When your mental model of a situation is working, you don't notice it — you just see the situation. That invisibility is exactly the problem. The American philosopher John Dewey, in his largely overlooked work on 'inquiry under uncertainty,' argued that our frameworks only become visible to us at the moment they break down — what he called the 'problematic situation.' Until then, the model isn't something we use; it's something we see through, like a lens we've forgotten we're wearing. The leadership trap this creates is subtle: high performers are especially susceptible, because their models break down less often, which means they get fewer involuntary moments of seeing the lens itself. Dewey's prescription was deliberate — engineer small collisions between your model and reality before the market, your team, or your product does it for you. This week, pick one assumption baked into how you run your roadmap or read your team, and actively try to break it in a low-stakes context. Don't wait for the model to fail loudly.

What is a situation you currently feel you understand well — and what would it take for that understanding to be completely wrong?

Drawing from American Pragmatism / Instrumentalism — John Dewey (Logic: The Theory of Inquiry, 1938)