What are the questions we should be asking about money?

Show me the money. Go ahead, say it out loud. Feels good, doesn't it? Now ask yourself why you hesitated.

That hesitation is exactly where this episode starts.

Dr. Patti Fletcher, Lynne Cuppernull, and Dan Ward go well past the balance sheet on this one. Because it turns out when you pull the thread on money, you don't end up talking about money for very long. You end up talking about fear, safety, power, and value. The working-class kid whose mother paid CCD tuition in installments while the teacher announced it to the whole first-grade class. The Armenian genocide and everything it stripped away, not just wealth but everything, passed down generation to generation in ways most of us never stop to examine. The women working three shifts, two of them unpaid, and getting brunch on Mother's Day once a year as compensation.

The questions get uncomfortable fast: Why is it easier for women to ask for money on someone else's behalf than for themselves? Who gets called ambitious for wanting more, and who gets called greedy for the exact same ask? Does money buy happiness, or is it just a proxy for the things we are actually afraid to name? And when the richest man in the world says money can't buy happiness, what exactly is he asking you to believe?

Also: Maud weighs in. Humans invented money. So why does it feel like money has power over humans rather than the other way around?

That one will stay with you.

Listening for the Questions is available wherever you get your podcasts. Subscribe, leave a review, and bring a question.

RESOURCES MENTIONED IN THIS POD EPISODE:

High Income Improves Evaluation of Life But Not Emotional Well-being, Daniel Kahneman & Angus Deaton, 2010

https://www.forbes.com/sites/johnjennings/2024/02/12/money-buys-happiness-after-all/

AI Boom is driving the economy, NYT Nov 2025

Billie Eilish asking “why are you a billionaire?” https://youtube.com/shorts/BB_buANeTS4?si=tlSfGneqKBJn3M6d

Listening for the Questions is where curiosity is our compass.

Transcript

Patti 0:14

Hello and welcome back to Listening for the Questions. I'm Dr. Patty Fletcher. I'm a recovering C-suite executive from Big Tech, a leadership futurist working at the intersection of people, business, technology, and data, a best-selling author, and the granddaughter of genocide survivors. Today's episode is a topic that touches on all of that: the tech, the people, the books, and the emotions we hold inherent and pass down to the next generation.

Dan 0:43

Hey everybody, my name is Dan Ward. I'm an engineer and a military technologist. I'm also an author, a juggler, and a punk. And I spent most of my professional career in the military and working at a nonprofit. And yes, even in those spaces, we spent a lot of time talking about today's topic.

Lynne 0:58

And I'm Lane Cuppernall. I'm a leadership coach and a healthcare consultant. I'm also a triathlete. And as a triathlete, I know how to do hard things. And that includes talking about today's topic. Like Dan, I've spent most of my professional career in nonprofit organizations. But that doesn't mean we didn't talk about what we're going to talk about today, which drumroll, that was a big buildup, is money. And specifically, what are the questions we should ask when we talk about money?

Dan 1:29

Sometimes we start these podcasts by defining our terms, like what is the difference between loneliness and being alone? Or what even is misinformation? And I don't think we need to do that today, right? Because everybody knows what money is, probably. So the first question I want to ask is: why do so many people find it so hard to talk about money? What is it about money that makes it such a fraught topic to ask questions about?

Patti 1:55

Let me be a little selfish here and go back to Jerry Maguire and shout it, shout it from the rooftops. Show me the money, people. So look, I always want to know how do I get more money? And what I'm really bad at and have been asking since, you know, I really thought about money is how do I stop going from being someone who thinks about only earning money to being someone who thinks about how that money can grow, whether I'm in the room or not?

Lynne 2:25

Ooh, Patty, I love that question. I was about to take a diversion down that road. But I actually want to connect the dots between the questions that Dan asked and the questions you just asked, which is, you know, why is it hard for some people to admit they're interested in having more money? Why do some of us get so squeamish about it and feel hesitant to say things like, show me the money?

