So how do you break the guilt/obligation/failure cycle?
I’m of the mind that you have to come to a place in your hunger for or relationship with a loving Father where you realize that guilt will not lead you to the life of the Father. Most of us were trained with it, however, and until you know how God and his Gospel works, guilt is an easy thing to follow because it preys on our fears. When I’m uncertain what God’s demeanor is, it seems better just to do what we think we should and hope we get brownie points for it, than to actually break it’s cycle.
I don’t know how to conquer it except to ignore it, which is way easier said than done, but guilt doesn’t last just for a few seconds; it gets stronger and stronger the longer you ignore it until it just seems best to go ahead and follow it to get out from under the guilt and fear.
So ignoring it takes a bit of doing and a whole lot of relationship, where God is in it with you to untangle its talons from your flesh so that you can begin to live out of love, which is where real transformation begins.