What Do You Do With Your Doubt? / Matthew 11:1-19
Welcome and Broken Paths
If you have your Bibles with you, turn to Matthew chapter 11. A special welcome to the guests who are with us today, especially those joining via video this weekend. I am especially mindful as we enter into this message of those who have maybe walked with God at some point, drifted away, and have now come back. If you find yourself identifying with the prodigal son, I just want to say to you: welcome to The Well.
We are a group of people who are trying to walk humbly with the Lord, who have come from broken paths and broken lifestyles ourselves, and who have embraced the grace of Jesus Christ who is making us anew. So if by chance you are sitting at our North campus or at Fig, kind of wondering, Is lightning going to strike because I’m here? I would just remind you: you are in a room full of lightning rods. We are all coming at the gospel from that same sense of brokenness and desperation. I’m just really thankful you are here.
Disciples vs. The Religious
We are in Matthew 11, looking at verses 1 through 19. A couple of weeks ago, at the end of chapter 9 and the beginning of chapter 10, Jesus was talking about what it meant to be an ambassador of the kingdom of God. In this kingdom, we live as representatives of the King. This life is not about you and me. We are not the center of the universe. Whatever people thought about you in high school, that ship has sailed—it is about Jesus, not us. We are His ambassadors.
Last week, we saw in Matthew 10 where Jesus introduced what it means to be a disciple.
Matthew 10:24 (NASB)
’A disciple is not above his teacher, nor a slave above his master.
A disciple is, by definition, a pupil, a learner, a student. But we need to put an asterisk next to the biblical definition, because it means that and much more. It is not simply knowing what Jesus knew that makes us disciples. What makes us disciples is when we reorient our lives so that we begin to live like He lived.
We made a distinction last week between a disciple and what we call “the religious.” A disciple reorients their life and says, “God, I’m going to do whatever Your Word tells me to do, even if it hurts.” The religious person says, “I’m going to do just enough so that you think I’m in, but I’m going to keep this other hustle over here that reminds me of my old life.” They want enough of the world and enough of Jesus, trying to manage the tension between guilt and indulgence.
That is a completely fruitless existence. Neither life is fulfilling at that point. You are not content walking with Jesus because you know what you did last night, and you are not fully content with what you did last night because you know you are going to church today. There is this constant sense of being trapped.
I want to invite you to another way, because that is what Jesus did. A disciple recognizes that the number one priority in life must be Christ and Christ alone, because He is worthy. He is the only one who died on the cross, paid for sin, and rose from the dead. There is no other pursuit worth making the primary focus of your life.
Following Jesus, however, is not always easy. In fact, when you begin to follow Jesus, do not be surprised if it causes division. If you are in a pitch-black room and someone flips on the light, it is almost blinding at first. If you live in the light of Christ in a dark world, people may be blinded at first. Our calling is to walk with Jesus in a way that is honoring to Him and not unnecessarily repulsive to the people around us. The gospel by its very nature is already offensive; we do not need to add our own offense to it.
The Ultimate Disciple on Death Row
In Matthew 11, Jesus finishes giving instructions to the twelve and departs to teach in Galilee. Then He introduces us to an interaction He has with John the Baptist.
Matthew 11:1 (NASB)
When Jesus had finished giving instructions to His twelve disciples, He departed from there to teach and preach in their cities.
Now, we need to make a distinction here. We are not talking about John the Apostle, the disciple whom Jesus loved. We are talking about John the Baptizer. The history of John the Baptist is fascinating. Jesus and John were related because their mothers were related. According to Luke 1, both experienced miraculous conceptions. Elizabeth, advanced in years, was given a child, and Mary experienced the virgin birth of Jesus. When Mary visited Elizabeth while they were both pregnant, the baby in Elizabeth’s womb leaped, and she was filled with the Holy Spirit. Elizabeth understood who Mary was carrying.
Luke 1:43 (NASB)
’And how has it [happened] to me, that the mother of my Lord would come to me?
John grew up with that same understanding. In Matthew 3, John is living an ascetic lifestyle out in the wilderness, likely near the northern portion of the Dead Sea by Qumran. He is preaching: “Repent, for the kingdom of heaven is at hand!”
