When God mentions being poor in spirit, he does not mean what we think, however, he holds a different perspective on this phrase. When hearing the word poor, many of us will more or likely think of a beggar, or perhaps a homeless man, in addition, one who is in lack of money. Nevertheless, the Lord sees the poor with a total better analogy, a man; woman or child who is in definite need of God's help. In other words, we need to humble ourselves to the lowest point, and realize that we are nothing without Christ.
A man or woman who is full of pride and an attitude of "two good for anything" also carries the mentality of not needing a God. When a situation as such occurs, no person can understand and see God's holiness because their mind is supposedly too high for such an imagination, as some may call it. Nonetheless, a man or woman with a poor spirit can see God's beauty, His holiness, His perfections, His goodness, and His unconditional love. The Greek word for poor is thus, 'ptoe-KOSS' which simply means, "Life is difficult" or perhaps even a better and clearer definition, "I am not going to make it without help."
We need to acknowledge that we are wretched creatures, and our life needs to depend solely in Christ alone. The lowly run to their God, however, the foolish say there is no God. The only ones, who can see God, are the poor in spirit, the ones who are just and lower themselves lower then dirt, as to say. A boastful person sees no one and no necessity of relying and asking others for help. All they see are themselves and have a "my" vision. They also picture life as going solo, alone and therefore are totally fine without God.
Often, we may find ourselves perhaps being a bit too prideful, thus we need to ask Christ to humble our boastful spirit, so that we can have the wonderful gift of seeing and grasping God's holiness. Sooner or later, the arrogant man will fall, and by God's grace, he will notice the importance of Christ and an attitude of gratitude!