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Trying Not to Lose (Pt. 2)

Turning Point / David Jeremiah
The Truth Network Radio
January 1, 2026 7:01 pm

Trying Not to Lose (Pt. 2)

Turning Point / David Jeremiah

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January 1, 2026 7:01 pm

Caleb's unwavering faith and trust in God's plan led him to make bold decisions, including volunteering for the hardest assignment in the land of Canaan. His story serves as a testament to the power of faith and the importance of living a life that is fully surrendered to God. As individuals and as a church, we must learn to trust in God's plan and not try to lose, but to win, just as Caleb did.

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Where you are today is the result of decisions you've made over your lifetime. In the Bible, there's one particular story where that truth is plain to see. Today, on Turning Point, Dr. David Jeremiah guides us through the story of Caleb and the nation of Israel. and why we should think of them in the choices we make today.

Here's David to introduce the conclusion of his message, trying not to lose. And thank you for joining us. And once again, welcome to this new year that is spread out before us with such opportunity and excitement. We wanted to kind of motivate you a little bit these first couple of days by reminding you that there are two ways to live life. One way is to live life in such a way that all you're trying to do is not to lose.

And the other way is to live life with a winning mentality. Obviously, you know I'm interested in sports and have sports in my family. This is a big deal in sports. If you ever watched games where people pull the ball out, try not to score, but try not to let anybody else score or try not to make any mistakes, doesn't usually turn out very well. We were not made as individuals to live life that way.

And the illustration we are studying is the life of Caleb.

So. Follow along today as we finish up this message, trying not to lose. Our promise book for this month is what God promises you. It's the resource that we make available to you when you make a gift to Turning Point during the month of January. Obviously, we need your help.

We can't do this by ourselves. We are able to reach out to the world because of a network of many people who faithfully give to Turning Point, our Bible-strong partners, and many people who discover us along the way and just want to help us. Maybe you're in that category. When you send a gift of any size to Turning Point during the month of January, all you have to do is ask for the book, What God Promises You. It's a 208-page hardback gift book.

It answers questions about the Christian walk and God's promises for the future, has timeless biblical wisdom and practical, easy-to-apply guidance. It's inspiring because it is spiritual transformation stuff that will really make a difference in your life, helping you to build that foundation strong for this new year. It's yours for the asking when you send your gift today, and we thank you in advance for your generosity.

Well, this is part two of Trying Not to Lose, The Life of Caleb. Here we go. I've always thought it interesting in the story of Katie Sparnilla. that the two reports can be explained on the basis of perspective. And the perspective goes like this.

The ten who went in and felt defeated after they saw the giants were comparing themselves. the enemy. Joshua and Caleb went in, they saw the same enemies, but they compared the enemies. Yeah. The ten were trying not to lose.

Joshua and Caleb. We're trying to win. And if only the people had listened to the voice of faith instead of to the voice of fear. In taking counsel, they doom themselves to a generation of emptiness and wandering. And we do the same thing when we listen to the wrong internal voices in our lives.

Caleb waited out the time through the punishment. That wasn't his to endure. Because he had not done anything to endure it, but he had to suffer along with the rest of the nation. He kept his heart young and his faith active. And now, at 85 years old, he told God.

what he wanted to do. Joshua 14:12, listen to these words.

Now therefore, he said, Give me this mountain, Hebron. Of which the Lord spoke in that day. For you heard in that day how the Anakim were there. And that the cities were great and fortified, it may be that the LORD will be with me, and I shall be able to drive them out, as the LORD said.

Now, remember, the tribes are being assigned to the different parts of the land. And each of them has to do a certain thing. Caleb comes up, he doesn't wait for his assignment, he volunteers. He comes before Joshua to request his portion of the land, and he asked for an area that was known as Hebron.

Now, let me explain to you why I think Caleb asked for that portion of land. You have to use a little bit of imagination with this, but hang with me. when he was marching through that land earlier with the spies. He saw Hebron and he maybe asked some questions, and it was pointed out to him that Hebron was a sacred place. In Canaan.

Do you know who was buried in Hebron? Sarah was buried there. And Abraham was buried there.

So were Isaac and Joseph and Rebekah. Hebron was the only sacred burial place in all of Canaan. And when Caleb found that out, it stuck in his heart. And when it got time for him to ask for the place he wanted to settle, He wanted to go to Hebron. And you know why that's interesting?

It's interesting because Caleb was not even a full-fledged Jew. Read again the record as we read it already, and you will discover that his father was a man by the name of Jephuna. And his father, Jephunah, was a Kenizzite. If you've read the Old Testament, you'll remember that the tribes that were driven out of the land of Canaan were the Hivites, the Jebusites, the Girgashites, and the Kenizzites. And somebody added the Termites, but they don't belong in there.

