Does Jesus -- unlike Pharisees and philosophers -- require His disciples to sacrifice our "digital abstraction of self" in order to confront the emotional distress that lurks beneath?

My impression, partly from the poem you shared but which I suspect is a gross misunderstanding on my part, is that you think that Jesus is demanding that we daily re-live the emotional distress of facing the death of our self.

Your impression is essentially correct, though perhaps not _quite_ as bad as you probably think...