen for Thirty Years. Here’s Why I Finally Stopped.

A note on why this project is built the way it is.

For most of my adult life, I’ve sat across from Westerners and tried to explain what Zen actually is.

Not the version sold in airport bookstores. Not the rebranded mindfulness app. The real thing — or at least, the version I grew up inside of, the one that entered my body through kendo and judo before I had words for it, the one that later led me to Kyoto, to monks, to years of sitting with questions that refused to resolve.

My success rate was roughly thirty percent. On a good day.

The other seventy percent left the conversation nodding politely, having received something that resembled what I’d said but wasn’t it. I could watch it happen in real time — the concept landing, being sorted into a familiar Western category, and quietly becoming something else. Zen becomes “concentration.” Mu becomes “emptiness” and then “nothingness” and then something vaguely Buddhist that sounds like it belongs on a meditation app.

I don’t blame anyone for this. The problem isn’t intelligence or open-mindedness. The problem is structural.

The Wall Isn’t Language. It’s Underneath Language.

My English was built in school. Grammar, vocabulary, and examination scores. Functional English, not philosophical English. When I tried to talk about Zen in depth, I would find myself standing in front of a wall — not because I lacked the words, but because the words I needed didn’t seem to exist.

I once asked a Japanese friend who had studied in the United States — fluent, articulate, deeply bilingual — to help me translate a particular concept. He thought about it for a long time and said something I’ve never forgotten: “There isn’t a word for this in English. Not because English is limited, but because the concept itself grew from a different soil.”

That phrase — different soil — stayed with me. Language doesn’t just carry meaning. It carries the ground on which the meaning grew. And that ground, in Japan, has been shaped by Zen, by Shinto, by Buddhism, by a relationship with nature and silence and ambiguity that developed over more than a thousand years.

You can’t transplant the fruit without the roots.

For a long time, this felt like an unsolvable problem.

What AI Changed — and What It Didn’t

Then AI arrived. And something genuinely shifted.

I want to be precise about what changed, because it wasn’t everything.

What changed: the language barrier lowered. I could now articulate nuanced ideas in English without losing them in translation. Concepts I had struggled to express for decades could finally be rendered in ways that felt accurate — not perfectly, but far more so than before. The gap between what I meant and what I could write narrowed considerably.

AI is my brush, not my brain

What didn’t change: the cultural distance.

Language was always the visible wall. But behind it was something harder to name — the absence of shared context. When a Japanese person hears the word en (縁), they feel something. A web of invisible connections, fate that isn’t quite fate, the way certain encounters seem to carry weight beyond coincidence. When an American hears the word translated as “fate” or “karma,” they hear something different. The word arrives, but the soil doesn’t come with it.

So the language barrier fell, and the cultural translation problem came into clearer view. They had always both existed. Now I could only see the second one.

Why Dialogue — and Why These Two Characters

Here is the part I want to be honest about.

Nicholas and Catherine are not real people. I say this clearly in my About page, and I’ll say it again here. They are composite characters — built from real conversations, real questions, real moments of confusion, and occasional breakthroughs that I’ve witnessed over many years of talking to Westerners about Japanese philosophy.

But they are also, in part, me.

The questions Nicholas asks — the impatient ones, the ones that demand practical application, the ones that push back — those are often questions I myself once asked, or questions I watched other people ask, or questions I could feel sitting unspoken in a room. Catherine’s confusion, her reaching toward something she can sense but not name, her frustration with her own perfectionism — I recognize all of it. I’ve felt versions of it myself.

I created these characters because a one-directional explanation of Zen is, in a very real sense, a contradiction in terms.

Let me explain what I mean.

When I was young, I asked several monks about satori — enlightenment. And about sunyata, the concept often translated as “emptiness.” I asked the same questions to different teachers and received entirely different answers. Not slightly different. Fundamentally different. Answers that didn’t fit together, answers that seemed to cancel each other out.

For a long time, I thought this meant the teachers were speaking from different traditions, different schools of thought. Eventually, I understood something else: they weren’t answering the question. They were responding to me asking it. And what they were each — in their different ways — pointing toward was the moment when I would stop looking for the answer and start noticing that the question itself might be the problem.

Zen is not transmitted through explanation. It is transmitted through the repeated experience of reaching for something and not finding it where you expected it to be. The understanding doesn’t come when you finally receive the right information. It comes, if it comes at all, when something shifts in the way you’re looking.

A solo essay can explain this. A dialogue can enact it.

When Nicholas pushes back, when Catherine reaches and misses, when I find myself unable to give a satisfying answer — that friction, that incompleteness, is not a failure of the format. It is the format doing what explanation alone cannot.

One More Thing I Want to Say Clearly

I am aware that using AI to write in English and using fictional characters to explore real philosophical questions might strike some readers as a kind of deception. Or at minimum, a workaround that undermines authenticity.

I’ve thought about this. I don’t think I can entirely argue against it. Reasonable people might read this project and feel that something is being constructed rather than genuinely encountered.

What I can say is this: everything Takeshi says in these dialogues reflects my actual thinking. Every answer I give is one I believe, or one I’m genuinely uncertain about, which I also believe is worth being honest about.

The characters asking the questions are fictional. The questions themselves are not.

And the AI — it gives me the ability to say what I actually mean, in a language capable of carrying it further than my school English ever could. It is a tool, the way a brush is a tool. What matters is what the brush is being used to draw.

What This Means to Me

I’ve been at this for a long time. Long enough to suspect that the teachers who gave me those contradictory answers about enlightenment might have been, on some level, still figuring it out themselves. Not deceiving me. Just reporting honestly from wherever they stood at that moment.

That suspicion used to unsettle me. Now it feels like the most honest thing about Zen that I know.

This project — the essays, the dialogues, the AI-assisted English, the characters who ask the questions I’ve been asked and the questions I’ve asked myself — is my attempt to build a space where that honesty can happen across a cultural distance that used to feel unbridgeable.

I’m not sure how well it works. I’m not sure Zen can be transmitted this way at all, or whether the attempt itself is the point.

But I keep writing. And that, I suppose, is its own kind of answer.

This project publishes two formats: solo essays and three-character dialogues. If this is the first thing you’ve read here, the rest of the work will make more sense with this context in mind.

Nicholas Caruso and Catherine Marsh are composite fictional characters. Their questions are drawn from real conversations and real confusions — including my own.