When Earning More Makes Your Financial Anxiety…Worse?

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In our “money dysmorphia” episode, a theme emerged that I wanted to revisit: Money anxiety increasing with income, not decreasing. This is a counterintuitive response to expanding your access to resources. While most of us are probably familiar with the law of diminishing marginal returns and accept that after a certain point, money won’t make us any happier, the idea that money could make us actively unhappier is pretty antithetical to the entire capitalist enterprise.

So to get the inside track, we invited Clay Cockrell, a therapist for the ultra high-net worth, to talk through some theories about why someone might experience enhanced anxiety as they ascend the income ladder—and what it might mean you need to do next.

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Mentioned in the Episode

• The Money with Katie Show episode on money dysmorphia

• Nick Maggiulli’s piece on “The Low Stability of High Income”

• Rich Girl Roundup  story on inheritance

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Clay:

Listen to me. I work with these people, I work with many of them. Money is not going to bring you happiness. A certain level of money is going to alleviate some stresses, remove some challenges, allow you to experience life on a higher level, but you have to understand what is enough. Enough is an incredibly difficult concept because I’ve worked with people who have a hundred million dollars in the bank and say, I almost feel safe.

Katie:

In one of the listener interviews that I did for our Financial Dysmorphia episode, someone mentioned rather casually that they noticed their money anxiety got worse as they proceeded up the income ladder. Here’s that clip:

[Money Dysmorphia episode]:

There was such a weird contradictory experience. As soon as I doubled my income when I was underearning, I was just in this survival mode. Well, I was educating myself on personal finance and learning what getting my shit together with money would actually look like, but it was all very theoretical and the day-to-day reality of my life was that I was still in a really scary place financially. And so in the back of my mind, I was kind of filing away all of this information that I would plan on using later because at that time, even though I knew kind of what I needed to be doing with money, I didn’t have the money to be doing it. So there was nothing that I was doing in my day-to-day that could actually make me feel better because the numbers that I wanted to see were not there.

And so when my income changed, I felt a lot of pressure to close that gap between where I was under earning and not putting away the money that I wanted to be for retirement and investments and things like that. And then I also had this backlog of just unprocessed guilt and fear and shame and embarrassment and anxiety about all of that time that I had lost because I was under earning and there was only so much that I could do. It was all of these little factors lining up to work against me at a time when I was expecting to feel an immense amount of relief. It was like all of that responsibility, all of that pressure, and all of this reckoning with what I had experienced as an under earner was really, really catching up to me. I was like, oh my gosh, now I will never be safe.

Katie:

That sentiment actually came up a lot during the interviews for that episode. This idea that becoming a higher earner actually exacerbated feelings of financial anxiety that weren’t there before or at the very least were different and maybe more understandable before. So this week I was interested in speaking with a therapist who specializes in financial anxiety that’s specifically tied to making and having more money, not less. As you can imagine, this is a relatively obscure niche for a therapist, but I think nosy people are going to get an extra kick out of this one. So welcome back to the Money with Katie Show, Rich Friends. I’m Katie Gatti Tassin. And today we are talking about the unexpected anxiety that accompanies the very thing you would expect to make your money worries melt away: getting more of it.

Now this topic is inherently interesting to me because it is so antithetical to the conventional wisdom that goes something like this. Being resource scarce causes anxiety. Once you have more money, your anxiety will go away. Now to be fair, the first part is definitely true. Being resource scarce does cause anxiety and depression and health issues and all sorts of maladaptive responses when human beings are starved of the things that they need to live. But what about the inverse relationship going from not thinking about money much at all beyond meeting your basic needs to feeling absolutely consumed by earning more of it?

