You'll Be Surprised Who Enters | Matthew 21:31

Devotional

Day 1: Yield Signs and Stoplights

Jesus faced religious leaders who recognized His authority but refused to submit. They questioned Him like drivers slowing at a yield sign—aware of the rules but unwilling to fully stop. When Jesus told the parable of two sons, He exposed their half-hearted obedience. The first son’s initial “no” turned to action, while the second’s polite “yes” led nowhere. [10:15]

Submission requires more than polite words. Like a red light, it demands we halt our plans to follow God’s direction. The Pharisees preferred debates over surrender, clinging to control while sinners embraced repentance. Jesus honors those who turn from rebellion to radical obedience.

Where are you slowing down instead of stopping? What habit, schedule, or attitude have you yielded to God without fully releasing it? Write down one area where you’ve said “I will” to God but haven’t moved. What concrete step will you take today to shift from yielding to submitting?

“What do you think? There was a man who had two sons. He went to the first and said, ‘Son, go and work today in the vineyard.’ ‘I will not,’ he answered, but later he changed his mind and went. Then the father went to the other son and said the same thing. He answered, ‘I will, sir,’ but he did not go. Which of the two did what his father wanted?”
(Matthew 21:28-31, NIV)

Prayer: Ask God to reveal one area where you’ve been yielding instead of submitting. Confess your resistance plainly.

Challenge: Write “STOP” on a sticky note. Place it where you’ll see it hourly as a reminder to surrender control.

Day 2: Vineyards and Watchtowers

The wicked tenants attacked servants sent to collect the harvest, rejecting the owner’s authority. They ignored the watchtower—a visible reminder of protection beyond themselves. Yet new tenants accepted their role as stewards, not owners, trusting the landowner’s care. [23:44]

God’s watchtower—His constant presence—still stands over your life. Like tax collectors who relied on Roman backing, we thrive when we trust His oversight. The Pharisees’ self-sufficiency blinded them to divine provision. True security comes from leaning into His guardianship, not our strategies.

What “vineyard” has God entrusted to you—your job, family, or gifts? How might you be acting as an owner rather than a steward? Identify one responsibility you’ve clutched tightly this week. How can you actively acknowledge God’s ownership today?

“He rented the vineyard to some farmers and moved to another place. When harvest time approached, he sent his servants to the tenants to collect his fruit.”
(Matthew 21:33-34, NIV)

Prayer: Thank God for three specific ways He’s protected you this month. Ask Him to deepen your trust in His oversight.

Challenge: Text one person: “How can I pray for your burdens today?” Actively lean into God’s care together.

Day 3: Sons Who Changed Their Minds

The first son’s gritty repentance—crushing his pride to obey—mirrored tax collectors and prostitutes. These “notorious sinners” didn’t hide their flaws. Like Zacchaeus scrambling up a tree, they embraced their need openly. [21:37]

God prioritizes raw honesty over polished performance. The second son’s empty “yes” satisfied religious expectations but left the vineyard untended. Jesus confronts our tendency to prioritize reputation over transformation. True submission starts when we stop pretending we’re already perfect.

Where have you polished your “yes” to God while avoiding action? What failure or weakness are you still trying to hide? Name one area where you need to trade appearances for authentic repentance.

“For John came to you to show you the way of righteousness, and you did not believe him, but the tax collectors and the prostitutes did. And even after you saw this, you did not repent and believe him.”
(Matthew 21:32, NIV)

Prayer: Confess one specific instance where you’ve valued appearances over obedience. Ask for courage to embrace messy growth.

Challenge: Initiate a conversation with three people today using the phrase, “I was wrong about…”

Day 4: Owners vs. Tenants

The original tenants murdered the heir, shouting, “This is ours!” Their rebellion flowed from believing the vineyard belonged to them. But the new tenants harvested with open hands, remembering the fruit wasn’t theirs to keep. [24:42]

Everything we have—time, talents, even our breath—is on loan. The Pharisees hoarded spiritual knowledge; tax collectors shared freely because they knew nothing was theirs. Submission flourishes when we release ownership and become joyful distributors.

