515: The Soul of Wealth: Bridging the Gap Between Money and Happiness with Daniel Crosby, PhD

[INTRODUCTION]

Casey Weade: There's undoubtedly been a lot of uncertainty in 2025, and today we're going to be discussing that uncertainty specifically but also comparing it to some of the experiences we had not that long ago in 2025. But we're also going to be focusing the bulk of this conversation on the intersection of money and meaning. Today, your guest is Chief Behavioral Officer at Orion Advisor Solutions, Dr. Daniel Crosby. He's a psychologist and behavioral finance expert who helps organizations understand the intersection of the mind and the markets. He has been named one of the 12 Thinkers to Watch by Monster.com and a financial blogger you should be reading by AARP. He’s also the host of the Standard Deviations Podcast and is a New York Times bestselling author.

We’ll be focusing the latter half of our discussion today around his newest book, The Soul of Wealth: 50 Reflections on Money and Meaning. If you don't remember Daniel, I encourage you to go back and listen to our 2020 episode five years ago, Episode #117 titled Coronavirus and Your Retirement, and now we're bringing him back. We're going to kick off the discussion. We're going to talk a little bit about what happened then, what's happening now, and what we can learn from some of the actions that we took back in 2020 and apply those to what you're experiencing today. We're also going to be exploring, as I said, his new books. We're going to be answering that age-old question, can money really buy happiness, how to align meaning with your money, and more great insight on how your emotions drive your financial behavior.

We also partnered up with Daniel to give away free copies of his latest book, The Soul of Wealth. If you'd like to get a free copy of his book, all you have to do is this: Open up your podcast app, write an honest rating and review of the podcast on iTunes, and then just shoot us a text. You can text us the word ‘BOOK’ to 888-599-4491. We'll send you a link so that you can get your free book.

[INTERVIEW]

Casey Weade: Daniel, welcome back to the show.

Daniel Crosby: Casey, great to be back with you.

Casey Weade: And what a timely return it is, Daniel. I was going back. I was listening to our conversation that we had five years ago this morning. And we kicked off that discussion talking about what was happening in the market at the time. And, yeah, that was kind of the open of our whole conversation that day, had to do with what's going on in March 2020. We opened up, the market's down 9.6%, and you said, "Uncertainty is what's driving the market.” And I look at what's happening today in the market here in 2025, and I wanted to see how you compare and contrast these two things. Do you still see uncertainty as the main driver of the volatility we've seen in the market this year?

Daniel Crosby: I do. You said something brilliant, and before we hit record, you said, "Look, it's been five years since we talked, but the more things change, the more they stay the same.” And while the individual players and the specifics of the market may be different, the thing that you've seen in both instances that's accounted for the sharp drop, and then the sharp return is uncertainty or a lessening of that uncertainty. To understand this, we have to understand the human mind, and people are surprised to hear this, but we actually hate uncertainty more than we hate bad news. There's a couple of interesting studies that look at this.

If you look at someone who's receiving a life-changing medical diagnosis, the point of maximum stress is the point of maximum uncertainty. It's not the moment when you find out that you have cancer. It's actually when you're waiting for the results of your biopsy. Because knowing you have cancer, getting that bad news, there is a silver lining there in that now you can fight it. You have some certainty. You know what's going on. You're ready to attack, you're ready to wage war against cancer, and you have a treatment plan with your doctor and your spouse and whoever, and you're ready to go. But when you're waiting for that biopsy, that's the agony. That's the agony. And we see the same thing in markets.

There's nothing markets hate more than not knowing. And because of a host of reasons that we could talk about in the absence of information, we just tend to assume the worst. And so, that's I think what you've seen in 2025 as well as in 2020, and 2020 we had this unprecedented health crisis. In 2025, we have these sort of unprecedented moves by the president to impose tariffs and all the uncertainty that went along with that. I think they actually have a lot in common, even though the underlying causes are quite different.

Casey Weade: Now, I can see some listening and arguing and saying, well, the market's a forward-looking beast, and it is looking at market fundamentals too. And that's why we see these reactions. It's saying, well, tariffs are going to have a negative impact. It's looking at the bond market, geopolitical tensions. Would you still say that psychology is what's driving the day-to-day market movements over market fundamentals?

