Go to any Christian bookstore (or browse one online) and you will find many titles concerning the issue of finding God’s will. It can be overwhelming, especially since there are some crazy ideas out there about how this should be done. Who should I marry? What job should I take? Where should I go to school? Etc.
If you are wanting to read a book on the topic, let me recommend a few:
1. Decision Making God’s Way, Gary T. Meadors
2. Decision Making and the Will of God, Garry Friesen
3. Just Do Something, Kevin DeYoung
All of the above are great books and biblically informed. However, if you do not want to read a book, you can just ponder the words of Augustine:
“Love God and do whatever you please.”
You should end up in the same place.
Theologically Speaking 
I think why it gets dicey is because our hearts are deceitfully wicked and people of God know that ,so they search to be sure that the affections they have are truly for God and not displaced and focussed on self. I know that is why I search. In an effort to know that what I desire is in line with God’s good and perfect will. To worship and honor Him in the way that would delight Him. 🙂