I Finally Understand Marshall McLuhan
It only took thirty years.
I run a software company.
Databases. APIs. Reporting engines. Scheduled jobs that wake up at 2:00 a.m. and punish you for your architectural sins.
I also have a philosophy degree.
And I started my working life as the personal assistant to Bill Marshall.
If you don’t know the name: Bill co-founded the Toronto International Film Festival in 1976. Conjured it, really, out of a terrace in Cannes and an argument that Toronto deserved to matter. He was a raconteur, a schemer, a genuine force of Canadian cultural will.
He was also one of the most devoted students of Marshall McLuhan who ever walked the earth.
I was twenty-something. I took notes. I answered phones. I sat in rooms where ideas moved fast and the reference points were dense. Bill talked about McLuhan the way some people talk about oxygen — as something you needed so constantly it barely seemed worth naming.
*The medium is the message.*
I nodded. I filed it. I moved on.
I spent the next three decades building software.
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Enterprise software has a fundamental problem that nobody talks about honestly.
It pretends reality can be finitely encoded.
It cannot.
Every client has different terminology, different workflows, different assumptions, different exceptions. One company’s “completed” means the learner watched the video. Another means they passed the assessment. Another means a manager signed off after a field observation they conducted in a hard hat in a refinery in northern Alberta at minus thirty degrees.
And what do we do?
We write another rule.
`if OntarioHealthcare and LegacyBranch and CompletionDate < ExpiryDate`
Another exception. Another configuration toggle. Another support ticket slowly building an infinite ontology, one semantic argument at a time.
I spent years doing this. Getting better at it. Thinking I understood the problem.
I didn’t understand the problem.
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The understanding came sideways.
I was thinking about report testing — the unglamorous engineering problem of how you verify that a highly configurable reporting system actually works. The traditional instinct is exhaustive: test every report, every permutation, every field, every edge case, every client scenario.
This approaches infinity immediately.
And something shifted.
*We are testing the wrong thing.*
We should not be testing whether the software perfectly understood every client’s business meaning. That problem is infinite. That problem will never be solved. That problem is a category error dressed up as a technical requirement.
We should be testing whether the system preserved supported data structures correctly through every stage of computation.
That problem is finite.
And once I saw it I couldn’t unsee it.
A bitmap preserves every point. A vector preserves the shape.
Enterprise software has been trying to be a bitmap of human meaning since the beginning. It will never be good enough. There are too many pixels in the universe.
The real work is the geometry.
---
I started thinking about why large language models work at all.
Not in the press release sense. In the actual sense.
They’re trained on tokens. Fragments. Individually, they mean almost nothing. Statistically, they’re noise with punctuation.
But something emerges. Something that can reason, connect, generate, surprise.
It doesn’t emerge from the tokens.
It emerges from the relationships between them. The topology. The latent geometry of meaning compressed across billions of examples into something that behaves, improbably, like understanding.
Intelligence is in the shape.
Not the dots.
And I sat with that for a while. And then it hit me all at once, decades late, slightly embarrassing in its tardiness:
*The medium is the message.*
Bill said this to me. Bill said this constantly. I nodded and filed it and moved on, because I was twenty-something and I thought I knew what it meant and I did not know what it meant at all.
It doesn’t mean the delivery mechanism is more important than the content.
It means the structure is where the meaning lives.
It means a television doesn’t just carry messages — it *is* a message, one that rewires how you process everything that comes through it. It means the shape of the container changes the shape of the thought.
Tokens are the content. Vectors are the medium. And the medium — the geometry of relationships baked into those billions of parameters — is what actually thinks.
McLuhan wasn’t being clever. He was describing something foundational about how meaning moves through systems. I just needed to build a few of those systems from scratch before I could hear it.
---
I think about Bill sometimes when I’m deep in an architectural decision.
He died in 2017. New Year’s Day. Which felt, to people who knew him, like an act of theatrical timing he probably would have appreciated.
He built something that remade Canadian culture, and he did it by understanding that the festival itself — the shape of the gathering, the public nature of it, the fact that it was for everyone and not just insiders — was not just the vehicle for the films.
It was the message.
Toronto became a film city not because of which movies played. Because of what kind of space Bill and Dusty and Henk built around the watching.
The medium.
I was twenty-something in those rooms. I didn’t know I was learning the most important thing I would ever learn about software architecture.
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The hardest problems in software are no longer computational.
They are ontological.
AI is making raw computation abundant. Which means the bottleneck shifts upward, into meaning. Into the question of what we are actually trying to preserve, and what shape that thing has, and whether we even know the difference between the pixels and the geometry.
The programmers who thrive in the next era won’t just write syntax.
They’ll be ontology designers. Shape-makers. People who understand that you are not encoding reality — you are constructing a stable approximation of it, and the approximation’s structure is where the truth lives or dies.
That turns out to be philosophy.
It also turns out to be what a loud, brilliant, McLuhan-quoting Scotsman was trying to tell a twenty-year-old who was too busy taking notes to actually listen.
I’m listening now, Bill.
Thirty years late.
But I finally got it.
Even if I still don’t understand the point of Robbie Burns Day.
But I’m young.