I wish it were this easy, to pick the least traveled road. But sometimes, as a friend ask me " why does it have to be this big wrong or right decision?" They went on to tell me that God spoke to men of old in the Bible just a couple of times in their whole lives. That call he gave that one time in their lives, was enough. Sometimes God won't hold your hand through every situation. It's not that he isn't there, but it is like he is saying I told you to "go" way back when, so nothing has changed. Sometimes I want to ask him, is this ok? if I go here? or maybe here? no wait... I think I feel you more here. God called me to "go" a long time ago. Nothing has changed.
Don't get me wrong, I think we should pray about everything, but on the other hand God leaves things up to us sometimes. We have to be listening the whole time to know when those times are and are not.