“The Disciple’s Character: Mourning Over Sin” (Matthew 5:4 sermon)

Many times over the years, people have come to my office, feeling very troubled over a sin or a habit in their life. And sometimes they will say something like: “I feel so bad about that sin; I am not even sure that I am a Christian.” But the truth is, oftentimes the OPPOSITE is true: if you are a real Christian, you will most likely feel worse about your sin than an unbeliever would.
— Jonathan Edwards, the great American pastor and theologian from the 1700’s, said that as a Christian, “I have had a vastly greater sense of my own wickedness and the badness of my heart than ever I had before my conversion.”
— Donald Whitney, in his book we studied in Discipleship here last fall, 10 Questions To Diagnose Your Spiritual Health, wrote “the fact that there is a struggle with sin, and a sense of grief because of sin, is good. Unbelievers have no such struggles or griefs.”
I’ve seen Christian guys who mourned and grieved over the fact that they had used pornography — but I’ve also seen that lost guys often just laugh and boast about it! So, far from feeling bad about your sin meaning that you are NOT a Christian; it may be the very sign that you really ARE a Christian — or that you are about to become one!

This morning we are continuing our study: “The Disciple’s Character” – the 8 character qualities of Jesus Christ that are found in the Beatitudes of Matthew 5:3-12, which He wants to build into each one of our lives. We have seen over the last weeks that the 8 qualities we find here are not 8 disparate and random qualities, but that together they form a picture of the character of Jesus Himself, and the character that God is causing “all things” to work together for good (Rom. 8:28-29) to form in our lives. Last Sunday we saw that the first quality was “poor in spirit”, which we saw is “spiritual dependence” – that we need to learn to depend upon God, first of all, for our salvation, but then also every hour, every minute, and every second in our Christian lives. If you missed that message, I hope you will go to the PRBC app and listen to it, or go to my website at shawnethomas.com and read it, because that principle is foundational to the Christian life. You MUST learn to depend upon God both to enter and to grow in the Kingdom of Heaven. But today we move to the 2nd character quality that Jesus gives us in this passage: “Blessed are those who mourn, for they shall be comforted.”


I. The Meaning of “Mourning”

The first thing we need to understand is what Jesus means here when He talks about “mourning.” This does not mean here what many people would take it to mean. A lot of people think it probably means something like: “God will comfort those who have lost loved ones” or something like that.
And yet that is NOT really the primary meaning here. You must remember what we learned in the Introductory message, that these Beatitudes are SPIRITUAL qualities. They deal with the spiritual realities in our lives. So what Jesus is really speaking of here is mourning over SIN, both in your own spiritual life, and in the lives of other people.
— James 4:9 says “be miserable, MOURN and weep” because of your sins
— In I Corinthians 5:2 Paul says the church should have MOURNED the sins of a man who was living immorally in the church.
This is the kind of thing Jesus is talking about here in Matthew 5:4. He is referring to mourning over SIN.

Now this may sound odd to us. We have been taught by our world that if we want to be happy, we shouldn’t dwell on our sins. So we justify them, blame them on someone else, forget them: “don’t worry, be happy, put it behind you and go on”, “sweep it under the rug”, etc. And the world would never call anyone a “sinner” – it would damage their “self-esteem”! Mourning over sin is the exact opposite of what popular opinion would encourage us to do.

But remember, Jesus “turns the world upside down” in this Sermon on the Mount. Or rather, He puts it “right side up”! He says that you must NOT skip over your sin, or minimize it. Instead, you need to be confronted with your sin, so you can mourn over it, and let your mourning over sin cause you to take it to the Lord so He can deal with it for you.

There are several examples of this in scripture; one of the best is found in Isaiah 6. When Isaiah has the vision in Isaiah 6 of God in the temple, with the angels calling out, “holy, holy, holy”, his first response to that vision of God is: “Woe is me, for I am undone; for I am a man of unclean lips, and I live among a people of unclean lips, for my eyes have seen the King, the Lord of hosts.” As soon as Isaiah saw the vision of the thrice-holy God, he was immediately convicted with a strong sense of his own sin.