Listen to me, Caleb. Came from Jephuna, his father, and his father was a Kenizzite, and the Kenizzites were inhabitants of the land of Canaan, where they were going in to drive them out. And you say, well, how in the world did Caleb ever get hooked up with Israel? I don't know the answer to that question, but somehow when the Jews were in Egypt, or maybe right after they came out of Egypt, Caleb became a part of their community. And Caleb, this Kenazite.

Has now so fallen in love with the people of Israel that he asks. that he be allowed to settle the sacred burial place in Canaan. known as Hebron. The Bible also tells us, as we have read, that in Hebron, There were many who were called the Anakim. And I don't want to get into a lot of detail about that, but the Anakim were the sons of Anak, and I'm sure that helps you a lot.

The Bible tells us that they were giants. They were kind of superhuman individuals. bigger, stronger. More valiant. frightening to be exact.

And that's the reason why, when the spies went into the land and they saw the Anakim, they said, in comparison to them, we're just like grasshoppers. The Etachim apparently were Consolidated In Hebron.

So it's not amusing, but it is interesting that up to this point, nobody had volunteered for that mountain. It was still available when Caleb came. It was still on the list of to be developed. And Caleb walked up and he said, I want Hebron. And if God will help me, I'll go there.

and we'll take those giants out and we'll claim the land of God. You see? Here is this 85-year-old man. When he gets a chance to choose the place where he wants to serve, he settles for the hardest assignment there is. Isn't it interesting that nobody had taken that land, nobody had volunteered, but Caleb at the age of 85 says, I want that mountain as my inheritance, and I will go there and I will subdue the giants in the land of Hebron.

He did not use his gray hair to beg off from the heavy lifting. He asked for a worthy challenge because he had the wisdom to know that with powerful quest comes powerful reward. If you knock down a giant, You become one yourself. And at age 85, Caleb still had a vision for the future. When you begin to lose that vision, you're already starting the process of dying.

And there's so many people that allow that to happen, and all of us have to fight off the urge to let that happen as we get older. If you've already started that process, it's a little bit like a bit of poetry I read not long ago. It goes like this. since I have retired from life's competition. Each day is filled with complete repetition.

I get up every morning and dust off my wits. Go pick up the paper and read the old bits. If my name isn't there, I know I'm not dead, so I get a good breakfast and go back to bed. That's the way to. That's the way some people end up their lives.

Not so, Caleb. I'm grateful for Caleb. He spent his life trying to win and not trying not to lose. Because of that, he accomplished the greatest thing in his whole life when he was 85 years of age. And then thirdly, Calem was a man who was energized by his assignment.

When you go through the record of what happened in the settling of the land, it's interesting to note that none of the tribes who were assigned the land did what they were supposed to do. Remember what they were told to do? To go in and drive out the inhabitants. I've just chosen some selective report cards on these people and what they did. Here's what the scripture says in verse 13 of Joshua 13.

Nevertheless, the children of Israel did not drive out. The Gesherites or the Macathites, but the Gesharites and the Macathites dwell among the Israelites until this day. Joshua 15, as for the Jebusites, the inhabitants of Jerusalem, the children of Judah, could not drive them out. Joshua 16, 10. And they did not drive out the Canaanites who dwelt in Gizar.

But the Canaanites dwell among the Ephraimites to this day and have become forced laborers. After the glorious crossing of the Jordan River, the Israelites left unfinished business in their wake. They were obviously trying not to lose. If they had done what they were told to do and tried to win, they would have driven out the various tribes who were the enemies of God, and their future would have been peaceful and secure in the land. Instead, the Canaanites remained a thorn in Israel's collective side for all the years to come.

Then there was Caleb. Oh. He refused to let the losing mentality of his younger and stronger brothers affect him. He was a winner clear through the heart, even though he was the oldest of the tribe. Here's what Joshua tells us about Caleb in chapter 15 and verse 14.

Caleb drove out the three sons of Anak from there, Sheshai, Aheman, and Telmai, the children of Anak. No one finished business with Caleb. He took the hardest assignment. the scariest place to settle. And he went in and he didn't settle for anything but absolute victory.

He was a different sort of guy. And you can't help but ask yourself as you read this story, at least I do. What made him that way? Why was Caleb so different? Do you ever do that when you see people that succeed?

Everybody does this. You read a book about somebody who succeeds, not necessarily to read about their success, but to see if you can figure out why they succeeded. Maybe they will show you something that you can do that they're doing and you can learn. We learn from successful people, from people who do what they do well. I'll be frank, I read everything I can about preachers who are good preachers so I can learn how to be a better one.

And we want to learn about Caleb. Why was he so successful? And I want to tell you, we don't have to be in doubt. Here's an amazing statistic. Thirty verses.

about Caleb's life. And in those thirty verses are six expressions as to why he was. successful.