Dan 2:51

I love that we're leaning into the Jerry Maguire thing. So squeamishness about money is a real thing. And it gets me thinking about how I prepared for today's episode. I literally went back onto YouTube and I re-watched the show me the money scene from Jerry Maguire like three or four times. And on probably the fourth time watching it, I noticed something I had overlooked the first couple times. So for those who haven't seen the movie, Cuba Gooding Jr.'s character is on the phone with Jerry Maguire, played by Tom Cruise, and he says, This is a family motto, and then the famous line, show me the money. And then, then it gets interesting because here's what I didn't notice before. He asks Jerry a great question. He says, Show me the money. And then he says, Doesn't it make you feel good just to say that? And I mean, wow, talk about a question we should ask when we talk about money. Doesn't it feel good just to say that?

Patti 3:42

Oh, Dan. Okay, I'm gonna steal your thunder and I'm gonna bring up a topic you usually bring up, which is gender, right? So I have to admit that you're helping me see that scene in a such a different lens that I'm embarrassed I didn't see it before. Because how does it feel from a gender perspective? It feels squeamish. Let's bring that word back in, right? It's really, and you know, you folks who are listening cannot see Lynn nodding her head, right? We're both bobbleheading here because we as women, aren't we conditioned, right? And then I get asked to do things for free all the time, to go on stages, to, to take my own time, to share my 25 years of earned, like, you know, school of hard knock sharings for free. And I have just started to go, I'll do one of those a quarter, but you gotta show me the money. And I have to tell you, as long as I've been in business and it's a lot easier for me to get money for someone or something else, it's really hard for me to do it myself. And I'm sitting here listening to you, Dan, and listening, remembering that interaction, and go, why is that so hard for me?

Lynne 4:57

Yeah, Patty, I'm right there with you. So much so that I rewrote show me the money to be something else. I was like, how about we say make it rain? And then I thought, no one knows what that means. Like, what? Where's the money in make it rain? That just sounds like I'm gonna need an umbrella. So it's a really good question. Why is women, at least you and me, right? N of two, feel squeamish about saying show me the money, about saying it out loud. And you know what? When they say it out loud, show me the money, it does feel good. So, what would happen if women started saying, show me the money more often? What if we didn't give something away for free, even once a quarter?

Dan 5:48

Yeah, I think and in that movie, it was even in the context of two men talking to each other, it was still sort of a countercultural moment where he said, show me the money and was was open about it, was explicit and clear about it. Uh, but I do agree that that the sentiment matters more than the specific words. If make it rain, which I think is from a different movie, uh, or some other phrase works better, great. I I think this concept of being willing to express the interest uh in getting paid for the work that we do, I think is an important one. But it makes me think about the concept of uh unpaid labor and the concept of seeing money versus not seeing the money for the work that we do. So I'm including like raising a family and everything that goes in that unpaid labor category, all kind of the important work that creates value but doesn't lead to an invoice that results in a paycheck. So, why do we tend to treat that work as less important just because it doesn't include showing anybody any money, right? So, how can we learn to see it differently, maybe, is the question here. Both the unpaid work we do, the unpaid work that other people do, and is there a way that we could honor that work even if it never earns a penny?

Lynne 7:02

Yes. I mean, I'm just yes. I guess I'm stuck with wanting to try and answer that question, Dan, even though I know that's not the point of this podcast. How might we? How might we like truly honor that unpaid work? And and I think probably the one that comes to mind the most is women, well, people, often it's women, people who stay home with children. Um, and that is an unpaid labor job. And actually, even if you go and make money during the day, then you're home working your second shift or your third shift, not getting paid. Uh, and you know, going to brunch on Mother's Day once a year does not count as showing me the money. So I think it's a really good question and one that, you know, we're not going to answer, but would love to have more people think about.

