Greek: talaiporhesate (2PAAM) kai penthesate (2PAAM) kai klausate; (2PAAM) o gelos humon eis penthos metatrapheto (3SAPM) kai e chara eis katepheian.

Amplified: [As you draw near to God] be deeply penitent and grieve, even weep [over your disloyalty]. Let your laughter be turned to grief and your mirth to dejection and heartfelt shame [for your sins]. (Amplified Bible - Lockman)
ASV: Be afflicted, and mourn, and weep: let your laughter be turned to mourning, and your joy to heaviness.
BBE: Be troubled, with sorrow and weeping; let your laughing be turned to sorrow and your joy to grief.
ESV: Be wretched and mourn and weep. Let your laughter be turned to mourning and your joy to gloom.  (ESV)

KJV: Be afflicted, and mourn, and weep: let your laughter be turned to mourning, and your joy to heaviness.
NET:  Grieve, mourn, and weep. Turn your laughter into mourning and your joy into despair. (NET Bible)

NJB: Appreciate your wretchedness, and weep for it in misery. Your laughter must be turned to grief, your happiness to gloom. (NJB)
NLT: Let there be tears for what you have done. Let there be sorrow and deep grief. Let there be sadness instead of laughter, and gloom instead of joy. (NLT - Tyndale House)
Phillips: As you come close to God you should be deeply sorry, you should be grieved, you should even be in tears. Your laughter will have to become mourning, your high spirits will have to become heartfelt dejection. (Phillips: Touchstone)

Be miserable and mourn and weep: talaiporhesate (2PAAM) kai penthesate (2PAAM) kai klausate (2PAAM): (Jas 5:1,2; Ps 119:67,71,136; 126:5,6; Eccl 7:2, 3, 4, 5; Isa 22:12,13; Jer 31:9,13,18, 19, 20; Ezek 7:16; 16:63; Zech 12:10, 11, 12, 13, 14; Mt 5:4; Luke 6:21; 2Co 7:10,11)

Hiebert feels that here James is calling for open repentance explaining that...

Three further aorist imperatives without any modifiers, "grieve, mourn and wail," unite to form an urgent demand for open and thorough repentance. The intensity of the demand is startling, intended to shake these double-minded believers.  (D Edmond Hiebert - James)

Be miserable...mourn...weep -- To the commands cleanse and purify themselves James adds this triad of commands (all aorist imperatives) which call for decisive, obvious, and perhaps even public acts of contrition reflective of genuine repentance (See discussion of repentance).

Spurgeon adds that...

If the previous verses have rightly accused you of sin, confess your guilt with shame and sorrow, and so come to Christ imploring pardon.

The Amplified Version renders it...

[As you draw near to God] be deeply penitent and grieve, even weep [over your disloyalty].  (Amplified Bible - Lockman)

John Stott writes...

I fear that we evangelical Christians, by making much of grace, sometimes thereby make light of sin. There is not enough sorrow for sin among us (2Co 7:10). We should experience more ‘godly grief’ of Christian penitence (Stott, J. The Message of the Sermon on the Mount: Inter-varsity Press)

The psalmist speaks of the positive effect of affliction in the context of sin...

Psalm 119:67-note Before I was afflicted I went astray, but now I keep Thy word.

Psalm 119:71-note It is good for me that I was afflicted, that I may learn Thy statutes.

Lenski adds that...

How oft, alas! this wretched heart
Has wandered from the Lord,
How oft my roving thoughts depart,
Forgetful of His Word.

Yet sovereign mercy calls, “Return”;
Dear Lord, and may I come?
My vile ingratitude I mourn;
O take the wanderer home.
(How Oft, Alas!)

Be miserable (5003) (talaiporeo) is a verb which Vine says "is derived from tlaō, to bear, undergo, and pōros, a hard substance, a callus, which metaphorically came to signify that which is miserable". Other sources say the root word is talas = suffering, wretched.

Talaiporeo means first to do hard work, and then to endure hardship or experience distress. The idea primarily denotes going through hardship and distressing circumstances which came to be used of the feeling of misery and wretchedness because of the outward circumstances.

To be afflicted. To be sorrowful over wretched circumstances. It speaks of the emotions that emanate from torment, whether external or internal.

In the present context (the only NT use), it describes the expression of this person's grief and sense of brokenness. James commands them to "suffer misery, be sorrowful, be devastated, feel afflicted and miserable" over their sins (worldliness, double-mindedness, etc).

Hiebert makes the important distinction that there is no indication...

that James is calling for ascetic practices, such as fasting in sackcloth and ashes, to induce this feeling. Mayor holds that, since James was known for his asceticism, this imperative "is best understood of voluntary abstinence from comforts and luxuries." Well aware that such practices were no satisfactory substitute for inner penitence, James is best understood as calling for a deeper inner feeling of wretchedness and shame because of their sins. The aorist imperative is probably ingressive: "become wretched." When a true realization of their sinfulness strikes home, the feeling of wretchedness and grief will follow. (Ibid)

Martin observes that...

The demands to cleanse oneself are followed quickly by the resounding call to an overt and explicit repentance. To be miserable, (a hapax legomenon = only NT use) is not an invitation to or a sanction of asceticism (so Mayor, 147). In prophetic language...James urges his readers to change their ways. The opening verb (talaiporeo)...in the sense of “be devastated”) is a favorite with Jeremiah (in LXX, e.g., Jer 6:26).... The day of the Lord is near (Jas 5:8) and God’s people must return to him (Joel 2:12). There is no allowance made for Christians to take a casual attitude toward sin (1Pe 4:17). Mourning and wailing are the accompaniments of repentance, not the substitutes for it (see 2Sa 19:1; Neh 8:9; Mt 5:5; Lk 6:21, 25; Acts 18:11, 15, 19; 2Co 7:10). What James is implying is that (while there is still time) genuine repentance is needed or else those who are unrepentant face the eschatological wrath of God. (Martin, R. P. Vol. 48: Word Biblical Commentary : James. Dallas: Word, Incorporated)

There are 13 uses of talaiporeo in the Septuagint (LXX) (Where we have meanings such as to endure distress, suffer misery, be in ruin, to trouble of afflict someone). It is notable that talaiporeo is used by the OT Prophets who generally convey news of a time of great and imminent danger.  Keeping this thought it mind, his Jewish readers (who would be familiar with the OT prophets) would understand that in using this verb (the only use in the NT) James has placed before his hearers a matter which is not trifle but conversely quite serious. Similarly, the idea of changing laughter to mourning was used in Amos 8:10 to spark a sudden awareness of guilt and repentance. By proclaiming such signs the OT prophets warned of sudden catastrophe that the people of Israel had brought on themselves by their indifference to the poor and therefore to God Himself!