Matthew 3:1-3 (NASB)
Now in those days John the Baptist came, preaching in the wilderness of Judea, saying, ‘Repent, for the kingdom of heaven is at hand.’ For this is the one referred to by Isaiah the prophet when he said, ’THE VOICE OF ONE CRYING IN THE WILDERNESS, ‘MAKE READY THE WAY OF THE LORD, MAKE HIS PATHS STRAIGHT!’’
John clearly understood his role and who Jesus was.
Matthew 3:11 (NASB)
’As for me, I baptize you with water for repentance, but He who is coming after me is mightier than I, and I am not fit to remove His sandals; He will baptize you with the Holy Spirit and fire.
When Jesus came to the Jordan River to be baptized, John protested, saying, “I need to be baptized by You, and do You come to me?” But Jesus told him to permit it to fulfill all righteousness.
Matthew 3:13-17 (NASB)
Then Jesus arrived from Galilee at the Jordan [coming] to John, to be baptized by him. But John tried to prevent Him, saying, ‘I have need to be baptized by You, and do You come to me?’ But Jesus answering said to him, ‘Permit [it] at this time; for in this way it is fitting for us to fulfill all righteousness.’ Then he permitted Him. After being baptized, Jesus came up immediately from the water; and behold, the heavens were opened, and he saw the Spirit of God descending as a dove [and] lighting on Him, and behold, a voice out of the heavens said, ‘This is My beloved Son, in whom I am well-pleased.’
John declared of himself that he was the voice crying in the wilderness, quoting Isaiah 40.
John 1:23 (NASB)
He said, ’I am A VOICE OF ONE CRYING IN THE WILDERNESS, ‘MAKE STRAIGHT THE WAY OF THE LORD,’ as Isaiah the prophet said.’
Isaiah 40:3 (NASB)
A voice is calling, ’Clear the way for the LORD in the wilderness; Make smooth in the desert a highway for our God.
John pointed people to Jesus: “Behold, the Lamb of God, who takes away the sin of the world!” When his own followers began leaving him to follow Jesus, John had no problem with it. He said, “He must increase, but I must decrease.” John was the ultimate disciple. He was fully committed to God’s Word, full of passion, completely all-in, having totally reoriented his life around Jesus.
Yet following Jesus was not easy for John. He took tremendous heat because he stood up for what was right. Herod Antipas, the ruler, came from a dynasty where they took whatever they wanted. Herod looked at his brother Philip’s wife, Herodias, and took her for himself. John confronted him directly.
Matthew 14:3-4 (NASB)
For when Herod had John arrested, he bound him and put him in prison because of Herodias, the wife of his brother Philip. For John had been saying to him, ‘It is not lawful for you to have her.’
When you hold to the Word of God, it will cause friction. John posted up to the governor and said, “It is not lawful for you to have her. That is immoral, it is wrong, and it is not honoring to God.” So Herod threw him into prison. Later, at Herod’s birthday party, Herodias’s daughter danced for him, and in front of his guests, Herod foolishly promised her whatever she wanted. She conferred with her mother and asked for John’s head on a platter.
John knew the risks. He knew Herod’s father had ordered the massacre of the infants in Bethlehem. He knew that calling out this corrupt ruler could cost him his life. And sure enough, he found himself sitting on death row.
The Question of Doubt
It is against that backdrop that we read verses 2 and 3.
Matthew 11:2-3 (NASB)
Now when John, while imprisoned, heard of the works of Christ, he sent [word] by his disciples and said to Him, ‘Are You the Expected One, or shall we look for someone else?’
John is in prison, and he sends his disciples to ask Jesus: “Are You the Expected One, or shall we look for someone else?”
Why is that such a shocking question? They were related. Their mothers knew each other. John had proclaimed the kingdom of God, baptized Jesus, seen the Spirit descend like a dove, and called Jesus the Lamb of God. If anyone in the Bible had the information, it was John. Why in the world is he asking this question?
Because John is human. He doubts. He feels fear, uncertainty, and insecurity. In a moment where his faith is intensely tested, he falters slightly and needs reassurance.
Can you relate to that? Can you relate to understanding the gospel intellectually, having memorized Scripture, and yet finding yourself in a dark valley wondering what God is doing? If you were on death row under the authority of a ruthless madman, knowing your life was on the line, wouldn’t you want a little reassurance?