What resource have you been treating as a personal possession? Your schedule? Expertise? Savings? Choose one to actively redistribute this week. How can you tangibly demonstrate it’s God’s, not yours?

“Therefore, when the owner of the vineyard comes, what will he do to those tenants? ‘He will bring those wretches to a wretched end,’ they replied, ‘and he will rent the vineyard to other tenants, who will give him his share of the crop at harvest time.’”
(Matthew 21:40-41, NIV)

Prayer: Hold your hands open palms-up for 60 seconds. Verbally release three “possessions” to God’s control.

Challenge: Donate or give away one physical item you’ve overvalued.

Day 5: From Harlots to Heirs

Prostitutes knew their reputation—crusts of bread, not banquets. Yet Jesus honored their raw awareness. Unlike the Pharisees scrambling to protect their status, these women had nothing to lose by surrendering. Their shame became the doorway to grace. [22:39]

In Christ, our true identity overrides every label. The second son’s polished “sir” masked rebellion, while the first son’s honest “no” led to transformation. God isn’t fooled by titles or tripped up by our past. He crowns those who trust His naming over their striving.

What false identity have you clung to—performer, victim, self-made success? Write the lie. Then write Christ’s truth over it from 2 Corinthians 5:17. Who can you affirm today in their God-given identity?

“Therefore, if anyone is in Christ, the new creation has come: The old has gone, the new is here!”
(2 Corinthians 5:17, NIV)

Prayer: Thank Jesus for making you new. Ask Him to highlight one person needing to hear this truth today.

Challenge: Text someone: “God calls you ___. How can I support that truth in you this week?”

Sermon Summary

Jesus plants a cold and prickly line right in the temple courts: Truly I tell you, the tax collectors and prostitutes are entering the kingdom of God ahead of you. The text puts that line in the long, single conversation of Matthew 21. The chief priests and elders recognize Jesus’ authority, but they still try to find an out. Their mouths say, show us the credentials. Their hearts say, why should anyone have to submit to this? The text exposes people pleasing, excuse making, and the refusal to stop doing life on their own terms.

The parable of the two sons shows what obedience looks like in real time. One son says, I will, sir, puts some respect on the father’s name, and then never moves. The other says no, then changes his mind and goes. The first did what the father wanted, not because he started with the right words, but because he stopped, changed posture, and entered the vineyard.

The parable of the tenants widens the frame. A landowner plants a vineyard, builds a wall, digs a winepress, and raises a watchtower. That tower is quiet protection staring over the field. The old tenants recognize the heir, but do not submit. They act like owners, not stewards, and kill the servants and the son. Judgment falls, and the vineyard is handed to tenants who will give the owner his share at harvest. The theme is steady: authority is acknowledged all over the passage, but the kingdom opens to those who submit.

The yellow light and the red light make the difference plain. Yielding slows down while staying in the same lane. Submission stops, waits on direction, and moves when the Father says move. The line about tax collectors and prostitutes fits because both groups, for all their sin, already live with certain postures God can redirect. They submit to a higher protection, operate with limited ownership, and know their reputation and identity. That posture is primed for repentance, like Zacchaeus sprinting ahead of the crowd to see Jesus. The new tenants mirror those postures: they trust the watchtower, give the owner his share, and act like farmers instead of thugs.

The call is to relent, not just talk about repentance. Stop being stubborn about authority, stop acting like an owner of time, money, and gifts, and start walking as a servant of Christ, a new creation. John came in the way of righteousness and the hardened still would not relent. The Son has come, and the vineyard is ready. The kingdom moves ahead with those who stop, believe, and submit.