Fortunately, I found someone who is a therapist for ultra-high net worth patients, so think tens of millions if not hundreds of millions of dollars. And I was excited to talk to him because I don’t think we often have conversations about what can go awry at a human level, when you take this dial and you turn it up to its most extreme level. I was curious if there were any themes that he notices in his clients. So my guest today, Clay Cockrell, is someone I found via an interview with New York Magazine‘s, Charlotte Cowles. He’s a therapist who specializes in rich people. Yes, seriously. And admittedly Clay’s clients are operating on a completely different financial scale than I’m talking about, which is for reference today, so we’re all on the same page, something much closer to our listener who went from earning in the $60K range to the $200K range. So you might notice in his examples that his clients are stressed about things like taking a private jet to Paris for dinner, whereas the listeners who inspire this episode are stressed about things like, am I upgrading my vehicle too quickly? Right?

But while the scale, while the volume may be radically different, there is something that tells me the emotional tenor, the psychological processes that the human brain undergoes when people come into more money are probably pretty similar. After all, we’re probably familiar by now with the idea of diminishing marginal returns. Old studies said that happiness plateaued after $75,000 per year. And while we have reason to believe the number is probably a lot higher than that, especially post inflation, it’s true that after your needs and wants are met, you really aren’t going to experience much in the way of lifestyle improvement from stacking ever more cash. But most of us probably don’t think it would ever start to degrade our quality of life. I know I didn’t until this conversation. We might accept that becoming richer beyond a certain threshold won’t make us any happier, but we also probably don’t believe it would actively make us less happy. That’s what I’m hoping Clay can shed some light on today using his 20 years of experience as a therapist after a quick break.

So before I talk to Clay, I want to lay out a few theories of my own for why this might happen. These are a couple observations that might help us chip away at the inscrutable problem that is having a bad relationship with money even after you technically have enough of it. My first theory is unmet expectations. So part of what people might have been describing in my listener interviews about money dysmorphia could be a sort of response to unmet increased expectations, especially if those expectations went unacknowledged or otherwise unexamined.

So in other words, you have a vision in your mind that is going unmet. For example, you may have had a narrative consciously or unconsciously that once you surpassed a certain level of income or wealth, that something about you or your life would feel different. And if you didn’t find that to be the case, being confronted with the reality that the problems you thought money would solve, like the problems you thought were about money are still around can be destabilizing.

It’s kind of like, okay, all this time I’ve been thinking that once I made six figures or once I hit XYZ net worth, I would feel better and I don’t. So now what? Do I need more money? Do I need something else or relatedly, you start making more. You start spending more. Your life is now scaled up to accommodate someone with your new income, and that means you’re now accustomed to a lifestyle that requires a certain level of income to uphold.

Usually the jobs that pay those types of incomes are harder to come by, they’re harder to keep. Usually they’re harder to work in some instances. In the newsletter, a couple weeks back I shared Nick Maggiulli’s thoughts on the instability of highly paid work based on the findings from a 2015 National Bureau of Economic Research paper that supported this idea. And so whether we’re aware of this ambient sense of insecurity or not, it seems reasonable to assume that climbing higher is often accompanied by a sense that one now has much farther to fall.

And I think this is related to the next theory, which is a fear of losing the ground that you have gained. That’s the paradox of my earlier point about problems you assumed would go away once you got a little money. Once you experienced financial stability like deep, deep financial stability, and you can now compare that to how instability feels, you now know how much better and how much easier life can feel. And I think the potential of losing that or going backward in some way can lead to intense anxiety and overthinking of financial decisions. It’s like the photo negative of the American dream.

You work really hard, you obtain this future that you have always dreamt of, and now you basically have to spend every waking minute defending what’s yours. There’s also the element of needing to keep up. And normally we talk about this in the context of the Joneses or the material arms race that occurs when you start hanging out with people in a higher socioeconomic class who might normalize spending behavior that you may now feel pressured to imitate. But if I had to guess based on some of the money dysmorphia submissions, conversations with friends, my own experiences, and quite frankly some garden variety r/FatFIRE subreddit creeping the comparison and pressure someone feels might actually be more about the literal dollars and cents the scoreboard.

