Discerning God's will would be so much easier if the choices were between good and bad, black and white, Godly and ungodly. But rarely are choices that simple. Most of the time, when you're in the midst of trying to discern God's will, there seem to be ten different choices and all of them have some good and bad in them. All of them could be God's will. And all of them could be terrible decisions. The only way to know for sure is by hindsight. But that's never helpful when you're right in the thick of things trying to discern.
This doesn't mean that there is no hope and that the entire will of God thing is just chance.
Look at God's word for guidance. God will will not contradict what has already been revealed in God's word.
Look at God's character. God's will will not contradict God's character and nature as revealed in God's word.
Pray and fast. God will give you guidance and direction. And when you are praying and fasting, don't forget to listen. If you want to hear God's guidance you must listen.