Which Direction Does Your Repentance Go

Aug 17, 2026

Devotional

Day 1: From No to Go: The Turn of True Repentance

The first son’s blunt refusal to work shifts to reluctant obedience, mirroring the raw honesty of repentance. His journey from defiance to action reveals repentance isn’t polished words but a gritty about-face. True repentance isn’t measured by eloquence but by the dust on sandals and sweat on brows. It’s the tax collector dropping his ledger, the prostitute leaving her corner—turning toward the vineyard despite pride’s resistance. Heaven celebrates the stumbles of those who finally walk, not the eloquence of those who never move. [17:38]

“A man had two sons, and he came to the first and said, ‘Son, go work today in the vineyard.’ But he answered, ‘I will not’; later he regretted it and went.”
(Matthew 21:28-29, NASB)

Reflection: Where is God asking you to move from refusal to action, even if your “yes” feels awkward or delayed? What practical step can you take today to turn regret into obedience?

Day 2: Lip Service and Empty Sandals: When Yes Means No

The second son’s eager “I will, sir” dissolves into inaction, his sandals never dusty from the vineyard. Polite agreement without follow-through insults the Father more than honest rebellion. Empty words dress rebellion in respectability, masking hearts that prefer comfort over costly obedience. Religious leaders mastered this art, honoring God with titles while rejecting His messengers. Jesus confronts the danger of mistaking verbal compliance for faithfulness. [20:33]

“The man came to the second son and said the same thing. But he answered, ‘I will, sir’; and he did not go.”
(Matthew 21:30, NASB)

Reflection: Where have your actions contradicted your spiritual affirmations? How can you align your daily choices this week with the “yes” you’ve spoken to God?

Day 3: Fishing Before Cleaning: Jesus Welcomes the Unwashed

Jesus doesn’t demand scrubbed hands before embracing sinners—He cleans what He catches. Tax collectors and prostitutes stumbled into the kingdom reeking of failure, trusting grace over self-reform. The religious elite polished their reputations but missed the Messiah; the broken recognized their stench and ran to the One who breathes life into rot. God’s kingdom prioritizes messy surrender over sanitized self-righteousness. [35:42]

“And hearing this, Jesus said to them, ‘It is not those who are healthy who need a physician, but those who are sick; I did not come to call the righteous, but sinners.’”
(Mark 2:17, NASB)

Reflection: Who in your life needs to encounter Jesus “as they are” before you pressure them to clean up? How can you model grace over judgment this week?

Day 4: Gates Open Wide: The Surprise Guests of Heaven

Prostitutes and tax collectors—the “professional sinners”—entered God’s kingdom first, shocking the pious. Their desperation became their salvation, their moral bankruptcy a runway for grace. Heaven’s gates swing wide for those who abandon self-justification, not for those clinging to résumés of goodness. The kingdom’s guest list favors honest rebels over polished hypocrites. [30:43]

“Truly I say to you that the tax collectors and prostitutes will get into the kingdom of God before you.”
(Matthew 21:31, NASB)

Reflection: What assumptions do you hold about who “belongs” in God’s family? How might your interactions change if you saw others through heaven’s surprise-guest lens?

Day 5: Regret vs. Repentance: The Stench That Demands Action

Regret mourns consequences; repentance murders the sin. The first son’s remorse led to movement; the religious leaders’ regret calcified into pride. True repentance isn’t a campfire emotion but a funeral for old ways—a refusal to let guilt fester into complacency. Jesus confronts those content to weep over trash without taking it to the cross. [24:20]

“For the sorrow that is according to the will of God produces a repentance without regret, leading to salvation, but the sorrow of the world produces death.”
(2 Corinthians 7:10, NASB)

Reflection: What sin have you mourned but not yet surrendered? What specific habit, relationship, or attitude needs a funeral, not just a tearful eulogy?

Sermon Summary

Matthew’s context puts Jesus in the temple during Holy Week, right after the triumphal entry and right after the cleansing of the temple. Jesus rides in on the donkey, hears the leaders want the Hosannas hushed up, and says the rocks will cry out because he made the rocks. Jesus then kicks over the tables, drives out the money changers, cleanses the temple, and comes back to teach. The temple is ready for God to show up, and the leaders show up asking, “Who do you think you are?”