This is sort of what someone else told me in those interviews. She said, when I was making $60K, I was not comparing myself to people who made $300K. I wasn’t even in the same universe as them. So it never occurred to me to compare myself. But now that I make great money, all I can think about is how I am not as successful as they are. And here’s the thing, even being able to recognize that that’s the sneaky source of your dissatisfaction is challenging because we don’t really have a cultural script for I’m successful beyond my wildest dreams, and yet I am unsatisfied because I am now aware of people who have done better than I have now. That is a very champagne problems psychological loop to find yourself stuck in which can make it hard to admit or even acknowledge without feeling intense guilt and shame.

These are stories and scripts that usually lurk under the surface of our consciousness, and unless you look at them directly, it can be easy to feel this way and not even realize that that is the source of your vague discontent with an otherwise great situation. So I intend to ask Clay about that, but we talk about systems on this show a lot. Most notably with a deep dive into capitalism a couple of weeks ago, this really does kind of feel like a slingshot from that episode. But there’s no more powerful system in our lives than that which drives us toward these goals. Most of the structures that we are compelled to pass through beginning early in our childhoods are in place to engineer this very outcome of compulsory striving and achievement, doing well in school so that you can get into a good college so that you can get a good job so that you can make money and so on.

All that to say, if you end up doing well for yourself and you still have a hard time with comparing yourself to people who are doing better, even if you are doing better than you ever thought you would, I do not think that that is a unique personality trait that belongs to you. I think that is just the predictable outcome of a system that is inherently rooted in engendering a sense of competition amongst individuals. Money just makes quantifying those outcomes that score easier. And finally, there are the complexities that accompany a heightened financial situation.

So these are problems that are probably pretty hard to sympathize with for sure, but having more money does usually up the ante, right? The nicer bigger house has more complicated, expensive problems. You have an estate, well, congratulations babe. You need an estate planning attorney. You earn a lot of money. Amazing. Well, you probably now need new and expensive types of insurance. And guess what? There are going to be a ton of people who want to sell it to you. You got an inheritance? Cool. Now you got to figure out what the hell you’re going to do with that inheritance. In fact, you’ve probably noticed a few recent Rich Girl Roundups. This has been an increasing theme in our submissions in which even the possibility that an inheritance is coming can send people into this hand wringing spiral about how their lives should change now. Now it’s a problem I’m sure we would all welcome, particularly if we are having a hard time, I don’t know, affording groceries, but it still introduces options and access that you simply didn’t have before and by extension obligations that you did not have before. If you exist in a set of systems that tell you over and over again that more money, more success, more right, more achievement, that this is always and unequivocally a good thing, you may not be anticipating these changes, which means you might feel unprepared to deal with the uncomfortable and destabilizing emotions they can bring.

I remember the first time I realized that I owed the IRS literally $50,000, which was a panic inducing problem that I did not have when I made $50k a year. Now obviously I was happy to make more money, I was happy to have a business that was doing well, but I was unprepared for what to do with it. I did not grow up in a house where people had accountants, so I did not know that I needed an accountant and boom, $50 grand mistake. It can feel really overwhelming and really high stakes because now there is money on the line for your mishaps. Alright, now that you’ve heard my baseline thesis for the operating principles that are at play here, we’re going to ask Clay what he thinks.

Our entire economic model is sort of built around the idea that becoming wealthier is like an aspirational thing and that money is something to sacrifice for and to be disciplined for that the experience of having access to more money is this inherently worthwhile pursuit. That is, I think at least the subtext of the system. You go to school, you do well, you try to get a scholarship in school so you can go to a good college and then you’re going to that good college so you can get a good job. And the whole point of the good job is that you can afford the good life and money is this motivating through line throughout this prize at the end of the race. But you told Charlotte Cowles for The Cut—who is a friend of mine, she’s wonderful, her work is great—that not only does money not solve all your problems, but that it can cause a lot of problems. And the stories that you tell about your clients are kind of this succession level of wealth that probably isn’t super relatable or sympathetic to the average person. But I’m curious thematically, when people who earn more money report feeling increased levels of anxiety, what do you typically attribute that to? Why do you think money brings anxiety with it?