Psalm 17:9 From the wicked who despoil me, My deadly enemies, who surround me.

Psalm 38:6 I am bent over (Heb = avah = bent; twisted; bewildered; Lxx = talaiporeo) and greatly bowed down; I go mourning all day long.

Hosea 10:2 Their heart is faithless; Now they must bear their guilt. The LORD will break down their altars And destroy (Heb = shadad = despoil, devastate; Lxx = talaiporeo) their sacred pillars.

Micah 2:4 "On that day they will take up against you a taunt And utter a bitter lamentation and say, 'We are completely destroyed (Heb = shadad = despoil, devastate; Lxx = talaiporeo)! He exchanges the portion of my people; How He removes it from me! To the apostate He apportions our fields.'

Joel 1:10 The field is ruined (Heb = shadad = despoil, devastate; Lxx = talaiporeo), The land mourns, For the grain is ruined (Heb = shadad = despoil, devastate; Lxx = talaiporeo), The new wine dries up, Fresh oil fails.

Zechariah 11:2 Wail (Heb = yalal = command to howl; Lxx = hololuzo [onomatopoetic verb] = make loud an inarticulate cries in context because of the painful circumstances associated with God's judgment), O cypress, for the cedar has fallen, Because the glorious trees have been destroyed (Heb = shadad = despoil, devastate; Lxx = talaiporeo); Wail, O oaks of Bashan, For the impenetrable forest has come down.3 There is a sound of the shepherds' wail, For their glory is ruined (Heb = shadad = despoil, devastate; Lxx = talaiporeo); There is a sound of the young lions' roar, For the pride of the Jordan is ruined (Heb = shadad = despoil, devastate; Lxx = talaiporeo).

Isaiah 33:1 Woe to you, O destroyer, While you were not destroyed (Heb = shadad = despoil, devastate; Lxx = talaiporeo); And he who is treacherous, while others did not deal treacherously with him. As soon as you shall finish destroying, you shall be destroyed; As soon as you shall cease to deal treacherously, others shall deal treacherously with you.

Jeremiah 4:13 "Behold, he goes up like clouds, And his chariots like the whirlwind; His horses are swifter than eagles. Woe to us, for we are ruined (Heb = shadad = despoil, devastate; Lxx = talaiporeo)!"...20 Disaster on disaster is proclaimed, For the whole land is devastated (Heb = shadad = despoil, devastate; Lxx = talaiporeo); Suddenly my tents are devastated (Heb = shadad = despoil, devastate; Lxx = talaiporeo), My curtains in an instant. (In this context Jeremiah like James gives a charge to "get right with God" -- Jeremiah 4:14 Wash [command] your heart from evil [cp Jer 4:4], O Jerusalem, that you may be saved. How long will your wicked thoughts Lodge within you?)

Jeremiah 9:19 "For a voice of wailing is heard from Zion, 'How are we ruined (Heb = shadad = despoil, devastate; Lxx = talaiporeo)! We are put to great shame, For we have left the land, Because they have cast down our dwellings.'"

Jeremiah 10:20 My tent is destroyed (Heb = shadad = despoil, devastate; Lxx = talaiporeo), And all my ropes are broken; My sons have gone from me and are no more. There is no one to stretch out my tent again Or to set up my curtains.

Jeremiah 12:12 "On all the bare heights in the wilderness Destroyers (Heb = shadad = despoil, devastate; Lxx = talaiporeo) have come, For a sword of the LORD is devouring From one end of the land even to the other; There is no peace for anyone.

The Lord wants us to mourn our sin,
To grieve what brings Him pain;
And if the sorrow changes us,
Our tears won't be in vain. —Sper

Mourn (3996) (pentheo [word study] from pénthos = mourning) means to mourn for, lament. Mourning is grief and sorrow caused by profound loss, and is often associated with death or great tragedy (as would or should occur as an outward manifestation of James' readers sense of wretchedness!)

Trapp says that pentheo here in James 4:9 speaks of a "funeral grief" which is not a bad thought considering the fact that sin kills our fellowship with God! This is a grief so deep and so profound that it simply cannot be contained nor concealed. Beloved, a true awareness of our sinful state should optimally always have such a deep impact on our psyche!

Mourning can reflect an outward expression of sorrow. It is to experience sadness or grief as the result of depressing circumstances or the condition of persons and so to be sad, to grieve, to bewail or to lament. 

Pentheo is the word which is used for mourning for the dead, for the passionate lament for one who was loved. This is the quality of mourning Jesus is calling for as we see our sins the way God sees them and His Spirit convicts us of sin. (cp John 16:8, Acts 2:37, Zech 12:10)

In Classical Greek in most uses of pentheo, it expresses a sorrow which is outwardly expressed in some way, such as by tear or laments. Among the Greeks the verb and noun (penthos) were used especially for public mourning. Not surprisingly, pentheo is often connected with the term "weep" and it describes the mourning which cannot be hidden. It describes not only a grief which brings an ache to the heart, but also a grief which brings tears to the eyes.

Weary of wandering from my God,
And now made willing to return
I hear and bow me to the rod
For thee, not without hope, I mourn:
I have an Advocate above
A Friend before the throne of love.
(Weary of Wandering from My God)

Pentheo - 10x in 10v in the NT - Mt 5:4; 9:15; Mark 16:10; Lk 6:25; 1Co 5:2; 2Co 12:21; Jas 4:9; Rev 18:11, 15, 19.

Matthew 5:4 (note) Blessed are those who mourn (present tense = speaks one exhibiting a lifestyle of mourning!), for they shall be comforted.

A W Pink explains that the mourning in Mt 5:4...

The first use of pentheo in the  Septuagint or LXX describes the mourning of Abraham for his wife Sarah (Ge 23:2). Pentheo describes Jacob mourning for his son Joseph whom he thought had been killed (Ge 37:34, 35). Samuel grieving over Saul and his failure to obey (1Sa 15:35, 16:1).  David for his son Absalom (2Sa 13:37, 19:1). All Judah and Jerusalem for King Josiah (2Chr 35:24). Ezra mourning over the unfaithfulness of the exiles in marrying foreign women. Ezra 10:6, cf Ezra 10:1, 2). Nehemiah mourning over the great distress of the remnant who were back in Jerusalem (Neh 1:4). The people weeping and mourning upon hearing the Words of the Law read (Neh 8:9). Figuratively of Zion or Jerusalem's gates mourning over the coming destruction (Isa 3:6). When Messiah returns to comfort all who mourn (Isa 61:2, 3). Daniel mourned for 3 entire weeks (Da 10:1) Several verses refer to "the land" (the land of Israel) mourning over the sin of the chosen people (cf Jer 23:10 because of the curse, Hos 4:3, Joel 1:10)

“Lord, let me weep for naught but sin,
And after none but thee;
And then I would-oh, that I might-
A constant mourner be!”
C H Spurgeon

Ps 51:17 The sacrifices of God are a broken spirit; A broken and a contrite (English = bruised, brokenhearted for sin, deeply affected with grief and sorrow for having offended God; humble) heart, O God, Thou wilt not despise.