Matthew makes authority a huge deal because Jesus is the King, and kings have the right to rule and reign. Jesus is not a confused teacher who got deified later. Jesus keeps saying “I am,” and that is why they killed him. Jesus is God the Son, the one they should have known, and the one they were now rejecting. The name of Jesus is not a sign-off at the end of a prayer, but the name that deserves glory because he is God the Son.

Jesus answers their trap with a question about John’s baptism. If John’s authority came from heaven, then the leaders had to answer why they did not believe him. If John’s authority came from men, then the crowd that flocked to John would turn on them. Their “we don’t know” was not ignorance. Their answer was fear of truth and fear of public opinion.

Jesus then tells about two sons. The first son says, “I will not,” with no respect for the father, but afterward he regrets it and goes. The second son says all the right respectful words, “I will, sir,” but he does not go. Regret is not repentance. Repentance is when regret gets up and walks in a new direction. The first son moves from no to go. The second son moves from go to no.

Jesus says tax collectors and prostitutes are entering the kingdom ahead of the religious leaders because they believed John and turned. The gates of the kingdom are wide open to bluntly ungodly sinners who repent. The gates are shut tight to precisely orthodox people who have all the right answers but refuse to repent. The gospel does not say people are basically good and Jesus makes them better. Sin is stinky, filthy garbage, and Jesus says, “Bring it to me and I’ll clean it up.” Fish do not get cleaned before they are caught. Jesus catches sinners, then cleans them.

The kingdom belongs to those who stop establishing their own righteousness and place faith in what Jesus has done. The test is not walking an aisle or filling out a card. The test is whether Christ is in a person, and whether repentance has gone from no to go.

Key Takeaways

1. Repentance moves from no to go. Regret can sit still and feel bad, but repentance gets up and heads toward the Father’s will. The first son’s change was not complete when he felt sorry. The change became real when his feet carried him into the vineyard. [28:40]
2. Authority belongs to God the Son. Jesus does not borrow authority from the temple leaders, the crowd, or public approval. Matthew presents Jesus as King, and the King has the right to rule and reign. A person cannot honor Jesus as a helpful religious figure while rejecting his claim to be “I am.” [10:44]
3. Heaven opens to honest sinners. Tax collectors and prostitutes had no good religious resume to hide behind. Their sin was obvious, but their repentance was real. The kingdom stood open because they believed the gospel instead of defending themselves. [30:18]
4. Right answers cannot replace surrender. The religious leaders knew the categories, the language, and the system, but they would not bow. Orthodoxy without repentance becomes a polished way to say no to God. The second son sounded obedient while his life walked the other direction. [36:28]
5. Jesus catches before he cleans. The gospel does not require sinners to scrub off the stink before coming to Christ. Jesus receives the trash, the filth, and the failure, and he is the one who cleans what no person can clean. Fish are caught first, then cleaned.

## [34:38]

Youtube Chapters

[00:00] - Welcome
[03:35] - Context Is Key
[04:20] - Jesus in the Temple
[05:23] - The Rocks Would Cry Out
[06:23] - The Cleansed Temple and God’s Authority
[10:44] - Matthew’s Theme of Kingdom Authority
[11:53] - Jesus Questions John’s Baptism
[17:38] - The Parable of Two Sons
[22:31] - Regret Is Not Repentance
[29:53] - The Right Direction of Repentance
[30:18] - Tax Collectors and Prostitutes Enter First
[34:38] - Jesus Cleans What He Catches
[39:28] - Entering the Kingdom by Faith
[43:19] - Testing the Reality of Faith

