Synopsis: This section of Proverbs is the first time that we are introduced to Lady Wisdom, the personification of wisdom that appears a few times throughout the book. Lady wisdom is found preaching and pleading with fools in the streets, that she might save some from the consequences of their foolish behavior. While some turn and find life in wisdom’s embrace, others refuse to listen and continue in their own destructive paths. This sermon will challenge us to reflect on the consequences of folly. It will ask us to search ourselves and consider if there are any areas of our life where we have been ignoring wisdom’s plea.

Text: Proverbs 1:20-33
Date: September 27, 2026

Introduction

Opening Illustration: When I was in college, I loved lifting weights. You could find me in the gym most days of the week. I remember one time an older wiser weight lifter gave me some coaching. And he said, “Young man, you’re very lop-sided.” I said “What do you mean.” He said, “Well you’re making the mistake that a lot of young men make. They lift all upper body and no lower body. You’ve got chicken legs son. And if you don’t even out you’re going to end up having back pain.” Well I didn’t listen to him because frankly I hated leg day. And today, I live with pretty consistent back pain.

Personal: Folly has consequences doesn’t it. Whether its something not morally significant like proper weight lifting, or something that really matterse, like choosing a spouse, managing your finances, navigating crisis and conflict, the path of folly has real world consequencs. My guess is, if you’re honest, you have your own fair share of stories regarding the consequences of your own foolishness. By God’s grace, as Christians we experience forgiveness. Because of Christ’s death and resurrection, we are truly free in Christ. Yet nevertheless, even Christians have often learn the hard way that our folly comes with a price.

Context: As we continue in our sermon series through Proverbs, we recall that Proverbs is trying to teach us as people of God, practical wisdom for life. We remember what we learned in week one, namely that underneath all of the wisdom that we discover in this book is one underlying principle.

Proverbs 1:7 “The fear of the Lord is the beginning of knowledge; fools despise wisdom and instruction.”

If you recall, the first 9 chapters of Proverbs are lengthy poems from Solomon, that are preparing us as readers, for the Proverbs that appear in chapters 10-31. And so many of themes that we will encounter later, begin here. The main idea of this section is as follows.

Main Idea: Rejecting Lady Wisdom’s counsel will only bring calamity in the end.

Proverbs 1:20–33 “Wisdom cries aloud in the street, in the markets she raises her voice; at the head of the noisy streets she cries out; at the entrance of the city gates she speaks: “How long, O simple ones, will you love being simple? How long will scoffers delight in their scoffing and fools hate knowledge? If you turn at my reproof, behold, I will pour out my spirit to you; I will make my words known to you. Because I have called and you refused to listen, have stretched out my hand and no one has heeded, because you have ignored all my counsel and would have none of my reproof, I also will laugh at your calamity; I will mock when terror strikes you, when terror strikes you like a storm and your calamity comes like a whirlwind, when distress and anguish come upon you. Then they will call upon me, but I will not answer; they will seek me diligently but will not find me. Because they hated knowledge and did not choose the fear of the Lord, would have none of my counsel and despised all my reproof, therefore they shall eat the fruit of their way, and have their fill of their own devices. For the simple are killed by their turning away, and the complacency of fools destroys them; but whoever listens to me will dwell secure and will be at ease, without dread of disaster.”

Exposition

WHO IS LADY WISDOM?

First, let us consider wisdom’s identity. In this passage, wisdom is personified as a woman.

Proverbs 1:20 “Wisdom cries aloud in the street, in the markets she raises her voice;”

“Lady Wisdom” as she if often called. Lady Wisdom is true street preacher, going into the city square and screaming loud for all who pass by to hear. Just as with most street preaching today, no matter how faithful and biblical the preacher is, the vast majority pass by, shake their head and scoff, and continue in their way.

Is This Christ?: Throughout the first nine chapters of Proverbs, Lady Wisdom will emerge a few times and begin to speak. Over the years, pastors and biblical scholars have looked the personification of wisdom in these chapters and have wondered about whether or not there is an intentional connection being made to the messiah, Jesus Christ. If so, this is pretty important for how we interpret this passage, and those like it. Why would they think this.

