Joe: could it possibly be that you are subconsciously only doing the comfortable photos because you don't want many losers? I think you have to act like you are in a home run contest. You have to think that a base hit, a double or even a triple is the same as a strike out, only home runs count. And no one is tracking your batting average. No one cares how many bad photos you made, even the good ones. Only the ones with potential to be great count.
Take chances. Convince yourself there is nothing wrong with shooting all day and editing everything out. No one cares about your 3th best photo of the day or your 50th best of the year, you shouldn't either. Be thrilled with the day where you busted your *ss all day and got one photo you really like.