This is such an important lesson from this text: a genuine encounter with God always convicts a person of sin. I would go so far as to say that if you had something that you thought was an encounter with God, and you did not have an awareness of your sin, you did not meet God. Hebrews says: “Our God is a consuming fire.” Even those who knew Him well – Isaiah, Moses, Abraham, John – fell as dead in His presence when they met Him. If you say that you have had an encounter with God, and have not been convicted of your sin, you are mistaken. You may have had a good feeling; you may have a vivid imagination, but if you have truly encountered God, you WILL be convicted of sin. (I think this is true even for a personal prayer time. One of the ways I know that I have not had the time with God that I should have had in prayer is if I was not convicted of sin. To really meet God, for us sinful human beings, is to be convicted of sin. If you were not shamefully made aware of your sin, you did not genuinely encounter the holy God!)

So Isaiah had this experience. As soon as he encountered God, he was made aware of his sin: “Woe is me! For I am a man of unclean lips, and I live among a people of unclean lips.” He mourned over his sin – specifically here, the sins of his lips. But his mourning led to his cleansing. As Isaiah mourned his sin, the Bible says one of the angels came to him with a coal from the altar, touched his lips with it, and said “Your iniquity is taken away, and your sin is forgiven.” And it was after that, that the Lord gave Isaiah his call to the ministry, and some of the greatest revelations in all of the Bible in the Book of Isaiah. But before he could have the comfort and the glory and the revelations – and even before his cleansing could come – he had to have the mourning over his sin.

That’s why Jesus says here that the one who mourns his sin is blessed — because THAT person takes his sin to the Lord and gets it taken care of.
(Hence, we need to be careful sometimes in our “comforting” people by telling them not to feel badly about their sins: listen, that deep sense of conviction they are experiencing may be a part of what God is trying to do in their lives! Let them mourn their sins; but point them in the right direction with their mourning of sin — and help them take it to the Lord!)
But only when we first mourn our sins will ever be truly happy (“blessed”!) Jesus says, “Blessed” – or truly, spiritually happy – is the one who mourns over his sin.

II. Mourning and Salvation

This is true first of all in regard to salvation. Blessed is the one who mourns over his sinful condition before God, because this is the one who will find salvation, and be comforted with a home in heaven.

— It is like the story of the Prodigal Son, who mourned over his sins, and his mourning led him to repent and turn back to his father—where he found forgiveness and restoration.
— We saw this last week, when the publican realized his “poverty in spirit”, so he mourned his sin and beat his chest – but Jesus said “he went to his house justified”! His mourning led to cleansing and forgiveness: “the mourner shall be comforted”!

It can be the same for you. The first step to salvation is a conviction of sin. Someone told me of how when they were a child, they committed a particular sin, and they felt so badly about it; they were just burdened by it – but that conviction and that burden – what Jesus calls here that “mourning” over sin – ended up bringing them to Jesus as their Savior. “The mourner was comforted”! But the mourning had to come first – then the cleansing and joy when you realize that Jesus died on the cross to pay for your sins, and that you can be forgiven by putting your faith in Him as your Lord & Savior.

This is how we knew that our son David was ready to be saved. When we were in Tulsa, one Sunday morning during the invitation, David came down front and said he wanted to be baptized. As I always do when I counsel children, I asked him if he knew what sin was. He said yes, so I asked him to name some sins, and he did. Then I asked him, “Have YOU done some of these sins?” He shook his head emphatically, “NO!” So I knew by that, that he was not ready to be saved. You aren’t ready for a Savior until you know that you are a sinner! It was some time later then, that David came down during an invitation, and this time when I asked him if he had sinned, tears fell from his eyes — in fact, people from our congregation told me later how they could see his big tears falling onto the Bible I was holding in my hand. And David trusted Jesus as his Savior that day, and ever since that time, He has had the comfort of knowing that he was saved and right with God. But first came his mourning, then the cleansing and comfort.

Maybe today you are feeling bad about the sins in your life. Maybe others are telling you to just “put it behind you” and forget it. Maybe you have tried to “cover up” your guilt with alcohol, or drugs, or entertainment. But God is telling you today in this word that your mourning is actually GOOD – because it is about to lead you to Jesus, where you can find forgiveness and cleansing and comfort. God is using that guilt in your life to bring you back to Himself. This verse may be about to come true for YOU today: “Blessed are those who mourn, for they shall be comforted.” Let your mourning lead you to Jesus for salvation.


III. Mourning in the Christian Life

Just like poverty in spirit does not stop when you depend upon God for salvation, so mourning over sin does not stop when you find forgiveness in Christ. It is a quality that God continues to use to mold you into the image of Christ. He will continue to bring a mourning over sin into your life, so that it will keep on bringing you to Him for continued cleansing and change in your life.

