The ancient Greek skeptics developed a practice they called 'suspension of judgment' — but their most underappreciated insight wasn't about withholding belief. It was about noticing the difference between first-order questions ('Is this true?') and second-order questions ('What kind of thing am I even evaluating right now?'). Sextus Empiricus, the second-century physician-philosopher, argued that most errors happen before the argument begins — in the silent classification that decides whether to treat something as a factual claim, a value judgment, or a social signal dressed in the clothes of evidence. The practical edge here, especially for anyone building mental models: before you apply your thinking process to a new piece of information, pause on the prior question — what mode of evaluation does this actually call for? A macro thesis requires different machinery than a character read on a management team, which requires different machinery than a base-rate check. Mismatching the tool to the type is where even rigorous thinkers reliably go wrong.

In the last week, which piece of information did you route to the wrong analytical tool — treating a signal about character as a data point, or a data point as a signal about character?

Drawing from Pyrrhonist Skepticism — Sextus Empiricus (Outlines of Pyrrhonism, c. 200 CE)