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Neat!

I'd consider tweaking the selection algorithm. Especially if word gets out you may be looking at a "frist psot" situation pretty quickly. Some human selection is probably unavoidable if you're going to avoid that. (Or spamming.) But big thumbs up on the core idea.

A fine stream of mediocrity.
Yes, though I find that answering this questionnaire can be an interesting personal tool, it doesn't mean that reading answers from random people can be interesting. Actually even Proust's answers are rather bland, which contrasts starkly with the deep psychology in his books.
I think a hacker Questionnaire should be more appropriate here. But this is not new, for example there is "my road to Lisp" that explains the motivation and context when learning Lisp.

HN is like an evolving Questionnaire filled with the technology news that shape the future of technology and start-ups.

Thanks for the mention (I made mechanical proust) - I agree that there's a lot of dross, but some responses are poignant, funny or interesting. It would be interesting to play around w/ how questions get posed.