Bible Study Guide

Bible Reading

Matthew 21:23-32
“When He entered the temple, the chief priests and the elders of the people came to Him while He was teaching, and said, ‘By what authority are You doing these things, and who gave You this authority?’ And Jesus answered and said to them, ‘I will also ask you one thing, which if you tell Me, I will also tell you by what authority I do these things. The baptism of John was from what source? From heaven or from men?’ And they began reasoning among themselves, saying, ‘If we say, "From heaven," He will say to us, "Then why did you not believe him?" But if we say, "From men," we fear the people; for they all regard John as a prophet.’ And answering Jesus, they said, ‘We do not know.’ He also said to them, ‘Neither will I tell you by what authority I do these things. But what do you think? A man had two sons, and he came to the first and said, "Son, go work today in the vineyard." And he answered, "I will not"; but afterward he regretted it and went. And he came to the second and said the same thing; and he answered, "I will, sir"; but he did not go. Which of the two did the will of his father?’ They said, ‘The first.’ Jesus said to them, ‘Truly I say to you that the tax collectors and prostitutes will get into the kingdom of God before you. For John came to you in the way of righteousness and you did not believe him; but the tax collectors and prostitutes did believe him; and you, seeing this, did not even feel remorse afterward so as to believe him.’” [03:35]

Luke 19:40
“Jesus answered, ‘I tell you, if these become silent, the stones will cry out!’” [05:56]

Matthew 21:12-13
“And Jesus entered the temple and drove out all those who were buying and selling in the temple, and overturned the tables of the money changers and the seats of those who were selling doves. And He said to them, ‘It is written, "My house shall be called a house of prayer"; but you are making it a robbers’ den.’” [06:23]

Acts 2:38
“Peter said to them, ‘Repent, and each of you be baptized in the name of Jesus Christ for the forgiveness of your sins; and you will receive the gift of the Holy Spirit.’” [21:52]

Observation questions

In Matthew 21, what question did the chief priests and elders ask Jesus, and what question did Jesus ask them in return? [11:53]
In the parable of the two sons, what did each son say at first, and what did each son actually do afterward? [20:10]
What details in the passage show that the religious leaders were more worried about consequences and public opinion than about telling the truth? [15:44]
According to Jesus in Matthew 21:31-32, which kinds of people were entering the kingdom ahead of the religious leaders, and why? [30:34]

Interpretation questions

Jesus ties his answer about authority to John’s baptism. Why does that connection matter? What does it reveal about the leaders’ refusal to believe both John and Jesus? [16:04]
The first son regretted his answer and then went. The second son spoke respectfully but did not go. What does that contrast show about the difference between outward religion and actual obedience? [22:31]
Jesus says tax collectors and prostitutes were entering the kingdom ahead of the religious leaders. How does that confront the idea that being morally polished or religiously informed is enough to make someone right with God? [36:12]
Repentance moves from “no” to “go.” Why is that a better picture of saving faith than simply feeling bad, making a promise, or having the right words? [28:40]

Application questions

Where is there a place in life right now where the heart has said “I will, sir,” but the life has not gone—home, work, school, marriage, private habits, or obedience to something already known? [44:31]
Is there a sin, pattern, or compromise that brings regret but has not yet led to a real turn? What would “getting up and going” look like in that specific area this week? [24:31]
Jesus receives people before he cleans them. Is there any reason someone has been keeping distance from Christ because of shame, filth, or a sense of being too far gone? What would it look like to bring that honestly to him instead of trying to fix it first? [34:38]
The religious leaders knew the right categories and still refused to bow. Where might a person hide behind Bible knowledge, church language, or a good reputation while resisting surrender to Jesus? [37:39]
Jesus is not asking for polite acknowledgment but for submission to his authority. In what part of life is it hardest to say, “You are King, and you have the right to rule here”? [10:44]
The kingdom opens to sinners who stop trying to establish their own righteousness and trust what Jesus has done. What are some practical ways people still try to prove themselves to God instead of resting in Christ? [40:41]
The real test is not a past moment alone, but whether Christ is truly in a person and repentance is showing up in real life. What fruit, desires, or changes give evidence of that reality—and where is there need for honest self-examination? [43:19]

Sermon Clips

44s

#BringYourTrashToJesus

“``So I think so often we we soft soap the gospel. We tell people, you know, you're basically a good person and if you'll just come to Jesus, he'll make you a better person. That is not true. Here's the reality. You're just like on that video we just saw. You're a person hauling around stinky, filthy, nasty garbage called sin. And no one wants to be around you. And no one wants to smell you. And no one wants to have anything to do with you except Jesus. The world will tell you, you stink, get away from me. The world will tell you that you can't bring that stuff in here. And Jesus says, bring it to me and I'll clean it up.”