A broken and a contrite heart, O God, thou wilt not despise.

A heart crushed is a fragrant heart. Men contemn (view with contempt) those who are contemptible in their own eyes, but the Lord sees not as man sees. He despises what men esteem, and values that which they despise. Never yet has God spurned a lowly, weeping penitent, and never will He while God is love, and while Jesus is called the man who receives sinners. Bullocks and rams He desires not, but contrite hearts He seeks after; yea, but one of them is better to Him than all the varied offerings of the old Jewish sanctuary.

THOMAS WATSON
ON MOURNING

The Puritan writer Thomas Watson in his exposition of Mt 5:4 (Beatitudes) has a treatise on mourning  which is too lengthy to quote in its entirety. Here are a few snippets to entice you to read his sobering exposition on an all too seldom contemplated subject...

We have in our hearts the seed of the unpardonable sin. We have the seed of all those sins for which the damned are now tormented! And shall we not mourn? He who does not mourn, has surely lost the use of his reason....

There is a fivefold mourning which is false and spurious.

A despairing kind of mourning. Such was Judas' mourning. He saw his sin, he was sorry, he made confession, he justifies Christ, he makes restitution (Matthew 27). Judas, who is in hell, did more than many nowadays! He confessed his sin...

A hypocritical mourning. The heart is very deceitful. It can betray as well by a tear—as by a kiss. Saul looks like a mourner, and as he was sometimes 'among the prophets' (1 Samuel 10:12) ...The true penitent labors to make the worst of his sin. Saul labors to make the best of sin...

A forced mourning. When tears are pumped out by God's judgments, these are like the tears of a man who has the stone, or that lies upon the rack. Such was Cain's mourning.  (Genesis 4:13). His punishment troubled him more than his sin! To mourn only for fear of hell is like a thief that weeps for the penalty, rather than the offence. The tears of the wicked are forced by the fire of affliction!

An external mourning; when sorrow lies only on the outside. 'They disfigure their faces' (Matthew 6:16-note). The eye is tender—but the heart is hard. Such was Ahab's mourning. 'He tore his clothes and put sackcloth on his flesh, and went softly' (1Ki 21:27). His clothes were torn—but his heart was not torn. He had sackcloth but no sorrow. He hung down his head like a bulrush—but his heart was like granite. There are many who may be compared to weeping marbles, they are both watery and flinty.

A vain fruitless mourning. Some will shed a few tears—but are as bad as ever. They will deceive and be unclean. Such a kind of mourning there is in hell. The damned weep—but the continue to blaspheme God.

What is the RIGHT gospel-mourning?...It is spontaneous and free. It must come as water out of a spring, not as fire out of a flint. Tears for sin must be like the myrrh which drops from the tree freely without cutting or forcing. Gospel-mourning is spiritual; that is, when we mourn for sin more than suffering. Pharaoh says, "Take away the plague!" He never thought of the plague of his heart. A sinner mourns because judgment follows at the heels of sin—but David cries out, 'My sin is ever before me' (Psalm 51:3-note). God had threatened that the sword should ride in circuit in his family—but David does not say, 'The sword is ever before me'—but 'My sin is ever before me'. The offence against God troubled him. He grieved more for his treason against God—than the bloody axe.

In particular, our mourning for sin, if it is spiritual, must be under this threefold notion:

1. We must mourn for sin, as it is an act of hostility and enmity against God. Sin not only makes us unlike God—but contrary to God: 'They have walked contrary unto me' (Leviticus 26:40). Sin affronts and resists the Holy Spirit (Acts 7:51). Sin is contrary to God's nature; God is holy; sin is an impure thing. Sin is contrary to his will. If God be of one mind—sin is of another. Sin does all it can to spite God. The Hebrew word for 'sin' signifies 'rebellion'. A sinner fights against God (Acts 5:39). Now when we mourn for sin as it is a walking contrary to heaven, this is a gospel-mourning.

2. We must mourn for sin, as it is the highest ingratitude against God. It is a kicking against the breasts of mercy. God sends his Son to redeem us, his Spirit to comfort us. We sin against the blood of Christ, the grace of the Spirit—and shall we not mourn? We complain of the unkindness of others, and shall we not lay to heart our own unkindness against God? Caesar took it unkindly that his son, Brutus, should stab him—'and you, my son!' May not the Lord say to us, 'These wounds I have received in the house of my friend!' (Zechariah 13:6). Israel took their jewels and earrings and made a golden calf of them. The sinner takes the jewels of God's mercies and makes use of them to sin. Ingratitude is a 'crimson sin' (Isaiah 1:18-note). Sins against gospel-love are worse in some sense, than the sins of the devils, for they never had an offer of grace offered to them. Now when we mourn for sin as it has its accent of ingratitude upon it, this is an evangelical mourning.

3. We must mourn for sin as it is a privation; it keeps good things from us; it hinders our communion with God. Mary wept for Christ's absence. 'They have taken away my Lord!' (John 20:13). So our sins have taken away our Lord. They have deprived us of his sweet presence. Will not he grieve, who has lost a rich jewel? When we mourn for sin under this notion, as it makes the Sun of Righteousness withdraw from our horizon; when we mourn not so much that peace is gone, and trading is gone—but God is gone, 'My beloved had withdrawn himself' (Song 5:6); this is a holy mourning. The mourning for the loss of God's favor—is the best way to regain His favor. If you have lost a friend, all your weeping will not fetch him again—but if you have lost God's presence, your mourning will bring your God again. (cp Jas 4:8-note)

Gospel-mourning sends the soul to God. When the prodigal son repented, he went to his father. 'I will arise and go to my father' (Lk 15:18). Jacob wept and prayed (Hosea 12:4). The people of Israel wept and offered sacrifice (Jdg 2:4,5). Gospel-mourning puts a man upon duty. The reason is, that in true sorrow there is a mixture of hope, and hope puts the soul upon the use of means. That mourning which like the 'flaming sword' keeps the soul from approaching to God, and beats it off from duty—is a sinful mourning. It is a sorrow hatched in hell. Such was Saul's grief—which drove him to the witch of Endor (1Sa 28:7). Evangelical mourning is a spur to prayer. The child who weeps for offending his father goes to his presence and will not leave until his father is reconciled to him. Absalom could not be quiet 'until he had seen the king's face' (2Sa 14:32, 33).

