I was just contemplating this very questions last week. I'm transferring the contents of my old EHD to a new one, and there is a lot of stuff I don't want to take with me moving forward.
I really like Marie Kondo's idea of being surrounded by the things you love, and I don't want to have to sort through a lot of stuff I don't love just to find the things that I do. But like any good hoarder, I worry that "someday I'll need it..."
So I guess that technically I'm not deleting old stuff, but I'm not necessarily keeping it, either.
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