Daniel Crosby: Well, so it's a little of both. I mean, it goes back to the old Ben Graham quote about in the short term, the market, it's the weighing machine, voting machine sort of consideration that Ben Graham talks about, right? In the short term, I think that emotions reign supreme. In the longer run, we see that fundamentals tend to matter more. But on any given day, emotions have the wheel. And what happens too is if you look at something like fundamentals like valuation, you see something like valuation. Markets can stray very, very far from their long-term averages in terms of their valuations. And oftentimes it is an emotional catalyst that sends it back towards the average.

So, let's say a market gets very, very expensive. Well, it can continue to get expensive for a very, very long time, years and years and years and years. It can be well, well north of its long-term average. That's in fact been the case in our stock market for some time. Oftentimes, though, it's an emotional catalyst that tends to send it careening back towards that average. Because even something like fundamentals are viewed through the lens of emotion, it is just simply impossible for humankind to interpret data in the total absence of emotion. So, even market fundamentals are looked at through a lens of emotion, and understanding the emotional lens of the moment becomes important because of that.

Casey Weade: Yeah. And you talk about the lens that we view things through, and I don't know if you see this, but I see quite a dichotomy in the way that investors view current changes in Washington, depending on how they view the current administration. How are you helping investors set aside their political bias, or at least recognize that political bias to help make better investment decisions?

Daniel Crosby: So, one of the things that we know is that we live in the most polarized political moment in the last 50 years here in the States. And the chasm between left and right has been widening for that entire 50 years. And today, it says the divide is as sharp as it has ever been. And you see this in political opinions and in economic opinions. We know that people tend to view the economy through the lens of whether or not their preferred candidate is in office. And we know empirically from research, thousands and thousands of data points have shown that when your person is in office, when your preferred party is in office, people tend to have better returns. They tend to take more risk, they tend to have lower bond allocations, lower cash allocations, and a higher concentration of US stocks.

When people's non-preferred party is in power, they hold more cash, they time the market more, they get more international exposure. So, people are in a very real way voting with their dollars. Now, the problem there is that when your non-preferred candidate is in power, which is half the country at any given point of time, these people tend to dramatically underperform the market because they're not taking as much risk. And this is a real problem because let's say half the time you're not happy with who's in the White House and you're going to, what, time the market and not take risk for that half the time. When we know that in red and blue administrations, the market has tended to be up into the right over long periods of time.

So, one of the things that I did, especially last year, and continuing into this year, was just try to help people divorce their political ideas from their investment ideas. And in fact, if you think about it, you're actually letting the “bad guys” win twice. If your non-preferred candidate is in office and your response to that is to handicap your earning potential, you've essentially lost twice. You didn't get what you wanted in the election, and now you're not getting what you want out of your investment portfolio. So, there are ways. I try to bucket those things. If you want to express a political opinion, you should. This country is founded on that, rather right or left, red or blue.

The way to do that is through activism, through voting, through getting out the vote, through campaigning, through supporting candidates, working a phone bank. That's how you support your political party. Don't try and support your political party with your investments because the engine of US excellence is larger than one person and one party.

Casey Weade: A big part of this, I think, is tuning out the noise and focusing on the information or the facts. And some would say, well, those things, those opinions, those are facts. These are things that are fact. They are information. You had an Orion behavioral finance article that came out last month that focuses on this concept of noise versus information. And right now is a really… It's always during COVID. It was very difficult to separate these two things, and we're right back to where we were back then. How do you help investors tune out the nonsense or even define the nonsense and remain calm?

Daniel Crosby: There's a few things that you want to look at. People use pressure and emotion when they're being noisy. You'll hear, "You've got to act now. You have limited time only. Operators are standing by.” Sort of time pressure is one of the hallmarks of noise. Emotion and bombast are also one of the hallmarks of noise. Good long-term critical thinking about markets tends to be pretty measured. So, if someone is screaming and shouting and pounding the table and turning red on cable financial news, that may be the information that it's noise. We also need to check people's credentials. I was at the gym the other day, and I saw there was a wrestler on, giving his opinion about the market. And you have to ask yourself, "Why should I listen to this person? What are their credentials?”

Then also hear what's in it for them. This is maybe the biggest one of all. We live in a day and age where so much of what gets promulgated on TV is really people talking their book and speaking to something that's going to provide them an economic or a political advantage. So, question the source, question the compensation model, question the melodrama. And then ask yourself if you're going to care about this in five years. You think about that is such a high bar, and we're actually perfectly positioned to talk about this here on the five-year anniversary of our last conversation. You think about something like COVID, which was literally earth-shattering. I've never lived through something as consequential as COVID, and a million Americans lost their lives, and millions and millions of people worldwide. And it truly was a very big deal.

