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Caleb: The Best Life

June 21, 2026
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Caleb: The Best LifeIn Joshua 14:6–14, Caleb’s unwavering faith and trust in God lead him to a life of courage and fulfillment. This message on Father’s Day reflects on perseverance, wholehearted devotion, and the lasting reward of following God fully. Please note that parts 1 and 2 of this series are unavailable online due to technical difficulties.Church at Wieuca is a Christ-centered community in Atlanta, Georgia. Learn more at ⁠wieuca.org⁠. To support this ministry financially, visit: https://www.lightsource.com/donate/1834/29

Dr. Kevin Head: As we've heard all morning, it is Father's Day. This is a day where we recognize our fathers and are thankful for them. We remember fathers are full of many things, but full of fatherly advice and full of wisdom. Many years ago, there was a young boy who got his driver's license and he asked his dad, who was a preacher, if he could start driving the family car.

His father said, "All right, I'll make a deal with you. If you can pull your grades up to an A average, and if you can start reading your Bible, participating in Sunday school a little bit more, and then get your hair cut, then maybe we can talk about you driving the family car." A couple of weeks went by and then the young man came back to his father and he said, "I just wanted to come back and ask about driving the car."

His dad said, "Son, I'm really proud of you. You pulled your grades up. I've noticed that. You've been studying your Bible. I've seen you participating in Sunday school. I'm really glad about that. But you still haven't gotten your hair cut. Your hair is still long." The young man said, "Dad, I've been thinking about that. When I read the Bible more, I saw Samson had long hair, Moses had long hair, John the Baptist had long hair. I think even Jesus had long hair." His dad said, "Yeah, and did you notice they walked everywhere they went?"

We're continuing our sermon series on women and men of the Bible. We've looked at several so far and this morning we come to a man who was a father. We come to Caleb. Caleb was the father of at least one daughter and several sons. I think if Caleb were here today, he would ask us an important question. I think if he were here today, he would ask us, "Do you want to live the best life you can possibly live?"

I invite you to think about that question as we hear our text for today. The text for today is a conversation between Caleb and his good friend, Joshua. They are well into their older years and Caleb is looking back over some experiences they've shared together over almost five decades now. Listen to the conversation. It's found in Joshua chapter 14, verses six through 14.

Scripture says, "Now the men of Judah approached Joshua at Gilgal, and Caleb son of Jephunneh the Kenizzite said to him, 'You know what the Lord said to Moses the man of God at Kadesh Barnea about you and me. I was 40 years old when Moses the servant of the Lord sent me from Kadesh Barnea to explore the land. And I brought him back a report according to my convictions.

But my brothers who went up with me made the hearts of the people melt with fear. I, however, followed the Lord my God wholeheartedly. So on that day Moses swore to me, 'The land on which your feet have walked will be your inheritance and that of your children forever because you have followed the Lord my God wholeheartedly.'

Now then, just as the Lord promised, he has kept me alive for 45 years since the time he said this to Moses, while Israel moved about in the desert. So here I am today, 85 years old. I am still as strong today as I was the day Moses sent me out. I am just as vigorous to go out to battle now as I was then. Now give me this hill country that the Lord has promised me that day.

You yourself heard that the Anakites were there and their cities were large and fortified. But the Lord helping me, I will drive them out just as he said.' Then Joshua blessed Caleb son of Jephunneh and gave him Hebron as his inheritance. So Hebron has belonged to Caleb son of Jephunneh the Kenizzite ever since, because he followed the Lord, the God of Israel, wholeheartedly." May God bless the reading and the hearing of this word today.

If Caleb were here and he were to ask us, "Do you want to live the best life you can possibly live?" all of us would say yes. All of us want to live the best life that is possible for us. But if we agree that that's what we want to do, then we should ask a follow-up question and that is, what does that life look like? What does the best life look like?

I was curious about that this week, so I went and did an internet search for "the best life." It's interesting if you do that, see what you can come up with. Several websites popped up. One website, it's called Best Life Online, and it says it is your one-stop destination for timely and research-backed lifestyle and wellness news. Others popped up saying they are the best life and health insurance.

YouTube videos popped up. These were interesting. One said nine habits to help you feel better for the best life. This one was very specific: 70 life lessons to fix 93% of your problems. That's what you'll find if you do an internet search for "best life." Well, it's 2026, so I also had to ask AI. I asked AI, "What is the best life?" AI gave me a short answer and a long answer.

