We live in a context of stratification where much of society is ordered into separate layers or castes. We are identified as upper class, middle class, or lower class. Our language reflects this up/down (superior/inferior) paradigm. We want to be at the top of the heap, climb the ladder of success, break through the glass ceiling, be king of the hill. This same kind of thinking seeps into our theology. When we talk about humility, we think mostly think in terms of lowering ourselves, willfully participating in downward mobility. This type of up/down language is certainly present in biblical texts (James 4:10 is one example), but I believe that the kind of humility we see in Jesus requires that we step outside of a strictly up/down paradigm. Instead of viewing humility as getting down low or stepping down a notch on the ladder of society, perhaps it is more helpful to think in terms of proximity and movement.
Jesuit theologian, James Keenan, notes that virtues and vices are not really opposites. Instead, virtues go against two extremes. So, in the case of humility, it means avoiding thinking too highly of oneself (pride) and avoiding thinking too lowly of oneself (self-deprecation). Therefore, humility is knowing our place in the community, and if we are out of place, moving. In other words, humility, like love, is always relational. It draws us close to others. We see this language of proximity every time Jesus proclaimed that the kingdom of God/heaven was near, close, at hand. Because God had come to the world as Jesus (movement), the kingdom was close (proximity).
Let's think for a moment about Jesus's position in society. Was he a servant or a king? An outcast or the chosen messiah? A despised rebel or a revered teacher? A suffering victim or a powerful overcomer? He was all of the above, depending on the context. We often think of Jesus as meek and humble during his time on earth and then as the just, Almighty King in the full expression of the kingdom of God. And yet, in the throne scene in Revelation, the writer identifies the one on the throne as the Lamb that was slain. For all eternity, we have a God who is marked by sacrifice and humility. When we see humility as movement and proximity, the various roles and relationships we observe in the life of Jesus (and the multiple aspects of the character of YHWH) cease to be in tension. Humility is not just about getting lower; it is about moving closer to the other.
A quick look at two stories will help to illustrate this. In Luke 7, Jesus is at the home of a Pharisee for a meal when a woman of ill repute bursts in and anoints his feet. She begins to cry, wiping his feet and kissing them. How's that for socially awkward? The Pharisee host and his friends are repulsed by the woman's intimate act and offended by Jesus's apparent lack of discernment. Jesus responds by pointing out that the host, Simon the Pharisee, offered Jesus no water for washing his dusty feet, no kiss of greeting, and no oil for freshening up. In effect, Jesus is saying that the woman of ill repute is a better host than the Pharisee. In a culture which highly values hospitality, that's a slap in the face. This woman is a despised outsider to the Jewish religious elite, but her bold expression of intimacy, her scandalous outpouring of affection and worship, moves her closer to Jesus. In contrast, Simon the Pharisee distances himself from them both.
The second story, found in Mark 7, is even more socially awkward, if that is possible. After spending time debating with the scribes and Pharisees about laws and purity, Jesus and his followers head out to Tyre in the region of Phoenicia, a busy and prosperous port city which is a centre for Greek culture. Shortly after they arrive, a Greek woman whose daughter has an unclean spirit comes to Jesus and prostrates herself. She asks Jesus to heal her daughter, and Jesus responds with a rather harsh answer, indicating that children should receive bread before it is fed to the family dogs. The woman replies that even the dogs under the table may eat the crumbs which fall from the children's meal. Jesus commends her for this answer and sends the woman back home, assuring her that her daughter is healed.
Why would Jesus speak such harsh words to this woman? Why would he treat her like a despised, unclean outsider? It is important to note the different contexts of the two stories. In the first story, Jesus is in the heart of Jewish religious culture, an invited guest of a Pharisee. In Tyre, Jesus is the outsider, an uncultured Jew, a person of little import or standing. My guess is that, much as the Jews looked down on the Samaritans for their lack of ancestral purity, the Phoenicians looked down on the Jews because of their lack of sophistication, their exclusivity, and their antiquated religious practices.