The Word of God: First, because Christ is the Word of God. That designation is given to Christ in the New Testament. And it captures the idea that God speaks. And in Christ, we see the entirety of the will of God on display. In a very direct sense, to look upon Jesus is to see God’s very Word embodied, living. And so, when we see in this passage, the Word of God going out in the streets, many scholars say, well this is Christ, God’s Word.

The Wisdom of God: Secondly, Christ is called the Wisdom of God in the Bible.

1 Corinthians 1:24 “… Christ the power of God and the wisdom of God.”

Then again

Colossians 2:2–3 “… Christ, in whom are hidden all the treasures of wisdom and knowledge.”

Quite literally, the New Testament teachings demonstrate that Christ is the full embodiment of wisdom. All that is wise, all that is just, all that is righteous, all that is worthy, all that is right, all that is true, is Christ.

Not Exact: Later, in Proverbs 8:22, we will see that Lady Wisdom boasts of being created by God. We know that the Word of God, the second person of the Trinity, was not created. And so when we see wisdom being personified in the Old Testament, we realize that wisdom was incarnate in the New Testament. It is not as if Lady Wisdom is Christ. And yet, Christ contains of all Lady Wisdom thoughts

Application: This is of such important to us, so let me slow down and make sure we hear this with clarity. The greatest folly in this world is to reject Christ, the Son of God, in whom are hidden all the treasures of wisdom. It is not just a folly of innocence to do so, but as we will see in this passage, it is a folly of the greatest kind. To reject Christ is to steer one’s life towards disaster. But Christ’s teachings will make you wise of heart, and wise of mind. Everything you could ever dream to know about God, about sin, about life, about death, about eternity, about predestination, about man’s responsibility, is all found in Christ. Further, anything that you find for yourself that does not come from Christ, is simply folly dressed up in wisdom’s wear.

Experimental: I ask you to examine yourselves right now. Have you set your heart and mind to know only the wisdom that comes from Christ, to apply it into every area of your life? Or have you, like so many fools, placed Christ alongside many other potentials paths of wisdom. A watered-down Christ is no Christ at all. Come to the fountains of living water and immerse yourself in the wisdom therein.

Lady wisdom is a personification of wisdom in Proverbs that obviously points us towards wisdom incarnate in Christ.

TO WHAT AREAS OF LIFE DOES HER WISDOM APPLY?

But second, let us consider wisdom’s scope. Hear in this passage we see Wisdom passionately pleading everywhere.

Proverbs 1:20–21 “Wisdom cries aloud in the street, in the markets she raises her voice; at the head of the noisy streets she cries out; at the entrance of the city gates she speaks:”

Public (20): First, Christ’s wisdom is public, crying “aloud in the street.” This is important because it is direct contrast to folly which we saw last week in Proverbs 1:11 takes counsel in secret, and lies in wait for ambush. Lady Wisdom out in the streets, in the public places, in the city gates. What this means is that wisdom is not simply something that is useful for overtly religious activities. Wisdom is not standing in the door’s of the temple. But wisdom is for all of life. We need wisdom for everyday life. There is no part of life where wisdom is not relevant. It’s in the board room. Its on social media. Its at home. It’s at school. It’s with your friends. Everywhere we go, wisdom speaks to us.

Crying Aloud (20): And look at the passion with which wisdom confronts us. Wisdom is “crying aloud.” This means that it is not just some academic counsel, some book that should be read. No! She preaches with full lungs and a clear booming voice above the hustle and the bustle of the city, so that all can hear her passionate pleas. In verse 20 she “raises her voice.” That language typically is used of those in deep emotional distress, and anguish. Christ pleads with “Seek and Apply Wisdom.” This is pulpit bashing and hell-fire preaching from Christ.