Clay:

Well, I’ll preface this that I’m sure there are a lot of wealthy people out there that are enjoying their money, but I typically don’t see them. They don’t go see a therapist with the problems related to it. But I believe that money at this level is dangerous and can be toxic. I think there is a numbness that goes, and therefore with that numbness, there is a pursuit of the next thing, the adrenaline of gambling, of climbing mountains, jumping out of airplanes, something just to feel alive, to have some kind of level of risk. So I see that a lot, and which goes back to my point of this can be very dangerous. People die of this, what the drug overdoses, suicide.

What it does is it isolates us from other people because we like to spend time with people who are like us. And I think that the anxiety comes from what happens if it goes away? How are other people looking at me? How am I going to be able to make new friends if I make a new friend? Is that person in my life because I can pay for dinner? It can be very isolating and create a place where you are distrustful of others. What do they want from me? How are they judging me? And it just brings a lot of issues that people without money don’t have to deal with.

Katie:

Yeah, I can appreciate that point about selection bias, but I do think that there’s a level of truth and depth in some of the observations that you have about your clients. There’s something you just said actually that sticks out to me about people who achieve a level of ultra abundance such that they now are searching for adrenaline in other places. I hear that and I think, okay, you become wealthy and successful to the point that you’re almost insulated from the normal ups and downs of life. And that numbness then to your point, you go out and you’re searching for that excitement, that texture in other ways. Is that a fair representation?

Clay:

Oh, absolutely. Absolutely. When you’ve eaten at all the best restaurants, stayed in all the best hotels and you’ve experienced all the very best of life, you’ve reached the pinnacle. It’s like, what’s next? What was Alexander the great wept because he conquered all his worlds. That’s kind of what these people are dealing with, and my heart goes out to them because there is a numbness to life of I’ve got all this, I should be happier.

Katie:

Well, immediately I’m thinking of some of the most, I’d say wheels off billionaires that are in the news and these people where they behave in such counterintuitive ways. I would think that if you got billions of dollars, I’m like, y’all would never hear from me again. I would not be anywhere. I would be so out of the loop. I would not be on Twitter. I would not be buying Twitter. I would not be trolling people. And so I think though that yes, having a billion dollars is an experience that an infant decimally small group of people has. There are 800 billionaires I think in the United States.

Clay:

Money allows us power. It’s is not good for you and you begin to make really poor choices because you are living in a bubble. Nobody’s going to say, hey buddy, that doesn’t make sense if what you’re doing doesn’t make sense. You are surrounded by people who are dependent upon you and therefore are going to make you happy and say, this is a great idea. Absolutely, you’re right on. I keep saying it’s not good for us.

Katie:

But I think that it is a sort of instructive use case for if you turn the dial of wealth and access up to its logical extreme, these are the sort of perverse outcomes that you get where I think a lot of us, or I’ll speak for myself, operate with this idea that there is some level of wealth, access, money, et cetera, that would make your life so frictionless and so easy and so lovely that your problems would kind of go away, but well, then I would really be happy.

And I almost feel like what I’m hearing you say is that you get to work with and speak to the people for whom this would ostensibly be true. And what you find is that they also thought that they would be happier than they are. And now it’s like, okay, it’s something wrong with me because this has not actually solved all the problems that I thought it was going to solve, which there’s a lot in there that is worthy of further inspection, I think.

Clay:

Absolutely. You hit it on the head and that life that you were looking at is incredibly complicated. It sounds like first world problems because it is first world problems, but they are problems. It is a complicated life because you think it’s going to be a frictionless experience. Now I have all this money. No, it’s true. More money, more problems, different problems, interesting problems, but problems are there.

Katie:

We will get right back to it after a quick break.

So you wrote a piece for the Guardian; in it, you tell this story about having clients whose access to lavish things often creates an obligation to do lavish things. And I’m curious, do you think it’s possible that suddenly having access to more options, and I’m talking now in my frame of reference, you are somebody that maybe went from making $70,000 a year to $250,000 a year. It’s like now your expectations for your life are going to be different, but that perhaps having access to more options creates this paradox of choice discomfort, like we overestimate the marginal utility, I guess is what I’m trying to say. I mean, do you think that that’s what’s happening here or is it something else?

