I suspect our inferential distance may be too high for agreement at this time. But, to clarify on one point
What meanings, and where do you think I'm using each?
You said "I frequently do things that, on the whole, I think I shouldn't do. Often while actually thinking, in so many words, 'I really shouldn't be doing this.'". This is a plausible rephrasing of "I frequently do things that I generally disapprove of and perhaps would prefer if people in general wouldn't do them, also I may sometimes feel guilty about doing things I disapprove of, especially if they're generally socially disapproved of in my culture, subculture, or social group. When I do these things, I think the words 'I shouldn't do this', by which I don't literally mean that I shouldn't do this, but that doing this is 'boo!'/'ugh'/low-status/seems to conflict with things I approve of/would not happen in a world I'd prefer to live in."
I suspect our inferential distance may be too high for agreement at this time.
Oh. Would you care to say more?
(meanings of "should")
So, your proposed expansion of my second "should": (1) on what grounds do you think it likely that I mean that, and (2) is it actually different from your proposed expansion of the first? ("Seems to conflict with things I approve of" and "would not happen in a world I'd prefer to live in" are not far from "things that I generally disapprove of" and "perhaps would pre...
Neal Stephenson's The Diamond Age takes place several decades in the future and this conversation is looking back on the present day:
I'm not sure if I agree with this characterization of the current political climate; in any case, that's not the point I'm interested in. I'm also not interested in moral relativism.
But the passage does point out a flaw which I recognize in myself: a preference for consistency over actually doing the right thing. I place a lot of stock--as I think many here do--on self-consistency. After all, clearly any moral code which is inconsistent is wrong. But dismissing a moral code for inconsistency or a person for hypocrisy is lazy. Morality is hard. It's easy to get a warm glow from the nice self-consistency of your own principles and mistake this for actually being right.
Placing too much emphasis on consistency led me to at least one embarrassing failure. I decided that no one who ate meat could be taken seriously when discussing animal rights: killing animals because they taste good seems completely inconsistent with placing any value on their lives. Furthermore, I myself ignored the whole concept of animal rights because I eat meat, so that it would be inconsistent for me to assign animals any rights. Consistency between my moral principles and my actions--not being a hypocrite--was more important to me than actually figuring out what the correct moral principles were.
To generalize: holding high moral ideals is going to produce cognitive dissonance when you are not able to live up to those ideals. It is always tempting--for me at least--to resolve this dissonance by backing down from those high ideals. An alternative we might try is to be more comfortable with hypocrisy.
Related: Self-deception: Hypocrisy or Akrasia?