SilasBarta comments on Best articles to link to when introducing someone to Less Wrong? - Less Wrong Discussion
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I suggest Truly Part of You, as it has the highest ratio of insight to length. My only concern is that the jargon is uses may violate your first criterion. However, the jargon is explained sufficiently where it's used in TPoY; it's only a problem if seeing such terms is intimidating to your friend. For example, there's the passage
I didn't know about gensyms at the time (and still don't have mastery of the concept), but you can see that in context it makes the point clear.