The short answer was, "The best life is one you build on purpose, not the one you drift into." I thought that's pretty good. The long answer was too long to explain. You can go back and look it up yourself for the best life possible on AI. So what is the best life? We've got all these websites, we've got artificial intelligence that can help us, we certainly have Scripture. What is the best life?

Picture the scene with me. Two friends. They've been friends for a long time, Joshua and Caleb. They are both in their 80s now and they are looking back on times they experienced before. They're looking back on the good old days, 45 plus years earlier. As the Bible records the conversation, Caleb does most of the talking here and Joshua listens, and I imagine he nods his head as he listens.

Caleb says, "Joshua, my friend, it was 45 years ago when we came to this place, the Promised Land. The Lord had led us out of Egypt, out of slavery in Egypt. We went across the Red Sea on dry land. We were in the wilderness following the pillar of fire by night and a cloud by day. God was good to us, feeding us with manna and quail in the middle of the desert, opening up the rock for us to drink when we were so thirsty we didn't think we could make it. It was God, Joshua, it was God, God who brought us to this place. Do you remember, Joshua?" Joshua nods his head yes.

Caleb goes on, "And do you remember that Moses appointed 12 of us to go as spies into this country to check out this land? For 40 days, we spied on this land. Remember, we were supposed to spy on this land to figure out how to take the land, not if we should take the land. That had already been promised to us by God. But we were to decide how to take the land, which paths to take, which rivers we needed to cross, what valleys and hills were there. Do you remember, Joshua?" Joshua nods his head yes.

"And then we brought our report back to Moses and the others. The other 10, they brought their report back also. The reports were similar in some ways. We all said the land flows with milk and honey. It's a beautiful land, a land rich beyond anything we could imagine. We also talked about the grapes that were there. Some of the other spies brought back grapes so big they carried them on those poles and they brought everything back to tell the people what they saw. Do you remember, Joshua?" Joshua says yes, shakes his head yes.

"But then some of the reports were different. You remember some of the others said there were too many obstacles. They said the land was occupied by giants who lived in walled cities, and inside these cities were many soldiers. The soldiers were so numerous and so mighty that we should all be afraid, and they thought it was impossible for us to go into this new land. They filled the people with fear. Do you remember that, Joshua?" Joshua nods his head yes.

"But you and I brought back a different report. We said yes, the land flows with milk and honey. Yes, it's an incredible land. Yes, there are cities, and yes, there are soldiers, and yes, they are numerous. But God has promised us this land. God has promised us that it is for us. We should do it. We should enter this land. We should take it. Do you remember that's what we said, Joshua?" Joshua nods his head yes.

"But at first they didn't listen to us. The people were afraid. The people thought the problems were too big, the obstacles too large. They rebelled against Moses and they said they wished that they could go back to Egypt, even back to slavery. God didn't like that. Remember, God said that no one over the age of 20 would enter the Promised Land because of the rebellion. No one over the age of 20, no one that is except me and you, Joshua. Do you remember?" Joshua nods his head yes.

"And now all these years later, here we are, looking at the Promised Land. We are well into our 80s, but God is still blessing us. Isn't God great?" Joshua nods his head yes. If that was all of the conversation, we would say what a beautiful conversation, two gentlemen looking back over the golden days, the good times of the past and cherishing God's blessings. That would be good enough, but the conversation doesn't end.

Caleb kept talking and Joshua continues to nod his head. Here's what Caleb said, "And now Joshua, here we are again back at the border of this great land. We have fought seven years to occupy it, but there are still some unclaimed territories here. It's time, Joshua. It's time as our leader for you to direct us to go in and to divide up this land and parcel it out among all of our people."

Then Caleb says the words that form our focus for this morning. He says, "Joshua, my friend, I am well into my 80s now, but I am still as active and still as strong as I was when I was 40. Remember Hebron, Joshua? The walled city on the hill where the Anakites and the giants live? When you divide up this land, give me Hebron. Give me the hill country. Give me the land where the giants live. Give me the land where the Anakites are. We will take this city. We will win the victory. Joshua, let me take this challenge."

