From “Falling Upward: A Spirituality for the Two Halves of Life” by Richard Rohr
Because none of us desire a downward path to growth through imperfection, seek it, or even suspect it, we have to get the message with the authority of a “divine revelation.” So Jesus makes it into a central axiom: the “last” really do have a head start in moving toward “first.” and those who spend too much time trying to be “first” will never get there. Jesus says this clearly in several places and in numerous parables, although those of us still on the first journey just cannot hear this. It has been considered mere religious fluff, as most of Western history has made rather clear. Our resistance to the message is so great that it could be called outright denial, even among sincere Christians. The human ego prefers anything, just about anything, to falling or changing or dying. The ego is that part of you that loves the status quo, even when it is not working. It attaches to past and present, and fears the future.
When you are in the first half of life, you cannot see any kind of failing or dying as even possible, much less as necessary or good. (Those who have never gone up, like the poor and the marginalized, may actually have a spiritual head start, according to Jesus!) But normally we need a few good successes to give us some ego structure and self-confidence, and to get us going.