Clay:

No, I think that there’s some truth in that, but too many options gives you a lot of pressure, especially when your options are infinite. I had a client who, for example, if my wife had a birthday and let’s say the Eagles were in town, I’d get her a ticket, we’d go see the Eagles. Her husband is having a birthday, she’s going to hire the Eagles to come and do a concert. Not kidding, not kidding at all. That is an option for her. And then you go, well, is that too much? Is that ostentatious? Is that showing off? What are my friends going to say?

Katie:

Well, and how do you typically counsel someone who might not even realize that they are feeling that pressure or obligation? How do you help them recognize and deconstruct that feeling? What does that look like?

Clay:

So my theory of therapy is that there is healing when we put a vocabulary around our internal thoughts and tell it to another person, helps us to understand it more. What I bring to the table is years of experience of working with this particular population, and there is so much relief and joy coming from them to be able to say what’s going on in their life without judgment. And also an awareness of here’s somebody that validates my experience that wealth is not all it’s cracked up to be. So that ability to talk about it with freedom, that validation of, Hey, this is problematic. Now we can get into a place of what can we do about this?

Let’s begin to think about how money has complicated your life and begin to change that to have a different relationship with your wealth, that your identity as a human being is separate from what your bank account shows. Maybe you’re funny, you’re loyal, you’re curious, you are depressed. Let’s deal with the person, the actual human being.

Katie:

In your conversation with Charlotte, you mentioned that you’ve seen people who accumulate a lot of money end up becoming so embroiled in lives that are so complicated by that money that it kind of ceases to be fun, that all the benefits that you expect as you gain wealth are sort of overshadowed by the complications that it introduces. And I can see that happening in two ways in a normal person’s life who may find themselves moving up the income ladder, especially if they are one of the first people in their family to find that type of financial success in life. I think the first is I now have become so accustomed to a lifestyle that requires my higher income and I feel a little bit trapped by that or that having these resources has isolated me from my friends and family who do not have these.

So sometimes I wonder personally, what would it look like to use intentional downsizing as a tool to prove to yourself that you are adaptable, that you are still resilient. There is a part of me that goes, maybe you should try moving back into an apartment, or you should try a smaller space just to prove to yourself that your happiness level is not going to change, that these material things are not really going to impact your baseline state, right? To prove to yourself that going backward isn’t scary.

But even as I say that, it occurs to me that that might be a sort of maladaptive response. And I’m curious how you think about that if someone who has begun earning more money and may have expanded their lifestyle a little bit, came to you and said, I’m feeling a little bit uncomfortable with the fact that I used to live pretty happily on a couple thousand dollars a month, and now before I know it, I’ve got a family, I’ve got kids. I bought this nice house, I drive this nice car and I can’t even believe how much I’m spending now, but I’ve feeling a little bit trapped by this reality.

Clay:

I hear that every day.

Absolutely. I hear that every day that my life has gotten too big. I’m not used to it. Now we’ve got to think about, there’s two buckets of people we’re talking about here right now. There are people who have earned their money and all this. They weren’t raised and they did not grow up with wealth. And then those people who did grow up with wealth, generational wealth, and they’re used to it and they’re two different, a lot of similar problems, but two different populations.

But that person who is not used to this larger life is uncomfortable. And there’s this degree of, I don’t want to go back. This is nice. And yet there’s a lot of pressure here to stay here because my wife’s depending on me, my kids are depending on me. If I screw up and the money goes all over, what am I going to do?

But the scenario you propose actually happened to a client of mine last year, and so I’ll change some of the details here, but for whatever reason, the home that they were going to be preparing was not quite right and just because of numerous factors had to move into a smaller apartment. It was a nice apartment, but it was much smaller, and the happiness that they found there of just being on top of one another was revealing. And that gave them a sense of security of what if we all had to go back? We could, and it would actually kind of be nice. It was a nice thing for them to experience, but without that actual lived experience, there’s a lot of fear that if I go there, this is not going to go well for me.

