nigerweiss comments on Philosophy Needs to Trust Your Rationality Even Though It Shouldn't - LessWrong
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There's a key distinction that I feel you may be glossing over here. In the case of the stick question, there is an extremely high probability that you and the person you're talking to, though you may not be using exactly the same definitions, are using definitions that are closely enough entangled with observable features of the world be broadly isomorphic.
In other words, there is a good chance that, without either of you adjusting your definitions, you and the neurotypical human you're talking to are likely to be able to come up with some answer that both of you will find satisfying, and will allow you to meaningfully predict future experiences.
With the three examples I raised, this isn't the case. There are a host of different definitions, which are not closely entangled with simple, observable features of the world. As such, even if you and the person you're talking to have similar life experiences, there is no guarantee that you will come to the same conclusions, because your definitions are likely to be personal, and the outcome of the question depends heavily upon those definitions.
Furthermore, in the three cases I mentioned, unlike the stick, if you hold a given position, it's not at all clear what evidence could persuade you to change your mind, for many possible (and common!) positions. This is a telltale sign of a confused question.
I believe that at least two of those definitions could be something like, "what kinds of humans would consider this art ?", or "will machines ever pass the Turing test". These questions are about human actions which express human thoughts, and are indeed observable features of the world. I do agree that there are many other, more personal definitions that are of little use.