46s

#JesusCleansTheBroken

“Here's the thing. We don't clean people up before they've come to Jesus. We invite them to Jesus so he can clean them up. And when you came to faith in Christ, if you have, you came to him with all that trash, all that filth, all that stench. And you know what he said? I love you. Let me take care of that for you. The prostitutes and tax collectors said, we have said no, but we now realize we need to do different, and we will go.”

40s

#SavedByGraceNotWorks

“Did you know that there'll be some people in heaven who spent almost their entire life shouting at the top of their lungs to whoever would listen, there is no God. And then at the last moment, God broke their heart, gave them a faith to believe, and they put their faith in Jesus. And they never went to a church service. They never went to Sunday school. They never got a gold star for perfect attendance, but they're in heaven. Why? Because we don't get there from what we do. We get there because of what he did.”

50s

#RepentanceIsAction

“And I come home from camp and I go, man, I feel so close to Jesus. And maybe even we walk an aisle and we pray, somebody tells us to pray a prayer and they fill out a card and they introduce this to somebody as a new believer, and we come home and nothing changes. Because all we got about Jesus was a contact high. Somebody was doing Jesus near us and we breathed in some of it and we got affected by it. But not enough to result in a life change. See, repentance repentance was not when he regretted it. Repentance was when he said, I had said no, but now I'll go.”

60s

#RegretIsNotRepentance

“Right? So you you, you you you did something, you stole money, so you got arrested, and you're sitting in jail well, maybe you I hope you didn't do that, but you stole money, you're sitting in jail, and you feel sorry because you're gonna spend the next certain percentage of your life behind bars because of the decision you made. Now, you don't really feel all that bad about stealing the money, but you feel bad about what's gonna happen to you because you stole the money. See, that's way a lot of people think that's repentance. But repentance is not feeling bad, not just feeling bad. Because you realize that you've sinned and you're separated from God and you deserve to be. See, repentance is when that regret leads you to different action.”

65s

#TurnAroundRepent

“And so what does God want us to do? What did what did Peter say when he preached that first sermon The Pentecost. They were broken. They were torn because they told him, you crucified the messiah. You killed Jesus. You killed God the son on a cross. And they said, oh, no. What do we do? And Jesus said, repent and go public with your repentance through baptism. But what was the what was the act? Repent. That that's a word that means to turn around, to turn around. It's not the same word as regret earlier. Remember? You still got your finger there? I said we'd come back to that. Because there's two different concepts here. One is he regretted how he had responded to the father, but that wasn't repentance. Repentance is when he got up and went.”

67s

#FaithEntersTheKingdom

“they were entering the kingdom because as soon as you place your faith in Jesus, you're part of the kingdom. Right? You go from being sinnerson to godson. You go from being dead to alive. You go you have your place in heaven secured the moment that you truly repent and place your faith in Jesus. Notice I didn't say the moment that you feel sorry for your sin or the moment that you're sorry for the things you've caused through your sin or sorry because you went to a camp and somebody preached about heaven and hell and scared you to death and now you feel bad. But when you repent from trying to establish your own righteousness and accept that God has already done everything needed for that, you become part of the kingdom. And they and they, the tax collectors and prostitutes, were believing it. The religious leaders were not. So guess who is going in first?”

45s

#DontBeYourOwnGod

“Think about that for a moment. If you've come to faith in Jesus, you may not have thought of yourself as a tax collector or a prostitute, but you said no to God in your own way. And the biggest way you said no to God was it you said, you're not gonna rule over me. I'm gonna make my own choices. Like a four year old whose mom's holding his hand as he crosses the street, you we pull our hand out of God's hand and we say, I do it myself. That's a way of saying, I'll be my own God. I don't need you.”

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