I love the Bible because it is so honest and relatable. John is sitting in a cold cell thinking, I knew following God was hard, but I stood up for righteousness. I defended God’s law. I pointed everyone to Jesus. Why am I on death row?
Many of us carry an unspoken version of the prosperity gospel. We assume that if we do what is right, read our Bibles, and live as disciples, everything will go smoothly. We treat God like a rabbit’s foot: do good things, get good luck; experience suffering, something must be wrong. But that is not the gospel. Following Jesus is costly. John is on death row, simply asking for reassurance.
Look at What Is Happening
Notice how Jesus responds. He does not give a quick, casual, “Hey bro, relax, you know I’m the guy.”
Matthew 11:4-6 (NASB)
Jesus answered and said to them, ’Go and report to John what you hear and see: [the] BLIND RECEIVE SIGHT and [the] lame walk, [the] lepers are cleansed and [the] deaf hear, [the] dead are raised up, and [the] POOR HAVE THE GOSPEL PREACHED TO THEM. ‘And blessed is he who does not take offense at Me.’
Jesus combines prophecies from Isaiah 26, 35, 42, and 61, and tells John’s disciples to report what they see and hear: the blind receive sight, the lame walk, lepers are cleansed, the deaf hear, the dead are raised, and the poor have good news preached to them.
Jesus does not give John special treatment just because they are cousins. Instead, He calls John to believe by faith. Scripture foretold what the Messiah would do; Jesus is doing those exact things. He sends the messengers back to tell John: look at the evidence of Scripture fulfilled, and do not stumble over Me.
As John’s disciples leave, Jesus turns to the crowd to address John’s character.
Matthew 11:7-10 (NASB)
As these men were going [away], Jesus began to speak to the crowds about John, ’What did you go out into the wilderness to see? A reed shaken by the wind? ‘But what did you go out to see? A man dressed in soft [clothing]? Those who wear soft [clothing] are in kings’ palaces! ’But what did you go out to see? A prophet? Yes, I tell you, and one who is more than a prophet. ’This is the one about whom it is written, ‘BEHOLD, I SEND MY MESSENGER AHEAD OF YOU, WHO WILL PREPARE YOUR WAY BEFORE YOU.’
John was not an everyday figure. He lived out in the wilderness, wore camel’s hair, and ate locusts and wild honey. Jesus asks the crowd, “What did you go out to see? A reed shaken by the wind? A man dressed in soft clothing? No, you went to see a prophet—and more than a prophet.”
Jesus quotes Malachi 3:1, confirming that John is the long-awaited messenger who would prepare the way for the Lord.
Malachi 3:1 (NASB)
‘Behold, I am going to send My messenger, and he will clear the way before Me. And the Lord, whom you seek, will suddenly come to His temple; and the messenger of the covenant, in whom you delight, behold, He is coming,’ says the LORD of hosts.
Greater Than the Prophets
Then Jesus makes an astonishing statement about John.
Matthew 11:11 (NASB)
’Truly I say to you, among those born of women there has not arisen [anyone] greater than John the Baptist! Yet the one who is least in the kingdom of heaven is greater than he.
Among those born of women, no one greater than John has arisen. Jesus looks at this man who just sent a message expressing doubt from a prison cell and calls him the greatest of all the prophets. That is incredible grace.
If you have ever doubted—if you have received an eviction notice, a cancer diagnosis, or a pink slip and wondered, Is God still good?—take heart. God does not discard you when you doubt. He meets you with truth.
Yet Jesus adds, “The one who is least in the kingdom of heaven is greater than he.” How can that be? John looked forward in anticipation of a gospel not yet fully revealed. John did not see the cross, the empty tomb, the ascension, Pentecost, or the birth of the global church. He anticipated the Messiah, but we live on this side of the resurrection. We experience the fullness of the gospel realized—the Holy Spirit indwelling us, the power of sin broken, and the sting of death removed.
Jesus continues teaching about the spiritual reality of His arrival.
Matthew 11:12-14 (NASB)
’From the days of John the Baptist until now the kingdom of heaven suffers violence, and violent men take it by force. ’For all the prophets and the Law prophesied until John. ’And if you are willing to accept [it], John himself is Elijah who was to come.