Experiential: As I have been preparing these sermons, I have had to do some real reflection both on my own life and on the patterns and behaviors I have seen among the many I have pastored over the years. There is no pattern I see in anyone else, that I cannot see in myself. Sin lurks in my own heart, and I often look on my actions in particular moments, and I think “I could have exhibited more wisdom there.” Let me tell you the number one pattern I see in my own heart and my own life, that I think is relevant on this point, ignoring my blindspot

Personal Illustration – Blind Spots: We all have blind spots. Just as in a car, there are particular angles that you can’t see when sitting in the driver’s seat. And if you’re not aware of those blindspots, eventually you can crash. Sometimes what happens is that because we sense about ourselves that we have wisdom in one area of our life (and perhaps a true “God-centered Christ exalting wisdom”), that necessarily we have are utilizing wisdom in all areas of our life. And simply put, it is often not the case. There are Wisdom Blind Spots. And we protect those blind spots. Sometimes we justify them. I do. Wisdom says

Proverbs 14:29 “Whoever is slow to anger has great understanding, but he who has a hasty temper exalts folly.”

My anger very rarely comes out in expressed ways. But And I have seen in myself that sometimes I jump to very clear and decisive reactions, that are tinged frustion and anger, without necessarily having all the understanding I need to evaluate a situation. This has been to my harm over the years. I share that with you as a personal example, not to dwell on my sin, but prompt you to examine yourself. Wisdom is for all areas of your life. It’s in the streets, in the gates, on the phone. Are there any areas where just maybe you have a blindspot? Lay these before the Lord. Seek wisdom.

There is no part of your life off limits from Wisdom’s searching eyes.

WHAT OFFER DOES LADY WISDOM MAKE US?

Third, what offer does lady wisdom make us?

Proverbs 1:22–23 ““How long, O simple ones, will you love being simple? How long will scoffers delight in their scoffing and fools hate knowledge? If you turn at my reproof, behold, I will pour out my spirit to you; I will make my words known to you.”

Audience: In verse 22, Lady Wisdom speaks to simple ones, scoffers, and fools. That covers a range of types of people, from the easily gullible, simple minded, to those who truly hate God and scoff at his word. But consider the offer in verse 23.

Reproof: The first side “If you turn at my reproof.” Isn’t it interesting that wisdom’s ultimatum hinges on what we personally do with “reproof”? What is reproof? That is when you are confronted with something that is unwise about your own behavior.

Illustation – Marriage Counseling: Many years ago I was asked by a couple to step in and help with a difficult marriage. We met a few times and I listened to this couple discuss the challenges they were facing. And it became fairly apparent to me that there was a particular hobby of the husband that was really at the center of a lot of the marriage struggles. And eventually I pulled the husband aside and said, “Hey, it seems that this hobby of yours is causing problems. You know, why don’t you just push pause for the time being. Focus on your marriage. And then let’s reevaluate when marriage is in a healthy place.” I thought it was fairly simple wisdom. And he looked at me and spent about twenty minutes justifying the hobby, and ultimately left frustrated with me that I had pointed to the wrong spot.

Self-Defense: It’s quite easy from a distance to judge that man. Who would do such a thing. Friends, this is the standard response to reproof. Our sinful flesh is so strong inside of us, that usually when we are reproved, even gently, our self-defense mechanisms kick in. We justify. We point the finger back the other way. It is a very rare thing for me as a pastor to offer gentle and loving reproof and not experience this. I almost never hear this, “Oh man… My sin… I still have so far to go. I want to work on that…” Sometimes I hear that, and then I start thinking, how can we get this person in leadership.

Poor in Spirit: Jesus teaches us

Matthew 5:3 “Blessed are the poor in spirit, for theirs is the kingdom of heaven.”

A man who is “poor in spirit” is someone who is aware of his own weakness. It’s not a soft weak person. Actually its a very strong person. But their strength is in the very fact that they are correctable. How do you receive reproof? Here’s an awkward test for you? Ask your spouse that question? And if they are afraid to give their answer—then you have your answer.

I Will Pour My Spirit: But what is the promise?

