When the Conversation Goes Blank

I’ll be in the middle of a good conversation—at least, I think it’s good. We’re talking about systems, ideas, strategy. It’s fluid, intelligent, insightful. The person across from me is keeping up, maybe even adding something valuable. Then I bring up something that veers just slightly into the practical—something real.

Scuba diving with someone you discover gets too drunk underwater with high partial pressures of nitrogen. Caving with someone who decided too late they didn’t want to come along. Flying in a pattern when turbulence hits. Sailing through a squall. Riding a motorcycle through unfamiliar terrain. Something lived.

And suddenly… blank.

Their eyes don’t just glaze over—they vanish. The spark is gone, the rhythm breaks. I didn’t ask them to calculate a physics equation or recall legal precedent. I asked them what they’d do if their regulator failed at 80 feet, something I know too well. Or how they felt the first time they looked over the edge of a cave drop. Or how they reacted when the wheels slipped on gravel at 60 miles an hour.

And they have nothing.

It’s not their fault, really. They were trained to think in theory. The world told them education was mastery, and their instructor told them doing it there that way was “doing it right”. That discussion was understanding. That empathy was the same as experience.

But experience leaves marks. It leaves you with a scar on your lip from a rock that hit you in the face when you were trying a new method of leverage for a cave squeeze. A scar on your leg from a preditor bite that you didn’t know you had invaded the territory of until it let you know. A scar on your arm from a small wound on a long passage that became a big problem that far from shore. It forces you to live with the consequences of your own decisions.

And when I talk to someone who doesn’t have those stories—who has knowledge but no scars—I feel the limit of the conversation close like a cliff’s edge.

It’s not that they’re unintelligent. It’s that their intelligence has no gravity. There’s no weight to it. No stories to hang it on. They might know what to say, but not why they’d say it—or how it would actually play out in the wild.

That’s the danger of theoretical. You risk becoming a speaker without substance. An analyst with no field time. A simulator that shuts down when the variables get real.

And increasingly, I’ve seen this accelerated by tools—AI included. People can hold a very convincing conversation because they’ve read the right summaries or used the right systems. But then I ask something simple: “how did you handle X or Y when you were there?”

And their eyes blur… they go blank.

If you don’t have your own stories, you’re standing on borrowed ground. And when the weather changes, it washes away.