Living in America, being "poor" is rarely a good thing. In school, our grades range from Excellent to Good to Poor. Poor is not good. From a young age we are taught there are no limits to our accomplishments. The "American Dream" is illustrated early and often with examples of people who have started with nothing (or not much) and have achieved success. And, the more material possessions we accumulate, the happier we'll be. Poor is not good.
In the counter-culture of the beatitudes, poor is good. Jesus said those who are poor in spirit will be blessed (Matthew 5:3). No, He wasn't talking about material possessions or passing grades. He was talking about coming to the realization that we have nothing to offer God. Because we are fallen creatures, we are spiritually bankrupt.
John Nolland says, "The poor in spirit will be those who sense the burden of their present (impoverished) state, and see it in terms of the absence of God; who patiently bear that state, but long for God to act on their behalf and decisively claim them again as His people."
Our problem is that we are middle-class in spirit! We certainly don't like being poor in spirit, but we know enough to avoid being totally full of ourselves. So we imagine that we are doing pretty well - not too great, but certainly self-sufficient. We are middle-class in spirit, and yet we find that Jesus offers nothing to the middle-class in spirit.
Like the rich in spirit, the middle-class in spirit see no need for God to intervene in their lives. God is certainly a helpful reality, but He's more like the GPS in our car than the Lord of our lives. We want Him around when things are tough, but otherwise, we think we can handle things ourselves. The middle-class in spirit are not blessed; only the poor. And it's only the poor in spirit that find entrance into the kingdom of heaven.
When we realize we are completely dependent upon the rich mercy of our great God, then we find approval (the meaning of "blessed") from God. And at that moment, we realize being poor is good.