Proverbs 1:23 “If you turn at my reproof, behold, I will pour out my spirit to you; I will make my words known to you.”

Turn = Repent: “Turn!” That word is the most important word that is in the Old Testament to refer to repentance. Repent!” says Christ. Respond to the preaching of the word with repentance. Repentance is the key to unlocking the blessed life. Repentance is the hallmark of a mature follower of Christ. They are soft. They are pliable. The Holy Spirit is always working in them. What does Repentance really mean? It means to turn! To repent is not simply to state the folly of your path, but it is to mourn the wickedness of your path, and turn your feet and walk after Christ instead.

Not Simply Uneasy-Conscience: Repentance is not simply an awareness of an uneasy conscience. Many sinners live daily with a sense of an uneasy conscience about their life. They may even use language that says they pray to God about their uneasy conscience. But this is not repentance. The passage requires a “turning.” In other words, repentance is ultimately taking sides with God over and against myself. Repentance alone does not save us, or change us. It is repentence tethered to faith in Christ and his finished work on the cross. That is where there is power!

My Spirit: Wisdom offers life! “I will pour out my spirit to you.” This language is obviously language that is most clearly seen in the New Testament with the giving of the Holy Spirit. All who turn from their ways and trust in Jesus Christ receive the Holy Spirit. God—through the Holy Spirit—quite literally dwells inside of us. That Holy Spirit begins to lead us in all wisdom, to reveal God’s Word in new ways, to teach us how to live practically and wisely.

Wrap Up: As Lady Wisdom says at the end of verse 33.

Proverbs 1:33 “… whoever listens to me will dwell secure and will be at ease, without dread of disaster.””

Wisdom is inviting you not just to avoid disaster, but to live a true life of being filled by the Spirit of God, of walking deeply with God, and experiencing all of his benefits along the way.

WHAT HAPPENS IF WE REJECT LADY WISDOM?

Fourth, what happens if we reject lady wisdom? The bulk of this passage, verses 24-31, display what I call the Boomerang Effect of Folly. The boomerang effect is simply that if you persist in folly, eventually it comes back to bite you in the rear. On the other hand, if you persist in wisdom, eventually it pays off nicely.

Their Callousness: First, in 24-25 we see their callousness.

Proverbs 1:24–25 “Because I have called and you refused to listen, have stretched out my hand and no one has heeded, because you have ignored all my counsel and would have none of my reproof,”

These people can no longer claim ignorance. They have actively chosen to ignore God’s counsel. Their hearts have become like great callouses that are rough on the outside, and no longer sensitive to God. Now they simply walk by the preacher and don’t even hear him or see him anymore. Their way is set. They have chosen their path.

Illustration – Quit Smoking: Christian, take note here. It is possible to be saved, and to be on a foolish path, and to allow spiritual callouses to develop in your heart. So often when we are made aware of our sin, we say “not yet.” And when we do that, we slowly begin building callouses towadrs God’s call on our life. We are like the smoker who says “I can always quit tomorrow.” Then the next day comes, “I will quit tomorrow.” And each time they say “I will quit tomorrow” the callous builds thicker and thicker until even they know there is no longer any intention or possibility that they will actually quit. Such is sin, even in a believer’s life. Christian, when you learn of sin in your life, or spot folly, turn quicky, lest you suddenly find yourself playing the fool.

The Boomerang Effect: Then, in verses 26-27 we see their calamity. Wisdom warns, that if a person stays on the foolish path they’re on, and never turns, eventually their folly will catch up with them.

Proverbs 1:26–27 “I also will laugh at your calamity; I will mock when terror strikes you, when terror strikes you like a storm and your calamity comes like a whirlwind, when distress and anguish come upon you.”

In the end, some way, somehow, their folly catches up to them. Isn’t this true? Haven’t you seen this play out time and time again in real life. I have.

The young man who refuses to address his growing addiction to sports gambling, eventually finds himself in so deep he’s placing multiple bets over multiple games multiple days a week. It’s a time bomb.

