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I'm not self-employed, and I once got a surprisingly conservative job (librarian for the county paper) even though I was covered with tattoos. It still matters, but not as much as it used to. Many companies don't care as long as you are behind the scenes and not up front dealing with the public. And besides, that's what turtlenecks and long sleeves are for.
As far as regretting them with age, some of the coolest chicks I've ever seen in tattoo magazines are the really old tattooed grandmas. You're going to look old one day whether you have tattoos or not.
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