eli_sennesh comments on Siren worlds and the perils of over-optimised search - Less Wrong
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My mind is throwing a type-error on reading your comment.
Liberty could well be like pornography: we know it when we see it, based on probabilistic classification. There might not actually be a formal definition of liberty that includes all actual humans' conceptions of such as special cases, but instead a broad range of classifier parameters defining the variation in where real human beings "draw the line".
The standard LW position (which I think is probably right) is that human brains can be modelled with Turing machines, and if that is so then a Turing machine can in theory do whatever it is we do when we decide that something ls liberty, or pornography.
There is a degree of fuzziness in these words to be sure, but the fact we are having this discussion at all means that we think we understand to some extent what the term means and that we value whatever it is that it refers to. Hence we must in theory be able to get a Turing machine to make the same distinction although it's of course beyond our current computer science or philosophy to do so.