The One Question I Now Ask AI Before Every Investment Decision

It came from a forty-year-old psychology paper. AI happens to be well-suited to running it. Image generated by AI A few months ago I was about to add to a position I’d already been wrong about twice. The thesis still felt clean. The price looked attractive. The chart had what I wanted to see. My finger was on the buy button and something nagged at me — couldn’t articulate what. So I closed the order, opened Claude, and typed one question. Eleven minutes later, I didn’t make the trade. The question wasn’t clever. It wasn’t proprietary. The technique behind it traces back to a 1989 paper by Deborah Mitchell, Jay Russo, and Nancy Pennington — three psychologists who found that imagining an event had already happened (rather than just imagining it might) made people roughly 30% better at identifying the actual reasons it could go wrong. Almost twenty years later, Gary Klein formalized this into a project planning technique called the pre-mortem, published in Harvard Business Review in Sept