Wei_Dai comments on Outside View(s) and MIRI's FAI Endgame - Less Wrong
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I can't provide a single example because it depends on the FAI design. I think multiple design approaches are possible but each involves its own hard philosophical problems.
At least one hard problem here is, at you point out, how to formalize "thought longer", or perhaps "remain in control". Obviously an AGI will inevitably influence the options we have and the choices we end up making, so what does "remain in control" mean? I don't understand your last point here, that "we must face these with or without machine intelligence". If people weren't trying to build AGI and thereby forcing us to solve these kinds of problems before they succeed, we'd have much more time to work on them and hence a much better chance of getting the answers right.
If we look at other empirical though hard-to-test questions (e.g., what security holes exist in this program) I don't see much reason to be optimistic either. What examples are you thinking of, that makes you say "these don't seem to be the kinds of questions that have proved challenging"?
I'm suspecting that even the disagreement we're current discussing isn't the most important one between us, and I'm still trying to figure out how to express what I think may be the most important disagreement. Since we'll be meeting soon for the decision theory workshop, maybe we'll get a chance to talk about it in person.
If you get anywhere, please share your conclusions here.