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Is there a name for that annoyed (yet slightly ashamed for being annoyed) feeling you get when the new and improved way of doing something breaks for some reason and you have to go back to doing it the old way, which worked perfectly well for many years and wasn't really that bad?

  • Captain hindsight would yell: "If it ain't broken, don't fix it!" – nl-x Jun 14 '14 at 9:15
  • If you felt surprise rather than dismay and shame, taken aback would be good :) – James Waldby - jwpat7 Jun 14 '14 at 19:33
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Assuming the key features of the feeling are the three given below, you'd be chagrined...

chagrin - a feeling of vexation, marked by disappointment or humiliation

In my experience, when people are described as chagrined it's very often because their bright idea for a new/better way to do something didn't work out, so they've had to admit humiliating defeat. And revert to the old way - bringing even more humiliation, since they were probably complaining at length about the old way before they optimistically tried something new against all advice.

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    This is close, but doesn't capture the feeling I was intending which is a bit of shame at even feeling annoyed given that I wasn't complaining about the old way. So "chagrinned but ashamed of it". – Andrew Sterian Jun 13 '14 at 23:50
  • @Andrew: You have me at a loss. You want a word that means a feeling of vexation, marked by disappointment or shame, but not marked by humiliation? Do you want jam on it too? I can't closevote as Too Localised, but I think your request is now too narrow to justify my upvote, which I've now withdrawn. – FumbleFingers Jun 13 '14 at 23:56
  • I'll upvote your answer anyway. – Jim Jun 14 '14 at 0:13
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    @Jim: Top man! We'll redefine the question as what we want it to mean, regardless of OP's strictures! Actually, I'm struggling to understand how humiliation differs from shame in any context, let alone this specific one. – FumbleFingers Jun 14 '14 at 0:15
  • The (admittedly nitpicky) difference between the humiliation built-in to the definition of chagrin vs. the shame I am requiring is that the humiliation is something that is done TO you, vs. the shame is something you feel for your own thoughts. If a teacher tells me that the answer I just gave is stupid, I would be chagrinned because of my humiliation in public. – Andrew Sterian Jun 14 '14 at 0:19
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In such a case (and in some others that are different from yours)

it's back to the drawing board.

or

it's back to square one.

While some may say that these don't name a 'feeling', I do believe these expressions strongly imply the negative feeling you describe. Evidence: "Let's fall back to the original plan" means much the same thing in practical terms, but has no negative valence.

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