Gospel-mourning is for sin in particular. The deceitful man is occupied with generalities. It is with a true penitent as it is with a wounded man. He comes to the surgeon and shows him all his wounds. Here I was cut with the sword; here I was shot with a bullet. So a true penitent bewails all his particular sins. 'We have served Baal' (Judges 10:10). They mourned for their idolatry. And David lays his fingers upon the sore—and points to that very sin which troubled him (Psalm 51:4-note). 'I have done this evil!' He means his blood-guiltiness. A wicked man will say he is a sinner—but a child of God says, 'I have done this evil!' Peter wept for that particular sin of denying Christ. It is reported that Peter never heard a rooster crow—but he fell a-weeping. There must be a particular repentance, before we have a general pardon.

Gospel tears must drop from the eye of faith. 'The father of the child cried out with tears, 'Lord, I believe' (Mark 9:24). Our disease must make us mourn—but when we look up to our Physician, who has made a remedy of his own blood, we must not mourn without hope. Believing tears are precious. When the clouds of sorrow have overcast the soul, some sunshine of faith must break forth. The soul will be swallowed up of sorrow, it will be drowned in tears—if faith does not keep it up from sinking. Though our tears drop to the earth—yet our faith must reach heaven. After the greatest rain, faith must appear as the rainbow in the cloud. The tears of faith are bottled as precious wine. 'You keep track of all my sorrows. You have collected all my tears in your bottle. You have recorded each one in your book' (Ps 56:8-note).

Gospel-mourning is joined with self-loathing. The sinner admires himself. The penitent loathes himself. 'You shall loath yourselves in your own sight for all your evils' (Ezekiel 20:43). A true penitent is troubled not only for the shameful consequence of sin—but for the loathsome nature of sin; not only the sting of sin—but the deformed face of sin. How did the leper loathe himself! (Leviticus 13:45). The true mourner cries out, O these impure eyes! this heart which is a conclave of wickedness! He not only leaves sin—but loathes sin. He who has fallen in the dirt loathes himself (Hosea 14:1).

Gospel-mourning must be purifying. Our tears must make us more holy. We must so weep for sin, as to weep out sin. Our tears must drown our sins. We must not only mourn—but turn. 'Turn to me with weeping' (Joel 2:12). What good is it, to have a watery eye and a whorish heart? It is foolish to say it is day, when the air is full of darkness; so to say you repent, when you draw dark shadows in your life. It is an excellent saying of Augustine, 'He truly bewails the sins he has committed, who never commits the sins he has bewailed'. True mourning is like the 'water of jealousy' (Nu 5:12-22). It makes the thigh of sin to rot. 'You broke the heads of the monster in the waters.' (Ps 74:13-note). The heads of our sins, these monsters, are broken in the waters of true repentance. True tears are cleansing. They are like a flood that carries away all the rubbish of our sins away with it. The waters of holy mourning are like the river Jordan wherein Naaman washed and was cleansed of his leprosy (2Ki 5:11, 12, 13, 14). It is reported that there is a river in Sicily where, if the blackest sheep are bathed, they become white; so, though our sins be as scarlet—yet by washing in this river of repentance, they become white as snow (Isaiah 1:18-note). Naturalists say of the serpent, before it goes to drink it vomits out its poison. In this 'be wise as serpents'. Before you think to drink down the sweet cordials of the promises, cast up the poison that lies at your heart. Do not only mourn for sin—but break from sin.

Gospel-mourning must be joined with hatred of sin. 'What indignation!' (2Cor 7:11). We must not only abstain from sin—but abhor sin. The dove hates the least feather of the hawk. A true mourner hates the least motion to sin. A true mourner is a sin-hater. Amnon hated Tamar more than ever he loved her (2Sa 13:15). To be a sin-hater implies two things: first, to look upon sin as the most deadly evil—as the essence of all evil. It looks more ghastly than death or hell. Second, to be implacably incensed against it. A sin-hater will never admit of any terms of peace. The war between him and sin is like the war between Rehoboam and Jeroboam. 'There was war between Rehoboam and Jeroboam all their days' (1Ki 14:30). Anger may be reconciled—hatred cannot. True mourning begins in the love of God—and ends in the hatred of sin.

Gospel-mourning in some cases is joined with restitution. It is as well a sin to violate the name of another—as the chastity of another. If we have eclipsed the good name of others, we are bound to ask them for forgiveness. If we have wronged them in their estate by unjust, fraudulent dealing, we must make them some compensation. Thus Zacchaeus, 'If I have taken anything from any man by false accusation, I restore him fourfold' (Luke 19:8), according to the law of Ex 22:1. James bids us not only look to the heart but the hand: 'Cleanse your hands, you sinners, and purify your hearts' (Jas 4:8-note). If you have wronged another, cleanse your hands by restitution. Be assured, without restitution—no remission.

Gospel-mourning must be a speedy mourning. We must take heed of adjourning our repentance, and putting it off until death. As David said, 'I will pay my vows now' (Psalm 116:18-note), so should a Christian say, 'I will mourn for sin now.' 'Blessed are you that weep now' (Lk 6:21). God has encircled us in the compass of a little time, and charges us immediately to bewail our sins. 'Now God calls all men everywhere to repent' (Acts 17:30). We know not whether we may have another day granted us. Oh let us not put off our mourning for sin until the making of our will. Do not think holy mourning is only a deathbed duty. You may seek the blessing with tears, as Esau when it is too late. How long shall I say that I will repent tomorrow? Why not at this instant? 'Delay brings danger'. Caesar's deferring to read his letter before he went to the Senate-house, cost him his life. The true mourner makes haste to meet an angry God, as Jacob did his brother; and the present he sends before, is the sacrifice of tears.

Gospel-mourning for sin is perpetual. There are some who at a sermon will shed a few tears—but they are soon dried up. The hypocrite's sorrow is like a vein opened and presently stopped. The Hebrew word for 'eye' signifies also 'a fountain', to show that the eye must run like a fountain for sin and not cease; but it must not be like the Libyan fountain which the ancients speak of—in the morning the water is hot, at midday cold. The waters of repentance must not overflow with more heat in the morning, at the first hearing of the gospel; and at midday, in the midst of health and prosperity, grow cold and be ready to freeze. No! it must be a daily weeping. As Paul said, 'I die daily' (1Cor 15:31), so a Christian should say, 'I mourn daily'. Therefore keep open an outflow of godly sorrow, and be sure it is not stopped until death. 'Let your tears flow like a river. Give yourselves no rest from weeping day or night' (Lam 2:18). It is reported of holy John Bradford that scarcely a day passed him wherein he did not shed some tears for sin. Daily mourning is a good antidote against backsliding. I have read of one that had an epilepsy, and being dipped in seawater, was cured. The washing of our souls daily in the brinish waters of repentance is the best way both to prevent and cure the falling into relapses.