So here's what happened. Joshua parceled out the land and he gave Hebron to Caleb. Caleb went in with his armies to the hill country where the Anakite giants lived. At the age of 85, when he could have taken the easy land, when he could have taken the land where there was no challenge, where there were no hills and there were no giants, Caleb begged for a challenge.

Caleb has been described as one who lived the best life. If we want to live the best life, I think there are some very important lessons we can learn from Caleb. First, like Ruth we talked about two weeks ago, the first thing we see in the life of Caleb is that he believed in the promises of God. He believed in the promises of God all the way back 40 plus years ago when he and Joshua had been spies.

Those two were the only ones who believed if God said we can take this land, we can do it. He believed in the promises of God. Believing in God's promises, if we want to live the best life we can live, that's where it starts. This book is not just a book of history, our Bible. It is filled with the promises of God for how we live our lives today.

In our passage for this morning, as we read Caleb talking to Joshua, there is at least five times in six verses that Caleb says something like this: "And the Lord promised. And the Lord said. And the Lord promised." On and on he goes. Caleb was saying to Joshua and he is saying to each one of us who want to live the best life possible that it starts with believing in God's promises for your life.

Even when Caleb faced tremendous obstacles in the past and now once again as he faces tremendous obstacles in his future that he doesn't even have to face but he chooses them, he believes if God says you can conquer this, if God says this belongs to you, if God promises it, I believe it. Caleb says he trusts in the promises of God.

What does that say to us? At the very least, it reminds us as Christians that we are not to be like those who hear the promises of God but are too afraid to claim them. As Christians, Caleb reminds us we are not to be like those Christians who read God's promises but are uncertain if it's true. We're not to be like the 10 spies who go into the Promised Land and say it looks great, but there are too many problems, there's no way we can do it.

Wayne Dehoney was one of my seminary professors, was one of my preaching professors in seminary, and he wrote a sermon on this very passage. In that sermon, he wrote some words I want to share with you what he wrote. He was preaching about Caleb believing in God's promises and here's what he said: "We have enough pious grasshopper philosophy among the people of God. It is a tragedy to hear someone of faith who is supposed to be a child of God shaking their head and saying the burdens of this life are so great, we are going to be defeated."

He wrote, "That kind of pious philosophy does not belong to the people of God. We are not weak. We are not small. We are mighty because we are with God and God is on our side. We can claim God's promises. We will march to victory," said Dr. Dehoney. That's the way Caleb lived. He didn't look at life thinking what could not be done. He didn't look at life thinking the pathway ahead is impossible. He looked through the eyes of faith and he said, "God, I have no idea how you're going to do this. I have no idea how this is going to work itself out, but I believe in what you have promised me and therefore I'm going to do whatever is my part to do to make this happen."

I'm reminded in the New Testament that Paul writes we are more than conquerors. More than conquerors because of God, not of our own doing but because of the work of God and our faith in the promises of God. Caleb says if you want to live a life that means something, if you want to live the very best life you can possibly live, it begins by trusting in the promises of God for your life.

But then as I look at Caleb, there's more to it. He was also someone who lived life without regrets. Think about that. Caleb is now well into his 80s but he's looking back and saying he doesn't regret the decisions he made, the choices he made, or the actions he made. He is living life now with no regrets. As Caleb is talking to Joshua, there's a word that stood out to me. We said it three times as we read this passage. Caleb believed in the promises of God wholeheartedly.

In other words, he put his whole life into this faith. He put all that he had into believing in God's promises wholeheartedly to the very best of his ability. Caleb knows now that because of his wholehearted faith, he can look back on the past without any regrets. Not all of us are able to do that. Sometimes in life, we find ourselves saying, "Well, if I had to do it all over again, or if I could go back, I would do some things differently."

Obviously, none of us are perfect. Caleb didn't live a perfect life. He made some decisions, he said things, he thought things, he did things he shouldn't have done. That's certainly true. But in the big picture of his life, as he thinks about how he believed in God and put his faith in God's promises, he now looks back without any regret for the decisions that he made.

Dwight Moody, a famous evangelist, tells about an experience in his life that was a real turning point for him. It wasn't his conversion and it wasn't his call to be an evangelist, but Moody says that one day early in his life, he was walking and he saw a man out in a field, out in a pasture, who was preaching. Very few people were gathered around this man, but he was standing in the middle of a field and he was preaching.