Patti 7:54

Yeah, I agree. I think, you know, when I think about that, and I know we need to move on for topics, but it's so important is does money and being paid money equate to value? And when we go to, you know, like in my world, it's premium pricing, right? You know, and and there if you are paying a premium, it's because that thing is perceived to have more value to the person like who is receiving it. And so when I think about that, Lynn, right, when I think about the three shifts that women work, right? The maintenance of the household, you know, their day, their day job, and then that they are constantly having to do more, learn more, right? To just be in the room. And yet we are continuing to be underpaid, which brings me to the next topic, if we can jump in. And so much of our podcast comes back to happiness, right? And if I don't feel valued, I don't feel happy. And we are, we do think a lot and we're told a lot about and asked the question does money buy happiness? And the the rich guy in the world, we all know who he is. He just, you know, offered to pay TSA, um, TSA employees who aren't getting who aren't getting paid. That, you know, can't can't happen. But it was interesting, Lynn. I think it was you who told me that, you know, he doesn't believe money can buy happiness. And that's the richest man in the world who said that, who likes money. Of course, I want to go, great, transfer the money out of your bank account and send it to me. Let's see how happy you are. But it also reminds me of 25 years of doing gender equity work of all of the male executives who have looked across, I talked about in my book, Disruptors, looked across the table to me and said, Well, it's an only 5% differential, that's not bad. And my response is great, then give me your 5%. How happy are you now? Right. So, you know, I I think seriously though, when we think about does money buy happiness, that's probably not the right question. But there's a guy, um, Dan Kahneman, um, and he published some research. Now, take take just keep in mind this was back in 2010, but he said that people um make a certain amount of money, and after that amount of money, it you you can't buy more happiness, right? So his threshold was 75k. I don't know what that would be in today's world, 150. I don't know the inflation rates, right? But he's saying if you made over that baseline, probably of being able to have a home and you know, not worry paycheck to paycheck, that it won't increase your happiness if you go over that, right? And so my question is, is that true? Right? Like, did he get that right?

Dan 10:39

Yeah, it's such an interesting question. And I love that somebody you know back in 2010 did some research and did some calculations and says, you know, if you're below this threshold, more money does make you happier, or and beyond that threshold, more money doesn't make you happier. And uh their research has been analyzed and debated, as as all research tends to be. But that gets me wondering like, if you're just a miserable person to start with, does having money make you less miserable? And really, I think what I'm asking is whether money gets to the underlying things that make us unhappy. Like if I can't afford food, that would make me sad. And so having money would make me happier, yes. But if I don't have friends, that would also make me sad, and more money wouldn't necessarily fix that, above or below that $75,000 threshold that Daniel Kahneman found out. Uh like if I suddenly won the lottery, I don't think I would suddenly have a lot more real friends, would I?

Lynne 11:31

Not real friends. Patty and I would still be your friends.

Dan 11:37

For sure. I will share my lottery winnings with you both.

Lynne 11:40

It is fascinating that so many discussions about money are actually discussions about happiness like we've just been having, or they become discussions about happiness. Now, why is that? And and how does this enough idea factor in as well? What is enough money? What is enough happiness? Can you have too much happiness? Like, can you have too much money? And I think this conversation is also making me think, maybe just because of the enough, about when I worked with multiple community-based health plans who served people getting health care via Medicaid. One of the things the Medicaid members told us over and over again was that yes, food trucks, food banks, prescriptions for fruit, all of the things that the health plans were trying to help people eat healthier on fixed incomes, those were nice. But the real issue was poverty. And wasn't that what we should be getting working on? And so it got me thinking about what it truly means to lead generously, have an open mind about what people actually need in the context of money.

Dan 12:52

Yeah, so you're right. I think maybe one of the questions we should be asking here when we talk about money is whether we're really talking about money or whether we're talking about something else, something that's related, that money's a proxy for.

Patti 13:06

I I love this. Um, this podcast episode is what are the questions we should be asking about money? And I'm hearing you two and going, wait a minute, is that really what we're focused on? Right. And that's so unique with this episode and the episode that we did about disinformation and misinformation, where we're like, wait a minute, are we talking about information? Are we talking about truth? Right? Are those two things separate or are they the same? And so it just makes me wonder with money, like, are we really talking about money? Because then you use the term happiness, right? As much, if not more, than you use the term money. I found myself doing that, right? In value. And Dan, the same with you. So, like, what is it? Just following your Medicaid example and you know, other examples that you guys have shared, what is it about money that makes it stand in for other things?

Lynne 13:58

Yes, yes. Essentially, what is money a proxy for? Like, what does it represent? What is it a stand-in for? And what if we talked about those things, the real things, like fear, safety rather than money?

Dan 14:17

Right. Fear, safety, poverty. I think poverty is a different topic than money. I think they are related. And so to go back to the Jerry Maguire thing, the phrase show me the money in that scene, I think it was really about respect, right? He might as well have been saying, show me the respect. It was about confidence. I'm showing you my confidence. It was maybe about security. And so maybe it was only peripherally about money, kind of as a proxy, like you were saying. So now I'm wondering, was my opening question incorrect when I said, hey, we all know what money is, right? Because maybe we don't. What if what if money isn't money?