(And the preceding is only a "snippet" of Thomas Watson's treatise on Mourning - highly recommended)

Hiebert points out that James' use of pentheo and klaio...

picture the emotional expressions of penitence, as Peter sobbing in shame when seized with a realization of his sin in denying Jesus (Mk 14:72).

Weep (2799) (klaio [word study]) means to cry with emphasis upon noise accompanying the weeping. Loud or audible weeping. Klaio expresses mourning and sorrow of all kinds. The picture is a person who laments with sobbing. There is shedding of tears accompanied by external expression. Klaio was used of wailing over the dead (Mt 2:18; Ge 37:34; Lxx = Dt 34:8). Indeed, an outflow of tears is a healthy sign that one is broken over their sin.

Klaio - 40x in 34v in the NT and is always translated weep(18), weeping(18), wept(4) - Mt 2:18; 26:75; Mk 5:38, 39; 14:72; 16:10; Lk 6:21, 25; 7:13, 32, 38; 8:52; 19:41; 22:62; 23:28; Jn 11:31, 33; 16:20; 20:11, 13, 15; Acts 9:39; 21:13; Ro 12:15-note; 1Co 7:30; Php 3:18-note; Jas 4:9; 5:1; Rev 5:4-note, Rev 4:5-note; Re 18:9, 11, 15, 19-note.

Klaio - 94x in the Non-apocryphal Septuagint (LXX) - Gen 21:16; 27:38; 29:11; 33:4; 37:35; 42:24; 43:30; 45:14f; 46:29; 50:1, 17; Ex 2:6; Lev 10:6; Nu 11:4, 10, 13, 18, 20; 14:1; 20:29; 25:6; Deut 1:45; 21:13; 34:8; Jdg 2:4; 9:7; 11:37f; 14:16f; 15:18; 16:28; 20:23, 26; 21:2; Ru 1:9, 14; 1Sa 1:7f, 10; 11:4f; 13:16; 20:41; 24:16; 30:4; 2 Sa 1:12, 24; 3:16, 32, 34; 12:21f; 13:36; 15:23, 30; 18:33; 19:1; 1Ki 18:45; 21:27; 2Ki 8:11f; 13:14; 20:3; 22:19; 2Chr 34:27; Ezra 3:12; 10:1; Neh 1:4; 8:9; Job 2:12; 30:25; 31:38; Ps 78:64; 95:6; 126:6; 137:1; Eccl 3:4; Isa 15:2, 5; 16:9; 22:4; 30:19; 33:7; 38:3; Jer 9:1; 13:17; 22:10, 18; 34:5; 41:6; 48:5; 50:4; Lam 1:1f, 15; Ezek 24:16, 23; Hos 12:4; Joel 1:5, 18; 2:17; Mic 2:6.

The Greek-English Lexicon of the Septuagint has the following entry for klaio...

Ge 21:16; 27:38; 29:11; 33:4; 37:35 to cry, to weep, to wail, to lament [abs.] Ge 21:16; to weep for, to lament for, to bewail. Ge 37:35; id. Nu 11:13; id.  Lv 10:6 he wept bitterly (semit., rendering 2Ki 20:3; cpr. Ge 46:29, Jdg 21:2, 2Sa 13:36, Is 30:19, Jer 22:10

Sin must have tears. While we carry the fire of sin about with us—we must carry the water of tears to quench it! (Ezekiel 7:16). 'They are not blessed' (says Chrysostom) 'who mourn for the dead—but rather those who mourn for sin.' And indeed it is with good reason we mourn for sin, if we consider the GUILT of sin, which binds over to wrath. Will not a guilty person weep, who is to be bound over to the penalty? Every sinner is to be tried for his life and is sure to be cast away—if sovereign mercy does not become an advocate for him. (Beatitudes)

How amazing it is that we have so few tears these days when there is so much to weep about! (From John Blanchard's highly recommended collection - The Complete Gathered Gold- A Treasury of Quotations) (On Wordsearchbible)

LET THE TEARS FLOW - A DEVOTIONAL - It isn't good to brood about our sins nor to lament constantly over our shortcomings. But neither should we take them too lightly. To disobey the moral law of a holy God is a serious thing. Although as Christians we bask in the warm glow of divine forgiveness, we must never minimize the awful reality of sin.

A young pastor visited Dundee, Scotland, shortly after Robert Murray McCheyne died at age thirty. Many people had come to Christ because of McCheyne's ministry, and the visitor wanted to know the secret of his great influence. The old sexton of McCheyne's church led the preacher into the rectory and showed him some of McCheyne's books lying on a table. Then he motioned to the chair the evangelist had used, and said, "Sit down and put your elbows on the table." The visitor obeyed. "Now put your head in your hands." He complied. "Now let the tears flow; that's what McCheyne did." Next he led him into the church and said, "Put your elbows on the pulpit." The visitor did. "Now put your face in your hands." He obeyed. "Now let the tears flow; that's what McCheyne used to do."

Robert Murray McCheyne cried freely over his sins and over those of his people. By contrast, our emotions are often hardened toward sin. We need to be more sensitive to the convicting voice of God's Spirit and more determined to live a separated life. We may rejoice in God's forgiveness, but we should never be afraid to mourn for our sins.—D. C. Egner (Our Daily Bread, Copyright RBC Ministries, Grand Rapids, MI. Reprinted by permission. All rights reserved)

Calvary proves that sin troubles God—
Does it trouble you?

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DRY EYES - A DEVOTIONAL - I read a news report about a woman who hadn't shed a tear in 18 years. The reason for her dry eyes was physical, not emotional. Doctors said she was a victim of a rare condition called Sjogren's syndrome. For some unknown reason, antibodies attacked her tear glands as if they were undesirable foreign organisms.

This reminds me of a spiritual problem among the people of God—people who should and could cry, but don't. They need to learn what Jesus meant when He said, "Blessed are those who mourn" (Mt 5:4-note).

Sometimes we think tears are a sign of weakness. But if this were the case, why did Jesus cry? (Lk 19:41). Why did James tell Christians to weep over their sins? (James 4:9).

