Sirach 21
What do you do the moment after you realize you have sinned? Sirach 21 begins exactly there, and its first word is not a rebuke but a hand on the shoulder: "My son, hast thou sinned? do so no more: but for thy former sins also pray that they may be forgiven thee." Two movements live in that single line. Turn from the sin you have just seen, and bring the old ones to God in prayer.
Only then does the chapter sharpen its warning. Sin is a serpent whose bite kills, a sword whose wound has no remedy. It is described this way not to crush the reader but to make us take seriously what we are tempted to treat lightly, so that we will actually flee.
From that opening the chapter unfolds the long contrast wisdom literature loves: the wise heart set against the fool's. The knowledge of the wise "shall abound like a flood," and his counsel "continueth like a fountain of life," while the heart of a fool is "like a broken vessel" that can hold no wisdom at all. The difference between the two is not cleverness. It is what each one does with a word of correction.
One hears it, praises it, and applies it to himself; the other is displeased and casts it behind his back. The chapter closes where it opened, at the place all of this finally shows itself - the tongue. "The heart of fools is in their mouth: and the mouth of wise men is in their heart." What we treasure within is what at last we speak.
Tap any highlighted phrase to jump to the commentary that unpacks it.

Sirach 21:1-5My Son, Hast Thou Sinned? Do So No More
1My son, hast thou sinned? do so no more: but for thy former sins also pray that they may be forgiven thee.
The chapter opens with the most pastoral words in it. The teacher does not begin by listing the reader's failures; he begins with "My son," the address of a father to a child he loves. And the counsel comes in two parts. First, "do so no more" - turn from the sin now in front of you, refuse to keep walking the path you have seen is wrong. Second, "for thy former sins also pray that they may be forgiven thee" - do not leave the old debts buried, but bring them into the open before God in prayer.
This is the rhythm of a heart coming home: stop, and ask. It is the same word the Lord would later speak to a woman everyone else had condemned, "Go, and sin no more" (John 8:11), sending her out forgiven and free.
2Flee from sins as from the face of a serpent: for if thou comest near them, they will take hold of thee. 3The teeth thereof are the teeth of a lion, killing the souls of men. 4All iniquity is like a two-edged sword, there is no remedy for the wound thereof.
Now the tenderness turns to urgency. Sin is pictured as a serpent, and the instruction is not to negotiate with it or study it from a safe distance but to flee - the way a person recoils from a snake before thought even forms. The reason is given plainly: "if thou comest near them, they will take hold of thee." Sin is not passive. Approach it, linger near it, and it reaches out and seizes you.
The teeth that follow "are the teeth of a lion," and what they kill is not the body but "the souls of men." Scripture keeps this same picture: an enemy who "walketh about, seeking whom he may devour" (1 Peter 5:8). The wise response to a predator is distance, and the only safe distance from sin is the far side of it.
The third image is the gravest: "All iniquity is like a two-edged sword, there is no remedy for the wound thereof." A two-edged sword cuts whichever way it moves; sin wounds the one it touches and the one who wields it. And the line warns that some wounds reach where ordinary healing cannot follow. This is sober realism about what sin does, and it is meant to make us cautious, not despairing. The chapter has already shown the way out before naming the danger - turn, and pray to be forgiven.
The warning about the wound is here so that we will take the open door of verse 1 while it stands open.
5Injuries and wrongs will waste riches: and the house that is very rich shall be brought to nothing by pride: so the substance of the proud shall be rooted out.
The teacher adds a social application. A fortune built on "injuries and wrongs" cannot stand; the wrongdoing that gathered it will scatter it. And "the house that is very rich shall be brought to nothing by pride." Pride is named as the rot at the foundation, the thing that hollows out even great prosperity until "the substance of the proud shall be rooted out." This is the same verdict Scripture pronounces everywhere: "Pride goeth before destruction, and an haughty spirit before a fall" (Proverbs 16:18).
What looks secure because it is large is not secure if it is proud. The fear of God, which the chapter will soon praise, is the only foundation a house can finally rest on.
Learn to recognize that moment and move. The wound the chapter warns about is real; so is the open door it sets before you first.
Sirach 21:6-11The Prayer of the Poor, and the End of the Sinner's Road
6The prayer out of the mouth of the poor shall reach the ears of God, and judgment shall come for him speedily. 7He that hateth to be reproved walketh in the trace of a sinner: and he that feareth God will turn to his own heart.