But I think here we are five years later, the markets are up sizably over that five years. And so, you have to tease out, “Does this matter to me on a human perspective?” versus "Does this matter to my portfolio five or ten years hence?” Because the human toll of COVID was enormous, and we should rightly be moved by that, and we should be charitable and be thoughtful and be tenderhearted about the humanitarian fallout from viruses or wars or political upheaval, right? But again, the economic fallout from that, the financial fallout from that tends to be very, very different. And I think a lot of times people will see a war or a disease or some bad news, and they'll confuse the human impact of that with the potential financial impact of that, and oftentimes they're very different.

Casey Weade: In your book, you share the importance of taming uncertainty by focusing on what we can control, the controllable aspects in our lives. What would you implore investors today to focus on that they actually have control over right now?

Daniel Crosby: Yeah. So, one of my previous books was sort of my ten commandments of investor behavior, and the first chapter was You Control What Matters Most. And I was very intentional about putting that chapter first because I want to help everyday investors take the power back. I imagine you have a similar experience. When people find out that I work in finance, I often get asked a host of questions, all of which are unknowable, uncontrollable, and candidly unimportant in the long term. People will say, "What's the Fed going to do this month? What's the president going to tweet about? What's the virus going to do?” On and on and on, I have no idea. Even if I did know, the market's reaction to that is a second-order further unknowable consideration.

So, what we do know, though, is that we can do what you just said, which is control the controllable. So, what do we control? We control whether or not we work with a professional. People who get professional advice make 2.7 times as much terminal returns as those who don't. They're happier. They're better prepared for an emergency. They're less likely to get divorced. They have higher levels of marital communication. Money touches every part of our lives. And so, when you get someone in your corner who can help you make sense of that, it tends to raise all boats. So, whether or not you're getting professional insight into your financial life is within your power. Your behavior is within your power, whether you remain calm and long-term in your thinking is within your power. Your media diet is within your power.

One of the best predictors of whether or not someone makes a behavior change is what they are surrounding themselves with. You and I talked before we hit record. I've lost a bunch of weight in the last year. And one of the ways that I did that was not by having superhuman willpower, but by just not having Double Stuf Oreos in my house because if the Double Stuf Oreo is in my house, like a whole sleeve is going down.

Casey Weade: Just a sleeve?

Daniel Crosby: Yeah, just a sleeve. Just one sleeve. Yeah.

Casey Weade: I'm more of a whole box kind of guy.

Daniel Crosby: Yeah, I get it. I get it. So, the same thing is true of financial news. Every investor wants to be patient and prudent, and long-term in their thinking. That becomes a whole lot easier when you're not filling your mind with panic-ridden, emotionally-laden news every day in the form of cable financial news, or doom scrolling, right? So, your media diet is material, and it's within your control. So, the last thing I'll say and I talk about a lot in The Soul of Wealth is the biggest predictor of your terminal wealth is your income, and the biggest predictor of your income is the level of education and training that you've received. In a very real sense, your income is the engine of your wealth.

And so, do you have the letters behind your name that you need? Do you need to go back to school? Do you need to go get a vocational training? Do you need to learn how to weld? Whatever it is, how can you figure out something that's going to crank up that engine of your wealth, which is a much more reliable predictor of you reaching your financial finish line than trying to squeeze another 1% or 2% out of the market?

Casey Weade: Yeah. I often will have that conversation with young individuals that, "Which stock should I buy?” and, "What can you do to increase your income?” That's going to be a much bigger long-term impact for you than what stock you're going to buy today. You had a LinkedIn quote that ties into this really closely, and it might be my favorite quote that you've put out there. You recently posted on LinkedIn, “Fear isn't always a stop sign. Sometimes it's a spotlight that shines a light on what matters most.” You went on to share, "The size of your fear might just match the size of your opportunity.” How can someone leverage their fear today and turn it into an opportunity?