Key Takeaways

1. Yielding slows down, submission stops [10:15] Submission does not mean adding spiritual awareness to the same old direction. It means a full stop before God to receive a new command, even if that reroutes cherished plans. Yellow lights create caution; red lights create obedience. The kingdom is entered by those who stop, not those who merely slow down. [10:15]
2. Authority recognized is not obedience [12:41] The leaders saw Jesus’ authority and still schemed for an exit ramp. Knowledge about who holds authority cannot replace surrender to that authority. People pleasing is often the mask rebellion wears to look respectable. The text calls that bluff and demands a yielded heart. [12:41]
3. God redirects a repentant posture [21:09] Tax collectors and prostitutes were not commended for sin but for a posture God could turn. They already lived under higher protection, handled what was not theirs, and knew they had a name problem. That kind of ground softens fast when truth lands. Like the first son, repentance becomes movement, not just apology. [21:09]
4. Ownership is limited, stewardship is worship [24:42] The vineyard belongs to the landowner, and harvest is his to claim. New tenants honor the watchtower and deliver the owner’s share, translating belief into practiced stewardship. Treating time, talent, and treasure as personal property breeds violence toward God’s claims. Returning the share is how worship walks into Monday. [24:42]
5. Identity in Christ resets direction [31:51] Old tenants acted like thugs because they forgot they were farmers. A Christian who clings to the old self will fight the Son instead of welcoming him. The gospel names a person anew as servant of Christ and new creation. Identity is not discovered by self-invention but received and lived under the Lord’s word. [31:51]

Youtube Chapters

[00:00] - Welcome
[00:15] - Gratitude and introduction
[02:39] - Praying for a West Valley church
[04:49] - "Cold and prickly" sayings of Jesus
[06:02] - Text: Matthew 21:31
[07:25] - Why tax collectors and prostitutes?
[09:55] - Yielding versus stopping with God
[11:18] - Authority questioned; submission avoided
[13:58] - Parable of the two sons
[16:48] - Parable of the tenants
[19:23] - Three traits God can redirect
[23:44] - New tenants and true identity
[25:58] - Confession, ownership, and second chances
[29:45] - Relent, repent, and respond
[34:16] - Salvation prayer

Bible Study Guide

Bible Reading
Matthew 21:28-32 (ESV)
“What do you think? A man had two sons. And he went to the first and said, ‘Son, go and work in the vineyard today.’ And he answered, ‘I will not,’ but afterward he changed his mind and went. And he went to the other son and said the same. And he answered, ‘I go, sir,’ but 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, the tax collectors and the prostitutes go 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 the prostitutes believed him. And even when you saw it, you did not afterward change your minds and believe him.”

Matthew 21:33-44 (ESV)
“Hear another parable. There was a master of a house who planted a vineyard and put a fence around it and dug a winepress in it and built a tower and leased it to tenants, and went into another country. When the season for fruit drew near, he sent his servants to the tenants to get his fruit. And the tenants took his servants and beat one, killed another, and stoned another. Again he sent other servants, more than the first. And they did the same to them. Finally he sent his son to them, saying, ‘They will respect my son.’ But when the tenants saw the son, they said to themselves, ‘This is the heir. Come, let us kill him and have his inheritance.’ And they took him and threw him out of the vineyard and killed him. When therefore the owner of the vineyard comes, what will he do to those tenants?” They said to him, “He will put those wretches to a miserable death and let out the vineyard to other tenants who will give him the fruits in their seasons.” Jesus said to them, “Have you never read in the Scriptures: ‘The stone that the builders rejected has become the cornerstone; this was the Lord’s doing, and it is marvelous in our eyes’? Therefore I tell you, the kingdom of God will be taken away from you and given to a people producing its fruits. And the one who falls on this stone will be broken to pieces; and when it falls on anyone, it will crush him.”

