I think one aspect of how to deal with the possibility of failure is how to deal with the possibility of accidental harm / downside risk—i.e., the possibility that an action would make the world worse in some ways (which may or may not outweigh the positive effects). Here is a collection of sources on that topic which people might find useful.
(But this is of course not a complete answer to your question, since the possibility of failure is not always about downside risk. It can also be about actions turning out to be more “expensive” (e.g., time-consuming) than one would like, actions turning out to achieve their intended objectives to a lesser extent than one expected/hoped, or other actions turning out to have probably been better choices than the action one took.)
I think one aspect of how to deal with the possibility of failure is how to deal with the possibility of accidental harm / downside risk—i.e., the possibility that an action would make the world worse in some ways (which may or may not outweigh the positive effects). Here is a collection of sources on that topic which people might find useful.
(But this is of course not a complete answer to your question, since the possibility of failure is not always about downside risk. It can also be about actions turning out to be more “expensive” (e.g., time-consuming) than one would like, actions turning out to achieve their intended objectives to a lesser extent than one expected/hoped, or other actions turning out to have probably been better choices than the action one took.)