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For me I think the trick with getting tattoos is to realize that they won’t be “perfect” forever, because styles and preferences change, both mine personally and in general. I think of them more as markers of some period in my life, of some context – this one’s design was drawn by that crazy girl I dated for a while, this one I got in university because of that one class, this one was right after I split up with so and so, this one I got because I read that one book, this one was my friend’s idea, etc. etc.
Some pieces can be timeless and I’ve got a few that I feel fall in that category, but some definitely look like they’re from a different time and were made for a different me, and that’s OK.