Blessed are the poor in spirit, for theirs is the kingdom of heaven. Matthew 5:3 This Beatitude has always been a little difficult for me to understand, but looking at Benson's commentary, I think the explanation is a good one. "Poor in Spirit" refers to a consistent attitude of humility in all areas of life so that (quoting Benson's) ... "whatever their outward situation in life may be, however affluent and exalted, think meanly of themselves, and neither desire the praise of men, nor covet high things in the world, but are content with the lot God assigns them, however low and poor. Their humility renders them teachable, submissive, resigned, patient, contented, and cheerful in all estates; and it enables them to receive prosperity or adversity, health or sickness, ease or pain, life or death, with an equal mind." It requires faith to live this way, because the way of the world is loud and pushy, manipulative and grasping. But Jesus is telling us there is another, better way to live, that is not naturally understood by mankind. In the Beatitudes, Jesus is showing us what His Kingdom will be like and the values that will matter. We are given a glimpse of heaven.
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