Now, again, we're back to this repetition thing. If God Wants us to know something, he'll say it once. If he really wants us to understand it, he'll say it twice. If he says it six times, You better take melt.

So I'm going to give you his secret. And it starts in chapter 14 of Numbers. But my servant Caleb, because he has a different spirit in him, we all know that. His spirit was different, wasn't he? He was different from all these other dudes.

He wasn't going to take settling for not losing. He wanted to win. He was going to do everything. He had a different spirit in him.

Now we're told what that spirit was. And he followed me forth. Fully. That's what the Lord said. In the 32nd chapter of Numbers, we read it again.

At the end of the verse, it says, And Joshua the son of Nun and Caleb the son of Jephunah, holy father. Followed The Lord. We read it again in Deuteronomy chapter 1. The Lord was angry and took an oath, saying, Surely not one of these men of this evil generation shall see the good land of which I swore to give your fathers, except for Caleb, the son of Jephunah. He shall see it, and to him and his children I am giving the land on which he walked, because.

He wholly followed The Lord. Joshua 14 verses 8 and 9. Here's Caleb saying, Nevertheless, my brethren who went up with me made the heart of the people melt, but I wholly followed the Lord my God.

So Moses swore on that day, saying, Surely the land where your foot has trodden shall be your inheritance and your children's forever, because you have wholly followed the Lord my God. In Joshua 14:14, Hebron therefore became the inheritance of Caleb, the son of Jephunah, the Kenizzite, to this day. Because Be holy. followed. the Lord God of Israel.

Now what do you think about all that? What was the secret? Man, if you don't get that, I'm quitting. He wholly Followed the Lord his God, not half-heartedly. Not almost, not trying not to lose.

He left nothing on the table. But he said, Lord God, whatever you want me to do, I'll do it. I'm in, all in, 100% in. I'm going to do this with everything I have. Holy follow the Lord my God.

Have you ever thought what might happen in your life? If you were able to say to the best of my ability, I wholly followed the Lord my God. Caleb's passion breaks through, so we can't miss it. He had a different spirit. He followed God with all of his heart.

By the time he was 85, while most of his generation had given up hope and died, Caleb still had a bright fire burning in his heart. He still wanted to leap on the greatest possible task that God could give him. and as we reflect on the principles of winning and losing. I'm going to tell you a Shadow Mountain story. And hopefully It will make the point.

that this message was intended to make. It was the early 90s. I had been the pastor of this church for about 10 years. Almost eight years of that had been struggling to try to build this building. For eight years we struggled.

We finally had the building up, and it was just a few months, and we were going to be moving in to our new worship center. We knew we were about to experience dramatic growth. And the fact is, in the first two years that we were in this worship center, we tripled in growth. One of the issues that we were discussing at that time had to do with how we gave our offerings to the Lord through our church. For many years prior to my coming to Shadow Mountain and for all of the years up to this point in our history, the people of the church had used what we called a two-line envelope.

One line gave them the opportunity to direct their gifts toward the general budget. and the other line was permissions giving. The pattern was usually like this. When someone came to the church, they would give all their money to the general budget for a while until they were educated about missions. Maybe we would have a missions conference or a mission speaker, and then little by little they would get energized about missions and they would begin to split up their offerings, some for the general and some for missions.

When we started to think about having three times at that time we thought maybe two times as many people What we knew was if we didn't do something different, missions was going to be left in the dust. We wouldn't be able to maintain what we were doing.

Now, we didn't have the mentality at that time that just leaving it the same was okay. Our concern as we anticipated the growth of the church was what would happen to the missions program. And so we began to have long discussions about that. in a meeting that I will never forget. We began talking about giving a percentage of our giving to missions.

Okay.

Someone suggested that if we gave 5% of our giving, we would not lose much in missions going forward. trying not to lose. Another suggested that if we ask our people to tithe to the church, maybe the church should tithe to missions. The room got very quiet. You mean take 10% of our offerings?

and give all of that to ministries outside our four walls? Up to this point in our discussion, we were all trying to figure out a way to keep from losing. Our mission's giving was what it was. We wanted to make sure that it stayed what it was, and we didn't want to lose what it was. And then I heard myself say something that I don't remember being motivated to say, it just popped out.

What do you think God would do for us if we gave 20% of our giving to missions going forward?

Now, this was a long time ago, and I don't remember everything that happened at that time, but I do remember how quiet it got. and how long it stayed quiet. And then a man by the name of Ralph Radford. spoke up. Ralph Radford's one of the great Patriarchs of Scott Memorial Baptist Church.

In Shadow Mountain Community Church, and I'm sorry that those of you who are new in this church never got to know him. He was the Chairman of the pulpit committee that brought me here. He was my friend. He was the man who came into me one day, and we were building this building, and we were only going to build the center part of it, like up to this. He said, Dr.

