The Gentle Work of Jesus

What Zacchaeus teaches us about repentance and the grace that transforms.

We often think of repentance as heavy, guilt-ridden, or even harsh. But what if true repentance feels more like opening the door to someone who brings healing, not harm? That’s what we see in the story of Zacchaeus—and it might just change how we view God’s work in our lives.

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We’ve Sanitized the Story

In both our childhood Sunday schools and our adult imaginations, we have a tendency to sanitize Scripture—scrubbing away its harder, messier, and more complicated truths. It makes sense when we’re talking to kids. They don’t need the full weight of David’s darkest chapters or the brutal honesty of certain psalms. But as adults, this sanitization becomes dangerous. We begin to form a curated version of faith—tidy, tame, and disconnected from the raw realities of our lives.

Take Zacchaeus, for example. We often reduce his story to a silly children’s song: “Zacchaeus was a wee little man…” But when we really sit with his story, we discover something far richer and more disruptive—a story that challenges how we think about Jesus, repentance, and transformation.

Zacchaeus Was the Worst

Luke’s Gospel tells us three things right away: Zacchaeus was rich, he was short, and he was a chief tax collector. That last detail is where things get especially problematic. First-century tax collectors were seen as moral outcasts. They weren’t just disliked—they were despised.

Imagine this: A foreign empire invades your country, strips away your freedoms, and imposes oppressive taxes. Now imagine one of your own neighbors signs up to enforce those taxes—then gets rich doing it. That’s Zacchaeus. It wasn’t just that he worked for Rome; he made his wealth by overcharging his own people and setting up a pyramid scheme of exploitation beneath him.

It’s hard to overstate how much this guy would have been hated. No one in the crowd that day would have looked at Zacchaeus and thought, “You know who deserves a second chance? That guy.” If anything, they were probably hoping he’d fall out of the sycamore tree he climbed to see Jesus.

And yet… Jesus stops, looks up, and calls him by name.

Jesus Always Sees the Outcast

Zacchaeus climbs the tree just to get a glimpse of Jesus. But Jesus sees more than a man in a tree. He sees a heart ready to be transformed. So He does the unthinkable—He invites Himself over to stay the night.

This wasn’t just a casual social call. In that culture, to share a meal was to extend relational acceptance. And the crowd could hardly believe it. “He’s gone to stay with a sinful man?” they grumbled.

It’s tempting to read this story and relate to Jesus—the one who sees the outcast and extends grace. But the truth is, most of us would have been in the crowd, confused and annoyed that grace would go to someone so clearly undeserving.

A Joyful, Repentant Heart

While the crowd murmured, Zacchaeus moved. “He quickly came down and welcomed Him joyfully.” That single sentence shows us so much. Zacchaeus didn’t wallow in shame. He didn’t delay. He received the grace offered to him without resistance. And in doing so, his heart was changed.

Though we don’t get the full dinner conversation, we see its fruit. Zacchaeus stands up and declares:

“Look, I’ll give half of my possessions to the poor, and if I have extorted anything from anyone, I’ll pay back four times as much.” (Luke 19:8, CSB)

This wasn’t performative guilt. It was genuine repentance—honest, costly, and transformative. It’s one of the clearest pictures in Scripture of what repentance looks like in action.

Welcoming Jesus’ Work

If repentance is at the heart of Zacchaeus’ story, and at the heart of Lent, then we need to understand what true repentance looks like in our own lives. Here are five invitations we see in Zacchaeus’ story:

1. Acknowledge Where You’ve Gone Wrong

Zacchaeus begins with honesty. He doesn’t defend his behavior or make excuses. He owns it. That’s where transformation always begins. Is there an area in your life where you’ve gone wrong and need to tell the truth—first to yourself, and then to God?

2. Bring Your Confession to God and Others

Confession isn’t about punishment—it’s about healing. We confess to God for forgiveness and to others for restoration. (James 5:16) Is there someone you need to confess to today?

3. Take Action to Restore What’s Broken

Repentance isn’t only internal. Zacchaeus’ heart change led to tangible restitution. He made things right. Who might you need to make amends with? What steps can you take toward restoration?

4. Grow Through the Lessons of Your Choices

While Scripture doesn’t track the rest of Zacchaeus’ life, some church tradition suggests he went on to become a leader in the early church. He didn’t stay stuck in shame. He let his past shape a wiser, more faithful future. What lessons is God trying to teach you through your past?

5. Receive the Grace God Freely Gives

Zacchaeus didn’t earn Jesus’ presence—he received it. His transformation wasn’t payment for grace; it was the result of it. Are you willing to let go of guilt and simply receive the grace Jesus offers?

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Let Grace Lead

There’s no part of Zacchaeus’ story that suggests he deserved anything but judgment. And yet, Jesus sought him out, called him by name, and extended an invitation that changed everything.

Maybe you’re feeling unworthy today. Maybe you’re weighed down by past choices or struggling to believe that change is even possible. If so, let Zacchaeus’ story speak to you:

Repentance isn’t about earning God’s love—it’s about welcoming Jesus’ gentle work of transformation.

Jesus doesn’t come to condemn you. He comes to call you by name, invite Himself into your life, and lead you into freedom.

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Before You Go…

Take a moment of stillness today. Ask:

“Where might I be resisting the gentle work of Jesus in my life?”

Then—like Zacchaeus—open the door.

Let Him in. Let Him lead. Let grace do what it does best.

Thanks for reading,

Ryan

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