We see this in the Apostle Paul. Paul had been Christian since he met Jesus on the Damascus road, but he continued to mourn the sin in his life. Romans 7 is one of the great examples of this. Paul was frustrated with the ongoing sin in his life, and he cried out: “For the good that I want, I do not do, but I practice the very evil that I do not want.” (:19) And he cried out in :24 “Wretched man that I am, who will set me free from the body of this death?” It is obvious that Paul was mourning his sin. But again, his mourning led him to forgiveness in Christ! In the next verse (:25) he calls out: “Thanks be to God, through Christ Jesus our Lord!” His mourning over sin, even as a Christian, led him to be comforted.

God commands us in the Book of James to take our sins seriously as Christians, and mourn over them: James 4:9 says: “Be miserable, mourn and weep; let your laughter be turned into mourning and your joy into gloom. Humble yourselves in the presence of the Lord and He will exalt you.”

Unfortunately, this kind of mourning our sins is too often missing from our lives as Christians. David Martyn Lloyd-Jones, probably THE foremost British preacher of the late 1900’s, wrote, “I cannot help feeling that the final explanation of the state of the Church today is a defective sense of sin and a defective doctrine of sin.” He went on to say that the flip side of that is that we also don’t have the true nature of Christian joy. And he says, don’t you see, they are RELATED?! Because we don’t have great mourning and grief over our sins, we don’t experience great comfort and joy in our forgiveness. Basically he’s saying that We can’t go “high” in joy, because we haven’t gone “low” in mourning first. God says it is the MOURNER who is comforted. It is the one who MOURNS his sins first, who then finds great comfort and joy. But we must first learn to Biblically mourn the grievousness of our sins before a holy God.
Now we need to notice an important thing about this quality of mourning: it is not just “feeling” bad about your sin. It is an inward conviction of sin that leads you to action to change it. Many people don’t understand this. They think that if they simply “feel bad” about their sin, that is what God wants. It is not. Real repentance is not just a feeling but involves action.

Paul makes this clear in II Corinthians 7:9, where he says: “I now rejoice, not that you were made sorrowful, but that you were made sorrowful to the point of repentance; for you were made sorrowful according to the will of God … for the sorrow that is according to God produces a repentance … but the sorrow of the world produces death.” Paul was saying there that there is a kind of “worldly sorrow” for sin – a “feeling bad” for what you have done, that never really changes anything. He said that kind of sorrow does not do you any good. But, he said, there is a “godly sorrow” – the kind of “mourning over sin” that Jesus is talking about here, that causes “repentance” – and that word “repentance” means a “u-turn” – a change in direction. So we see here that Biblical mourning is not just a feeling, it takes ACTION to do things differently!

It is one thing to feel badly about your sin; it is another to DO something about it. It is like the character Caleb in the Christian movie “Fireproof” that came out a few years back. He had been involved in internet pornography, and he was mourning over what it had done to his marriage. So at one point in the movie, he takes the computer outside and just starts hammering it with a baseball bat! Now, I am not recommending that this is the step of action you take (just get some screening software and save your computer!) but the point is, where there is real “mourning”, real conviction of sin, you don’t just feel badly about your sin; you don’t just say you are “sorry”; you DO SOMETHING about it!

Some of you may say: “I feel really bad about a sin in my life today.” Well, feeling badly can be a first step. But if what you have is Biblical “mourning” over your sin, a godly sorrow brought about by the conviction of the Holy Spirit, you will not only feel badly about it, it will lead you to DO something about it.I believe God is speaking to some of you here today about taking some specific steps of action about a sin in your life. Write down what God is leading you to do; tell somebody about it who will pray with you, and take those steps with God’s help (remember “poor in spirit”; depend on Him!) But Godly sorrow/repentance does not just “feel sorry”; it takes action about their sin.


IV. Mourning for OTHERS.

We have seen how mourning applies to our own sin. But it also applies to mourning over the sins of other people as well. In fact, this is where we find this as a character quality of Christ. As we have seen, each of the Beatitudes are first and foremost, character qualities of Jesus Christ. But Jesus had no sins of His own to mourn! The Bible makes that clear. Hebrews 4:15 says “He was tempted in all things as we are, yet without sin.” Satan never had a single foothold in Jesus’ life. He never sinned. But that does not mean that He did not mourn over sin. He did. Jesus did not mourn over His OWN sins, but He did mourn over the sins of OTHERS. We see this throughout the Gospels:

— Jesus wept outside of Lazarus’ tomb in John 11 – not because Lazarus had died; He was about to raise him from the dead! He was weeping over the sin-hardened hearts of people who were standing there, about to see a man come back to life, and yet who would not believe! He mourned their sins!
— Jesus repeatedly mourned the sins of His disciples, saying things like: “oh, ye of little faith, why did you doubt?”
— One of my favorite examples of Jesus mourning sin is found in Matthew 23:37, when He looks over the city and cries out: “Jerusalem, Jerusalem, who kills the prophets, and stones those who are sent to her. How often I wanted to gather your children together the way a hen gathers her chicks under her wings, but you were unwilling.” Those were the words of a mourner; as He looked over the city that was the apple of His eye, His chosen people; knowing what their sins were going to cost them.