Jeremiah, you're making a huge mistake. You know, a lot of people have told me that, but not anyone like that who I respected so much. He said, We need to build the sides, or we're going to be in trouble. I said, Ralph, we don't have enough money. He says, Well, let's pray, let's ask God for it, let's tell the people about it, and we have two weeks.

In two weeks, we took another million dollars worth of pledges and we built this building. What would we have done if we hadn't? Ralph Radford was the voice in all of that. And I'll never forget when he said in that meeting. He said This is something that's God.

Size. Let's do this. And he encouraged us to take the challenge. He predicted that God would bless us if we did it.

Someone reminded us in that meeting that missions was the closest thing to the heart of God. In the Bible, and that God had sent His own Son into this world to be the very first missionary of all missionaries. Long story short. We made that decision and we've carried it out without interruption from that day until now. And now we have a chance to look back over our shoulders.

and see what's happened because of that. trying to win decision.

Some of you will remember up until that time. Every year we were struggling with our general budget. We couldn't make budget. We would try. We'd have to have meetings and make cuts.

I need to tell you something that's truly amazing. After we made this decision and we gave 20% of our income to missions, Every year since then, we have never had a year when the church gave less than it gave the year before. But we have always given more. in the current year than we gave the year before. It is a reminder to me that when we do things God's way, He always takes care of the other things that we might be prone to worry about.

This church has literally experienced the tithing experience twice over. We have learned as a congregation that when we put God first and we put missions first, God will always bless what we do in the other parts of ministry. I tell you the truth, men and women. You cannot out-give God. You cannot out-trust God.

When you put your faith in God, God will bless you. And without faith, it's impossible to please God. What are you doing that's easy for you to do? What are you doing that's in the comfort zone? I wrote down in my notes, please forgive me for mixing the metaphors again, but God doesn't want us to live in the comfort zone.

He wants us to be in the end zone. You know, that's a very important principle. Here's the final point in all of this. If God would do what he has done for us as a body of believers, It's only because he's already doing it for individuals who are part of that body. The church isn't Ubiquitous thing.

The church is made up of individual believers. There is no such thing as a church without the people.

So if the church is doing what we said it has done, then it's because the people are doing what they are supposed to do. And it's a reminder to me that God is willing to do for anyone who will follow Him and refuse to live by fear and not try not to lose, but to try to win. The way we are living our lives now is also a reminder to us that that's how the future will be written about us. Years earlier, we made this decision, and look what God has done. How many of you know decisions determine destiny?

That decision made among a few people in the church that many years ago, look what it accomplished. It seemed like a scary moment. It was a moment of faith, but God took it and showed us in this Looking back over your shoulder picture. How marvelous God is. As long as our church continues to believe that God honors faith.

He will continue to see his mighty hand working in our lives. Let's hold each other accountable. to live by faith. and not to lose by fear. God has a wonderful thing He wants to do in your life and in mine and in the life of this church.

And the only thing that will keep him from doing it is our unbelief. God had a great plan for the people of Israel. It was already there. He had already promised it to them. That would have, of course, included victory over their enemies.

It was there for them to take, but because of their unbelief, they never got it for four decades. I don't know about the rest of you, I want everything God has for me. I don't want it after it's too late to enjoy it. or too late to know it. I want to accept his word at face value, and most of all, like Caleb.

Holy. Follow the Lord, my God. Amen, amen. I hope you took good notes. This is one of the most motivating stories in the Bible for me personally.

to always make sure that you're Vision is greater than your memories. Keep looking forward and keep trusting God. And the Bible says, in many ways, you're never too old to do something great for Him. Caleb was in the end of his life and his waning years, but he did some great things, and he still had this great heart of vision to do something that never had been done before, and he did it. And he's a testimony to all of us.

Keep looking to the future, keep trusting God, keep doing great things for his name and for his glory. Hey, we have a magazine I'd like to tell you about briefly. I hope you have. Had a chance to receive it. If you're not getting it, You can receive it by simply asking for it and will be sent to your home when the next edition comes out.

You can have all the devotional content downloaded into your email box. Ask about that as well. We'll see you next time right here on this good station. Thanks for listening. Our message today originated from Shadow Mountain Community Church and Dr.

David Jeremiah, the senior pastor. Turning Point is also on radio and TV this weekend. To learn where to find it, visit our website davidjeremiah.org slash radio. That's davidjeremiah.org slash radio or call 800-947-1993. Ask for your copy of David's new book, What God Promises You, Seven Truths That Will Change the Way You Live.

It's yours for a gift of any amount. You can also purchase the Jeremiah Study Bible in the English Standard New International and New King James Versions, available in your choice of attractive and durable cover options. Tell us how this ministry helps you grow. Write to Turning Point, PO Box 3838, San Diego, California, 92163. This is David Michael Jeremiah.

Join us Monday as we begin the series Investing for Eternity on Turning Point with Dr. David Jeremiah.

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