Blessed are they that mourn: for they shall be comforted. (Matthew 5:4)
On one level, this verse says simply that one feels better after a good bout of weeping. But its deeper significance may be difficult for many to accept because it is culturally contrary to the way we think: To be truly happy, we must adopt a spirit of grievousness over our lives and the world in which we live.
Blessed, of course, is from the Greek verb μακάριος (makarios — blessed or happy).
But it may be easier to ponder what Jesus Christ meant when he said “blessed” by defining what precisely “mourning” was. Mourn is from the Greek verb — πενθέω (pentheo): to mourn or lament, especially for the dead.
We are blessed (happy) when we mourn our dead, old selves. Blessed Theophylact said, “‘Blessed are they that mourn” for their sins, not for the things of this life. Christ said, ‘They that mourn,” that is, they that are mourning incessantly and not just one time; and not only for our own sins, but for those of our neighbor.”
This seems to be a polar opposite to the concept of maintaining health self-esteem that today’s psychologists, counselors and teachers would profess. In fact, God wants us broken.
A sacrifice unto God is a broken spirit; a heart that is broken and humbled God will not despise. (LXX, Psalm 50)
The context of mourn appears also in James:
Be afflicted, and mourn, and weep: let your laughter be turned to mourning, and your joy to heaviness. (Jms 4:8)
Let us dissect this verse, defining the words:
Be afflicted [ταλαιπωρέω (talaiporeo) — to toil heavily, endure labor and hardship] and mourn [πενθέω (pentheo) — to mourn, lament], and weep: Let your laughter be turned to mourning [same root as “mourn” — lamenting, mourning] and your joy [χαρά (chara) — joy or gladness] (be turned also) to heaviness [κατήφεια (kateiphea) shame, dejection, gloom].
Putting it in context of James’ epistle: Draw closer to God and submit to Him, flee from the devil, be pure both outwardly and inwardly and cut the hypocritical living (verses 7-9), endure hardship and lament and weep for your true sinful nature from which only God can rescue you. Don’t laugh but tear in your eyes, and instead of glee — show the shamed and downcast look of someone whose only pick-me-up can come from God.
Spiritual mourning is a state akin to mourning for a loved one — where we care for nothing except for our grief at our loss. That leads to the Lord’s promised comfort.
The consolation comes by God’s innate design. People feel better after a good cry. But when we actually mourn and weep for own pathetic condition, not solely because of losses to us, then we are gaining in spiritual strength. Comforted stems from Greek παρακαλέω (parakaleo), which carries a variety of shades of meaning — to animate, encourage, comfort, console, to be cheered, comforted. Said Blessed Theophylact, “‘Comforted,’ both in this life, for he who mourns for his sins rejoices spiritually, and even moreso in the next life.”
This message probably grates at many of the happy go-lucky westerners (like myself) who view living a spiritual life through the New Age distortions of secularism and equate spirituality as a “self-help” that promotes self-esteem and enhanced productivity. But what Christ had been saying that was so revolutionary to his audience at the time was this: A man is blessed not when he is graced by wealth, luck, or happiness, but when he is wailing in a fetal position at the loss of a loved one or hitting the sharp shoals clustering the shores of repentance.