Dispatches from the AI Trenches: The Illusion of Control

As I think you know, I earn my keep in property management. Most of my day-to-day responsibilities revolve around leasing space and keeping commercial tenants happy—and paying the rent. I’ve been doing this for 30 years.

Last week, something happened that I’ve never seen before. Twice.

I sent a draft lease to two different tenants. In both cases, it came back within an hour with detailed commentary and questions.

That shouldn’t be possible.

Our commercial lease isn’t standard. It’s fifty pages long, built and refined over decades by the owner of our company, who is a lawyer. It’s dense. It’s thorough. It has, at times, scared off prospective tenants simply because of its complexity. There is no realistic way either of these tenants read and analyzed it in under an hour.

More to the point, these weren’t large, sophisticated tenants. They were renting small spaces on relatively short terms. In my experience, tenants like this don’t hire lawyers. The financial commitment isn’t large enough to justify it. Typically, they skim—or don’t read at all—and ask me to flag the key financial clauses before signing.

And when lawyers do get involved, negotiations stretch into weeks.

But this was different. The comments came back quickly, and more interestingly, they looked similar—in tone, structure, even in the types of issues raised.

I knew immediately what I was dealing with: AI.

Both tenants had almost certainly run the lease through ChatGPT or Claude and received a clean set of concerns and questions in return.

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Something else happened this week.

We had our annual meeting with partners to review property performance, approve last year’s financial statements, and sign off on this year’s budget (late, as usual).

The owner of our company typically gets nervous before these meetings. He’s meticulous with numbers and tends to revise reports right up to the last minute.

That said, we run a fairly tight operation. The properties perform quite well. Our partners trust us. These meetings are usually perfunctory—more social than substantive. We present, they approve, everyone leaves with a cheque. It’s always been that way.

This year was different.

His anxiety wasn’t just elevated—it was bordering on paranoia. I couldn’t understand it at first.

Then it clicked: AI.

He’s worried the partners—who historically haven’t read much beyond the bottom line—are going to run our reports through AI, giving them the tools, or at least the language, to question our decisions, our assumptions, maybe even our competence.

For thirty years, a certain balance held. Leases were too long to dissect quickly. Financial reports were too dense to interrogate casually. Most people didn’t have the time, expertise, or incentive to dig deeply. That balance is gone.

Now, anyone can upload a fifty-page lease and get a list of risks in minutes. Anyone can run financials through a model and generate discrepancies.

Whether those questions are always insightful is almost beside the point.

They now exist and present a challenge.

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These two small stories capture something larger happening in the workplace.

On one hand, AI empowers. It gives people access to information that once required hiring expertise. It allows them to ask better questions, to feel more protected, more in control.

On the other hand, it quietly displaces the very expertise it imitates.

In my own experience, when clients came back with AI-generated questions, there was often no real follow-up. The questions sounded sophisticated, but they weren’t grounded in understanding. When I answered them, the conversation ended quickly. The space that would normally be filled by experience—judgment, sequencing, knowing what matters next—was simply empty.

What AI provides is not expertise, but the appearance of it. It allows people to perform knowledge without possessing it.

And for now, that may be enough. It saves money. It creates the feeling of control.

But scraping a database is no substitute for experience.

The risk is that we trade away expertise for its simulation, only to rediscover—too late—that knowing what to ask is not the same as knowing what to do.

The real cost will not just be job loss, but the erosion of judgment, the thinning out of skill, and a quiet loss of dignity in work itself.

Mother Earth

I'm thinking about the term Mother Earth. Not in the flaky, Gaia, New Age woo-woo metaphoric sense. In the sense that the term is literally true. 

We have literally emerged out of the Earth. We are made from the very chemical compounds that formed with the Earth's creation. We have been shaped and developed along with the evolutionary timeline of the planet and in response to it. Life emerged from its material, its energies, its climate, its forces. What we call “life” is not something placed on top of the Earth. It is something the Earth does.

Nerve by nerve, instinct by instinct, perception by perception, we are calibrated to the Earth's rhythms: light and dark, season and scarcity, sound and silence. Even things that seem esotheric, our sense of beauty for example, is not arbitrary. It's recognition of the conditions that made us possible.

We don't live in nature, we are nature. It's why when you go for a walk in the forest something inside you settles. The noise in your head drops a notch. That response isn’t spiritual, it’s biological. What some researchers call the Biophilia Hypothesis: we feel at home in the conditions that made us.

Think of the opposite, how it feels to live in the city. Towers of glass and steel, lengths of asphalt and endless right angles. Artificial light overriding circadian rhythm. Environments designed not for human coherence, but for efficiency, extraction, and control. It produces anxiety, alienation, and numbness—as though it were a malfunction of the individual rather than a predictable response to an unnatural environment.

We like to imagine that human ingenuity has freed us from dependence on the Earth. That we can engineer substitutes, optimize inputs, transcend limits. But everything we eat is still a variation on a single theme: plants, animals, fungi. All of it grown, fed, or assembled from the same planetary chemistry. We do not create nourishment. We reorganize it.

The illusion of independence is made possible by layers of abstraction. And the more layers there are, the more we forget where things actually come from, and the more distant we become from who we are.

The further we push into environments that ignore this fact, the more we should expect not just ecological breakdown, but psychological and social fragmentation as well. 

Every harm we do to the environment, the more we bury our heads under digital covers, the more we lose a sense of ourselves. 

This summer, I'm going for more walks in the woods.