Which tree have you been climbing, and roughly how high up are you?

Tom Brady was twenty-seven years old with three Super Bowl rings, married to the number one supermodel in the world, and on camera he asked why he had all of it and still thought there was something greater out there. It has to be more than this, he said. I have done it. I am twenty-seven. What else is there? Then: I wish I knew. That is Zacchaeus in this passage, at the top of the top. Jericho was a city of enormous affluence and influence. He was not simply wealthy, he was chief tax collector — he had climbed as high as the ladder went. And then a grown man runs. In that culture, dignified men did not run, and they certainly did not climb trees. He does both, in public, in front of the people who hate him, because he is that desperate. Maybe your tree is not a sycamore. Maybe it is s

When did you last let him call you down, instead of climbing higher to be seen?

Here is the irony of the whole story, and it is easy to read straight past. Zacchaeus thinks he is the one searching. He runs, he climbs, he positions himself. And Jesus walks up to the tree already knowing exactly where he is, and already knowing his name. Zacchaeus, hurry and come down, for I must stay at your house today. In our culture that lands as presumptuous. Let me check my calendar. In the Middle East it is an honor — you tell people to come over any time and you mean it, and when someone says they are coming, you get the food ready. Remember who is in that tree. A man with no friends. The people below him had all been overcharged by him, by design, and they hated him for it. He is lonely at the top of everything he built. And Jesus offers the outsider a place inside, before

Who do you know who looks like an insider and is starving?

They all grumbled. He has gone in to be the guest of a man who is a sinner. And here is the uncomfortable part: the crowd was not wrong about the facts. Zacchaeus really had overcharged them. He really had bought the franchise knowing his people would hate him and his family would be embarrassed by him, and he did it anyway because he saw opportunity. The crowd had the facts right and the heart wrong, which is a combination available to religious people in every century. James serves as the chaplain for the Miami Marlins, so he is around people who look like insiders from the outside. After a game one night, in the locker room, a player said: Chap, there's got to be something more. Best season of my life. More fans than ever. All these people know my name and follow me. But I don't think

Is there anyone you owe — not legally, but truly? What is your fourfold?

Watch what Zacchaeus does the moment his feet hit the ground. Half of everything to the poor. And anyone he defrauded — which is essentially everyone standing there watching — paid back fourfold. Nobody asked him for it. There is no demand anywhere in the passage. And the law of the day required twenty percent restitution, so he could have satisfied every legal obligation he had and kept the rest with a clear conscience. He did not ask what the standard was. That is what tells you something actually happened to him. He had just been handed extravagant grace, and extravagant grace was the only currency he had left to spend. You cannot receive that and then go looking for the minimum. There is an old hymn called Just As I Am. A lot of people come to Christ just as they are — and then lea

Who is up a tree near you — and will you use their name?

The Son of Man came to seek and to save the lost. One sentence, and it settles who has been doing the searching this whole time. Zacchaeus ran and climbed and craned his neck, and none of that is why the story ends the way it does. Jesus came looking. The tree was never the point. And notice the direction it moves. He takes outsiders and brings them in. Then he takes insiders and sends them back out to the outsiders. That is what a faith family on mission means, and it is why a church that only gathers has stopped halfway through the sentence. He does not save you so you can hold eternal fire insurance. He saves you and hands you something to live for — his kingdom, not yours. So there is something more, and it is not a thing. Not a title. Not a follower count. Not a number in an accou

Read Luke 19:1-10. James pointed out the irony: Zacchaeus thinks he is the one searching, but Jesus already knows where he is and already knows his name. Look at verse 10 — who is doing the seeking in this story, and how does that reframe the whole scene?

Finding True Meaning: What Zacchaeus Teaches Us About Life's Purpose

James explained that a chief tax collector bought the franchise from Rome and kept everything he could squeeze above what Rome required — so every person in that crowd had been overcharged by him. Read the crowd's reaction in verse 7. How far outside was this man, and what did it cost him to climb that tree in public?

Finding True Meaning: What Zacchaeus Teaches Us About Life's Purpose

James named three trees people climb: success, relationships, and reputation. He said Zacchaeus reached the very top of his and still knew something was missing. Which tree have you been climbing, and roughly how high up are you?

Finding True Meaning: What Zacchaeus Teaches Us About Life's Purpose

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Inside Out

When Success Isn't Enough · Group Guide

Luke 19

James Drake Sunday, September 7, 2025

Icebreaker

Think of something you worked hard for and actually got. How long did the good feeling last before you started looking at the next thing?

Discussion Questions

1
Read Luke 19:1-10. James pointed out the irony: Zacchaeus thinks he is the one searching, but Jesus already knows where he is and already knows his name. Look at verse 10 — who is doing the seeking in this story, and how does that reframe the whole scene?
2
James explained that a chief tax collector bought the franchise from Rome and kept everything he could squeeze above what Rome required — so every person in that crowd had been overcharged by him. Read the crowd's reaction in verse 7. How far outside was this man, and what did it cost him to climb that tree in public?
3
James named three trees people climb: success, relationships, and reputation. He said Zacchaeus reached the very top of his and still knew something was missing. Which tree have you been climbing, and roughly how high up are you?
4
The law of the day required paying back what you took plus twenty percent. Nobody asked Zacchaeus for anything, and he offered fourfold and half his estate on top of it. What does that number tell you about what had just happened inside him?
5
A Marlins player told James after the best season of his career that thousands of people knew his name, but if he took the jersey off he did not think any of them would care. Where does your own sense of worth get quietly tied to what you produce?
6
James said Jesus makes outsiders into insiders and then sends insiders back out — and that the overwhelming majority of people who come to faith do so through one person who actually cared about them. Who is the outsider in your life right now? Name one specific thing you will do for them before we meet again.

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When Success Isn't Enough · Group Guide

Luke 19

Discussion Questions

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