A bright promise interrupts the warnings: "The prayer out of the mouth of the poor shall reach the ears of God, and judgment shall come for him speedily." The one with no power to defend himself, no wealth to buy a hearing, is heard at once in heaven. God leans toward the cry of the lowly, and the help that the world withholds from them He gives. This is woven through all of Scripture - "this poor man cried, and the LORD heard him, and saved him out of all his troubles" (Psalm 34:6).
The verse stands deliberately near the warning about proud houses being rooted out. The rich man trusting his fortune is not heard for his riches; the poor man with nothing but his cry is heard for his need.
Verse 7 draws the dividing line of the whole chapter. "He that hateth to be reproved walketh in the trace of a sinner" - to refuse correction is already to be walking in the sinner's footprints, on his road, heading where he is headed. But "he that feareth God will turn to his own heart." The one who reveres God does not deflect a hard word outward onto others; he turns inward, examines himself, lets the reproof do its work.
This turning to one's own heart is the quiet hinge between the wise and the fool. The same correction comes to both; one resents it and keeps walking, the other receives it and turns.
8He that is mighty by a bold tongue is known afar off, but a wise man knoweth to slip by him. 9He that buildeth his house at other men’s charges, is as he that gathereth himself stones to build in the winter.
Two pictures of folly built on a bad foundation. The loud man, "mighty by a bold tongue," makes himself "known afar off" - his volume carries, his bluster impresses at a distance. But the wise man "knoweth to slip by him," declining to be drawn into the contest, recognizing noise for what it is. And the one who "buildeth his house at other men's charges," raising his life on what rightly belongs to others, is gathering stones "to build in the winter" - cold, hard labor on a foundation that will not hold.
Both the loud and the grasping look like they are getting ahead. The chapter sees the frost already in the mortar.
10The congregation of sinners is like tow heaped together, and the end of them is a flame of fire. 11The way of sinners is made plain with stones, and in their end is hell, and darkness, and pains.
The chapter names where the two roads arrive. The crowd of sinners gathered together is "like tow heaped together" - dry, bundled flax, ready to catch, and "the end of them is a flame of fire." Then a haunting line: "The way of sinners is made plain with stones." Their road is smooth, paved, easy to walk, pleasant underfoot. That is exactly its danger. The broad and comfortable way asks nothing and warns of nothing, yet "in their end is hell, and darkness, and pains."
Jesus would draw the same contrast: "broad is the way, that leadeth to destruction" (Matthew 7:13). A road is not safe because it is smooth. What matters is where it lets out.
You do not have to be impressive to be heard. You have only to be honest, and to come.
Sirach 21:12-17A Fountain of Life, and a Broken Vessel
12He that keepeth justice shall get the understanding thereof. 13The perfection of the fear of God is wisdom and understanding.
Two verses set the root of wisdom in place before the chapter pictures its fruit. "He that keepeth justice shall get the understanding thereof" - understanding is not handed to the spectator but grows in the one who actually does what is right. Wisdom is learned in the doing. Then the summary line: "The perfection of the fear of God is wisdom and understanding." The fear of God, that reverent awe before the Holy One, is not the lowest rung of religion to be left behind; brought to its fullness, it simply is wisdom.
This is the conviction at the heart of all the wisdom books: "The fear of the LORD is the beginning of wisdom" (Proverbs 9:10). Everything the chapter says about the wise and the fool flows from whether or not this reverence lives in a person.
15But there is a wisdom that aboundeth in evil: and there is no understanding where there is bitterness. 16The knowledge of a wise man shall abound like a flood, and his counsel continueth like a fountain of life.
The chapter pauses to warn that not all cleverness is wisdom: "there is a wisdom that aboundeth in evil," a shrewdness bent to wicked ends, and "there is no understanding where there is bitterness." A heart soured by bitterness cannot see clearly, however sharp its mind. Set against that comes one of the loveliest images in the book: "The knowledge of a wise man shall abound like a flood, and his counsel continueth like a fountain of life."
The wise person is a spring. What he knows does not sit stagnant; it overflows and waters others, and his counsel keeps flowing like a fountain that never runs dry. Wisdom, rightly held, is not a private hoard. It is a source of life for everyone who comes near it.
17The heart of a fool is like a broken vessel, and no wisdom at all shall it hold.
The opposite image lands with quiet force: "The heart of a fool is like a broken vessel, and no wisdom at all shall it hold." Pour wisdom into a cracked jar and it runs straight out the bottom; nothing stays. The fool may hear a thousand good words and retain none of them, not because none reached him but because his heart cannot keep what it receives. Set the two pictures side by side and the whole chapter comes into focus.
