The will of God is a tough nut to crack, or is it?

Dear all,

I was working on a post about sheep vs. our intellect, and the more I got to thinking about the will of God and how to interpret it, the more difficult it became. I started out talking about how the will of God is vague when it comes to instructions for our everyday lives, issuing out instead broader strokes for how to live an ethical life but not specific about what to do in our careers, marriage, our finances, et cetera.
Then I thought perhaps I'm wrong. Perhaps I'm avoiding the idea that really I and all of us have been called to surrender all our money, our ideas of job security, healthcare, comfort and careers, and live like Christ did, in voluntary poverty, serving the needy. And that's a scary thought.
I remember trying to read some of Thomas Merton's New Seeds of Contemplation, or worse Thomas A Kempis' The Imitation of Christ, and I found myself often not being able to take it because there was such a rejection, bordering on loathing, of the self and the joys of this world, versus the joy of Christ. I LIKE myself. I LIKE my desires. I LIKE my goals, my ambitions, my passions for things other than God. And for these texts to call me to shed that existence is a hard pill to swallow.
Sometimes I feel like you can't commit yourself to following Christ's words to the letter while also going after a successful career and raise a healthy secure family. Christ rejected his family and lived his life as a nomad: I do not long for that existence.
So to what degree are we called to follow absolutely in his and the apostles' footsteps, and to what degree are we called to do as they say, but not as they do? And do I have less faith if I say "No, I'm not going to give all my possessions to the poor and go around with only a robe and walking stick, thank you very much"? Am I ignoring the will of God? Am I a lost sheep, no longer following my shepherd?
All I can think of are questions for now. There's a book called "The Year of Living Biblically" which seems to apply to my predicament. I think I'll look it up.
Next up...a look at Suze Orman's teachings vs. the Gospels on money.