Katie:

There’s a bit of a larger theme here that I feel like we’re kind of circling, which is the idea that the grass is not always greener. And I know that feels really trite when we exist in a world where so many people lack access to things like food and shelter or are experiencing resource scarcity. But I actually think the point that I’m about to make is more compatible without reality than it might sound on the surface.

So if you’ll indulge me, I think if we accept the premise for a moment that having a boatload of money is actually in many ways like one headache after another, and that constantly aspiring to more and always kind of arranging your life around wanting to gain more and more and more turns out to be this profoundly soul-sucking human experience. And that once you get there, you’re kind of like, well, now what?

Now I have to go parasailing to feel a little bit excitement in my day. I have basically paid to remove any friction. What do you think that says about the fundamental logic of the existing system that I kind of described or laid out for us? In the first question, we ardently defend the right to accumulate as much money as possible in the us. It is this very powerful economic narrative of paramount importance to the lore of America that your success can be infinite and the more infinite it is, the better your life will be and the happier you are and the more successful you are and the economic importance of that ability to accumulate as much money as possible, hundreds of millions, if not billions of dollars is sort of by my estimation, used to justify then whatever societal issues it’s going to create that important that people are able to do this. But I just sit here and I go, man, what does it mean if even the winningest of winners still don’t really feel like they are winning?

Clay:

Yeah, I’ve learned to not read the comment section because the anger that I receive from people of being the therapist to the ultra-high net worth individuals, and I think it’s because it’s challenging to people. Here I am, I’m getting up every morning, I’m going to work. I’m busting my butt to make a living to get there. And you’re saying that when I get there, I’m not going to be happy. That’s incredibly challenging and anger producing because it is challenging their fundamental belief system. And I think that’s good. Listen to me. I work with these people, again, skewed, but I worked with many of them. Money is not going to bring you happiness. A certain level of money is going to alleviate some stresses,

Remove some challenges, allow you to experience life on a higher level, but you have to understand what is enough. Enough is an incredibly difficult concept because I’ve worked with people who have a hundred million dollars in the bank and say, I almost feel safe. Yes, there an addiction level to this that is important, that just a little bit more and then I’m going to feel safe. I’m going to feel good. I’m finally going to have no joy comes from spending time with your family, pursuing pursuits that make you happy, hobbies, travel, working hard, having a challenge in your life that you are working hard to overcome. That is where joy comes from. We have complicated our bank accounts. That number in there of just a little bit more, that’s where joy is going to come from. That’s where contentment and fulfillment, and I’m talking to you from the other side, that’s not where it is, which then is actually hopeful.

Pull back, pull back. You’re spending 80, a hundred hours a week or whatever it is away from your family trying to build something, trying to get a little bit more. And I understand if you are not middle class and you are struggling, but if you’ve gotten to a certain level and you’re still doing that pull back, joy comes from watching your kids get up in the morning and reading them bedtime stories at night and sitting on the porch with your wife. This is where joy is. I think that there’s something hopeful in that to remove this rap race that we’re all in and go, I don’t have to do that.

Katie:

I think it’s a John Steinbeck quote, “Socialism never took root in America because the poor see themselves not as an exploited proletariat, but as temporarily embarrassed millionaires.” I can’t help but think about that quote. Though when we talk about this idea of it’s the anger you’re describing. I think the surface level read of that anger is like, yeah, people are, life is hard. The economy is kicking the shit out of everybody. And so if you are having a hard time and you’re working really hard and then you’re hearing someone be like mmm, my yacht, it’s like, shut up. So I get the surface level anger, but then the deeper story, and I think the more interesting story and interesting piece of this is what’s actually fueling that wellspring of fury is that challenge of the fundamental belief of the worldview that if I were there, I wouldn’t be unhappy.

