maia comments on Argument by lexical overloading, or, Don't cut your wants with shoulds - Less Wrong
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When I have something that I want to do, then categorize it as something I "should" do, I generally want to do it less. Attaching the sense of moral obligation makes me forget that the original reason I put it in that bucket was because it was something I would actually enjoy doing. This seems to line up with your hypothesis that people conflate these two and cause problems for themselves. But this also seems to imply that there is, in fact, a relevant difference between "want" and "should," at least in one's own head.
I suspect you have cause and effect reversed there. If you want to do something a lot, you don't categorize it as a "should" you just do it. Thus the things you categorize as "should" are the things you want to do not quiet as much.