Lynne 14:52

Well, it wouldn't be listening for the questions if we didn't get a little meta. So I love that, Dan. And again, you know, we've we've sort of really talked about this Jerry McGuire example. Uh, but the other thing you pointed out that Cuba Gooding Jr. says is this is a family thing. Uh, and this is a family saying. And so I want to pivot a little bit on that and ask you two and our listeners are, you know, what are your earliest memories that involve money? Like, when was the first time you became aware that money was a thing? When did we learn that money is or is not something we are supposed to have? I'm I'm guessing that you did not have Cuba Gooding Jr. as your father, teaching you that thing from the get-go. But maybe I'm wrong.

Patti 15:40

Whatever your concept of money and your feelings about it, not your thoughts, your feelings, which then lead to your thoughts. Like, where did that concept come from? Right. And to your point, Lynn. Like, as a kid, like, let's really think about question, what did you believe about money when you were a child? And were the where did those concepts come from? And as I'm listening to you, Lynn, I'm going, wait a minute, nature versus nurture, right? So we're conditioned to believe things based on the environments that we were formed in, right? Those formative years. And then what reinforced those things moving forward? And it's it's so interesting. And like, do you know anybody who doesn't have judgment when it comes around money, right? Like doesn't have a feeling, you know, or you know, like uh who has it and who doesn't have it kind of opinion. So like when we look at certain working class backgrounds, people with money are not trusted, right? They've done something bad. Um, certain backgrounds, like in the world we're living in now, people with money get a blank check literally for everything because they're seen as better. But like it's not necessarily what people are thinking, Lynn and Dan, when I listen to you, it's why and the how they got there in the first place. And my next question is, and can it change?

Dan 16:59

Oh, yes. This has me trying to remember like, what were some of the first things that I did to earn money? Earn like my own money, not an allowance from my parents. And then that makes me think: when was the first time you became aware of economic inequality? Whether it was like an awareness that some people have more than than you and your family, or awareness that some people have less than you and your family. When do we become aware of that? And how did that feel? Either to be on either side of that more or less. And how does that then affect our decisions and our attitudes and our actions when it comes to money?

Lynne 17:36

Yeah, I definitely remember becoming aware of that inequality pretty early age, both in terms of having more and having less. And I not to minimize this, but I can distinctly remember, you know, guess jeans and wanting guest jeans. And my mom's like, no way, those are so expensive. Why would we spend the money on that? And but that was a thing, right? And that was kind of a marker about for everyone to see who had more and who had less. Um which makes me even start to think more about economic inequality. Like, oh, why is it a thing? Why does it exist? Why do we tolerate it? I think that's a question a lot of people have been asking for a long time, and we don't have an answer.

Dan 18:24

Yeah, and you might have heard uh Billie Eilish recently asked a room full of rather wealthy people if you're a billionaire, why are you a billionaire? I think it's a great question, and I'm pretty sure that means she listens to our show.

Lynne 18:37

Well, if she doesn't yet, she will be now. Hi, Billy Eilish.

Dan 18:41

Thanks for listening.

Lynne 18:44

I do think I know at least part of the answer around this conversation we've been having with inequality and money. It relates to power. Uh, money maybe doesn't buy happiness, as we've talked about, but it does appear to buy power. Uh, maybe one day we can also ask questions about whether a universal basic income program will ever actually be a thing.