The wise heart is a fountain that gives life away; the foolish heart is a broken vessel that cannot even hold its own. The difference is what each does with what it is given - and that is precisely the difference the next verses will draw.
The chapter says the wise man becomes a spring that never runs dry; Christ is the source from which that spring is fed. Even the broken vessel is met by Him, for He came to heal what cannot hold itself together and to make the cracked heart able to keep the wisdom it receives. To fear God and come to Christ is to be turned from a broken jar into a fountain of life.
Do one true thing today that you have only been hearing about, and you take a step from broken vessel toward fountain.
Sirach 21:18-22One Lays It to Heart, Another Casts It Behind His Back
18A man of sense will praise every wise word he shall hear, and will apply it to himself: the luxurious man hath heard it, and it shall displease him, and he will cast it behind his back.
Here is the dividing line of the whole chapter, drawn in a single verse. Two people hear the same wise word. "A man of sense will praise every wise word he shall hear, and will apply it to himself" - he welcomes the truth and, more, he turns it on himself, asking what it means for his own life. The other, the self-indulgent man, "hath heard it, and it shall displease him, and he will cast it behind his back."
Same word, opposite response. One lays it to heart; the other flings it where he will not have to look at it. This is what separates wisdom from folly in practice. It is rarely a matter of who has access to truth. It is a matter of who is willing to be changed by it. James says it the same way: be "doers of the word, and not hearers only" (James 1:22).
19The talking of a fool is like a burden in the way: but in the lips of the wise, grace shall be found. 20The mouth of the prudent is sought after in the church, and they will think upon his words in their hearts.
The contrast moves to how each person's speech lands on others. The fool's talk is "like a burden in the way" - it tires those who must carry it, a weight that wearies a journey. But "in the lips of the wise, grace shall be found"; their words come with a kind of grace that lifts rather than burdens. So "the mouth of the prudent is sought after in the church," in the gathered assembly of God's people, and others "will think upon his words in their hearts," carrying them home to ponder.
Wise speech earns a hearing not by force or volume but by the weight of its truth. People come back to words that proved trustworthy.
21As a house that is destroyed, so is wisdom to a fool: and the knowledge of the unwise is as words without sense. 22Doctrine to a fool is as fetters on the feet, and like manacles on the right hand.
The chapter returns to the fool to show how teaching feels to a heart unwilling to receive it. To the fool, wisdom is "as a house that is destroyed" - a ruin he wanders through without making it home, getting no shelter from it. And "doctrine to a fool is as fetters on the feet, and like manacles on the right hand." The very instruction meant to set him free feels like chains; correction strikes him as imprisonment rather than rescue.
This is the tragedy of the closed heart. What would have freed him he experiences as bondage, and so he shakes it off. The same teaching that the wise receive as light, the fool resents as weight, and the difference is entirely in the one who hears.
And ask whether the teaching that corrects you feels like fetters or like freedom. If it feels like chains, the obstacle may not be the teaching. It may be a heart not yet willing to be led.
Sirach 21:23-31The Fool's Heart Is in His Mouth
23A fool lifteth up his voice in laughter: but a wise man will scarce laugh low to himself. 24Learning to the prudent is as an ornament of gold, and like a bracelet upon his right arm.
A cluster of small portraits sketches the bearing of the wise against the fool. The fool "lifteth up his voice in laughter," loud and unrestrained, drawing all eyes; the wise man "will scarce laugh low to himself," not joyless but measured, his mirth governed rather than spilling everywhere. And to the prudent, "learning is as an ornament of gold, and like a bracelet upon his right arm." Where the fool felt instruction as fetters and manacles on that same right hand, the wise wears the very same learning as a thing of beauty and honor.
The image is deliberately matched to verse 22. The identical instruction is chains to one and gold to the other; the metal has not changed, only the heart that receives it.
25The foot of a fool is soon in his neighbour’s house: but a man of experience will be abashed at the person of the mighty. 26A fool will peep through the window into the house: but he that is well taught will stand without. 27It is the folly of a man to hearken at the door: and a wise man will be grieved with the disgrace.
These verses paint folly as a failure of restraint and respect. The fool's foot is "soon in his neighbour's house," intruding where he was not invited, while a person of discretion holds back even before the great. The fool "will peep through the window," pry, snoop, gather what is not his to know; "he that is well taught will stand without," keeping a respectful distance. And "it is the folly of a man to hearken at the door," to eavesdrop, to listen where he has no right - while "a wise man will be grieved with the disgrace" of it, ashamed even to be caught in such a thing.