Moody says he stopped to listen to the sermon for a while and he said for the most part, it was a very forgettable sermon. I understand that. I've preached many of those. But he says in that forgettable sermon, the preacher said one thing he said he never forgot. The preacher said this: "The world has yet to see what God can do in and through a person who is wholly committed to God. Yes, the world has yet to see what God can really do through a person, in a person, for a person, with a person who is totally committed, totally committed to God."

Moody would later say that at that very moment in that forgettable sermon, he resolved to be that person. He resolved in that moment he would be that person. Not a perfect Christian, but like Caleb, Moody decided to live life with no regrets, to follow God no matter what the cost was, to believe in God's promises despite what life's circumstances looked like. Caleb teaches us if we want to live that best life, then we must follow God wholly and completely, living without regrets.

It's not too late to live that way. It doesn't matter what decisions you've made in your life. It doesn't matter what has happened in your past. It doesn't matter where you are today. It doesn't matter what's happening in your life at this moment. It doesn't matter how young you are. It doesn't matter how old you are. Today you can decide that from this day forward, you will believe in God's promises to the best of your ability and live life without regrets as you follow God. Caleb says that is how to live the best life possible.

The last thing I want to mention about Caleb is that I think his best life was possible because he continued to choose to face the challenges that were in front of him. Caleb said to Joshua, "When you divide up the land, give me the greatest challenge. Give me the hill, Hebron. Give me the place where the giants live. Give me the place where all the soldiers are. I know I'm 85 years old. I know I've already done my part. I know Hebron is a huge hill and giants live there, but listen, life is about challenge. I want to live the best life I can possibly live. So I'm 85, but give me the hill country. Give me the giants. I want the challenge."

What an incredible statement of faith from a person who had already done so much. He could have easily said, "God, I've already done that. It's time for somebody else to do it." But he chose the challenge. I think Caleb teaches us regardless of our youth or our elderly status, if we want the best life, then we must be ready to take on the challenge that God gives us.

If we're not ready for the next challenge, if we're not interested in the challenges of life, then basically it's like we've already given up the best life we could live. There's a wonderful line in the great movie "The Shawshank Redemption." There's a line that I absolutely love in that movie and it goes like this: "Get busy living or get busy dying. Get busy living or get busy dying."

I think that was Caleb's approach to living the best life he could possibly live. Life is about challenges. Regardless of our current situation, regardless of our position, regardless of any other factor in our life, be ready for the challenges that God puts before you. The challenges that God wants you to take on as you believe in God's promises.

I'm reminded Helen Keller said, "Life is either a daring experience or it is nothing at all." Do you want the best life? Do you want a life that is more than just making it through every day? I think Caleb would say to us, "Believe in God's promises. Live from this day forward with no regrets, following God's will and purpose for your life, and relish the challenges God places before you. For life is either a daring experience or it is nothing at all." Caleb, an example of the very best life.

Let us pray. Good and gracious God, what a blessing it is to read, to learn about, and to know the people who have gone before us. Our forefathers, those who have given us examples of faith. The women and men of Scripture who serve as our examples. Today we're grateful for Caleb for the example he gives to us about how we can live the best life we can possibly live through our faith in you.

Lead us and guide us, Lord, that we too might follow in those footsteps and serve you as you call. For we make this our prayer in the precious and holy name of Jesus Christ, our Lord and our Savior. Amen. Our song of commitment today is a wonderful song that gives us a chance to make our commitments to God. So I invite you to do so as we stand and sing or by coming forward if God has spoken. Would you respond? Let's stand together as we sing "He Knows My Name."

This transcript is provided as a written companion to the original message and may contain inaccuracies or transcription errors. For complete context and clarity, please refer to the original audio recording. Time-sensitive references or promotional details may be outdated. This material is intended for personal use and informational purposes only.

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About Church at Wieuca

Church at Wieuca is a warm, welcoming church that has served the North Atlanta community since 1956. We gather each week for meaningful worship, faithful community, and hope rooted in Christ. With ministries for all ages, including children and families, and outreach opportunities for our neighborhood and city, we continue to follow God forward together.

About Dr. Kevin Head

Dr. Kevin Head joined Church at Wieuca in January 2025 and brings more than 25 years of pastoral ministry experience. A thoughtful preacher and steady leader, he is passionate about caring for people, strengthening the church, and helping communities grow in faith and purpose.

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