I would be so happy and I would be so much better at being rich than that person is. It becomes very insidious and very easy to slowly without even realizing it, shape your life around and arrange your life and your decisions around that kind of empty pursuit. And to be patted on the back for it by society like, yes, good job. Look how successful you are. Yes, keep going, keep going. Without really taking that step back to question, I have enough, should I be shifting my priorities now because I’ve already reached the point that I decided 10 years ago would feel like enough. Also talk about in some of the pieces you’ve written, the way that your clients have this range of personal narratives about how they have gotten where they are, and I think this narrativizing is also a really crucial piece of what enables and what is necessary for economic systems and inequalities like the ones we have that you have these extreme spectrum of outcomes to perpetuate. And I think that the stories that we tell ourselves about our lives, how we’ve gotten where we are, how what we have are very powerful. And you mentioned that many of the very wealthy people that you’ve worked with tend to believe that there is something special about them that led to their financial success.

Clay:

I think that you’ve hit upon a really good point here. It is the story we tell ourselves about ourselves that help us understand our life. And when you’re in such an unusual situation, you have to be able to explain that to yourself. So I think there’s a dichotomy too. There is a part of them that goes, I’m here because I am special, and if that guy standing on the street begging for money, if he just worked a little harder or figured things out, if I did it, then he could do it. So there’s that thought process, but then there’s that I am special, but then I’m not special and that this could go away at any moment.

Katie:

Interesting.

Clay:

So there is this degree of guilt and fear that is factored into all this, but the story keeps changing of I made it here because of all my hard work or because I’m somewhat special or because my family gene is a certain way so that this is just how we’re made. But then also looking down on another person of if I can do this, then they could probably do it too. Therefore I’m not special. It’s a complicated mess inside people’s heads, depending from one moment to another. I think that’s true for all of us, but I think that they also, it is that story inside of us, that narrative that helps us come to terms with any unusual situation.

Katie:

Yeah, it’s like a constant effort to resolve that cognitive dissonance, I guess. Well, you mentioned guilt and I think one of the things that I enjoy about this sociologist named Matt Desmond’s work is that he talks about the psychological degradation that humans experience in the midst of visibly intense, that conscious or subconscious sense of unfairness. And I think that if you end up as the winner in a system like this and you’re feeling both the need to justify your position as a winner, but also guilt because you can see that you have so much more than you need and there are so many people that do not have what they need. So yeah, you have to tell yourself a story about the guy on the street corner who’s begging for money and why he’s not you and why you’re better than him and why you deserve to be here and if he just did this.

So I just think that most people morally are going to feel funny about that, and I think that that feeling funny happens a lot sooner than a hundred million dollars. I think most people who start to feel extremely secure and enough are then running up against that kind of dual track. To your point about the complicated mess of like, well, I’m not that rich, so I should keep striving and keep hoarding and keep accumulating while at the same time you do have that sense of I have plenty, I have enough. I need to be finding ways to give back to make the world around me better and to not be so singularly focused on what I can do to make the number in my bank account go up.

Clay:

You look around and go, this is not good for any of us. I don’t have an alternative. I don’t have a different proposal. I’m just dealing with the impacts of this system on people

Katie:

And on the winners.

Clay:

And on the winners, absolutely.

Katie:

You’re dealing with the impact on the winners, the people that we are. I don’t know. Again, it’s like all kind of told that that’s what you get when you win the game,

Clay:

Which can be very challenging for people like me who are still playing the game trying to figure out how to pay my mortgage and all this other stuff, but it is not good for any of us. Therefore, we come up with these stories that are untrue on both sides of the argument. I’m special and I’m not special, and that’s hard to take in.

Katie:

Are there any signs that you notice themes, trends, patterns of when someone’s relationship to money, wealth, striving, et cetera, is maybe turning maladaptive or has gone beyond the sort of what I would call, I guess healthy and normal striving within the context we exist within where some of this isn’t necessary to survive and has kind of surpassed that and is now taking a turn where it might be leading them down this sort of path?

Clay:

The word that comes to mind is loneliness. You look around and you don’t feel a connection with your kids and your spouse friends. It may be because you’ve made some choices that have driven people away, and I think that that’s a sign to maybe begin looking at, maybe this is not going well for me. On top of that stress, why are you so stressed? You’ve got all these resources. They’re complicating factor, but loneliness because a lot of the wealthy people that I work with have really isolated themselves with only other wealthy people because it just easier, we like hanging out with people who are similar to us, so they push people away from their childhood because it feels weird and all of a sudden they wake up and they feel lonely. And I think that’s a sign that maybe this is not going well for you.

