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I'm seeking a word or phrase that conveys a person's heightened caution or risk aversion regarding a task that stems from prior failure. Something like "gun shy," but perhaps more specific?

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"Once bitten, twice shy."

"Older and (or but) wiser."

ChrisW
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  • The 'once bitten, twice shy' saying, apart from being elliptical (not a sentence), uses 'once' in the 'wrong' position. It's in the 'on a previous occasion' position but carries the 'a single time' sense. But 'bitten once ...' just wouldn't sound the same. – Edwin Ashworth Apr 05 '15 at 13:34
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    It implies "previous occasion" and "single occasion". – ChrisW Apr 05 '15 at 13:36
  • No; the 'bitten' references the past. 'Once there / Once we are there, we can rest' obviously doesn't. // It's an unusual usage is all that I'm saying. English is awash with them. – Edwin Ashworth Apr 05 '15 at 14:02
  • The saying puns between the two separate senses of once. – Brian Donovan Apr 05 '15 at 14:06
  • @EdwinAshworth - Regardless of how "improper" it is, "once bitten, twice shy" is a very familiar idiom in (US) English. It perhaps comes closest to the OP's desired meaning, but is a bit wordier than some alternatives. – Hot Licks Apr 05 '15 at 14:27
  • @Hot Licks I upvoted it. I implied that it was acceptable (But 'bitten once ...' just wouldn't sound the same. // It's an unusual usage is all that I'm saying. English is awash with them') Unusual in the sense that the positioning of 'once' is idiosyncratic. It's a common usage over here too. – Edwin Ashworth Apr 05 '15 at 14:34
  • "It's an unusual usage is all that I'm saying" - Perhaps you're right. Maybe it's synonymous with 'when': "when bitten, shy" or "one we're done, we'll move on". I might not be good at spotting strangeness, because I never studied/learned English grammar, usual or unusual is whatever I've heard in the past (if you know what I mean). For example "Christ is risen" didn't sound a bit unusual to me. – ChrisW Apr 05 '15 at 14:38
  • The phrase also (IMO) implies that the shyness will last twice as long or occur twice as often as the original negative stimulus. (related example) – ChrisW Apr 05 '15 at 14:42
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Circumspect - Unwilling to take risks as there may be danger involved.

Eg. The batsman was very circumspect in playing deliveries outside off-stump, having got away by edging a few early on in his innings. (You'd hear a lot of this in Cricket commentary.)