Patti 19:06

Yeah, for sure. And and I'm with you, Lynn, right? When I think about there's a reason why if a law is broken or something happens, it's always follow the money. There is a reason why the World Economic Forum focuses in on always follow the money, because where there's money that equates to power. And does power equal happiness? Now, these are all really interesting combos, right? For another, another episode. But you know, just in kind of wrapping this up around the origins and thinking about our money origins and how we talked about money growing up, do those still hold true for you today, right? So how you were taught to think and feel and talk about money is that reflect, and for me, I'm gonna tell you it's not. And I can ask myself why, and and I know why, right? What I grew up with at very working class, I too remember very early on being called out, like my, you know, you have to pay for CCD. My mother had to pay in installments and the teacher telling everybody in the first grade about that. And it was awful. Yeah, it was awful. And so it was really this, like, oh, you know, this this feeling. So when I think about am I different and how I talk about it, and I ask myself why, I have to ask myself, do I think and talk about money differently? Because I now am presented with different viewpoints on money because I have more of it and I have more access. And yes, that access gives me power. And then the other thing that I am thinking about is who I talk to about money. Because we didn't, you know, you keep that stuff inside your house, right? You don't talk about money, and yet I'm finding myself talking pretty freely about money and pretty freely about having it and not having it, and you know, you know, the universal pay and all of that stuff. Whereas in my upbringing, I did not. And so, you know, I have to ask, is it because I have had exposure based on the good fortune of the career and then the people I get access to who were raised differently on the topic of money?

Dan 21:08

Yeah. So speaking of differences, uh, Patty, I know you already started us on the gender and equity questions early on, but I've got a few to add uh on the topic of gender and differences as well. So, first, do men and women ask different questions about money? And then are we told different things about money? And then if we're asking different questions and being told different things, do men and women then land in different places when they're thinking and planning about money?

Lynne 21:35

Yeah, maybe I'm not sure if men and women ask different questions about money. Although for anybody who ever played a mother against a father, there's probably different beliefs about money. Um, I do think it goes back to the environment in which people grew up talking about money. Many Gen Xers, like we all are, the three of us, likely grew up with parents who Grown up in the shadow of the Great Depression, which probably really impacted how they related to money. Um, and I do think, just getting back to the women-men question that you asked, Dan, I think women historically have negotiated about money differently than men. It's why there are so many salary negotiate negotiation programs for women, which makes me wonder you know, what did we learn about money from watching the women in our family? And who gets called ambitious for wanting more money? And who gets called greedy?

Patti 22:37

Oh, God, I love these questions, which of course I think about more, you know, demographic changes, right? So, like, what about people from different socioeconomic backgrounds and circumstances, and you know, people who started with nothing at all and earned their money like I did, versus people who inherited their wealth, right? Did they think differently, talk differently, feel differently about money? And what about the people who experienced the extreme loss of money? Right. I know in my own experience and what's been handed down generation to generation of my grandmother, my grandfather, their families having everything taken away from them, not just money, of course, but everything taken away from them in 1915 with the Armenian genocide. And, you know, listening as we prep for this and listening to you talk and go, I can't think of one part of how I feel and thought about money that was not informed by that. And quite frankly, my fear of money. And so, like, I just I these there are so many questions we should be asking. And that is for me, just a takeaway from me is wow, really wow.

Dan 23:53

Right. The fear of money. Why is money scary in some cases? And I think there's also this expectation, maybe building on some of that fear, particularly in America, there's an expectation that we'll make more money than our parents. And there's an expectation that every family is just on the same upward trajectory indefinitely and infinitely. Why do so many of us seem to think that? Is that a reasonable expectation? How many families actually do experience that and have that happen? And then what happens when the trajectory reverses? Back to your fear question, Matty.

Patti 24:24

Yeah, it's it's true. And now let's bring in another element of fear because you know I'm going to, and that's going to be all about our two favorite letters, AI, right? And we know because we believe it, we've seen it, we've read it, read it, including that New York Times article last November, which I know many of us have cited, including me, that the AI boom is driving the economy. What happens if it falters? And many of us have said, not if, when it falters. So maybe the question I, you know, should start asking myself or we should start thinking about is what's the relationship between AI and money?

Lynne 25:08

I love that question. And I'm I'm really curious about you know why AI is responsible for so much economic growth right now. Is it sustainable? Is it real? I mean, you think about so many booms and what tends to follow them, right? Bust. Uh, so is this AI boom sustainable and real? And why is it happening?

Dan 25:35

Yeah, you know, I think a lot of the investment that I'm seeing is in infrastructure right now, so building big data centers. And whenever I read about that, I always wonder how many people remember the telecom bubble that burst around 2000, 2001. So there's all these companies making massive investments in fiber optics and saying, oh, the internet changes everything, the old rules don't apply anymore. We can just continue building this indefinitely and the economics will work out eventually. And then it all collapsed. So, what are the lessons that we should be learning from that era? And more importantly, what are the implications if we don't learn them?

