New Wine, Old Wineskins, and the Giving Culture You Actually Have

After more than 30 years of working with churches on generosity, I’ve sat across the table from hundreds of senior pastors and executive pastors who share some version of the same frustration: “We preach biblical stewardship. We believe in generosity. But our giving culture just isn’t where it needs to be.”

I’ve heard every version of this. And almost every time, the problem isn’t what they think it is.

It isn’t the theology. It isn’t the congregation’s willingness. It almost certainly isn’t the staff’s commitment to the mission.

The problem is the wineskin.

Luke 5:36–39 is one of the most misapplied passages in leadership conversations. We typically read it as a lesson about change management — don’t mix old and new. But Jesus is making a far more specific point: the container determines what the content can do.

Old wineskins can’t expand. New wine ferments and expands. Pour new wine into an old wineskin and you don’t get a bad result — you get no result. The wineskin bursts. The wine is lost.

Here’s what the old wineskin looks like in most churches. See if any of this is familiar.

Giving discussed only when money is needed. Offering moments that are functional and forgettable. Communication centered on budgets and needs. Donors at every level treated the same. Little storytelling about life change. No pastoral discipleship around generosity.

The old wineskin — and it’s in more churches than leaders want to admit

Most of the time, the result is predictable: flat or declining giving, a small percentage of households carrying the financial weight of the whole church, ongoing anxiety around the budget, and leaders who dread talking about money because they know the response will be lukewarm at best.

But the problem usually isn’t the people. The problem is the wineskin.

The New Wine: Generosity as Discipleship

Here’s what I’ve seen in the healthiest, most generosity-driven churches I’ve worked with: they’ve stopped treating generosity as a fundraising activity and started treating it as a discipleship pathway.

This isn’t semantic. It’s structural.

Jesus talked about money more than almost any other topic — not because the early church had a budget to meet, but because He understood something we often miss: money is a discipleship issue before it is ever a financial one. What people do with their resources reveals what they actually believe. It exposes what they trust. It shows what they love.

When a church starts teaching generosity that way — as spiritual formation, as an act of worship, as participation in the mission of God, as a step of faith — something changes in the congregation. People don’t just give more. They give differently. With joy. With intentionality. With increasing capacity.

That kind of generosity cannot flourish inside a purely transactional structure. You can’t pour discipleship-level generosity into a fundraising-only system. The wineskin will burst.

Why Good Theology Isn’t Enough

This is the part of the conversation that leaders find most challenging, because it requires them to look at the system — not just the sermon series.

I see it constantly: a church invests in a beautifully crafted stewardship series. The pastor teaches with conviction. The theology is sound. The people are moved. And then the series ends, the plate gets passed the following Sunday with a one-sentence prayer, and nothing changes.

Why? Because the message said “generosity is a way of life” while the structure said “this is a transaction.”

You cannot sustain a new wine generosity culture with old wineskin practices. If the offering moment in your weekend service is purely functional, you’re communicating something, whether you intend to or not. If your only written communication to donors talks about need and budget, you’re communicating something. If your high-capacity givers receive the exact same content as first-time visitors, you’re communicating something.

And what you’re communicating is: generosity is a financial transaction, not a spiritual one.

WORTH NOTING

In 30 years of consulting, I have sat with pastors who have well-developed theologies of spiritual warfare, who preach it, teach it, take it seriously, and who have never once connected it to their congregation’s giving culture. They’ve never asked: what if the resistance to generosity in our church isn’t just behavioral? What if it’s structural? The wineskin itself can be an obstacle to what God wants to do.

What New Wineskins Actually Look Like

Churches that develop strong, sustained generosity cultures don’t just preach better, they build better structures. Here’s what I consistently see in churches where giving culture is genuinely healthy:

A clear theology of generosity. Not just a stewardship series — an ongoing, integrated biblical framework that helps your people understand what Scripture actually teaches about money, ownership, and the purpose of wealth. This becomes the foundation everything else is built on.

A pastor who leads with transparency. The most powerful generosity accelerator in any church is a senior leader who is willing to share their own journey — not a pledge amount, but a story. Generosity is caught more than it’s taught, and people are watching their pastor.

Compelling weekly offering moments. The two minutes surrounding your offering are among the highest-leverage minutes of your entire service. A brief, well-told story of life change, connected to mission, can reframe giving as participation rather than obligation. Every single week.

Personalized, giver-centric communication. Your high-capacity givers deserve more than a generic thank-you letter. Your first-time givers deserve a response that welcomes them into generosity as a spiritual journey. Treating all givers the same communicates that you see them as donors, not disciples.

Thoughtful giver segmentation. Different givers need different conversations. Some need theological formation. Some need a pastoral relationship. Some need a challenge to step up. A generosity culture that serves people well requires intentional thinking about who those people are and what they need.

None of this is complicated in concept. But it does require intentional restructuring — new wineskins that can actually hold the new wine.

The Leadership Challenge Nobody Warns You About

Jesus adds one more observation in Luke 5:39 that I think is the most honest verse in the passage: “No one after drinking old wine wants the new, for they say, ‘The old is good.’”

Resistance to generosity culture change rarely comes from people who don’t believe in generosity. It comes from people who are comfortable with the familiar.

You’ll hear it as:

“We don’t want to talk about money too much — our people don’t like it.”

“This is how we’ve always done the offering.”

“Our congregation is different. They won’t respond to that.”

Luke 5:39 — “No one after drinking old wine wants the new, for they say, ‘The old is good.’”

I’ve heard every version of this across hundreds of churches. And almost universally, it’s not true. What’s true is that leaders haven’t yet seen what their people look like when generosity is framed as discipleship rather than obligation.

Once a church experiences genuine new wine generosity culture — once they see their people give with joy, grow in faith, and fund the mission with abundance — they never want to go back.

The challenge isn’t convincing the congregation. The challenge is convincing the leadership to let go of the old wineskin.

One Question That Diagnoses Everything

If you want to do a quick assessment of your church’s giving culture, here’s the question I always ask: What happens in the two minutes when you receive the offering?

That moment is a diagnostic. It reveals your theology, your leadership clarity, and your cultural assumptions about money. It tells you whether your people are being invited into an act of worship — or asked to fulfill a financial obligation.

If those two minutes are purely transactional, the rest of your generosity culture probably is too — regardless of what you preach.

The good news is that the wineskin can change. The structure can be rebuilt. And when it is — when the systems and practices align with a discipleship-based theology of generosity — the results are consistently remarkable.

Not because people suddenly became more generous. Because the structure finally gave them room to be.

At Generis, we’ve spent more than three decades helping churches do exactly that. Because what looks like a giving problem is almost always a discipleship problem. And what looks like a discipleship problem is, more often than leaders recognize, a structural problem.

The question is simply whether you’re willing to change the wineskin.

About the Author

Jim Sheppard is the Chairman and Principal of Generis, and with more than 30 years of experience guiding leaders and congregations, he is a trusted voice in stewardship, generosity, and organizational health.

This blog post originally appeared on Church Leader Insider. For more information or to subscribe to Church Leader Insider, click HERE.