The hardest shot in the world is the pitch back to the fairway. Take your chances when the opportunity presents itself. If you feel a reasonable chance to make a play at the green from the trees, go for it. You need the confidence to hit the shot. Without it, make the prudent play.
Golf is tough enough and perfect shots at the perfect time are far too rare.
Stop playing for the perfect shot. Nine time sout of 10, you should take your medicine and make the safe play. Nobody likes to hit the ball off the planet, but keep your score in mind. Find a route that eliminates the big numbers and still gives you a chance to save par or make bogey at worse. Successful course management is a guaranteed way to bring you lower scores.