Why Money Conversations Still Feel Awkward in Church
Why do conversations about money still feel difficult in so many churches?
In this episode of the Next Sunday podcast, Jim Shepard and Frank reflect on what has—and hasn’t—changed across more than three decades of church generosity work. The tools look different, but familiar pastoral questions remain.
Together, they explore the discomfort surrounding money conversations, the importance of a pastor’s personal conviction, and the relationship between generosity and discipleship. They also consider how culture and consumerism shape the messages people hear about money throughout the week.
For pastors shaping vision and leading its implementation, the conversation offers a reason to revisit how the church teaches, communicates, and equips its people.
Listen, then bring one observation into a conversation with your team.
Key Takeaways
Generosity is a discipleship conversation. Jim connects biblical teaching about money to the condition of the heart, giving pastors a deeper purpose for addressing the subject. He explains: “It's about who or what owns your heart.”
The pastor’s personal conviction matters in a giving initiative. Jim describes the difference between participating out of compliance and leading from a changed heart. That conviction becomes visible in how pastors guide others: “Because once the pastor's heart has changed, then you can't help but try to help everybody else change.”
Culture is already shaping how people think about money. The conversation challenges churches to consider how consistently they equip people alongside the messages of consumerism. Jim emphasizes the responsibility to engage: “It's not an optional conversation, Frank. It's a necessary conversation”
Jim: Hi, friends. Jim Shepard here with the one and only, the amazing Frank.
Frank: Thanks, Jim. It’s good to see you, sir.
Jim: I was going to continue.
Frank: You ran out of words to say because you were like, “I don’t even know if those are true. I’m going to stop.”
Jim: Father to Isaac, Leila—
Frank: Yep.
Jim: Zeke—
Frank: Yep.
Jim: Mali—
Frank: Yep.
Jim: James—
Frank: Yep.
Jim: Micah.
Frank: You remembered them all.
Jim: I called the roll. Six. Not in order.
Frank: Kind of a random order. I’ll say this: a lot of times, I’ve called them the wrong name. That happens all the time. “James, Isaac—no, Zeke.” I just get all fussy.
Jim: Call the roll.
Frank: Call the roll. I’m going to get it right at some point.
Well, it’s always good to be back here with you guys in the Next Sunday podcast room, talking about things that we hope are helpful to you.
We do believe that what happens next Sunday could literally change everything. But we want to give you things that are transferable, that are workable, that are not just hypothetical, but things that we’ve actually seen work.
Jim: And today, we’re going to reflect back a little bit. Frank wants me to go back to the ’90s.
Frank: Take me back to the ’90s.
Jim: Let’s say, even better yet, the early ’90s.
Frank: Oh, the early ’90s. Jim, you’ve been doing this work for a long time.
Jim: By the time you watch this episode, it will have been 34 years. My 34th anniversary is in the next two weeks as we’re sitting here today.
Frank: Thirty-four years.
Jim: And I never dreamed that I would still be doing this 34 years later.
I came out of the corporate world. I was senior vice president and CFO of a big division of a publicly held company. The company got bought out, and then they moved my job, and I was out of a job.
I spent the summer of 1992 trying to figure out what I was going to do next. Landed here, consultant number five, if I remember correctly. And here I am all these years later.
I thought that I might do this for a couple of years and then go back into the public sector. Never happened.
Frank: Never happened.
Jim: And here I am.
Frank: I’m glad you didn’t go back. Fun fact: it was a little different back then than it is now.
Jim: A little different.
Frank: Fall of 1992, the hit song on the radio was Boyz II Men, “End of the Road.”
Jim: I remember.
Frank: And this is not a hint that we are at the end of the road, because Jim’s not going anywhere. But it’s been a minute since 1992.
Jim: Fall of ’92. Do you remember?
Frank: Let’s see here. I actually was pulling this up. Fall of ’92.
Jim: Sometimes it all gets a little blurry.
Frank: A lot of rappers. Eric Clapton did “Tears in Heaven.”
Jim: I remember “Tears in Heaven.”
Frank: Red Hot Chili Peppers was “Under the Bridge.”
Jim: Yeah, they were just kind of getting their groove on.
Frank: Billy Ray Cyrus had “Achy Breaky Heart.”
Jim: It wouldn’t be the same without “Achy Breaky Heart,” would it?
Frank: Guns N’ Roses.
Jim: For [unclear reference to “Achy Breaky Heart”], just tune in. Watch just three or four chords. You’ll have seen enough. You won’t go further.
Frank: You got it. You’ve got Nirvana with “Smells Like Teen Spirit” came out that year.
Jim: Yeah, grunge.
Frank: There was a lot going on back then. There’s a few that I’m just not going to reference on this podcast. They just don’t fit here. It’s fine.
Moving on. Jim, the question is—it’s kind of like being on the hot seat—what are just a few of the things that haven’t changed in 30-plus years of you doing this work? What’s been true?
