"Blessed are the poor in spirit, for theirs is the Kingdom of Heaven."
The beatitudes are a serious of principles that Jesus taught to his followers, and this is the first, in my opinion because it is the most fundamental. The less "poor in spirit" we are, the less able we will be to be blessed in any other way.
In addition to being the most fundamental beatitude, it is also perhaps the most ironic. We have to be poor in order to inherit the Kingdom of Heaven. When I think Kingdom, I think major bling. I think significant wealth. But it is only by being "poor in spirit" that I can inherit the significant wealth of Heaven. If I fill up my heart with the insignificant wealth of this world, there will be no room for what God wants me to have.
But what does "poor in spirit" mean? It means recognizing that we are nothing without God. It also means recognizing that no possessions that we may acquire, no lesser goods like notoriety or money, can give our lives the sense of meaning or joy that comes from being with God. Being poor in spirit means nothing else besides God preoccupies us.
Being poor in spirit means that we recognize that nothing else can make us happy -- that is, nothing can satisfy the deepest desires of our hearts -- other than Jesus. It doesn't mean that we must never enjoy any of the gifts that he wants us to have. Lent takes up only a little over ten percent of the calendar year. But none of those gifts can make us happy. Not even doing what God wants us to do can make us happy.
What does it take to be poor in spirit? In short, it takes letting go. It takes emptying ourselves, as Jesus did, of all the things that we rely on to give us joy and to keep us going -- whether it's our job (should we be blessed to have one) or our social life or whatever. Again, it doesn't mean we can't derive joy from these things, or be thankful to God for them. In fact, we should.
But there is only One who can occupy the very center of our hearts. That's Jesus, who himself gave us a model of spiritual poverty when He was being tempted by the devil in the desert, as Pope Benedict observed in his Angelus message on Sunday:
Of the three temptations of Jesus, the first "had its origin in hunger, in material want", said the Pope. "But Jesus responded with the words: 'One does not live by bread alone'". The second temptation came when the devil showed Christ all the kingdoms of the earth; this, the Holy Father explained, "is the lure of power which Jesus unmasked and rejected". To the third temptation, the proposal to perform a miracle that everyone might believe in Him, Jesus responded: "Do not put the Lord your God to the test."Making constant reference to Holy Scripture", the Pope added, Jesus "made human criteria subject to the only true criterion: obedience to the will of God. This is a fundamental lesson for us too: if we carry the Word of God in our minds and hearts, if it enters our lives, then we too can reject all the tricks of the Tempter".
The devil (who did not know who Jesus truly was at that point) was tempting Jesus to put something other than his closeness to God first in His life. Jesus refuses.
Jesus says, "I cannot do anything on my own; I judge as I hear, and my judgment is just, because I do not seek my own will but the will of the one who sent me." Jesus constantly relied upon His Father, surrendering to Him. So we must constantly recognize that we are poor, that we have nothing spiritually to sustain us, to give us joy, to make us capable of loving. We have to constantly rely on Jesus.
He says "Without me you can do nothing." Jesus can love without me. He can love an eternity without me, and He has. He can love all of creation and the whole human race, without me. But I can't love in any real sense without Him. Recognizing that, every single day, is the key to inheriting the Kingdom of Heaven.

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