From the days of John until now, the kingdom has faced intense opposition and forceful men. All the Law and the Prophets pointed toward this moment. Everything in the Old Testament anticipated the Messiah, and the prophetic era culminated with John. Why? Because the King Himself has arrived. If the people are willing to accept it, John fulfilled the prophecy of Elijah found in the very closing words of the Old Testament.
Malachi 4:4-6 (NASB)
’Remember the law of Moses My servant, [even the] statutes and ordinances which I commanded him in Horeb for all Israel. ’Behold, I am going to send you Elijah the prophet before the coming of the great and terrible day of the LORD. ‘He will restore the hearts of the fathers to [their] children and the hearts of the children to their fathers, so that I will not come and smite the land with a curse.’
For four hundred years, the people of God waited in silence. Jesus declares that the silence is broken: John was that messenger, and the Messiah is standing right before them.
Children in the Marketplace: Hope vs. Skepticism
Jesus then illustrates the stubbornness of that generation.
Matthew 11:16-19 (NASB)
’But to what shall I compare this generation? It is like children sitting in the market places, who call out to the other [children], and say, ‘We played the flute for you, and you did not dance; we sang a dirge, and you did not mourn.’ ’For John came neither eating nor drinking, and they say, ‘He has a demon!’ ’The Son of Man came eating and drinking, and they say, ‘Behold, a gluttonous man and a drunkard, a friend of tax collectors and sinners!’ Yet wisdom is vindicated by her deeds.’
He compares them to fickle children playing games in the marketplace. When wedding music is played on the flute, they refuse to dance. When a funeral dirge is played, they refuse to mourn. Nothing satisfies them.
John came fasting and living an ascetic life, and they said, “He has a demon.” Jesus came eating, drinking, and celebrating with people, and they said, “Look at Him, a glutton and a drunkard, a friend of tax collectors and sinners!”
They were impossible to please because their hearts were cynical.
Look at the contrast: John asked questions from a heart of hope. He asked, “Are You the One?” because he desperately wanted Jesus to be the Messiah. He was all-in and needed confirmation. The religious leaders, on the other hand, asked questions from a heart of skepticism. They were “yeah, but” people.
“Yeah, but He heals on the Sabbath.” “Yeah, but He eats with sinners.” “Yeah, but where is He from?”
If you have a heart of skepticism, no amount of evidence will ever be enough. You can read every book, watch every video, and study every argument, but for every answer you receive, you will find another excuse. Skepticism does not want truth; it wants an exit strategy to avoid surrendering to Christ.
Jesus says, “Wisdom is vindicated by her deeds.” Over time, the truth is revealed. Was John’s hope vindicated? Absolutely. Jesus is the Son of God. He continues to heal the brokenhearted, forgive sin, and set captives free. What did empty religion produce? It only weighed people down with guilt and legalism, over-promising and under-delivering.
Faith in the Middle of Our Doubts
If you find yourself questioning today with a heart of hope, wondering, Is Jesus truly who He says He is?—the answer is yes. He is faithful. He invites you: “Come to Me, all who are weary and heavy-laden, and I will give you rest.”
I love that Scripture is candid enough to show us John the Baptist—the greatest born among women—wrestling with doubt. There are moments when all of us look at circumstances or Scripture and think, Lord, help my unbelief. God is not afraid of your honest questions. It is not about pretending you never have doubt; it is about bringing your questions to Jesus with a heart that genuinely desires truth.
Jesus will not give you every minor detail or remove every mystery, but He gives you enough evidence to trust Him by faith. He has proven His goodness through His life, His death, and His resurrection.
Do you have a heart of skepticism, or a heart of hope? Bring your doubts, your fears, and your questions to the King who welcomes you.
Let’s pray.
Father, thank You for the reminder that You are faithful even when our faith falters. Thank You for the honest testimony of John the Baptist—a faithful disciple who wrestled with doubt in a dark cell, and to whom You responded with truth and grace. We thank You that Jesus is indeed the Expected One, the Lamb of God who takes away the sin of the world.
Give us hearts of hope rather than hearts of cynicism. Meet us in our questions, strengthen our faith, and help us live as devoted disciples who follow You wholeheartedly. We commit our lives to You and pray all these things in Jesus’ name. Amen.