Dare Something Greater
Before we get into the text, I want to be honest with you about who was on my mind while I was writing this.
When I prepare a sermon, I don’t think about individuals — I think in groups. What about the person wrestling with an addiction? What about the one who keeps asking God for something and hearing nothing back? What about the person drowning in doubt?
Kids, you weren’t the first group I had in mind. That doesn’t mean today isn’t for you — it is, and I’ll aim a few points squarely at you. Ladies, you weren’t first either, and the same holds: everything here is for you.
Who was on my heart were the guys. For two reasons.
First, the content. If Hollywood adapted today’s story, it would be marketed at men. It’s a manly kind of story.
Second, the context of my own life. Wrestling season is about to start, and I have the privilege of helping the Wartburg wrestling team in a couple of small ways — organizing a Tuesday gathering and hosting a Bible study at my house on Thursdays. This year the team is large, and there’s a women’s team too. So I’ve been asking what would genuinely serve them. I kept circling back to a story I first encountered years ago, one I think would encourage and challenge a believer and still have something real in it for someone who isn’t. And when it became clear a couple of weeks ago that I’d be preaching this Sunday, I thought: some of that belongs to the whole church, and especially to our men.
But guys — here’s my promise. So often when I hear a “men’s sermon,” I feel like the pastor has dragged me into an MMA ring to verbally work me over. Mother’s Day sermons run, “Ladies, you are wonderful” — which is true. Father’s Day sermons run, “You’re failing. Do better.”
Shame and guilt are lousy motivators. They work in the short term, but my goal isn’t to squeeze better behavior out of you for the next month. My goal is to see Jesus work in you across your life. So the last thing I want is to pile guilt on you. I’d rather draw you out and inspire you toward the life I believe God wants for you.
Or, to use today’s language: I think God wants you to dare something greater.
How Saul Got Here
Open to 1 Samuel 14. But first, some background.
Saul is Israel’s first king. Not long after being named king, God used him to rally the nation when the Ammonites threatened one of the tribes. Israel went out, defeated them, and experienced a unity they hadn’t known in a very long time.
People liked Saul, because Saul looked like a king. He was taller than everyone else and strikingly handsome — in other words, my opposite. He looked the part completely.
The problem was that he didn’t have a king’s heart. He was deeply insecure and profoundly selfish. He cared more about his reputation than his people, more about his throne than God’s throne. And that combination led him to do real damage.
The prophet Samuel told Saul to go to Gilgal, wait seven days, and Samuel would come, offer the sacrifice, and deliver further instructions. But when Saul arrived at Gilgal, the situation was obvious — battle with the Philistines was coming.
And the math was terrible. Saul had roughly three thousand men. The Philistines fielded thirty thousand chariots and six thousand horsemen, and that’s before counting foot soldiers. We’re talking about an army of at least thirty-six thousand, likely forty or fifty. Israel had just defeated a small Philistine detachment, so now the Philistines were furious and had come out in force.
Saul began to panic. So did his men. Of those three thousand, soldiers started slipping away to hide in caves. Some defected outright and joined the Philistines — if you can’t beat them, join them. By the time we reach chapter 14, only six hundred Israelites remain.
And there’s one more detail from chapter 13 that changes everything: the Philistines controlled the blacksmithing in the region. They made the tools and sharpened the blades, and they charged the Israelites exorbitant prices — so exorbitant that in the entire army, only Saul and his son Jonathan owned swords. The other six hundred were preparing to fight with farm implements.
So: overwhelming odds, an army evaporating, and two swords. Saul panics. And rather than wait out the seven days for Samuel, he takes matters into his own hands and offers the sacrifice himself.
But Saul is a king, not a priest. Only priests offered sacrifices. In that moment he dishonors God and reveals that he doesn’t actually trust Him. Had he waited a few more minutes, Samuel would have arrived — and in fact Samuel walks up to find the sacrifice already made.
“What have you done?”
And Saul launches into excuses. There are so many Philistines. We have no weapons. The men are deserting. I needed God’s help, and I needed the people to see God was with us so they’d stop running. It seemed like the right thing.
Samuel’s answer: because you would not trust God, the kingdom will be taken from you and given to a man after God’s own heart. If you know your Bible, you know that man becomes David — the ancestor of Jesus.
So as chapter 14 opens, put yourself in Saul’s head for a moment. Yes, he’s a bad king. But you can also feel it: insurmountable odds, no weapons, deserting troops, the sense that he’s a failure nobody wants to follow, and the conviction that engaging in battle means dying.
And we find him sitting. Some translations put him in a cave, others under a pomegranate tree. Either way — sitting, doing nothing.
That’s when his son kickstarts the story.
