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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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    I think "gun-shy" is probably about as specific as you can get in a terse phrase. – Hot Licks Apr 5 '15 at 14:24
  • risk averse or gun shy – Drew Apr 5 '15 at 16:26
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"Once bitten, twice shy."

"Older and (or but) wiser."

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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 5 '15 at 13:34
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    It implies "previous occasion" and "single occasion". – ChrisW Apr 5 '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 5 '15 at 14:02
  • The saying puns between the two separate senses of once. – Brian Donovan Apr 5 '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 5 '15 at 14:27
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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.)

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  • We could also say the batsman was circumspect in his approach given his failure in the previous innings. – Andy Semyonov Apr 5 '15 at 14:10

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