“Blessed are the poor in spirit (humble-minded) for theirs is the kingdom of heaven.” 

The Greek word translated “poor” has the significance of utter destitution, extreme poverty. Thus, a full appreciation of our own spiritual destitution is essential in order to receive the divine grace provided by Jesus, our Lord. And not only must our poverty be realized at the beginning of our walk, but we must constantly be dependent on divine grace. We must always realize our own insufficiency in order to be acceptable to God. 

To be poor in spirit is to be humble, not making yourself seem more important than you are. But it doesn’t mean having so little self-esteem that we are feel worthless.  

Proverbs 29:23: (NASB) A man’s pride will bring him low, but a humble spirit will obtain honor.

Being poor in spirit means having an accurate assessment of who we are. We aren’t automatically great if we don’t have money. Greatness comes from a humble approach to godliness.

There is nothing in this text to teach earthly poverty. Nevertheless, not many rich or great, but chiefly the “poor” of this world, rich in faith, shall be heirs of the kingdom. (1 Corinthians 1:26-28) In our present weak and fallen state, earthly prosperity and riches very frequently tend to choke the new nature. Prosperity hinders us from bringing forth the peaceable fruits of righteousness. Instead, earthly riches may develop a spirit of self-sufficiency, pride, etc. As our Lord Jesus expressed it, The cares of this life and the deceitfulness of riches choke the Word, and it becomes unfruitful. (Matthew 13:22) 

We do not seek to accumulate earthly riches. The faithful Christian will use all of his resources (finances, abilities, time, etc.) in the Lord’s service. The saints have “made a covenant by sacrifice” (of their wills and their all) to serve God. (Psalm 50:5)

Let us all then, as we strive to develop a Christ-like character, seek more and more continually this humility of mind. So far from being boastful and self-sufficient, the poor in self-spirit will humbly accept with gratitude every good and every perfect gift as coming from the Father of Lights. (James 1:17)

Additional Resource: 
Christian Questions Podcast 
Episode #1213: “Is God Happy With My Attitude? (Part I)” 
Uncovering the life-directing principles in the Beatitudes of Jesus
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