Ask yourself this: If I played this same situation 100 times going for it and 100 times playing safe and counted the scores for each, which would score better?
If I go for it, will I make enough pars to offset the double bogeys when I don't pull it off?
In my experience, if you're asking yourself this question the answer is usually to play it safe and get those strokes back elsewhere.
I went out the other day to our toughest course and only played the half dozen holes that give me the most trouble. I threw every shot I know on each hole multiple times trying to find the best way to minimize the chance of a big number. One of them I've decided to play for bogey from the tee.
A stroke is a stroke. Whether it is a birdie or a bogey that you didn't let become a double bogey, same value.
Yeah, there's a nasty par 5 near me. If I go for a 4 or a 5, I usually end up with an 8. If I play for the 6, I get the 6.