True, people differ in the way they express their emotions. But literal tears aren't the real issue. What's important is the attitude of the heart. The real issue is how deeply we sense the implications of our sins. Are we filled with Godly sorrow? Are we pained by the tragic consequences our sin creates in our relationships with others? I'm not talking about putting on a phony show of sorrow, but do we feel some of the same sorrow God feels about evil? Are we willing to turn from it? Or do we have dry eyes? — Mart De Haan (Our Daily Bread, Copyright RBC Ministries, Grand Rapids, MI. Reprinted by permission. All rights reserved)

The Lord wants us to mourn our sin,
To grieve what brings Him pain;
And if the sorrow changes us,
Our tears won't be in vain. —Sper

Indifference to evil is a great evil.

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A GODLY MAN WEEPS
from Thomas Watson's
The Godly Mans Picture

David sometimes sang with his harp; and sometimes the organ of his eye wept: "I water my couch with my tears" (Psalm 6:6). Christ calls his spouse his "dove" (Song 2:14). The dove is a weeping creature. Grace dissolves and liquefies the soul, causing a spiritual thaw. The sorrow of the heart, runs out at the eye (Psalm 31:9).

The Rabbis report that the same night on which Israel departed from Egypt towards Canaan, all the idols of Egypt were broken down by lightning and earthquake. Just so, at that very time at which men go forth from their natural condition towards heaven, all the idols of sin in the heart must be broken down by repentance! A melting heart is the chief branch of the covenant of grace (Ezek. 36:26), and the product of the Spirit: "I will pour upon the house of David the spirit of grace, and they shall look upon me whom they have pierced, and they shall mourn for him" (Zech. 12:10).

Question: But why is a godly man a weeper? Is not sin pardoned, which is the ground of joy? Has he not had a transforming work upon his heart? Why, then, does he weep?

Answer: A godly man finds enough reasons for weeping:

1. He weeps for indwelling sin, the law in his members (Ro 7:23), the outbursts and first risings of sin. His nature is a poisoned fountain. A regenerate person grieves that he carries with him, that which is enmity to God! His heart is like a wide sea in which there are innumerable creeping things (Ps 104:25)—vain, sinful thoughts. A child of God laments hidden wickedness; he has more evil in him than he knows of. There are those windings in his heart which he cannot trace—an unknown world of sin. "Who can understand his errors?" (Ps 19:12).

2. A godly man weeps for clinging corruption. If he could get rid of sin, there would be some comfort—but he cannot shake off this viper! Sin cleaves to him like leprosy! Though a child of God forsakes his sin—yet sin will not forsake him. "Concerning the rest of the beasts, they had their dominion taken away: yet their lives were prolonged for a season" (Da 7:12). So though the dominion of sin is taken away—yet its life is prolonged for a season; and while sin lives, it molests! The Persians were daily enemies to the Romans and would always be invading their frontiers. So sin "wars against the soul" (1Pe. 2:11). And there is no cessation of war—until death. Will not this cause tears?

3. A child of God weeps that he is sometimes overcome by the prevalence of corruption. "For I do not do the good that I want to do, but I practice the evil that I do not want to do." (Ro 7:19). Paul was like a man carried downstream. How often a saint is overpowered by pride and passion! When David had sinned, he steeped his soul in the brinish tears of repentance. It cannot but grieve a regenerate person to think he should be so foolish as, after he has felt the smart of sin—still to put this fire in his bosom again!

4. A godly heart grieves that he can be no more holy. It troubles him that he shoots so short of the rule and standard which God has set. "I would", says he, "love the Lord with all my heart. But how defective my love is! How far short I come of what I should be; no, of what I might have been! What can I see in my life—but either blanks or blots?"

5. A godly man sometimes weeps out of the sense of God's love. Gold is the finest and most solid of all the metals—yet it is soonest melted in the fire. Gracious hearts, which are golden hearts, are the soonest melted into tears by the fire of God's love. I once knew a holy man, who was walking in his garden and shedding plenty of tears, when a friend came on him accidentally and asked him why he wept. He broke forth into this pathetic expression: "Oh, the love of Christ! Oh, the love of Christ!" Thus have we seen the cloud melted into water, by the sunbeams.

6. A godly person weeps because the sins he commits are in some sense worse than the sins of other men. The sin of a justified person is very odious:

(i) The sin of a justified person is odious—because he acts contrary to his own principles. He sins not only against the rule—but against his principles, against his knowledge, vows, prayers, hopes, experiences. He knows how dearly sin will cost him—yet he adventures upon the forbidden fruit!

(ii) The sin of a justified person is odious, because it is a sin of unkindness (1 Kings 11:9). Peter's denying of Christ was a sin against love. Christ had enrolled him among the apostles. He had taken him up into the Mount of Transfiguration and shown him the glory of heaven in a vision. Yet after all this dazzling mercy—it was base ingratitude, that he should deny Christ! This made him go out and "weep bitterly" (Matt. 26:75). He baptized himself, as it were, in his own tears! The sins of the godly go nearest to God's heart. The sins of others anger God; the sins of the godly grieve him! The sins of the wicked pierce Christ's side! The sins of the godly wound his heart! The unkindness of a spouse, goes nearest to the heart of her husband.

(iii) The sin of a justified person is odious, because it reflects more dishonor upon God. "By this deed you have given great occasion to the enemies of the Lord to blaspheme" (2Sa 12:14). The sins of God's people put black spots on the face of piety. Thus we see what cause there is why a child of God should weep even after conversion. "Can whoever sows such things refrain from tears?"

Now this sorrow of a godly man for sin, is not a despairing sorrow. He does not mourn without hope. "Iniquities prevail against me" (Ps 65:3)—there is the holy soul weeping. "As for our transgressions, you shall purge them away"—there is faith triumphing.

Godly sorrow is excellent. There is as much difference between the sorrow of a godly man, and the sorrow of a wicked man—as between the water of a spring which is clear and sweet, and the water of the sea which is salt and brackish. A godly man's sorrow has these three qualifications:

(a) Godly sorrow is INWARD. It is a sorrow of soul. Hypocrites "disfigure their faces" (Matt. 6:16). Godly sorrow goes deep. It is a "pricking at the heart" (Acts 2:37). True sorrow is a spiritual martyrdom, therefore called "soul affliction" (Lev. 23:29).

(b) Godly sorrow is SINCERE. It is more for the evil that is in sin—than the evil which follows after sin. It is more for the spot—than the sting. Hypocrites weep for sin only as it brings affliction. Hypocrites never send forth the streams of their tears, except when God's judgments are approaching.

(c) Godly sorrow is INFLUENTIAL. It makes the heart better: "by the sadness of the countenance, the heart is made better" (Eccles. 7:3). Divine tears not only wet—but wash; they purge out the love of sin!

