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What does it mean to be blessed?

In Matthew chapter five we find the Beatitudes.
You know them as the “Blessed are the ….” statements.
Blessed are the poor in spirit: for theirs is the kingdom of heaven.
The Sermon of the Beatitudes (1886-96) by Jame...
The Sermon of the Beatitudes (1886-96) by James Tissot from the series The Life of Christ, Brooklyn Museum (Photo credit: Wikipedia)
Blessed are they that mourn: for they shall be comforted.
Blessed are the meek: for they shall inherit the earth.
(Matthew 5:3-5 KJV)

What does it mean to be blessed?

The Greek word from which we get blessed is: makarios – meaning, supremely blest; by extension fortunate, or well off.
So, if I look at this first blessed statement and restate it, I get this: “Well off are the poor in spirit: for theirs is the kingdom of heaven.”
This alone gives me problems because I see this condition in recovery every time I go there. People that are poor in spirit because of their hangups, but they are anything but well off. So this must have a meaning beyond the idea of bouncing around like a cheerleader, leading people into the kingdom with our phony smiles.
One of the men in our Monday morning bible study responded to some of the foolishness that was being voiced with, Consider that these statements were made to the disciples, while the crowd – in general - was excluded. This information was deeper than Jesus wanted or needed to go with the crowd that followed him around because they wanted to get something out of him.
This entire talk was meant to build something inside the disciples that would sustain them in the future, help them to understand this journey they were going to embark on, and in time, sustain us – the church – as well.
Now I want to know too.
Being well off, does not put smiles on people's faces all the time. Why not? Because it is never enough.
"Blessed are the poor in spirit, for theirs is the kingdom of heaven. (Matthew 5:3 NASB)
Let's try looking at this in another version.
"You're blessed when you're at the end of your rope. With less of you there is more of God and his rule”. (Matthew 5:3 MSG)
Now it is making more sense to me because this is the typical reason you find people in recovery, as they finally hit the end of their rope.
the poor in spirit”
Poor is the Greek word ptōchos – pto-khosFrom πτώσσω ptōssō (to crouch; akin to G4422 and the alternate of G4098); a beggar (as cringing), that is, pauper (strictly denoting absolute or public mendicancy,
MEND'ICANCY, a. [L. medicans.] Beggary; a state of begging.
This person is definitely hurting, but are they willing to be honest. I can just about guarantee you that the community around you are aware of your brokenness.
Spirit is the same word that we use for the Holy Spirit or human spirit.
If the implication here is a human with the Spirit of God in them – and it is, then we are talking about a member of the church body. Look, I get it, we are not all super-fans, or body builders in church. Some don't even know what a protein shake looks like (that is my analogy to opening their bible.) They are however on the same team, and found in this condition they are broken and desperately needing help, not a baseball bat to the head.
An aspect of the nonsense heard at bible study was the weekly barrage of guilt and condemnation over sin. If you are a follower of Christ, you have received your forgiveness for your sins, and that put you into the arms of the Father, never to be released. So if I continue to “sin” then I need to change my thinking and or surroundings, because I am certainly not thinking as clearly as I should.
"and God's servants must not be troublemakers. They must be kind to everyone, and they must be good teachers and very patient. Be humble when you correct people who oppose you. Maybe God will lead them to turn to him and learn the truth. They have been trapped by the devil, and he makes them obey him, but God may help them escape." (2 Timothy 2:24-26 CEV)
If sin is merely missing the bulls-eye, we are all capable of doing that, but in reality the target is large, and for the most part easy to hit. Doesn't that show that most of us are trying, and really do not wish to find themselves in a beggarly state.
We understand that “blessed” really has little to do with joy or the condition of your face – as in a smile, but could.
Paul wrote to the church in Rome:
May the God of your hope so fill you with all joy and peace in your faith, that you may be overflowing with hope by the power of the holy Spirit! (Romans 15:13 Moffatt NT)
Joy is the Greek word chara, and means cheerfulness. So while one might obtain a cheerfulness from possessing some thing, like a sixty foot luxury ocean power cruiser, it is not what God wanted us to learn here. I will show you why:
For all that is in the world--the desires of the flesh and the desires of the eyes and pride of life--is not from the Father but is from the world. (1 John 2:16 ESV)
For me, the bottom line here is this. I am better off when I live like this:
"You're blessed when you're at the end of your rope. With less of you there is more of God and his rule. "You're blessed when you feel you've lost what is most dear to you. Only then can you be embraced by the One most dear to you. "You're blessed when you're content with just who you are--no more, no lessThat's the moment you find yourselves proud owners of everything that can't be bought(Matthew 5:3-5 MSG)

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