Some people have to really work hard at keeping their ego in check. They are by circumstance, by upbringing or just quite naturally- arrogant. Pride is their downfall and many battle hard to remain humble. I recall a time, I was around 15 or 16, when I went to a local family reunion with my parents. The reunion was attended by distant cousins, I guess, and I knew from the beginning of the event that they were not "my kind of people". Some were in straw cowboy hats of all things, big shiny belt buckles and dusty boots. Some men wore overalls, the women had their hair in buns and wore big flowered-print polyester dresses. They were poorly educated and obviously people of humble means.
I remember clearly, at some point, turning to my dad and saying something like, "We're related to these yahoos? Has anybody hauled granny and the rocker down from Uncle Jed's truck, yet?" I will never forget his response. He looked me square in the eye and said, "These are relatives of yours who make an honest days pay with an honest day's work. They are poor but good people. You have no right to look down upon them." Wow. That exchange rocked me- I was ashamed and humbled- and I deserved every bit of it. On the surface, that wake up call from my dad may not seem a very significant exchange, but for whatever reason that single event transformed the way I looked at people then and today.
Yes, Jesus was very clear on the subject. It's the meek (the humble, gentle and kind) that will inherit the kingdom of God. But stop for a moment and think of the far end of that spectrum. Think beyond meekness or humility. There are people, me and you at times, who are paralyzed by fear of failure. Low self-esteem and self-doubt are as big a hindrance in serving God (and others) as is pride or egotism. They are two polar ends of a scale that serve to isolate you and keep you from your full potential as a person- and your full potential as a representative of Christ. Pride is destructive, but a lack of faith or confidence in your own God given abilities will have the same outcome when you are allowed an opportunity to serve. And we all are called to serve.
Meek, humble yes. But frozen by your own fear of failure or perceived lack of unworthiness misses the mark. And perhaps it even misses the mark with a similar outcome as looking down upon others of lesser means or a different upbringing- your relatives or not.