Lynne 26:10

I'm just gonna pause so people can ponder that question. We're not gonna answer it, but it's a biggie Dan. So I knew we were gonna talk about AI, because we always talk about AI on this show. And so I asked my AI, you long-term listeners know I call her Maud, uh, about what are the questions that I should be asking about money? And she asked, humans invented money. So, why does it feel like money has power over humans rather than the other way around? Such a good question. She also asked, What would change if everyone knew exactly what everyone else earned? I love this question. And this is an area where I do think generations are different.

Patti 26:59

I I'm gonna sit with that question that humans invented money, so why does it feel like money has power over humans rather than the other way around? Darn you, Maud. I mean, that is absolutely brilliant. And I do want to just put in a little plug. So I was part of a group of people in uh the state of Massachusetts that got a bill passed um a few years ago that makes it legal for employees to share how much they make with each other and talk about taking away power from the employer when that happens, right? So it's so interesting, and we're not doing that enough. And it's also very interesting to me as I was going through that process and asking myself, why are some people embarrassed by the money that they make if they are doing a comparable job to someone else making more money? Why is that guilt sitting with them versus with the HR department? Um, so you know, let's talk about this a little bit more of a macro perspective, right? So when it comes to the impacts of gross domestic product, right? The the money we make inside of the lines of where we live and gross national, right? Like what the things that we can export out of a country, how it impacts us as individuals. When we think about that, like should the question be like we talked about before, like following the money and like what that represents when we do, right? Is it power? Is it dominance? Is it freedom? I think we can all answer these questions, right? But we really do need to be asking them. We can point at other people and say, we believe this is what it means to them, greed, power, blah, blah, blah. But we should be pointing at ourselves as well. And what does that mean, right? People who may be good people are looking at a $50,000, you know, bonus to sign up for ice. What does that tell you? Right? People would rather not be unemployed, they'd rather have money in the bank, they'd rather put food on the table, but at what cost, right? And, you know, as I'm thinking through this, I'm realizing how hard it is for me to ask questions about money without assuming human emotion to its meaning, like ice, right? And what brings us back to square one, like is this question is just a more personal run, is like, what is the role money plays in my life and Lynn? Going back to what Maud asked you, am I allowing that to have power over me versus me have power over it? And that might be the central question. I really think that's important.

Dan 29:34

Yeah, well, I love it. And you know, I'm struck that when we talk about people's personal financial situations, we often use terms like doing well or in the comparative doing better than. Like if someone's making a lot of money, we don't say they're doing well financially, we just say they're doing well. And people fill in financially as if those two just automatically go together. I think that language choice really highlights how central money is to our view of success and happiness and all of that. And that makes me wonder what would happen if we changed our language around money and broadened our understanding of well-being. And then despite this entire conversation, why do I still want to jump up and shout, show me the money?

Patti 30:13

I'm gonna answer that because you didn't let me answer a question today. Um, I think it's because it feels good, Dan. Like looking at you and Lynn and even myself when we have said show me the money, we're all smiling when we do it. Like it's joy-inducing for some reason. And Lynn, you know, it kind of reminds me of what your response was in the beginning. Like, it just feels good. Why does it feel good, right? And who gets to feel good about that? So I love it.

Lynne 30:38

And I love it too. And I'm sad, but that's our time for today. What a great set of questions we ask today about money. Like, what is enough? What is enough money, happiness, power? What is enough AI? And what questions should I be asking about my origin story and how it is impacting me now?

Patti 31:02

I'm not embarrassed to say that my takeaway here comes from Lynn's best friend, Maud. And that is really me wondering what is the role money plays in my life? And am I allowing money to have power over me versus me having power over money?

Dan 31:18

I think my big takeaway is the question: what are we really talking about when we talk about money? I think it's possible to have too much money. I don't think it's possible to have too much happiness. And so that's that's where I'm going for. Show me the money, but only enough to maintain happiness. And beyond that, I want to give it away.

Patti 31:37

Dan, that's why you're such a good guy.

Dan 31:39

So thanks for listening, folks. Today's episode was sponsored by happiness because when we're talking about money, isn't that what we're really talking about?

Patti 31:46

Our music was composed by Jake Cuprinol. Our cover art was created by Matt.