It’s interesting that Jesus opens His sermon on the Mount with, “Blessed are the poor in spirit, for theirs is the kingdom of heaven (Matthew 5:3, NASB).” The NASB footnote describes poor as, “those who are not spiritually arrogant.” To me it means those who are open to hearing God’s word. They are hungry for the bread of life and living water.
There have been times in my life where my spirit has been drained. I’ve felt poor in spirit, not self confident or self sufficient, but empty inside. Those were the times, as the Psalmists often did, where I cried out to the Lord (Psalm 88:13 and 130:1 as examples).
In that emptied state, I was more open to receiving the blessings Jesus mentioned in Matthew 5:4-10: comfort (4); inheritance (5); satisfaction (6); mercy (7); seeing God (8); being a child of God (9); the kingdom of Heaven (10). By making ourselves vulnerable to God, we are better equipped to love Him with our heart, soul, mind, and strength (Deuteronomy 6:5).
140 Character Christian 
I’ve just experienced a short poor in spirit season,
Chris. It was 48 hours of tripping over my own two spiritual feet, while not looking or feeling Christ-like in the process. I started the journey out by swallowing my pride, which is much easier to write about than do. Your thoughts here may very well be the starting point for my own recent experience. I’m tagging myself it, brother. Thank you for your blog ministry. As you like to say, blessings!
You’re not alone in the journey of being more Christ-like. I’ve read these verses many times and recently the phrase “poor in spirit” struck me—lower case spirit is an invitation to the upper case Spirit to work in our lives. Too many times my own pride has been a barrier to this. Thanks for sharing. I walk with you in prayer, as I do other readers, as we seek more of Jesus in our life. Blessings.