Jesus was mourned over the sins of people, and God wants to form that same character quality in each one of us as His disciples.

The Apostle Paul had this quality. In Romans 9:1 He said, “I have great sorrow and unceasing grief in my heart” – and he said it was because of his brother Israelites, who had rejected God’s plan for them in Christ. In II Cor. 12:21 he says when he comes back to Corinth he may have to “mourn” over the sins of immorality that the people there had not repented of.

We see godly people all through scripture who mourn the sins of others. In Psalm 119:136, David says: “My eyes shed streams of water, because THEY do not keep Your Law.” David said at that point that he was not crying about his OWN sins, but at the sins of others who were breaking God’s word. Nehemiah was so smitten over the desolation of Jerusalem that he couldn’t hide his mournful countenance from the king. And on and on; godly people have this quality of mourning the sins of others.

We SHOULD mourn the sin we see around us. This week, they announced that the people who secretly videoed the Planned Parenthood officials selling the body parts of babies they had aborted, were being indicted by a grand jury. But the Planned Parenthood people, who had actually murdered the innocent babies, got nothing! What is wrong with our society? We should be troubled by this; we should mourn what is going on around us.

In fact, those who claim to be Christians and who do NOT mourn the sins around us are rebuked in scripture! In I Cor. 5, the Apostle Paul reprimands the Corinthian church for boasting about how “tolerant” they were over allowing immoral people to remain members of their church. He said, “You have become arrogant and have not MOURNED instead, so that the one who had done this deed would be removed from your midst.” He was saying that church members should mourn the sins of their fellow members.

But just like mourning over sin in our personal lives is not just a feeling, but a conviction that leads to action, so it is true with our mourning for others as well:
— When Paul told the Corinthians church that they should mourn over the sin of the church member, he didn’t indicate that they should stop with merely mourning. He told them that their mourning should lead them to remove the member who was so blatantly sinning from their membership, to preserve the purity and witness of the church. Their mourning was to lead to action.
— In Romans 9 Paul spoke of how he had unceasing grief in his heart for his unsaved countrymen – and then in Romans 10:1 he writes: “My heart’s desire and my prayer to God for them is for their salvation.” The mourning of Paul’s heart led him to action: to be a fervent intercessor for their salvation.

It will be the same with you and me. As we become “conformed to the image of Christ”, we will mourn over the sins of others in such a way that motivates us to action. And one of the best actions you can take is to pray. The real mourner prays; he is an intercessor. We saw last week that the depth of your dependence upon God is measured by your prayers; in the same way, the depth of your mourning for others can be measured by your intercessions for them: if you are really mourning, you are going to be praying. So ask yourself then: how much is your mourning over your loved ones leading you to pray? If you actually put a clock to it, how much are you really praying for the people you say that you care about? If you are really mourning the sins and needs of others, you will be constantly praying for them! And when we turn to God in Biblical, mournful, intercession, He does hear our prayers.

Most of you have probably heard of St. Augustine, who lived well over 1000 years ago. He was not always “Saint” Augustine, however! Despite having a very godly mother, Monica, he rebelled against the teaching he grew up with, drank to excess, and lived immorally. But his mother never gave up on him. She “mourned” the sins of her son. In fact, Augustine would write later that his mother Monica mourned his spiritual death more than most parents mourn their children’s physical deaths. She was often found weeping and praying to God for Augustine’s salvation. One day, she was at her church, crying out again at the altar for her son’s soul. The pastor came up to her and said, “Fear not; a son of such tears shall never perish.” Monica took that as a sign from God, and sure enough, not long afterwards, Augustine came under conviction by God’s Holy Spirit while listening to a sermon, and he was saved, and grew to become the “St. Augustine” who has influenced so many throughout history.