Daniel Crosby: I'm glad you liked that one. So, I've been doing, on my podcast this year, I've been talking about meaning and purpose in life, and I think it actually ties into our financial lives as well. We could talk about that in a moment. But when people look back on their lives, okay, they tend to regret not the things that they did, but the things that they didn't do. And what I was talking there in that post and in that podcast was a lot of times we try and play it safe. We let a practical sensibility talk us out of experiencing parts of life and perhaps even taking risks in markets that would ultimately lead us to the promised land to where we want to go. And I say there that, "Look, if you're scared of something, that isn't always a marker that you're being irresponsible. Sometimes it's a marker that you've landed on something that's deeply important to you.”

And I think the best way that I can illustrate this, Casey, is with a story from my days as a therapist. It's actually the first client I ever saw in therapy. I was 23 years old, which is a hilarious age to be giving life advice to other people. But here I am, I'm 23 years old, and I have my first ever therapy patient, and she comes in and she hands me six, like large manila-type envelopes. And I'm like, “What is happening? I was not ready for this. I was hoping for some garden variety depression or something.” And so, she hands me these six envelopes and says, “Hey, here's what brings me in today. All of my life, I've wanted to be a physician. All of my life, I've wanted to be a doctor. I've applied to six medical schools. I've heard back from six medical schools, and I cannot bring myself to open these letters, these responses from these schools, because if I didn't get in, everything I've worked for is for nothing. Everything I've worked for is for naught.”

And so, I was deeply confused for a minute. I'm like, "What do I say? What do I do?” And then, eventually, it dawns on me, having recently been through the grad school application process myself. I was like, “Hey, you've got a window of time to respond to these schools after they've admitted you, and if you don't respond, your spot goes to someone else.” And I said to her, effectively like, “Hey, it seems to me that in your best efforts to make yourself safe, to bubble wrap yourself against disappointment, you are bringing about the inevitability of the thing that you are most afraid of. The thing that you are most afraid of in the world is not getting into medical school. And guess what happens if you don't open these damn envelopes? You don't get into medical school.”

And that resonated with her. And she was able to open them, and she got in, and thank goodness, because then I really would've been out of ideas if she had not gotten into them. But I think we do this in markets too. People are so scared of not eating cat food in retirement. So, they sit in cash for a decade or two decades, thereby increasing the chances that you're going to eat cat food in retirement because you're not keeping up with inflation. So, a lot of times, the treasure that we seek is behind the door that we fear the most, and we've got to embrace that fear. And that fear is, actually, a gauge of how important or how valuable something is to us.

Casey Weade: Yeah. I've noticed that your conversations, your writings, the conversations you're having on the podcast, your posts over the last few years have shifted a bit. They're not as much about behavioral finance specifically, I want to say, or investing as they are about wealth and happiness. What's been going on? You've got another book that you're either just finishing up, that is specifically around purpose. What's happened for you over the last few years that shifted your mindset to be focused so much on wealth and happiness right now?

Daniel Crosby: A couple of things. On the micro level, two things. I had a health scare that I won't spoil it because I want people to read the book, but I had a health scare that ended up being nothing. But it was very scary for a moment, and very painful for a moment, where I did not know what was up with me or what was causing me all this pain. I started having really bad migraines, in particular, and couldn't pinpoint the source of the problem. And there was this moment where my wife was driving me to the emergency room after we had just spent the last couple of weeks going to all these specialists who could find nothing. And I was sitting in the front seat of my wife's car, and I'm crying and I can't figure it out, and I think I have a brain tumor or something. And I'm like, my three children are going to grow up fatherless. All these catastrophic things are going through my head.

And I told my wife like, "Look, I would give it all up for relief from this pain,” all up meaning money, right? Like, I would give it all up for answers and for relief from this pain. And luckily, a couple of weeks later, I got those answers and I got that relief, and it was no big deal. But in that moment, you see that a sick person only wants one thing, and it's not more money. So, that was really formative for me. That was on the micro level. On the macro level, when this country was founded, we're coming up on 250 years, when this country was founded, not quite 250 years ago, 85% of the world was living in poverty. So, again, this is not that long ago. 250 years on if you condensed human history down to a one-year timeline, 250 years ago is like December 30th at noon or something like that, like this is not that long ago.

And yet at that time, 85% of the world was living in abject poverty. So, that's $2 or less a day in today's dollars that they have access to. Today, that number is about 8.5%. So, for most of human history, we have just been squeaking by, trying to get enough calories and enough safety to eke out 30 or 40 years of a very tough life. But because of capitalism and because of democracy and because of technological innovations, medical innovations, life is materially richer than it's ever been before. And yet, we see that despite the fact that the average American home size has tripled post-World War II, people feel less well off than they did then. People are sadder. Suicide is spiking. Teens are more isolated. People are lonelier. We have a mental health epidemic in the richest country that the world has ever seen, the most prosperous time.