Wisdom honors the boundaries of others. It does not need to know everything, and it will not stoop to learn by prying what it was not given to share.
28The lips of the unwise will be telling foolish things but the words of the wise shall be weighed in a balance. 29The heart of fools is in their mouth: and the mouth of wise men is in their heart.
Now the chapter gives the line that gathers everything it has said: "The heart of fools is in their mouth: and the mouth of wise men is in their heart." The fool's heart is in his mouth - whatever rises within spills out instantly, unfiltered, unweighed; he speaks first and there is no thinking behind the words, only behind the regret. The wise man's mouth is in his heart - his speech is governed from within, weighed before it is spoken, so that "the words of the wise shall be weighed in a balance."
The image is exact. For one, the mouth runs ahead of the heart; for the other, the heart rules the mouth. The Lord put the same truth at the root: "out of the abundance of the heart the mouth speaketh" (Matthew 12:34). Guard the heart, and the mouth is guarded with it.
30While the ungodly curseth the devil, he curseth his own soul. 31The talebearer shall defile his own soul, and shall be hated by all: and he that shall abide with him shall be hateful: the silent and wise man shall be honoured.
The chapter ends on the tongue's power to harm the one who wields it. The ungodly man who "curseth the devil" while clinging to his own sin only "curseth his own soul" - blaming the tempter changes nothing while the heart stays bent toward evil. And "the talebearer," the one who carries gossip from house to house, "shall defile his own soul." The damage is first to himself; the gossip stains the gossiper. He "shall be hated by all," and his company contaminates - "he that shall abide with him shall be hateful."
Against all this stands the closing word, quiet and luminous: "the silent and wise man shall be honoured." The chapter that opened with a serpent to be fled ends with a mouth to be governed, and the highest honor it can name is given to the one wise enough to be still.
And remember the chapter's last word - the silent and wise are honored. Sometimes the wisest thing your mouth can do is stay closed.
Where this echoes in Scripture
My Son, Hast Thou Sinned? Do So No More
- John 8:11Neither do I condemn thee: go, and sin no more.The Lord speaks the chapter's first counsel to a forgiven sinner: turn, and walk free.
- Proverbs 16:18Pride goeth before destruction, and an haughty spirit before a fall.The same verdict on the proud house that is "rooted out."
- 1 Peter 5:8Your adversary the devil, as a roaring lion, walketh about, seeking whom he may devour.Sin pictured as a predator whose teeth are "the teeth of a lion."
The Prayer of the Poor, and the End of the Sinner's Road
- Psalm 34:6This poor man cried, and the LORD heard him, and saved him out of all his troubles.The cry of the poor that "shall reach the ears of God."
- Matthew 7:13Wide is the gate, and broad is the way, that leadeth to destruction, and many there be which go in thereat.The road "made plain with stones" whose end is ruin.
- Proverbs 9:8Rebuke a wise man, and he will love thee.The one who fears God receives reproof instead of hating it.
A Fountain of Life, and a Broken Vessel
- Proverbs 9:10The fear of the LORD is the beginning of wisdom: and the knowledge of the holy is understanding.The same root: reverence for God is where wisdom begins.
- John 4:14The water that I shall give him shall be in him a well of water springing up into everlasting life.Christ gives the "fountain of life" this chapter sees in the wise.
- John 7:38He that believeth on me... out of his belly shall flow rivers of living water.The believer becomes a spring that overflows, "like a fountain of life."
One Lays It to Heart, Another Casts It Behind His Back
- James 1:22Be ye doers of the word, and not hearers only, deceiving your own selves.The man of sense applies the word to himself instead of casting it away.
- Proverbs 1:7Fools despise wisdom and instruction.To the fool, "doctrine is as fetters" rather than freedom.
- Colossians 4:6Let your speech be alway with grace, seasoned with salt.In the lips of the wise, "grace shall be found."
The Fool's Heart Is in His Mouth
- Matthew 12:34Out of the abundance of the heart the mouth speaketh.The chapter's summary: the heart of fools is in their mouth.
- Proverbs 17:28Even a fool, when he holdeth his peace, is counted wise.The closing honor given to "the silent and wise man."
- James 1:19Let every man be swift to hear, slow to speak, slow to wrath.The wise man whose mouth is governed from within his heart.