Psalm 126:5 says: “Those who sow in tears shall reap with joyful shouting. He who goes to and fro weeping, carrying his bag of seed, shall indeed come again with a shout of joy, bringing his sheaves with him.” What a picture that is. It foreshadows in the Old Testament just what Jesus teaches here as a principle of the Kingdom: sow in tears and mournful prayers for those who are on your heart, and then go forth to action – and you will “reap with joy”! God will comfort you as He blesses your tearful prayers for those who are on your heart.

But the problem that many of us have is that we are trying to circumvent the process. We just want the comfort, but we don’t want to mourn first:
— We want the joy of salvation, but do not want to mourn and face our sins first.
— We want the joy of the Christian life, but without mourning our individual sins first.
— We want to “reap” with joy the answered prayers in the lives of our loved ones, but we do not want to “sow in tears” in intercessory prayer first.
— We want to have the joy of “Easter Sunday” – but we don’t want the pain of “Good Friday” that has to come first. Well, the truth is, there is no Easter Sunday without the Good Friday first. There is no resurrection without the death first. And there is no real joy without the mourning of a godly sorrow that leads to real repentance and action first.


This week as I was reading in Isaiah in my morning Bible reading I came across Isaiah 66:1-2, where God says: “Heaven is My throne, and the earth is My footstool. Where then is a house you could build for Me? … But to this one I will look, to him who is humble and contrite of spirit, and who trembles at My word.” In other words, God is saying, we can’t build a “place” here on earth, where we can find and meet God: not the temple in Israel, and not in our own worship centers here in America. Really meeting God is not about going to a certain “place”; it is about the kind of HEARTS of people that God will meet!

And what kind of heart does God say that He engage with? “Him who is humble and contrite of spirit …”. Those words “humble” and “contrite of spirit” virtually describe the first two Beatitudes! To be “Poor in spirit” is to be “humble”; and to “mourn” is to be “contrite.”
God is saying here, I don’t meet you just because you come to a certain physical location; He says I will come to you and help you when you are poor in spirit, and when you mourn over your sins. These first two Beatitudes are related: when you realize you’re poor in spirit, it leads you to mourn your sin. And both of them together will lead you to truly meet God. That’s why Jesus tells us here: “Blessed are those who mourn — for THEY shall be comforted”!


— Perhaps you came into this room today with a strong sense of mourning over your sin. Maybe you’ve thought, or people have told you, that you just needed to “get over it” – but God is showing you today that your mourning is actually a GOOD thing, that is leading you to Him. Bring your sin to Jesus, find His forgiveness. If you need to talk to someone about how to be saved, come forward and let me get you to a counselor who will help you and pray with you.

— Or if you are a Christian, and you are feeling guilty over your sins, use that conviction God is giving you as a motivation to pray, and to take some specific actions that He lays on your heart. Tell somebody about it, so you can be accountable to them, and they can pray for you — and then ask God to help you take the steps you need to.

— Others of us have children, or grandchildren, or other loved ones who are not saved on our hearts. Don’t just become “resigned” to it, and accept it. Mourn their rebellion against God; let this verse cause you to call out to God in a new way today. And God grant that it may be said of you with your loved one, like it was of Monica and her son Augustine, that “a son of such tears shall never perish”! Let’s make this altar a place of prayer for our loved ones this morning, as we respond to the Lord …

About Shawn Thomas

My blog, shawnethomas.com, features the text of my sermons, book reviews, family life experiences -- as well as a brief overview of the Lifeway "Explore the Bible" lesson for Southern Baptist Sunday School teachers.
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3 Responses to “The Disciple’s Character: Mourning Over Sin” (Matthew 5:4 sermon)

  1. Vivian Dyson says:

    Hallelujah in the name of Jesus! I declare and decree, and it is so in the name.of Jesus Christ of Nazareth, Amen, Amen, Amen, and Thank you Jesus, Thank you Lord!, Glory to God. God can do anything but fail. I say yes to God’s will, yes to his way. I love this post, and I needed it for some of my relatives about to marry in the obomination lifestyle. I mourn this, I mourn this so much and ask God to help our family. I sow years for this and ask for God’s guidance and action. First I pray continuously and vow to never give up on my cousin sin. I vow for my.other relatives sins. God delivered me from the bondage of fornication. I pray for deliverance from my relative of O bomination. Also deliverance in our other family in our finances. I pray for them to have an encounter with God. Repent, get born again.

  2. mary says:

    thanks for this post!! it has encouraged me to pray for my relatives and not just be sad about their spiritual state. it has shown me the heart of Jesus!

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