The Text
One day Jonathan the son of Saul said to the young man who carried his armor, “Come, let us go over to the Philistine garrison on the other side.” But he did not tell his father. Saul was staying in the outskirts of Gibeah in the pomegranate cave at Migron. The people who were with him were about six hundred men, including Ahijah the son of Ahitub, Ichabod’s brother, son of Phinehas, son of Eli, the priest of the Lord in Shiloh, wearing an ephod. And the people did not know that Jonathan had gone.
Within the passes by which Jonathan sought to go over to the Philistine garrison there was a rocky crag on the one side and a rocky crag on the other side. The name of the one was Bozez, and the name of the other Seneh.
Jonathan said to the young man who carried his armor, “Come, let us go over to the garrison of these uncircumcised. It may be that the Lord will work for us, for nothing can hinder the Lord from saving by many or by few.” And his armor-bearer said to him, “Do all that is in your heart. Do as you wish. Behold, I am with you heart and soul.”
Then Jonathan said, “Behold, we will cross over to the men, and we will show ourselves to them. If they say to us, ‘Wait until we come to you,’ then we will stand still in our place, and we will not go up to them. But if they say, ‘Come up to us,’ then we will go up, for the Lord has given them into our hand. And this shall be the sign to us.”
So both of them showed themselves to the garrison of the Philistines. And the Philistines said, “Look, Hebrews are coming out of the holes where they have hidden themselves.” And the men of the garrison hailed Jonathan and his armor-bearer and said, “Come up to us, and we will show you a thing.”
And Jonathan said to his armor-bearer, “Come up after me, for the Lord has given them into the hand of Israel.” Then Jonathan climbed up on his hands and feet, and his armor-bearer after him. And they fell before Jonathan, and his armor-bearer killed them after him. And that first strike, which Jonathan and his armor-bearer made, killed about twenty men within as it were half a furrow’s length in an acre of land.
And there was a panic in the camp, in the field, and among all the people. The garrison and even the raiders trembled, the earth quaked, and it became a very great panic.
Far More Than You Could Ask or Imagine
In Ephesians 3, Paul closes a prayer by declaring that God is able to do far more abundantly than all we ask or imagine.
I think those words are God’s invitation to seek Him, to trust Him — to dare something greater. I don’t believe God put us here to chase the American dream and grind along on the daily treadmill. I believe He wants to do more in us and through us than we could hope or imagine.
Over and over in Scripture we watch Him do exactly that. And we watch it here with Jonathan. So let me pull five things out of this story.
1. Jonathan Made a Choice
If you’re going to dare something greater, you first have to choose to.
Saul was also making a choice — the choice to do nothing. He sits under that tree because he’s convinced that going means dying, and he is far more concerned with himself than with anything else. Doing nothing is still a decision.
Jonathan chooses the opposite. God has called us to this battle. We have to obey. I choose to go.
Yes, the odds were absurd. But in Jonathan’s mind, if God is for us, who can be against us? If God can split a sea, if God can bring plagues on Egypt, if God can collapse the walls of Jericho — God can defeat fifty thousand Philistines with nothing but a prince and an armor-bearer.
Kids, this one’s for you too. Choosing is where everything starts.
2. Jonathan Followed Through
Have you ever made a decision and then simply not done it?
If you’ve ever made a New Year’s resolution, you know exactly what I mean. That’s it, I’m losing the weight — and you weigh the same. I’m going to start exercising — and you haven’t. I’m going to ask her out — and weeks go by.
Choosing isn’t enough. You have to initiate. You have to engage. You have to follow through. That’s the difference between Jonathan and his father. Saul won’t move. Jonathan says, “Let’s go,” and goes.
When I first sensed God calling me toward church planting, I behaved a lot more like Saul than Jonathan. It took me a long time to get my head and heart around the idea that God wanted to use me to start a church. I didn’t think I’d be a good lead pastor. I had every doubt. So I sat under my pomegranate tree.
Eventually the day came when I realized God wasn’t letting this go — and that it would be better to plant a church and fail than to stay where it was safe and comfortable and live with regret. Because my failure wouldn’t be failure in God’s eyes. My real failure would be refusing to move. I could honor God by obeying, even if the whole thing collapsed and I fell flat on my face.
Here’s where this bites. Too often we behave like Adam. Go read Genesis 3 and notice the detail we skip: after the serpent deceives Eve and she eats, she turns and hands it to her husband — who was with her. Adam was standing right there. He heard the entire conversation. And he did nothing.
What I notice in myself and in other men is exactly that. We stay silent. We don’t initiate. We don’t engage. We stay on the sidelines, under our pomegranate tree.
