The point of complex debates is not to prove your side right and the other wrong. Smart people make this mistake most often, and end up losing before they ever get started. The point of complex debate is always seduction: winning-over rather than winning. You do this not through logic or even novel insight, but by demonstrating a more fertile way of thinking. One that promises to throw up an indefinitely extended stream of surprises within an ever-widening scope.
Such intellectual seduction settles the original issue not by establishing an unassailable position around it, but by turning it into a portal to a hidden universe of thought. You cannot win over everybody, only the adventurous. But winning over an adventurous minority that joins you in passing through a portal, on a journey of discovery is enough. It allows you to eventually overwhelm those who prefer to plant a flag on a conquered hill of browbeaten minds, and sit around by it awarding each other medals of honor. Because adventures tend to yield riches that make whatever was originally being contested seem worthless by comparison.
There is a role for logic within a seduction: but it isn’t to dismantle arguments. The role of logic is to undermine seduction efforts that offer more predictable increase of pleasure and decrease of pain, rather than unpredictable adventure and surprisal. To show such false seductions to be simple arrangements of carrots and sticks. That is the larger purpose of fallacy-spotting in particular: demonstrating the poverty of a promised land. There is also a role for novel insight, but it isn’t to surprise the opponent in the sense of a clever, “gotcha” reframing judo move. The role of insight — a “seeing into” — is to expose limiting assumptions and motivations that people may want to voluntarily abandon upon recognition.
In other words, logic is for warning people against simple temptations and fears, insight is for liberating them from self-limiting patterns of thought, and visibly modeled fertility of thought is for seducing them onto intellectually adventurous paths. There is nothing adversarial about any of these motives. But that does not mean they will not be resisted, because taken together they are an invitation to give up power and control, which is usually the scariest thing humans can attempt to do.
And perhaps most surprisingly, this kind of seduction does not take much skill, wisdom-of-age or intellectual depth. I’ve seen young, inexperienced and rather shallow people do it very well. All it takes is giving up the desire to “win” and the innate openness to experience that allows you to signal a readiness for adventure without even being conscious of it. Even children can do it. In fact children are often really good at seducing and winning over much smarter adults.
So next time you find yourself in a complex debate, decide what your intent is: to seduce through a portal, or to plant a flag.
Endnote: I originally posted this on Facebook. Two interesting links were posted in the comments: a Farnam Street compilation of resources on winning arguments (HT Mick Costigan), and a link to an online translation of Schopenhauer’s Die Kunst, Recht zu behalten (The Art Of Controversy, HT Jean-Luc Delatre).