Technology has changed. We were talking earlier about how you used to travel around with binders, with all this paper. How many pages a year did Generis print at our peak, when we were printing binders and we had scaled the business and had some momentum?
Jim: Frank, are you ready for this?
Frank: I’m ready.
Jim: Two million pages a year.
Frank: How do we know that?
Jim: Because back then they had a clicker, and you paid for supplies, but then you paid per click as well. So we knew how many clicks we were doing through our machine.
We paid a lot of money back then. We slayed a lot of trees. I’m glad we don’t have to do that anymore. Now it’s just a quick email.
Frank: So that was then. But over these 30 years—about to be 34 years—what hasn’t changed?
Jim: One thing that hasn’t changed is it’s still, for many churches, the most challenging, awkward, weird conversation. You know what I’m talking about.
Frank: Yeah, totally.
Jim: Frank, you’ve heard me say this before in front of groups. Why is it that in culture today, to my knowledge, there’s only one place where the conversation about money is weird and/or awkward, and it’s the church?
And it feels to me like it’s the one place where it shouldn’t be weird or awkward.
I think it’s because we just think it’s a money conversation. It’s not a money conversation. Never has been, never will be.
We said it at the end of the last episode: when the Bible talks about money, it’s never talking about money.
Now, come on. There’s a few commercial transactions in there where somebody’s buying something. I’m not talking about that.
I’m talking about when the Bible talks about the parable of the talents. That is literally a currency measure: 6,000 denarii, 20 years’ wages. And he’s telling a story about stewardship.
When we see the story of the rich young ruler, it’s not really about the money. It’s about how much heart his money owns. Because his money owns his heart.
And the same thing is true about Zacchaeus: how much it owned his heart, and then how little it owned his heart all of a sudden.
Frank: Incredible.
Jim: When the Bible talks about money, it’s never about money. Never. Never. It’s about who or what owns your heart.
That was true then, and it’s true now. And I think that has something to do with why people make it such an awkward and weird conversation, because they won’t acknowledge the reality: it’s a discipleship conversation.
And if it’s a discipleship conversation, then it’s not optional. It’s necessary.
Unfortunately, Frank, I feel like we really haven’t made as much progress as we would like to have made on that.
At Generis, we don’t talk about this a lot, but our mission is to accelerate generosity toward God-inspired vision. Our vision is to change the conversation about faith and money, starting in the American church, which includes the conversation about giving to nonprofits. It’s all part of one conversation.
And while I feel like we’ve changed some churches, I feel like there’s a lot of work left to be done. It’s because some of that just hasn’t changed in 30 years.
I think number two is the realization that if you don’t have the pastor’s voice in a giving initiative, and have it tuned and refined and messaged correctly, it’s going to be hard.
And that means it really has to resonate in the pastor’s heart.
I had a conversation just earlier today with someone about a church client where the board’s sense is that the pastor is doing this as a matter of compliance, not as a matter of heart.
Frank: Wow.
Jim: And it’s a Generosity 360 [unclear term]. We’re trying to change the culture.
When we hear things like that, then we’re like, “Okay, is this a compliance issue, or is this a true ‘my heart is changed’ conversation?”
Because once the pastor’s heart has changed, then you can’t help but try to help everybody else change. And it becomes evident in the leadership.
I’ve seen that over and over again. When I have had pastors who really lean in on the conversation, I don’t really worry about the initiative going well or not. I feel like we’ve got it.
And that hasn’t changed in the last 30 years. I may have realized it a little bit back then, but every time I see it again and again and again, I realize, “Yeah, it’s still a thing, man. It’s still a real issue.”
The idea that a lot of people can walk into a church and think that giving is optional—I don’t think that’s changed over 30 years, Frank. I think in some ways it’s gotten a little bit worse.
We talk about that sometimes when we talk about the way tax law shifts motivations. It’s not that tax law is the end, but for people who are undeveloped spiritually, the tax deduction seems to matter.
And now tax deductibility has shifted. You get this big standard deduction. And you know what? Only 9% of the American population is now receiving a standard deduction. [Statistic and deduction terminology need verification.]
So tax motivations have shifted giving habits, and you can see it in the giving data that you and I look at all the time. A lot more people showing up in that under-a-thousand category than we might have seen even 34 years ago.
Frank: So the audience knows, I told him we were going to talk about this topic a few minutes before we recorded. So you’re hearing him processing fresh, just real information here. I knew it would be low-hanging fruit for you.
I will say this: you just shared three things that could also almost feel like one thing, because we’re talking about the people, their heart, their preparedness, the pastor’s heart, how the church talks about money.
The people are going to have a weird relationship with money if the pastor is not teaching on it or comfortable with it himself or herself.
And the same is true if we’re not going to talk about it in a normal, healthy way in the church.
The feeling that I have is that, for whatever reason, over the last 30-plus years, there’s this reality that we have tried to abdicate, as the church, to someone else to disciple our people when it comes to generosity.