So husbands: initiate a date. Initiate a conversation. Ask your wife how she’s actually doing. You might even initiate praying together. Yes, it’ll be awkward the first few times because you aren’t used to it. It gets easier.
Dads: many of you want to be a great father, which means initiating your way into your kids’ lives. Put the phone down. Turn the TV off. Set work aside and get on the floor for Legos or dolls or a tea party. Go throw the ball in the backyard. Be at the game, the school play, the piano recital. Let your children know they matter more than your team and more than your hobby.
Employees: go beyond the assignment. Teammates: initiate encouragement. If you live in a dorm or a neighborhood, initiate serving a neighbor.
It is one thing to have nice ideas. It means nothing if you only thought it.
3. There Will Be Risk
When Jonathan laid out his plan, he had no idea how it would go.
Look at verses 8 through 10. We’ll show ourselves. If they say “wait, we’ll come down to you,” we stand still — which probably means we die. But if they’re arrogant enough to say “come up here,” that’s our sign that God has handed them over.
How Jonathan knew that, I don’t know. What I know is that he understood the risk. This could cost him his life. And he judged it worth taking.
By nature I am not a risk-taker — I blame being a firstborn. When my wife and I were dating, she was the one saying, “Let’s go do something mildly illegal on campus, let’s get up into the ceiling of the chapel,” and I’d be thinking, we’ll get expelled. I’m a good boy. I don’t do those things.
And yet, as I said, I eventually realized that even if I risked planting a church and failed, God could still be glorified.
Most of the choices in front of you carry inherent risk — and ultimately you’ll be fine.
Kids, it’s a risk to stand up to the bully picking on the outcast in your class. Ladies, it’s a risk to ask a woman you barely know how she’s really doing. Husbands, it’s a risk to ask your wife for honest feedback. College students, young adults, singles — it’s a risk to refuse the pressure of a culture insisting something is perfectly fine when you know deep down it won’t help you become who God wants you to be.
Thankfully your risks aren’t at Jonathan’s level. You’re most likely not putting your life on the line. What’s actually exposed is your reputation and your heart. And yes, if you stand up to the bully you might take a fist to the face — but you’ll live to see tomorrow, get up, keep following God, and keep being a blessing.
So you can take the risk when you’re taking it for God’s glory. I’m not asking you to do stupid things — swallow fireworks or run country roads at a hundred miles an hour in the dark. Not that I would know from experience. I’m asking you to make choices that honor God, and to recognize that doing so involves an unknown.
You follow the God who knows the future. Keep giving Him your life as you step into it.
4. You Have Influence
Watch what Jonathan’s life does to his armor-bearer.
I used to picture the armor-bearer as essentially a slave — assigned to Jonathan, carrying his helmet and shield. That’s not it. Armor-bearers were closer to partners, almost apprentices. Jonathan almost certainly hand-picked this young man, and they had worked closely together.
Which means that even though Jonathan is a prince, the armor-bearer had standing to push back — if you’re ordering me to expose us to a Philistine garrison, I’ll do it, but let’s talk about this first.
He doesn’t. Look at verse 7: “Do as you wish. Behold, I am with you heart and soul.”
That tells me Jonathan had been living with such integrity that this young man simply trusted him. The plan is insane, and the answer is still, I’ve watched how you live. I know you follow God. So even though this is nuts, I’m with you.
Are you living in such a way that people would say that to you?
It’s hard to reach that place — especially when you say things like, “I think we need to leave our church and go plant one, somewhere, who knows where.” And yet my wife was able to say I’m with you heart and soul. Honestly, I think she was more in than I was. I was more the one saying, “Okay, I’m with you — I have no idea how this works out.”
Whether you realize it or not, you have influence. The only question is what you’re doing with it. Are you using it for your own gain? Is it pushing people away from God, or toward Him?
And the way you build that kind of influence is unglamorous: be consistent in small things. Do the little things over and over until trust accumulates — so that when you finally say something crazy like “I think God is calling us to…” people answer, “I’m with you.”
That means doing it today. And when you fail, confess it, admit it, go after God. His mercies are new every morning and you begin again.
But notice the other side too. Do you realize how powerful it is to have someone say I’m with you heart and soul? It’s life-giving.
So some of you don’t need to be Jonathan today — you need to be the armor-bearer. You need to say it to someone. That’s what marriage is supposed to be. That’s what friendship is supposed to be. That’s what the church is supposed to be. That’s what following Jesus is supposed to be. And when you give yourself to a person or a cause like that, God does something in you even as you influence them.
5. Your Influence Makes an Impact
If we kept reading past verse 15, we’d see what these two set off.
