Well, reading Irina Levontina's article made me realize (yet again) that close cognates or even borrowings can have interestingly different shades of meaning in Russian and English. But since there are often differences within one language across subcultures on such evaluative words, I'm not even sure how representative my own intuitions about "unambitious" are. But I checked some quotations on a dictionary site (http://www.thefreelibrary.com/_/search/Search.aspx?By=0&SearchBy=4&Word=unambitious)
and they mostly seemed to fit my intuition that an unambitious person is quite passive, not really aiming to accomplish anything at all for any reason. So it seems to negate the whole idea of working hard with any goal, not only the goals suggested by "ambitious".
"Enterprising" is good (I think for everyone), and it's pretty close to "ambitious", which for me is somewhat bad. So it needs real research of the sort Irina Levontina did for the Russian usage. (Her article suggests to me that "aggressive" is also different in Russian and English, although I can think of some contexts where "aggressive" is positive in English too.)

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Irina Levontina's claim seems to be that агрессивный is nowadays used by some people as a positive characteristic; but this usage is new, so other people (and I belong to them) haven't yet adopted it and consider it strange and/or striking. For me, агрессивный макияж or агрессивная тактика (whatever it means) is not something I might find pleasant.

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