Katie:

It tracks I think, feeling lonely and this idea of feeling constantly stressed. If you are someone who used to feel constantly stressed for reasons like resource scarcity, you are living paycheck to paycheck or sort of paycheck to paycheck. And so you get into that mindset of like, I am constantly hustling to try to make ends meet and then ends start meeting, and then they’re more than meeting and now you’re really cruising and now things are going really well, and now, oh my gosh, you’re accumulating all this money. But that I can see how that underlying feeling or mode of kind, I got to keep going. That stress becomes almost a, it’s almost like the devil you know. It’s the predictable feeling that you’re used to being in that mindset and now you’re being really rewarded for being in that mindset because you have this quantitative feedback mechanism that the harder you work and the more stressed you allow yourself to be, and the more you burrow into that feeling and assure yourself that, well, no one else gets it. There’s no mechanism in society that’s going to tell you to stop—short of, I would note really the only time I’ve ever talked to anybody for this show that has been in that zone and has been in that mode and then stopped was because they had a health condition. They had a problem, they were diagnosed with cancer that someone died. There was some major shakeup that made them see their lives differently, but they had gone on for years lonely, stressed, and accumulating more money than they know what to do with.

Clay:

People drink alcohol because it works. People, they work at work and they get more money and it works. I’m outside of my one bedroom apartment and now I have bedrooms for my kids. I’m going to work a little harder this year. I’m going to go on a nice vacation. So it works until it doesn’t.

It’s this magical level, and I think it’s different for everybody. And of course it also different on what part of the country or world you live in, but there is a level and we’ve got to understand what is enough. This works, working hard, making more money, it’s going to solve a lot of your problems until you go cross over that threshold, and then it just stops working as well. And then it becomes to work against you.

Katie:

And the threshold you mentioned, it’s not like, I mean, I wish there was a formula. I wish it could be like, well, once you have 25 times assets in the bank and then you’ll know. But it’s like that is I think a level of discernment. And I think those two points that you highlighted, loneliness and stress are kind of the, I’ll say, the two horsemen of the has been crossed.

Clay:

Yeah, yeah, I think so.

Katie:

I can imagine. How do you deal with that? Do you ever feel a little bit, you must be constantly having to do your own kind of mental recentering?

Clay:

Absolutely. Because you lose touch with reality. You really do of what is normal. And I’ve had to check myself going, okay, wait a minute. I talk with these people all day long. That’s not my world. And I’ve worked with people who private butler and money managers and other people that have to interact with them, and we all talk about it. It’s a little complicated. We are in that world, but we’re not of that world and we’ve got to remain grounded. And I don’t want that world. That’s something that I have to remind myself all the time of. I don’t want to, no, I don’t want that. That’s not good. It looks attractive, but I’ve seen inside and I don’t want that. So staying grounded, I think among the people who interact with ultra-high network individuals is a priority.

Katie:

Well, thank you. Thank you for joining me to talk about this. It’s such an interesting subject, the lifestyles and the problems of the rich and famous, and maybe why the lifestyles are not as aspirational as we have been led to believe.

Clay:

Absolutely.

Katie:

As we produced this episode, I think we all on the production side felt like it was in such stark contrast to the conversation with Grace Blakeley about the project of creating a truly democratic society and a truly democratic economy. Like I said, it kind of feels like we slingshot from one end of the spectrum to the other, from imagining a world that might do away with these psychological hangups by prioritizing humanity to understanding how we might be able to duct tape all the maladaptive responses in the meantime. And if that doesn’t encapsulate our project at the Money with Katie Show, I’m not sure what does.

So that is all for this week, and we will see you next week, same time, same place. Our show is a production of Morning Brew and is produced by Henah Velez and me, Katie Gatti Tassin with our audio engineering and sound design from Nick Torres. Devin Emery is our chief content officer, and additional fact checking comes from Scott Wilson.