Use 1. How far from being godly are those who scarcely ever shed a tear for sin! If they lose a near relation—they weep. But though they are in danger of losing God and their souls—they do not weep. How few know what it is to be in an agony for sin, or what a broken heart means! Their eyes are not like the "fishpools in Heshbon", full of water (Song 7:4)—but rather like the mountains of Gilboa, which had "no dew" upon them (2 Sam. 1:21). It was a greater plague for Pharaoh to have his heart turned into stone—than to have his rivers turned into blood.

The wicked, if they sometimes shed a tear—are never the better. They go on in wickedness, and do not drown their sins in their tears!

Use 2: Let us strive for this divine characteristic. Be weepers! This is "a repentance not to be repented of" (2Co 7:10). It is reported of Bradford, the martyr, that he was of a melting spirit; he seldom sat down to his meal but some tears trickled down his cheeks. There are two lavers to wash away sin: blood and tears. The blood of Christ washes away the guilt of sin; our tears wash away the filth of sin.

Repenting tears are precious. God puts them in his bottle (Psalm 56:8). Repenting tears are beautifying. To God—a tear in the eye, adorns more than a ring on the finger. Oil makes the face shine (Ps 104:15). Tears make the heart shine. Repenting tears are comforting. A sinner's mirth turns to melancholy. A saint's mourning turns to music! Repentance may be compared to myrrh, which though it is bitter to the taste—is comforting to the spirits. Repentance may be bitter to the flesh, but it is most refreshing to the soul. Wax which melts is fit for the seal. A melting soul is fit to take the stamp of all heavenly blessing. Let us give Christ the water of our tears—and he will give us the wine of his blood! (Read the entire book The Godly Mans Picture)

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Let your laughter be turned into mourning and your joy to gloom: o gelos humon eis penthos metatrapheto (3SAPM) kai e chara eis katepheian: (Job 30:31; Pr 14:13; Eccl 2:2; 7:6; Lam 5:15; Lk 6:25; 16:25; Rev 18:7,8)

James is calling for a striking reversal of their emotional expression.

The Amplified Version renders it...

Let your laughter be turned to grief and your mirth to dejection and heartfelt shame [for your sins]. (Amplified Bible - Lockman)

Barton comments...

The sorrow being described in this verse is not a public show. We should not attempt to impress God with elaborate displays of repentance. There may be a time of public confession, but the grief-work over sin is largely private and interior. The presence of close friends may help, for sometimes they know us better than we know ourselves. They can also hold us accountable to our confession. But the outcome of this entire process must result in submission to God. (Barton, B. B., et al. Life Application Bible Commentary. Romans: Tyndale House Publishers or Logos)

Hughes writes that there are some...

who are so insensitive and superficial that they are laughing when they ought to be weeping! Some laughter indicates a sickness of soul which only tears can cure. Have we wept over our sins? (Hughes, R. K. James : Faith that works. Preaching the Word. Crossway Books or Logos)

Let...be turned (3344) (metastrepho from meta = change + strepho = to twist, turn around or reverse; Note some more modern transcripts have the verb metatrepo = turn around, change the mind) means literally to turn about and figuratively to cause a change from one state to another. In some secular contexts the idea of metastrepho was to change one's mind. The idea is to cause a change of state, with emphasis upon the difference in the resulting state.

Hiebert says that the verb metastrepho is in the...

aorist passive third person singular (which) points to a force outside of themselves (see passive voice) producing the reversal, whereas the imperative calls upon their will to let it work. The change will occur as Spirit-wrought conviction seizes them. The demanded reversal relates to their past sinful pleasures. This does not mean that laughter in itself is evil (cf. Ps. 126:2-note), nor is James prohibiting future laughter for his readers. "James is no killjoy," Moo asserts and then points out, "But `laughter' in the Old Testament and Judaism is often the scornful laughter of the fool (Eccl 7:6) who blithely refuses to take sin seriously." (Ibid)

Metastrepho is used to translate the warning by the OT prophet Amos issued against faithless Israel (primarily directed at the northern 10 tribes but some prophecies included the southern nation of Judah)...

Amos 8:10 "Then I shall turn your festivals into mourning and all your songs into lamentation; And I will bring sackcloth on everyone's loins And baldness on every head. And I will make it like a time of mourning for an only son, And the end of it will be like a bitter day.

As someone has well said joys are our wings; sorrows are our spurs and every lock of sorrow has a key of promise to fit it.

Laughter (1071)(gelos from geláo = to laugh) means laughter and by metonymy merrymaking, rejoicing. Gelos was used of the leisurely, merry laughter of "gods" and men in their pleasures. This laughter is that of the fool who rejects God as the One Who determines reality and believes man to be an autonomous being.

The verb gelao is used in Lk 6:21, 25 where it signifies loud laughter in contrast to demonstrative weeping.  In the account of Jairus’ daughter, the related verb katagelao describes the scornful, superior laughter of those who ridiculed Jesus, believing that he could do nothing about someone already dead  (Mt. 9:24, cp Sarah's scornful laughter in Ge 18:12).

Luke 6:21 "Blessed are you who hunger now, for you shall be satisfied. Blessed are you who weep now, for you shall laugh.

Luke 6:25 "Woe to you who are well-fed now, for you shall be hungry. Woe to you who laugh now, for you shall mourn and weep.

John MacArthur makes the point that...

James is not condemning legitimate laughter or joy but rather the flippant, trivial, worldly, self-centered, sensual kinds that unbelievers revel in, despite, and often because of, their sinful pleasures. It corresponds to Jesus’ warning: “Woe to you who laugh now, for you shall mourn and weep” (Lk 6:25), and is the opposite of a beatitude given a few verses earlier that is recorded only in Luke: “Blessed are you who weep now, for you shall laugh” (Lk 6:21). In both verses Jesus used a verb form of the noun that in the present text is rendered laughter.

NIDNTT notes that...

The word group as a whole was in use in Greek literature from the time of Homer onwards and covered a whole range of meanings from free and joyous laughter to ridicule and scorn. The compound katagelao is an intensification, meaning either laugh loudly or sneer. The words were not only applied to men but also to the gods. K. H. Rengstorf (TDNT I 661) notes that for the Romans and the Greeks merry laughter was a divine characteristic which featured in the theophanies (cf. Virgil, Eclogues 4, 60 ff. where laughter following the birth of a child denoted its divine character). “gelos is a mark of deity which also spreads gelos in the world around” (K. H. Rengstorf, ibid.). (Brown, Colin, Editor. New International Dictionary of NT Theology. 1986. Zondervan)

There are 14 uses of gelos in the Septuagint - Gen 21:6; Job 8:21; 17:6; Pr 10:23; Eccl 2:2; 7:3, 6; 10:19; Jer 20:7; 48:26, 39; Lam 3:14; Amos 7:9; Mic 1:10

Genesis 21:6 And Sarah said, "God has made laughter for me; everyone who hears will laugh with me."