Some interpreters suggest that this story is a lesson for the disciples. At first, Jesus voices what would be a normalized Jewish prejudice toward outsiders, then turns that prejudice on its head. This view has some merit, but it fails to give adequate weight to the woman's response which proves to be a pivotal point in the exchange. Other interpreters suggest that because the word for dog here is a diminutive form (little dog), this is a pretty friendly exchange, that Jesus could almost be seen as teasing the woman, but this downplays the harshness of Jesus's words. In this encounter, we have one of the first times that a non-Jew receives the ministry of Jesus, hinting at the full inclusion of the Gentiles still to be revealed. It is important to note that in this scenario, Jesus is not the one who initiates inclusion; the Greek woman persists until Jesus accepts her and her request, and Jesus commends her for this bold display of humility. The importance of the woman's words cannot be underestimated. If we read this narrative through a chiastic lens, the Greek woman's retort in verse 28 stands at the centre of the story.
Recently, I heard a talk by David Moore in which he suggested that Jesus's words here were an invitation for a woman of higher cultural standing to humble herself, to bring herself down to Jesus's level (that of an outsider), in order to receive healing for her daughter.  It is remarkable that she was willing to do just that, to identify herself with a dog. One could say that Jesus was asking her to identify with himself, for, as a Jew, he might have been considered a despised dog in her cultured, Greek society. Again, it is helpful to think of this exchange in terms of proximity and movement instead of stratification. Jesus is not trying to humiliate the woman or make her grovel (she had already prostrated herself before him), but inviting her to identify with the outcast, the despised, the hungry. These were the ones to whom Jesus was always drawing near.
Of special significance in this exchange is the fact that a Gentile woman is given the honour of revealing the non-exclusivity of the Jewish God. Jesus did not declare it; the woman did! "Humility ... allows us to enter into a discourse rather than to tower above it. By relinquishing the power of certitude, it discovers a new authority, an authority in which the admission of ignorance might actually be a way to truth. If truth is found, then, not by me but by us, then there must be certain virtues that aid us in our pursuit of truth."  Not only do we see the movement of humility on the part of the woman (being willing to identify with outsiders), but we also see the movement of humility on the part of Jesus (healing the woman's daughter and allowing her to unveil God's inclusivity to all who were present). It was a genuine "we" moment. 
Because humility is relational, it invites us to operate outside of the stratification which happens in society and view ourselves not in terms of superiority or inferiority, but in terms of coming alongside others, especially outsiders. Humility invites us to think and speak and act in terms of "we" and to learn from each other (just as Jesus modeled in his exchange with the Syrophoenician woman). Humility is an invitation to intimacy, to move closer to Jesus and to the other. By doing so, we find our rightful place in community. Jesus was always raising up the lowly and taking the powerful down a notch, not because he was a rebel, but because he wanted to bring people closer to him, the Just One. This was the same message proclaimed by the prophet Isaiah and again by John the Baptist: "Every low place will be lifted and every high mountain, every hill will be humbled; the crooked road will be straightened out and rough places ironed out smooth; Then the radiant glory of the Eternal One will be revealed. All flesh together will take it in." (Luke 3, The Voice)
In order for all humanity to see the radiant glory of the Eternal One, and to see it together, the playing field (so to speak) must be equalized, and this requires the movement of humility. Sometimes we are called to lower ourselves, sometimes we are called to rise up, sometimes we are called to come near to someone we despise, sometimes we are called to learn from someone we disagree with, sometimes we are called to sacrifice, sometimes we are called to persist, sometimes we are called to stand with courage, sometimes we are called to keep silent, sometimes we are call to say, "No more!" Humility takes many forms, but it always moves us closer to Jesus and those he loves and cares for.
 James Keenan, "Jesus, Paul, and Virtue Ethics" (lecture, Boston College, March 29, 2011).
 Christopher E. Alt, "The Dynamic of Humility and Wisdom: The Syrophoenician Woman and Jesus in Mark 7:24-31," Lumen et Vita, vol. 2 (2012).
 This idea is also found in his book. David N. Moore, Make America Great Again: Fairy Tale? Horror Story? Dream Come True? (Crowdscribed, 2017), 82-84.
 Daniel J. Harrington, and James F. Keenan, Paul and Virtue Ethics (Chicago: Sheed & Ward, 2002), 146.
 This type of back and forth exchange where someone conversing with the divine is given the privilege of unveiling the mercy and justice of God is nothing new. When Moses bargains with God for the salvation of Sodom and Gomorrah (Genesis 18), we see how willing YHWH is to move, to respond with mercy, to come close.
Image from thegospelside.com