Stop Playing it Safe

Series:

Summary

Stop Playing It Safe: What Jonathan's Faith Teaches Us About Trusting God

Most of us say we believe God can do the impossible. But when it comes to actually stepping out in faith, we hesitate. We wait for certainty. We stay under our proverbial pomegranate tree. The story of Jonathan in 1 Samuel 14 challenges that tendency head-on and shows us what real, active faith looks like.

What Is the Context of 1 Samuel 14?

To understand Jonathan's faith, you have to understand the situation God's people were in. The Philistines had assembled a massive army against Israel. First Samuel 13:5 describes it this way: "The Philistines assembled to fight Israel with 3,000 chariots, 6,000 charioteers and soldiers as numerous as the sand on the seashore." - 1 Samuel 13:5

The Israelites saw the situation and were terrified. They hid in caves, thickets, rocks, pits, and cisterns. Some fled across the Jordan entirely. Saul's army shrank from 3,000 soldiers down to 600. The Philistines had a stronger army, a stronger position, and stronger weapons. The situation looked completely hopeless.

And where was Saul, the king? He was sitting on the outskirts under a pomegranate tree. On the sidelines. Playing it safe.

Why Do We Play It Safe When God Is Calling Us Forward?

Saul's posture under that pomegranate tree is easy to understand. The longer you live, the easier it is to play it safe. The more success you've had, the easier it is to settle for what God did in the past. You start thinking you've already done enough, proven enough, sacrificed enough.

But that posture costs us. It costs us the experience of watching God move. And it costs others the blessing that comes through our obedience.

Jonathan refused to sit still. While everyone else was paralyzed, he turned to his armor bearer and said, "Come, let's go over to the outpost of those uncircumcised men. Perhaps the Lord will act on our behalf because nothing can hinder the Lord from saving, whether by many or by few." - 1 Samuel 14:6

What Does Faith Actually See?

Everyone around Jonathan saw the same obstacles. A stronger enemy. A nearly impossible path. Two cliffs with a ravine in between, and a Philistine outpost waiting at the top. The path itself looked impossible before the battle even started.

But that was not all Jonathan saw.

When Jonathan called the Philistines "uncircumcised," he was not just using a random insult. In the Old Testament, circumcision was a sign of God's covenant with His people. Jonathan was making a theological statement. He was saying: they have a stronger army, a stronger position, stronger weapons. But they do not have what we have. We have a covenant relationship with the Almighty God.

That changes everything.

Your biggest obstacle is not the size of your problem. Your biggest obstacle is the size of your view of God.

Second Kings 6:16-17 captures this same truth when Elisha prays for his terrified servant: "Don't be afraid. Those who are with us are more than those who are with them. And Elisha prayed, 'Open his eyes, Lord, so that He may see.' Then the Lord opened the servant's eyes, and He looked and saw the hills full of horses and chariots of fire all around Elisha." - 2 Kings 6:16-17

Faith sees what others miss. It sees a God who is bigger than our limitations and our circumstances.

What Does Faith Actually Do?

Jonathan did not just see differently. He acted differently. He told his armor bearer the plan: they would cross over and let the Philistines see them. If the soldiers said "wait there," they would stay. If the soldiers said "come up to us," that would be their sign that God was giving them the victory.

This is where it gets honest and a little uncomfortable.

Does Faith Require Certainty?

Jonathan did not know for sure how this was going to turn out. He said "perhaps the Lord will act." Not "God told me this is definitely going to work." Not "I have a guaranteed word." Just perhaps. Maybe. It may be that God will work for us.

Sometimes faith is just a strong maybe.

A lot of us will not move until we know exactly how it is going to turn out. We want the full picture before we take the first step. But God does not always give us the full picture. His Word is described as a lamp to our feet and a light to our path. A lamp gives you enough light to see the next step, not the whole road.

Faith is not certainty in a particular outcome. Faith is confidence in God. It is trusting Him enough to take the next clear step, even when you cannot see what comes after it.

The best way to get over what you do not know is to act on what you do know.

Who You Let Into Your Circle Matters

Jonathan's armor bearer responded immediately: "Do all that you have in mind. Go ahead; I am with you heart and soul." - 1 Samuel 14:7

That kind of alignment is rare and valuable. Not everyone in your circle can see what God has shown you. Not everyone will say "I'm with you heart and soul." Be careful who you allow into the vision God has given you, because not everyone is aligned with where God is taking you.

What Does Faith Experience on the Other Side?

Jonathan and his armor bearer climbed down into the ravine and up the other side on their hands and knees. They took out the first 20 soldiers guarding the camp. That alone would have been worth celebrating.

But that was not the end of the story.

Verse 15 says: "Then panic struck the whole army, those in the camp and field, and those in the outposts and raiding parties, and the ground shook. It was a panic sent by God." - 1 Samuel 14:15

Jonathan and his armor bearer did not cause the entire Philistine army to panic. God did. They did not cause the Philistines to turn their swords on each other. God did. They did not inspire the rest of the scared Israelites to come out of hiding. God did. They did not save Israel. God did.

Jonathan took a step of faith. God did everything else.

One step of faith became an invitation to experience something far bigger than anything Jonathan could have planned or imagined. And his courage woke up an entire generation of Israelites who had been hiding in caves.

How Does This Point Us to Jesus?

Jonathan was an imperfect man. He could only do so much. And if all we had was his example, it would not be enough for the situations we actually face.

Our greatest problem is not an army, a government, or difficult circumstances. Our greatest problem is sin against a holy God. And we were powerless to fix it ourselves.

But when we could not save ourselves, Jesus stepped forward. Jonathan went down into a ravine. Jesus went down into death itself. Jonathan climbed a hill to reach a Philistine outpost. Jesus climbed a hill called Calvary and gave His life for our sins. And three days later, He rose from the grave.

If Jesus can solve our greatest problem, what obstacle do you face that He cannot walk you through? If you trusted Him enough to save you from sin and give you eternal life, why are you still hesitating to take the next step of faith He is calling you toward?

Life Application

This week, identify one area of your life where you have been waiting for certainty before taking a step of faith. It might be a conversation you have been avoiding, a calling you have been sitting on, a relationship that needs reconciliation, or a decision you know God has been nudging you toward. Stop waiting for the full picture. Take the next clear step and trust God with what comes after it.

Ask yourself these questions as you reflect:

  • Where am I sitting under a pomegranate tree, playing it safe, when God is calling me into the fight?
  • What do I say I believe about God that I am not actually trusting Him enough to act on?
  • What is the next clear step of faith in front of me, and what is keeping me from taking it?
  • Am I waiting for certainty, or am I willing to move forward with a strong "perhaps" and trust God with the outcome?

Nothing can hinder the Lord from saving, whether by many or by few. The question is whether you are willing to stop playing it safe and find out what is waiting on the other side of your obedience.

Speaker: Pastor Michael Kelsey, Jr.

October 18, 2026

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