Here comes the Blasphemy Train...Jake, great post. I can tell you put thought into it, which I think is what we are hoping happens here.
To further discuss this point, however, I will stick by my guns...and throw in a touch of good ol' evangelical theology (because I, too, cannot quite get it out of my system). I am more comfortable saying that I could have just as easily been in "God's will" at Geneva or Waynesburg or Spring Arbor, than saying that this I am positive that of all the things in the world I could be doing, I am absolutely positive that I am doing the one thing that I am suppose to, in regard to my occupation. It seems to me that people that try something and then claim "it is not God's will" may be mistaken as well. What leads people to draw these conclusions. If it's not comfortable or easy, does that mean it is not God's will. Or on the other hand, just because it is comfortable or easy, it is God's Will? What do we have to measure God's will in specific circumstances in our lives?
I believe that God will hinder something from us if it is not His will (such as when Paul was hindered from visiting certain churches at specific times), but we should still try to work towards it if we believe it could be God's will. Possibly God's will is just to learn from the process of attempting to discover God's will. Should we be throwing out fleeces for God to show us his will??? Well, that may have just been more examples of what I already had been saying, but I think it relates to Jake's post because I think at the heart is how do we know when we are doing God's will? I am not comfortable with the concept of Christian hedonism (Piper), but I think the things that we are gifted in are often things God wants to use for His purposes. See the life of Henri Nouwen to see someone who went to a place where his gifts were being "under utilized" from an outsider perspective, but the change on the inside with him was immeasurable, which I think illustrates Jake's point as well.
I guess I have gotten all the way down here just to say, the question is not just how to discern God's will for the future, but when were in a situation is comfort the best measuring stick of it??
That's it for now,