You're blessed when you're at the end of your rope. With less of you there is more of God and his rule.
Matthew 5:3, MSG
Let's try to regain the shock value in the way Jesus opened His Sermon on the Mount. We're too familiar with the statements and too far removed from the time to hear it like the original listeners. Imagine going to a fast food restaurant, ordering an enormous value meal, and the cashier hitting you with this question: "Would you like to down-size your meal for a dollar less?" Or imagine a car salesperson pausing before you sign the papers and saying, "You know what? That extended warranty is overpriced. Let's get rid of it."
Now you have an idea how much impact Jesus had and why the audience was so astounded. Just like we expect people to push us to buy more, the Jews at the time expected their rabbis to tell them the things they needed to do, the rules they needed to abide by. They came expecting to learn the ten steps required to earn God's favor, but Jesus crumpled up that idea and threw it out. Instead, He revealed that God's favor and blessings come to those who are poor in spirit.
There's more to it, however, than simply feeling beaten down or contrite. The poor in spirit—the ones at the end of their ropes—are those who realize they've gone as far as human effort can get them. In terms of salvation, that's not very far. Here's how John Gill puts it:
The greater part of mankind are insensible of this their condition; but think themselves rich, and increased with goods: there are some who are sensible of it, who see their poverty and want, freely acknowledge it, bewail it, and mourn over it; are humbled for it, and are broken under a sense of it; entertain low and mean thoughts of themselves; seek after the true riches, both of grace and glory; and frankly acknowledge, that all they have, or hope to have, is owing to the free grace of God. (John Gill, commentary on matthew 5:3)
The poor in spirit don't just feel bad; they feel bad because they realize how destitute their condition. When we truly understand that "karma points" and charitable acts amount to nothing more than drops of food coloring in the ocean, then we've gotten the point: We can't even approach the kingdom of God, let alone enter it, through our own efforts.
But those who look down and see the filth (and pre-salvation, our spiritual appearance is just that) are those who realize the need for God. And with that realization comes the increase of God in our lives and the decrease of self.
Intersecting Faith & Life: The beatitudes are much more than good ideas or suggestions. They crush preconceptions and expose us as we truly are. Each one reveals our need for God, our need for the work only He could do. When we're poor in spirit (that is, realizing our condition), we're rich in Him.