Observation Questions

In the parable of the two sons (Matthew 21:28-32), what specific actions distinguish the son who initially refused but later obeyed from the one who verbally agreed but did nothing?
The tenants in Matthew 21:33-44 repeatedly reject the landowner’s messengers and even kill his son. What does their refusal to honor the landowner’s authority reveal about their view of ownership?
How does Jesus contrast the responses of the religious leaders with those of tax collectors and prostitutes in Matthew 21:31-32?

Interpretation Questions

Why might Jesus have specifically used tax collectors and prostitutes as examples of those entering the kingdom “ahead” of the religious leaders? What postures did these groups embody that made them open to repentance?
The parable of the tenants mentions a watchtower built in the vineyard (Matthew 21:33). What might the watchtower symbolize about God’s role in our lives, and how did the tenants’ actions ignore this?
Jesus says the kingdom is given to those who “produce its fruits” (Matthew 21:43). What does “fruit” represent in this context, and how does it connect to submission?

Application Questions

Yielding to God’s authority often means slowing down without changing direction, while submission requires a full stop and redirection. Where in your life are you currently yielding (slowing down) but avoiding submission (stopping entirely)? [10:15]
The tenants acted like owners instead of stewards. What areas (time, money, relationships) do you struggle to treat as gifts from God rather than personal property? How could stewarding these differently reflect trust in His ownership? [24:42]
Tax collectors and prostitutes were aware of their flawed reputations, which positioned them to repent quickly. How might acknowledging your weaknesses or past mistakes actually help you respond faster to God’s correction? [21:09]
The first son’s obedience began with a “changed mind” (Matthew 21:29). What is one decision or habit you’ve been resisting that requires a change of posture, not just words?
The watchtower in the vineyard symbolizes God’s protection and oversight. How can intentionally recognizing His presence in your daily life shift your response to challenges or fears? [23:44]
Jesus says the kingdom is for those who “produce fruit.” What practical step could you take this week to align your work, relationships, or priorities with His purposes instead of your own?

Sermon Clips

They talk about, oh, just go out there and you'll find yourself. You're not the architect of your life. You are not the one who can self make yourself. You didn't you didn't birth yourself. So what makes you think you can make your own identity going forward? Our identity is in Christ. It's Christ. And that's when we have to align ourselves with that. And that's how we enter the kingdom. And that's when we can become repentant and submit and stop doing it our way and start doing it God's way. [00:31:32] (26 seconds)

Authority is easy to see, we have bosses, our parents, routines, schedules, traffic laws. Some of us let our kids be our authorities when we shouldn't, but we let them do it. But it's easy to see authority. But there's a difference between yielding to authority and submitting to it. There's that yellow light in traffic, you yield to that. But ultimately, when you're yielding, you just slow down. You're still moving in the same direction. You're becoming aware, you're looking around, but you're still just slowing down. Right? And I think a lot of us do that with our spiritual walk. We yield to God's authority, but we don't actually submit to him. Because the red light, that's submission. [00:09:30] (45 seconds)

When they came to the temple courts, they recognized Jesus' authority. It says it right there. They said it twice to him. Who gave you this authority, and by what authority are you doing this? So they knew that he had authority, and the question they were asking really wasn't who gave you the authority. What they were really asking was, why don't we have to submit to it? They were looking for an out. And sometimes we do that on our walk. We come in, we question the pastor, we question the word, we question what God's telling us, and we're like, but what about this? What about that? I'm just looking for that out. And Jesus knew that. He knew their hearts. [00:11:36] (41 seconds)

And that word relent has a different meaning than repent. That word relent means to stop. And specifically, it actually is to stop after being stubborn to something. So how do we we have to stop being stubborn to just seeing God's authority and start to submit to God. We have to see that stoplight and that red light and say, alright, you know what? I want to stop doing it my way. I'm gonna walk in the direction that God told me to go. I need to surrender and move in a new direction. [00:29:47] (33 seconds)

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You'll Be Surprised Who Enters | Matthew 21:31 | Orbit Church