Saul and the Israelites notice a commotion up on the ridge and realize a battle has started. They do a headcount — wait, where’s Jonathan? Where’s his armor-bearer? And suddenly the king who wouldn’t move discovers his son is up there, and that activates him. They take off toward the fight.
The men hiding in caves see the army moving and come out to join. And as the tide turns, the Israelites who had defected to the Philistines realize they’re on the wrong side and defect back. The Philistines break and run.
Two men made that happen.
At Easter of 2020 we couldn’t gather because of the pandemic. I was genuinely disappointed — I’d had an idea for that sermon for months and suddenly couldn’t deliver it. So I got the harebrained notion to shoot it as a short film instead. Someone grabbed a camera, recruited a family member to hold the boom mic, and we managed something halfway decent. It’s still on our YouTube page.
My opening illustration was a story about being out on a walk and passing a bench with a memorial plaque on it, someone’s name engraved. I think that can be a beautiful memorial. But as I stood there the thought landed hard: when my life is over, I don’t want the last remaining thing about me to be a bench.
I want the same for you. If someone builds a bench with your name on it, I will gladly come sit on it. But as I sit there, I don’t want to only recall your name. I don’t want to only recall your job title, or the activities you signed up for. I want to remember the life you lived. I want to remember the people you impacted. I want to remember a funeral where tears were shed because of how much you meant.
To get that day, you have to make the choice now — day in and day out, knowing there will be risk and knowing you’ll fail along the way.
What I Got Wrong Twenty Years Ago
This past Friday, while working on this sermon, I had a nagging feeling that I’d preached this text before. I dug into my digital archives and sure enough — twenty years ago. I was annoyed, because it would have saved me a lot of time this week. It was also interesting to see what I pulled out then versus now.
But then I got genuinely disappointed. Not about the time. Because looking at that old manuscript, I realized I had failed.
Twenty years ago I reached roughly this point and ended with: go be like Jonathan, do these things, and God will be glorified. The end.
If I stopped here, I’d be setting you up to fail. You might be inspired. You might be ready to climb the cliff. And then you’d walk out the door straight back onto the treadmill.
There are two more things in this passage that I have to show you, so you don’t leave saying “I can do this,” but instead “God can do this.”
Jonathan and the armor-bearer did not win that battle.
Think it through. They had one sword between them. I like to imagine Jonathan cutting down the first man, the armor-bearer scooping up that man’s weapon, the two of them back to back like something out of an action movie.
But even if they were the two greatest swordsmen who ever lived — even if the pair of them somehow killed a thousand Philistines — there are forty-nine thousand more. Eventually their arms give out, they die, and the story ends.
The only reason we have this story is that one line: and the earth quaked.
That’s the author’s way of saying God entered the fight. Suddenly the Philistines understood they weren’t facing two men. They were facing Jonathan, his armor-bearer, and their God. That is what sent panic through the camp.
So this victory wasn’t Jonathan’s, and it wasn’t Israel’s. It was God’s.
The same holds for you. As you dare something greater — as you fight temptation, addiction, entrenched patterns of thought, habits of lying or laziness or financial carelessness — if you try to muster it up on your own, you’ll eventually fail, and all that produces is guilt, shame, and a sense of defeat.
You win when you let the Lord win.
If you follow Jesus, Scripture says you’ve been given the Holy Spirit. In Romans, that Spirit is described as the one who raised Christ from the dead — and Paul says that same Spirit now dwells in you.
So don’t walk out of here saying, “I’m going to grind this out.” Walk out saying, “God, I give You my life. Through the power of the Holy Spirit, do this in me. I want to live this way. I want to initiate. I know there’s risk. And the only thing that will keep me going is You.”
And when you watch God work, it will amaze and humble you in a way that produces far greater joy than anything you managed on your own. Then, on the days you fail, it drives you to your knees to confess — and His mercies are new every morning, and you begin again.
The goal is not to be like Jonathan.
That’s the second thing I failed to say twenty years ago. Our goal isn’t to be Jonathan. Our goal is to be like Jesus.
And when you look at this story closely, everything Jonathan did, Jesus has already done. Jesus made the choice to come to this earth. He initiated the plan and put it into action. He followed through.
You might object that Jesus risked nothing, because He knew exactly what was coming. That’s true — there was no unknown for Him. But sit with what that means. He knew He would be brutally beaten, and He came anyway. He was driven by love, because He wanted to work in you.
So I don’t want you leaving here looking at yourself, thinking you can summon this. I want you leaving here looking at Jesus — the one who left His throne in heaven and came to earth for you.
Let us live for Jesus by looking to Jesus. Let us go make a difference because of the difference He has made in us.
Let us dare something greater.


