Messing up our status quo

Why does Jesus always have to mess things up? I read Matthew 20 today and right after telling a story where the point was that many who were first would be last and vise vesa in the Kingdom of Heaven, James and John's mother comes and wants them to be the two right-hand men in His kingdom. He replies and ends up telling them the same thing (First-last, last-first) and that our way of viewing greatness, is way off. Jesus thinks that greatness has to do with becoming a servant, even a 'slave' to others. He sure does like to turn things on their head. Funny that we still struggle with theses issues 2000 years later, after we've been so Christianized. ;)