This humility may, in fact, be one of Jesus' toughest teachings for anyone to follow. Humanity has, since long before Jesus came along, tended to develop pecking orders and hierarchies. I mean, he says right in Matt 23:9, "9 And call no one your father on earth, for you have one Father—the one in heaven." But what title is given priests in the oldest Christian traditions?
OTOH, without any social structure, of which titles are a part, you end up with a kind of anarchic community that really isn't going to sustain or grow beyond a certain, very small, size. Perhaps that's ultimately a good thing, but I doubt Christianity as we know it would exist without the structure that the Church brought to it. It would have splintered even earlier and maybe even to the point where there was no "Christianity" beyond scattered house churches and communities. A cult rather than a religion.
So, how do you have a sustainable community structure without hierarchy? How do you encourage humility while still having some kind of order? It's been tried many times politically and socially without much success. The US got rid of hereditary power only to have elected power become just as hierarchical in its own way. In the end, those who want greatness find a way to put themselves on top, don't they? And if no one wants to be on top, to be the one in charge, then nothing gets done, or so it seems to me. Servant leadership gets talked about a lot, but somehow the leader still has more privilege and power than the follower even in many organizations that profess it.