And there is no one else other than culture and consumerism that seems to be doing it. And they’re very good at it and unapologetic about it.
And yet, because we get a little squeamish, we’re a little unclear, we’re cautious, we don’t want to talk about it too much, we don’t want to talk about it too little—we get in our head and our feelings about it.
It feels like, in many ways, those three things you just shared intertwine together.
Jim: When you were saying this, Frank, just a second ago, I was thinking, “Gosh, this is the parable of the shrewd manager, isn’t it?”
What he was saying is the people of the world are better at talking about this than you are.
I think I’ve confessed it: for several years after I became a Christ follower, I was like, “Jesus, you’re commending a lying man.”
Well, that’s not the point. The point is not about his deceit. The point is about his shrewdness in taking on his responsibility.
The culture and the world are really, really good at talking about money. And if we don’t counteract that, then we’re losing the battle.
Again, you know this because I talk about it so much: it really comes down to a choice between two altars.
And Jesus made that very, very clear in two distinctly different places: in the parable of the dishonest manager and in Matthew 6:24. Completely different stories. One in Luke, one in Matthew.
You cannot serve two masters, right? You’re going to hate the one and love the other. You’re going to love the one and hate the other. You cannot worship—serve—both God and Mammon.
So we’ve got the altar of the one true God, and we’ve got the altar of Mammon.
And as long as the altar of Mammon is really good at speaking into the altar of Mammon, even in just the benign cultural sense of Mammon—not to speak of even the darker world of Mammon—we have to speak against that.
Otherwise, people are being discipled 24/7, 365 over here, and almost none over here.
And we look at our giving numbers like, “Why are we not—?”
Well, I don’t know, Pastor. If it’s a discipleship issue, and they’ve been discipled over here regularly and not so much in the church, why would you think there would be a reason for us to win this battle?
It’s not an optional conversation, Frank. It’s a necessary conversation. And that hasn’t changed since 1992.
Frank: Has not changed.
Jim: Because the whole idea is that money is an idol. It is over here at this other altar.
And anytime there are two altars competing for your affection—this is going to scare some people maybe a little bit—there’s only one two-word phrase that you can use for that. And most people don’t think about that in terms of their giving.
And that is spiritual warfare.
You are engaged in spiritual warfare with your money. You’re trying to tell it, “I’m not going to worship at that altar. I’m going to worship at the altar of the one true God.”
And that is a discipleship issue. Nothing more, nothing less. So that you can do battle with the other altar and [unclear wording].
Again, I don’t think that’s changed in 34 years. We’re still battling that other altar.
Frank: Wow.
Jim: And I think it’s why Jesus told us the story. He knew we’d be battling that.
Frank: Jim, that’s so good.
You know what has changed, though? We’re not making two million pages a year.
I know you’ve got your study Bible here. That’s not a consulting manual right there. That is our source of consulting.
Jim: This is our source document, but it’s not our consulting manual.
Frank: So true. Jim, we have the smallest little printer in this office now. It’s a little guy.
Jim: When I needed reams of paper, I went looking the other day. Couldn’t find a ream. Couldn’t find any paper.
Frank: Funny story: we had the opportunity to update our lease here at the Generis office, and I walked into this room that I’ve been in many times before. There’s a little copier. There’s all these shelves.
And I said, “Guys, why do we have such a big closet?”
They’re like, “Well, it used to be our print factory, basically. We just had to have all these massive printers and operations.”
But we didn’t need all that anymore. So now we’re down to a little guy.
Jim: Little guy.
Frank: I don’t even know if it counts the number of pages anymore.
Jim: I think we just own it.
Frank: I know.
Jim: Frank, literally, nobody can see this here, but the printer that we had that we put the two million through—it had all these big sorter bins. It was probably from here to the end of this.
Frank: It was the size of our podcasting studio and then some.
Jim: That is correct. And now it doesn’t even cover up a quarter of this table.
Frank: You could miss it if you weren’t looking for it. You might look right past it: “What is it?”
So that has changed. Jim, I appreciate the insights on what hasn’t changed and where there’s still a real need.
I guess I will say this: of the things that haven’t changed, if they had changed in a significant way, if this wasn’t a battle that we were still fighting in America and among the church—the needs that would be met, the problems that would be solved.
I think Jesus, in all his wisdom, taught on money so many times because he knew this was going to be an ongoing battle.
So we’ve got to do our part and be faithful in trying to steward well and help serve where we can.
We hope conversations like this spark you into having conversations with your team around how we are fighting this battle and equipping our church members and leaders to navigate these really difficult waters.
Guys, it’s been another episode of the Next Sunday podcast. Jim Shepard, thank you for sharing all those years of memories and wisdom.
And if they’ll let us, we’ll end this show by playing “End of the Road.”
Jim: Let’s go.
Frank: Let’s go.
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