Jesus, the most high, came humbly.
Nazareth was an obscure place with low esteem. In the eyes of the world Mary was an insignificant person, and Joseph was simply a carpenter. At the time Jesus' birth was not met with widespread fanfare. Jesus was born in a manger since there was no room at the inn, not dignified for someone of His nature. The angels appeared to shepherds so they would be the first witnesses, people who were not highly regarded or trusted in their society. Jesus and His family were being persecuted by the king, not exalted. His life would be full of incidents like this. Jesus's friends and disciples were not dignitaries of any sort. He would also associate with those society would not consider holy. The Son of God would be the one to wash his disciples' feet. He would be scorned and killed in a manner no one would expect for the Son of God.
Even if Jesus had all the riches of the world, that would have been a demotion compared to where He came from. And yet He came as a baby in one of the lowest earthly positions. Compare this with Satan who was one of the greatest angels, but he wanted to become greater than God.
Why would God do this? Pride is a great sin. Jesus came to conquer sin in His life and through His death. He is an example for us and we should strive to live a life like Jesus.
Jesus came this humble way so that everyone and anyone would be welcome to see Him. If He were born in a palace, a shepherd would not be given access. He came in a way so none would be intimidated.
Jesus came in the form of a servant to reveal who God is. It was not a disguise.
Jesus made many bold statements. Humility does not mean you give up strong convictions for the truth. We can be humble in our actions and by listening, but do not compromise the truth.
This story shows that no one is too low for God to want to connect with. Do not feel too unworthy for God's attention and love, do not despise others for their lowliness. Challenge our pride with Jesus's story.