Sometimes it can be difficult to discern God's will. I think that is because we often try to "sort things out" using our intellect. We consider pros and cons, the logic of our choices. Basically, we try to rationalize our way to a decision.
This is not a bad thing, however . . .
Any discernment we make must also be a discernment of heart. That is not the same thing as a discernment through emotion. This is not to say that our decisions should be led by our feelings.
Discernment of heart is an opening up of ourselves to God. It is prayer to God, asking for help. It is submission to God's will when we recognize our stony heart is unmoved because our logic is hardening it.
Sometimes difficultly with discernment comes from interior debate in the absence of a desire for God! It is our own logic vs. our personal wants, and that is not the debate that will help us reach a decision!
If you want to know God's will, ask him to remove your wants and your rationale and replace them with the desire to follow Him. Although you may need to patiently wait for a nudge as to what you should do, you can be confident that your personal wants have either been set aside, or are at least in line with God. This will bring you to a good decision.
And that's the second part of discernment. We want to line up our desires with God's plan for our life, rather than try to fit God's plan to ours.