The young woman who is so eager to get married and frustrated that she hasn’t found a husband in the church yet, begins dating a non-Christian. It’s a time bomb.

Folly boomerangs.

Brief Side – Sports Gambling: Men, permit me a very brief side while we are on the topic of gambling. Sports gambling among young men is the largest undiscussed sin plaguing men today. And I have not addressed it from this pulpit yet. Now is as good a time as ever. Get out! Don’t touch it! Flee! Don’t say “I’ll do it after this next bet.” If you have an account, delete it. Sports gambling is not wise. It is folly.

God Laughs: There is important language in there about God “laughing” and “mocking” their circumstance. The terms “laughing” and “mocking” are poetic terms used to describe the full permission of God’s judgment. It’s a way God saying, “I warned you this would happen. You didn’t listen. And it happened. I told you so.” Similar language to this is used in Psalm 2, when the Psalmist confronts the nations of this world that refuse to bow to God’s Messiah.

Psalm 2:4 “He who sits in the heavens laughs; the Lord holds them in derision.”

This language is meant to say, “What did you think was going to happen?” You built your life against God and his law? What did you think you would play the game long enough to not get caught? What a foolish and absurd and ridiculous notion. He’s God. This is his world. You are on his borrowed time. He has every atom of the universe at his disposal to execute his justice. You cannot run away from it.

Galatians 6:7 “Do not be deceived: God is not mocked, for whatever one sows, that will he also reap.”

Their Futility: Then, in verse 28-30 we see their futility. After the disaster strikes they call out to God, but they have no answer.

Proverbs 1:28–30 “Then they will call upon me, but I will not answer; they will seek me diligently but will not find me. Because they hated knowledge and did not choose the fear of the Lord, would have none of my counsel and despised all my reproof,”

Now this is interesting, because didn’t we earlier say that God is longsuffering and no matter how much sin and how deep the sin, God will always receive someone who is ready to repent. Yes and Amen! And so what is happening here is something other than genuine turning. These people are calling on God in their calamity, not in repentance or faith, but simply as all people do when their folly catches up to them. They want nothing to do with wisdom. They want nothing to do with God’s law. They just hope some cosmic being get them out of their jam. And God says, “No, I’m not your play thing.”

Illustration – Plane Crash: They are like people who rejected God all their life, refused God’s wisdom, built their own path for life, felt proud of it. One day they find themselves on an airplane that has hit violent turbulence. In their moment of being terrified they cry out “Oh God! Hear me now! Save me God!” God says “No.” That’s not repentance, it’s just self-preservation. Make sure you understand, if in that moment, the fool repents of his sin, falls to his knees and pleads for mercy from the one true and living God, accepts the blood of Jesus payment for his sin, will God respond with compassion? You better believe it. But that is not what we see in verses 28-30.

Application: Lady Wisdom tell us their end.

Proverbs 1:31–32 “therefore they shall eat the fruit of their way, and have their fill of their own devices. For the simple are killed by their turning away, and the complacency of fools destroys them;”

Conclusion

I do not know what Christ is particularly working on you right now. But I want to end this sermon by inviting you to consider three questions.

Have you authentically begun the journey of wisdom, by repenting of sin and trusting in the finished work of Jesus? If not, there is no other step you can take before taking that step. Make it. Avoid the destruction of a life outside of Christ and outside of wisdom! I plead with you, before it is too late.

Christian – Is there any area of your life that just maybe, if you’re very honest with yourself and with God, you ignoring Lady Wisdom’s offer. This is hard work. Let the Spirit search you. If you sense something rise up in your conscience, don’t bury it or dismiss it. That may be the Holy Spirit prodding you, and prompting to take action now, before calamity strikes.

Third, to the Christian again. Remember that you are ongoingly saved by grace. If you are in Christ, your folly does not disqualify you. Christ has certified your position in Him with his own blood. Thank God that his mercies are new every morning. Thank God that he is able to bend and mold fools like we often are, to be wise practitioners of God’s counsel.