The Strength to Disappoint: Finding Freedom in Matthew 11

What This Matthew 11 Sermon Is About

Are you exhausted from the constant pressure of keeping up appearances or managing everyone else's expectations? In this study of Matthew 11, we explore how Jesus’ easy yoke redefines humility and gentleness to give us an unshakeable inner resolve, granting us the freedom and true strength to disappoint others.

Introduction: The Prison of Pretense

Text: Matthew 11

Before moving to New York in 2016, we lived in Orange County, California. There’s a lot to do there: beaches, events, drive up to LA or down to San Diego. One day, on my day off, I decided to do something exotic: I visited the Richard Nixon Presidential Library and Museum in Yorba Linda.

That library is on the exact site where Nixon’s father built a small farmhouse for the family. I went inside Marine One, that green helicopter he flew in from time to time. If I remember correctly, his last day as president he flew away in that helicopter.

The library has tapes, actual recordings of Nixon’s conversations in the Oval Office. They have transcripts of him discussing the illicit spying done on the opposing political party at a hotel named Watergate. They have what historians call the “smoking gun” tape from June 1972, just days after the break-in, where you can hear him ordering the FBI to stop the investigation. It’s all there, public. You can listen to it, and you can read it.

Imagine my surprise this week when I was watching an interview with a politically prominent woman. A nationally known journalist was asking her about Watergate, about Nixon’s guilt, about the evidence. And no matter what was presented to her, she would not budge. Because if she did, it would undermine her entire narrative about, in her words, a deep state conspiracy against an unfairly treated president.

She had made up her mind, and no amount of proof would persuade her otherwise. We think that’s just politics, but it’s not. It’s a human condition. We all do this from time to time.

We all have our defensive positions. We have made our minds up. We find reasons to dismiss evidence. We reframe what doesn’t fit. We make excuses. All of this because admitting we were wrong or possibly wrong would mean admitting something deeper: that we are not as competent, righteous, as put-together as we want everyone to believe.

It's exhausting. The constant work of keeping up appearances, of defending the self we’ve constructed. Most people carry that weight their whole lives without ever naming it.

Two Sides of the Same Coin

The thing you might expect from this passage, is this: Jesus says, no matter the method or message, you dig your heels in, and you won’t budge. Stop that. Then he talks about humility and gentleness, and we might think that being a good Christian means not voicing an opinion that upsets others. You know, “Christians are supposed to be nice.”

They seem like polar opposites, don’t they? The one digging in looks prideful, unmovable. Arrogant. The “nice” person, we think, is humble, and that often means not rocking the boat.

But they’re not opposites. They are both driven by the same thing: what other people think about them.

One person refuses to budge because admitting an error would destroy their image. They are not strong enough inside of themselves to let other people have a differing opinion. So, you see, the rigid person is not free. They are trapped by caring about what other people think. The other collapses because standing firm might upset someone. One is rigid, the other spineless. They are just different reactions from the same fear: the opinion of others.

You cannot follow what’s true if your entire sense of self is built on being right, on being approved, on not admitting you were wrong. You cannot follow what’s true if your north star, what you are guided by, is not making anyone disappointed.

Unpacking the Drama of Matthew 11

This exact tension between the prison of pleasing people and the freedom of truth is exactly what is at play in our text today.

John the Baptist, an amazing man, is now in prison. A year or so earlier, John was preaching in the wilderness and proclaimed the coming of the Messiah, with urgency. “Right now,” he said, “the axe is laid at the foot of tree.” In other words, this is urgent. Your time is coming. God’s justice is sure, certain, and swift.

And now? The tree is still standing. He sends messengers to Jesus with this question: "Are you the one we were waiting for, or should we be looking for someone else?” In other words, “Jesus, you aren’t fitting into the box I built for you. Either you change, or I have to admit I was wrong about you.”

Jesus is confronted by John’s doubt and his disappointment. He didn’t meet John’s expectations. John is living in rigidity.

And here is what Jesus does: he doesn’t crumble. He doesn’t say, “You’re right. I’ll start doing things your way.” He doesn’t dig his heels in defensively either: “How dare you question me.” Instead, he models humility and gentleness.

Jesus puts it back on John, whom he loves. He gives the evidence: The blind see. The lame walk. The dead are raised. John, I’m doing what I’m supposed to do. I’m fulfilling my call. Your expectations of me are on you. Your opinion on whether or not you like what I’m doing, that’s on you, not me.

Jesus had learned something crucial: his worth wasn’t dependent on John’s approval. At his baptism, Jesus had heard the voice of God say, “I am pleased with you.” And he let that truth soak into his soul. His understanding and confidence in himself did not depend on whether people understood him or agreed with him. His confidence was rooted somewhere else entirely.

The Fickle Generation and Closed Ears

Then Jesus turns to the crowd, the same generation that had seen John, and now was face-to-face with Jesus. They are fickle.

Here’s the picture: children are in the marketplace trying to get other children to play. One group plays a cheerful tune on the flute: surely, you’ll play with us. Nothing. So, they switch tactics. They sing a sad song: surely now you will mourn. Still nothing.

The children have tried everything, both joy and sorrow, and the others won’t play. No matter what the first group does, the other group will not be moved.

