Righteousness has more to do with judgment than it does with personal morality. Judgment is an attribute of God. We are all gods in embryo and one of the purposes of the nursery school which we all are attending is to “learn how to be gods ourselves”, as Joseph Smith put it. We learn judgment by exercising judgment. i.e. making decisions.
What is God’s will? God’s will is not to much what we decide as THAT we decide. If our decision has undesirable consequences, we can always repent and decide again. If our decision has desirable consequences, we can continue to pursue that course. That is God’s will. There is no guesswork. There is only an application of eternal principle. The only times eternal principles don’t work is when we fail to apply them.
The Doctrine & Covenants has clearly spelled out how we may discern the will of God. Sometimes, its obvious. Sometimes, we have to think about it or consult others. Sometimes, we have to plunge into the darkness and “guess”. But, there’s no harm in guessing as long as you know you are guessing, and you are prepared to take responsibility for the consequences, whatever they may be.
Here is a good, workable definition of humility: know where you are on the path and act accordingly.