A famous anecdote between Bertrand Russell and Ludwig Wittgenstein was the debate they had in Bertrand's study about whether or not there was a rhinoceros in the room. Bertrand claimed that Wittgenstein would not budge even after hours of debate and looking under tables, desks, chairs, and behind bookshelves, curtains, and paintings. Wittgenstein claimed that it was impossible to know, for certain, that there were no rhinoceroses in the room--no matter how hard you looked. Over time, this anecdote has probably been embellished a bit (Did Bertrand really start looking around the room for a rhinoceros? Did they really debate for hours and hours about this single topic?), and the people in them have become more like archetypes for philosophical ideals rather than simply two people who spent more time thinking about abstract things than is healthy, but for some reason I still love this story.
I imagine a slightly different scenario where Wittgenstein invites Russell over to a specially made studio, say a yellow room, for the purposes of asking him this question again, "Are there any rhinoceroses in the room?" Because this studio was made explicitly for the purposes of asking this question, Russell has to take into consideration that maybe there actually is a rhinoceros in the room--planted by Wittgenstein. Maybe it is a trick question. If Wittgenstein gave Russell the opportunity to bet on either answer, which would he choose? What if the stakes were life and death? Wouldn't you be stuck in a constant loop of doubt thinking that maybe Wittgenstein is a bit more clever than you and has tricked you into thinking that there is or is not a rhinoceros in the room when in fact the opposite is the case? The Princess Bride "which chalice has the poison" problem. If your opponent has a possibility of being smarter than you, is there any way to be certain?
When I listen to the radio in the car there's this certain level of volume that I always like to exceed... it's that level where the music ceases to be simply playing on the radio and suddenly seems to be surrounding you from all angles, you are immersed in the sound.
I think regarding most things involving certainty, there is a similar threshold... where the "certainty" of a certain fact for a while has a distant, third-party-ish, feel to it... it seems true but it doesn't feel true. And then, after a certain amount of thinking has occurred, or a certain amount of investigation, and enough doubt has been wittled away, the volume of the fact becomes loud enough that it surrounds you and feels real. And that, I think more than anything else, is when we stop doubting and when we say we are "certain". Unless you're Wittgenstein. Because, really, this isn't certainty so much as benefit-of-the-doubt combined with some strong pattern-matching and a weird bulb in our heads that goes off when something qualifies as worth adding to our list of assumptions.
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