That’s his generation. They want John to lighten up: John, why so serious? And they want Jesus to tighten up: You’re not a serious person. Look at your eating and drinking and feasting with sinners. And because he welcomes sinners and eats with them, they smear him and call him a glutton and a drunk.

Same message about God communicated in two very distinct ways. The people reject both. So, the problem, Jesus says, is not the message. It’s the people.

They won’t dance. They won’t mourn. Not because the music is wrong, but because they’ve already decided. No matter what you say, I will not be open to you.

The Freedom of Jesus’ Way

Jesus had to figure out how to live with that – with people doubting him, being angry at him, being disappointed with him. He had to absorb disappointment. He had to feel the weight of people’s misunderstanding him, feel their rejection.

A people-pleasing leader would have heard the crowd’s critique (He’s a glutton and a drunkard!) and immediately changed his behavior to win them back. An arrogant, rigid leader would rage-tweet at them or try to force them into submission.

Jesus does neither. He says, “Wisdom is vindicated by her deeds.” In essence, “I’m not going to change my life and ministry to suit your fickle tastes, and I’m not going to manage your emotions. The fruit of my life will speak for itself.”

You see, in his work of becoming a soul deeply connected to God, of having his confidence rooted in God and not in the opinion of others, Jesus discovered a different way. Not rigidity. Not spinelessness. Freedom. And that is what he offers us in something he calls a yoke.

Redefining the Yoke: Gentleness and Humility

"Come to me, all you that are weary and are carrying heavy loads, and I will give you rest. Take my yoke upon you and learn from me; for I am gentle and humble in heart, and you will find rest for your souls. For my yoke is easy and my burden is light.”

In first-century Palestine, a yoke was used to describe a rabbi’s teaching and outlook on life. The rabbi’s learners, called disciples, would take the rabbi’s yoke upon them, basically saying, “I want to learn from you and live like you.”

So when Jesus says, “Take my yoke upon you, and learn from me,” it is an invitation to be a student of his way of life, to have your confidence and identity rooted where his is rooted.

And what does his yoke look like? He says, “I am gentle and humble in heart.”

You may think, gentleness and humility? Those sound soft. How are they going to help me speak truth to my boss, or stand up to my family members? How are they going to help me not become a doormat?

But you see, humility isn’t weakness. It isn’t thinking less of yourself. It’s the willingness to look honestly at yourself. It says: “I might be wrong. Let me examine my motives. Let me find out why I have that opinion.”

You do the work. Maybe you realize you do need to change. Maybe you realize that you don’t. Maybe you need to stay with your conviction or opinion, or maybe you can say, “I don’t know.”

This process leads you to something precious: resolve. That is how humility helps you get a backbone.

Gentleness. Gentleness frees you from the need to manipulate. When we are enslaved to approval, we try to force everyone to see things our way. Coercion isn’t strength; it’s anxiety. Gentleness says, “I have done my work. I am resolved. I will stand on my conviction, but I don’t need to force it on you to validate myself.”

Gentleness and humility do not mean you become squishy. It means you land on something solid. You find your bedrock, your core. It means you are strong enough to take a second look at yourself. And, you are strong enough to be yourself and to have an opinion, a choice, and values. And you are willing to stand on them.

That is the way to freedom.

Standing on Business: The Example of Christ

And that is what Jesus our rabbi, our Lord, offers us to be our way of life because it was his way of life.

He did the work. He studied, reflected, and the gospels say he withdrew to desolate places to have space to think, feel, and pray. That’s why his resolve jumps off the pages of Scripture. That’s why he could stand on business even though there was so much animosity toward him and misunderstanding of him. He didn’t coerce anyone into following him. At least once, he questioned whether or not a person should follow him.

As I read the gospels, I see a man living in freedom. That’s why he could stand before Pontius Pilate with resolve. Pilate said, “Shouldn’t you defer to me? I have the power to take your life.” And Jesus responds, “No one takes my life. I lay it down by my own choice.” Resolve. Strength. Humility. Gentleness.

Conclusion: The Lightness of Freedom

A while back, I was talking with someone who openly admitted to something most of us would do anything to avoid confessing. They just looked at me and said, “Yeah. I was wrong. My fault.” Not in the way in which people sometimes defensively say, “No one’s perfect.”

There was no pretense. No face-saving. No excuses. No minimizing.

Later that day, as I reflected on the conversation, a single thought kept coming back to me: That person is free.

That is what the lightness of Jesus’ yoke actually looks like. When your identity is anchored in the massive, unshakeable reality that you are a deeply loved child of God, the pressure lifts. You can make a mistake, or disappoint someone, and it doesn’t destroy you. Someone can disagree with you, and you don’t feel a frantic need to destroy them or crush their individuality to validate yourself.

Under that yoke, you are finally free.

And when you begin to carry it, you will notice a transformation happening inside you. Over time, you will develop the strength to disappoint, even if it means getting it wrong occasionally. You will find the strength to be honest, to apologize, even when it feels vulnerable or embarrassing. You’ll please yourself because you know that God is pleased with you.

The strength to stand. The strength to love without needing to be right. The ability to have a community that allows for diversity of thought.

That is what Jesus is offering.

The yoke is there. We need only choose to carry it.