Ecclesiastes 2:2 I said of laughter, "It is madness," and of pleasure, "What does it accomplish?"

Ecclesiastes 7:3 Sorrow is better than laughter, For when a face is sad a heart may be happy.

As Ryrie says...

Laughter is sometimes desirable (cp Ps. 126:2-note), but not when it reflects worldly frivolity.

Martin observes that laughter to mourning while negative in one sense...

should not be construed as though the preacher were a kill-joy. What the writer is saying is that the actions of (foolish) laughing and (senseless) rejoicing hold no place for Christians who refuse to turn to God’s paths. (Martin, R. P. Vol. 48: Word Biblical Commentary : James. Dallas: Word, Incorporated)

Thomas Manton writes that...

In this context he describes them as being worldly and as glorying in oppressing one another; he means here the sort of joy and laughter by which complacent sinners please themselves in their present success, putting off all thoughts of imminent judgment.

Zodhiates comments that...

Somebody said, “If you want to know whether a man’s life is made up of frivolous or serious things, watch what he laughs at.” If the Christian has to look at the same things as the worldly and unconverted people in order to laugh, then there is something radically wrong with his Christianity. A Christian believer cannot laugh at sin; he rather mourns because of it. The things that caused him to laugh before he became a Christian ought to cause him to mourn now after his repentance and regeneration. The laughter of his sinful life ought to become the mourning of his Christian life. The unconverted will not enjoy the believer’s company in their ungodly mirth, and he should not be able to enjoy the company of the unconverted. A Christian will enjoy laughter, probably even more than the unconverted, because he is really happy, but he will not laugh at the same things or with the same persons. (Zodhiates, S. Faith, Love, & Hope: An Exposition of the Epistle of James. Exegetical Commentary Series. Chattanooga, TN: AMG Publishers)

David Brainerd's journal on October 18, 1740 has this entry...

My soul before Thee prostrate lies;
To Thee, her Source, my spirit flies;
My wants I mourn, my chains I see;
O let Thy presence set me free.
(My Soul Before Thee Prostrate Lies)

Mourning (3997) (penthos) means grief or sorrow. Our English noun mourning describes an outward sign of grief (such as wearing of black clothing) or a period of time during which such signs of grief are shown. As someone has well said we should mourn over sin as long as we have sin to mourn over!

Penthos occurs 5x in 4v in the NT...
 

James 4:9 Be miserable and mourn and weep; let your laughter be turned into mourning, and your joy to gloom.

Revelation 18:7 (note) "To the degree that she (Mystery Babylon) glorified herself and lived sensuously, to the same degree give her torment and mourning; for she says in her heart, 'I sit as a queen and I am not a widow, and will never see mourning.' 8 "For this reason in one day her plagues will come, pestilence and mourning and famine, and she will be burned up with fire; for the Lord God who judges her is strong.

Revelation 21:4 (note) and He shall wipe away every tear from their eyes; and there shall no longer be any death; there shall no longer be any mourning, or crying, or pain; the first things have passed away."

Penthos - 28v in the non-apocryphal Septuagint (LXX) (Most of these uses are in the context of death) - Ge 27:41; 35:8; 50:4, 10, 11; Deut 34:8; 2Sa 11:27; 19:2; Esther 4:3, 17; 9:22; Pr 10:6; 14:13; Eccl 5:17; 7:2, 4; Isa 16:3; 17:14; 60:20; Jer 6:26; 16:7; 31:13; La 5:15; Ezek 24:17; Hos 9:4; Amos 5:16; 8:10; Mic 1:8

Lamentations 5:15 The joy of our hearts has ceased; Our dancing has been turned into mourning. (Comment: The sins of Jerusalem led to God's destruction and thus the "death" of the city, and as a consequence the people mourned.)

Jeremiah 31:13 "Then (Ed: When is then? When the Deliverer, the Messiah, comes from Zion to ransom captive Israel [cp Ro 11:26, 27-note] and inaugurate the glorious Millennium - [or see Millennium Part 3 for Biblical descriptions of the Messianic Age] ) the virgin shall rejoice in the dance, And the young men and the old, together, For I will turn their mourning into joy, And will comfort them, and give them joy for their sorrow.

George Barlow was right when he said...

There is no progress possible to the man who does not see and mourn over his defects.

John R. W. Stott spoke of the value of mourning when he said that

We can stand before the cross only with a bowed head and a broken spirit.

J C Ryle writes that those who turn laughter to mourning refers to

the man that feels his sin and hates it, that mourns that he should have rebelled against God, and desires to find mercy. Now, God will come to such, because there is purity in that heart. “Oh,” saith the contrite spirit, “I do not see any purity in my heart.” No, but what do you see, then? “Oh, I see all manner of sin and evil, and I hate myself because it is so.” There is purity in that hatred; at any rate there is a something that God loves in that hatred in your soul, of the sin that is within, and He will come to you, for there is something there that is akin to His own holiness: He has put it there. You have begun to appeal for mercy. Oh, then, God’s mercy will come, for mercy delights to visit misery. Mercy is always at home where there is a sinner confessing sin. (From his sermon on Isa 66:1,2 - Living Temples for the Living God)

Thomas Brooks writes (1662) in his book The Crown and Glory of Christianity or, HOLINESS, the Only Way to Happiness

Joy (5479) (chara [word study]) is a feeling of inner gladness, delight or rejoicing.  Secular dictionaries define joy as the emotion evoked by well-being, success, or good fortune or the emotion evoked by the prospect of possessing what one desires. The world's definition of joy is therefore virtually synonymous with the definition of happiness, for both of these "emotions" are dependent on what "happens".

Joy is that inner feeling which often expresses itself in laughter. James is calling for an about face reversal from joy to gloom or dejection!

Gloom  (2726) (katepheia from kata = down + phaino = shine) means downcast in look or the condition of one whose eyes are cast down. It pictures a dejected, sorrowful countenance that reflects a heavy heart.

Although katepheia is not used by our Lord in His description of the tax collector in Luke 18, his description of this man gives us an good sense of the meaning of downcast...

But the tax-gatherer, standing some distance away, was even unwilling to lift up his eyes to heaven, but was beating his breast, saying, 'God, be merciful to me, the sinner (hamartolos)!' (Luke 18:13)

VGNT writes that of a secular use of katepheia that...

the context suggests...“with eyes cast down for shame” and the same reference to the outward expression of the countenance underlies the only occurrence in Jas 4:9.

Martin Luther

You learn your theology most where your sorrows take you. (From John Blanchard's highly recommended collection - The Complete Gathered Gold- A Treasury of Quotations) (On Wordsearchbible)

Chrysostom put it well when he said that...