As far as im concerned, theres really 3 general ways to play a shot. Safe, risky, and stupid. Where do you draw the line between shots that are risky and shots that are stupid?
It depends on the context. I play Skins every weekend, and if i hit a bad drive, i might go for a shot that i'll only pull off once in 100 times to get myself in birdie position on a hole i know par wont win on. If i was playing stroke play, it would be downright stupid to do that, so i play more conservatively. There is no 'line' that seperates the two, just what you feel the probability of you making a successful shot are, and what the consequences are if you don't make the shot