“Blessed are those who mourn, for they will be comforted” (Matthew 5:4).
Jesus throws our minds into confusion once again with this maxim that runs in direct contradiction to the world’s logic. The literal definition of the word ‘mourn’, according to the Cambridge dictionary, means “to feel or express great sadness…” If that’s the case, Jesus’s statement here is synonymous to saying, “Happy are those who are unhappy…”
If you mourn, then how on earth are you happy?
Further contemplation of this biblical text is key to understanding this paradox. The first thing worth noting is that Jesus is referring to a specific type of mourning. Not all types of mourning lead the way to blessedness and there are at least two terribly wrong ways to mourn.
The apostle Paul talks about the first one when he asserts that there is a worldly grief that focuses exclusively on the painful repercussions of sin rather than the sin itself (2 Corinthians 7:10). The second type of worldly grief can be found in numerous accounts and examples in the Old Testament, where we read of evil rulers who mourn over their unfulfilled lustful desires for wealth and fame. King Ahab mourned over Naboth’s vineyard because he couldn’t take possession of it: “He lay on his bed sulking and refused to eat.” (1 Kings 21:4).
Both of these types of mournings are abysmal and will only produce death (2 Corinthians 7:10). It stands to reason, then, that the mourning Christ had in mind was a kind that is firstly restricted to the acknowledgment of transgression against the Judge. The mourner must be overwhelmed by guilt, not because they have broken God’s law (and thus incurred its consequences), but because they have broken God’s heart.
But that is only the first step. If this step was all there is to attain blessedness, then Judas would have passed the test! When Judas felt the weight of his betrayal, he acknowledged his sin and was filled with great remorse. He even confessed to the specific sin he had committed (see Matthew 27:3-4a). So then, what went wrong for Judas? Where he went wrong was that his mourning buried him in the pits of despair, and it crippled him from seeking help for his own depravity.
So how do you mourn the right way? To mourn over our loss of communion with God is the next step. A holy mourning over our sin against God should drive us to our knees in repentance, in the hopes that our joy from being in His presence will be restored (see Psalm 51:12). This is where good news comes for the spiritually poor and contrite: “If we confess our sins, he is faithful and just and will forgive us our sins and purify us from all unrighteousness.” (1 John 1:9).
Assurance and comfort is given freely to those who possess penitent hearts. The Spirit gives refreshment to their souls and affirmation that their sins have been forgiven, echoing the words of Jesus, “Take heart, son; your sins are forgiven.” (Matthew 9:2). Though they will grieve over their constant failure to please God, and feel the burden upon their conscience due to these failures, they can be comforted by the restoration of their joy and blessings through the blood of Christ which covers all their sins (1 John 1:7).
Therefore, as we strive to live holy lives for the glory of God, mourning over sin needs to be normative in the Christian life. This is the mourner’s paradox – as Thomas Watson aptly states, “The valley of tears brings the soul into a paradise of joy.”  For the sake of our joy and for His glory, may we plead with God that by the Spirit He will pour into our hearts the power to cry out the words of the prodigal, “Father, I have sinned against heaven and against you.”
 – Watson, T. (1975). Beatitudes. Banner of Truth, Trust, p.90.