And so, I've become obsessed with this question, and that The Soul of Wealth book was the first step into this world. How do we bridge that gap between material abundance, which we have in great supply, and happiness or a life of fulfillment and purpose? Because that's a connection we haven't societally been able to make in a meaningful way yet.

Casey Weade: It makes me think of the studies around income and happiness and how they, well, at 75,000, 125,000, depends on which study you look at. Somewhere around 100,000, you're going to be happy, and you won't have to worry about anything. And yet what we're finding is as people are getting wealthier and society has become wealthier, especially here in the United States, depression is at all-time highs. Loneliness is at an all-time high. So, should we be putting any weight in these income and happiness studies?

Daniel Crosby: Yeah. So, I did a whole chapter on that in The Soul of Wealth, the study that you talked about. So, it originally said $75,000. It would be a hundred in today's dollars, right? So, $100,000 today is where up to that point of $100,000 of income a year, you see large gains in happiness for every incremental dollar. And then about $100,000 a year, it flatlines greatly. But there's a little nuance that we need to introduce to that conversation because that study that there's no blood test for happiness, right? I can't give you a thermometer or prick your finger and see how happy you are in any objective way. We have to operationalize and standardize this measure for happiness.

And the measure for happiness they used in that study was leaned heavily on physical symptoms. So, one thing that money does well is it makes you physically comfortable. You have enough money to go to the doctor when you're sick. You have a warm bed to sleep in. You have enough food to eat. You're not worried about gunshots at night if you make enough money. And so, money does a good job, really good job of buying us an absence of physical misery. And that's meaningful. That's worth caring about. But when you look at those studies, you see a couple of things. First of all, 30% of people, their happiness plateaus until they hit $100,000 and then it takes off north of $100,000 because now they can really do the thing that they are excited about.

Gandhi said, I'm paraphrasing, but Gandhi said, "To a poor person, bread is God,” because if you're poor enough, you spend all your time sort of scrounging for your next meal and worrying about how to get enough calories or a safe place to stay. And once you've got that squared away, now you can worry about love and friendship and purpose and religion and all the higher-order human stuff. And that's nice. So, for about a third of people, happiness really takes off north of $100,000. We also see that happiness is very genetically linked like people have a set point for happiness, the way that they have a set point for weight or certain other types of body composition considerations.

So, one thing you can do to be happier is to pick better parents. And we see that about 15% of people, there’s no relationship between money and happiness. They just have different problems. Like, either something is going on in their life like a tough situation or there’s a strong organic or genetic component to the reasons for their unhappiness. And so, money just doesn’t help much and it doesn’t hurt much. So, it’s really complicated. But I guess the final thing that I would say is this. The first thing is money does a good job of buying you the absence of misery and it buys you a ticket to try. Like money can buy you enough freedom and enough time and enough health to try and do the stuff that matters, but you’ve still got to go get it. Like you’ve still got to go get after it.

The other thing we know is that how you spend your money, it makes a big difference. People who spend on experiences over things are more happy. People who buy their time back who get out of a hated chore, for me, it’s mowing the lawn, like I’ll never do that again, God willing. Never mow my lawn again. And then the other thing that I’ll say the final thing, there was a cool study in the book about relationships and happiness. So, people who buy a fancy car with their money tend to have very limited boost in happiness, and it’s very short lived relative to how expensive a car is.

But people who join a car club, right, people who buy a Porsche not to flex on their neighbors or to just try and show off, but people who buy a Porsche to join the Porsche Club of Carmel, Indiana, these people have an enormous boost in happiness because now they got new friends and they can deepen their interest and they have a place to go on Saturday and they have people to go on road trips with. And so, relationships are the best predictor. Good relationships are the best predictor of a fulfilling life. So, anything you can do to spend money to deepen your relationships, even if it’s by a Porsche, is going to help you a lot.

Casey Weade: Yeah, it makes a lot of sense when you’re on your way to retirement. You get to a certain level of income and now you have the opportunity to only focus on the things that you want to do or you create more time freedom to focus on those activities that bring you more meaning in your life. However, it seems like there’s another paradox here. There is some research that you point to your book that says that we are in a time famine with a lack of available hours to contribute to our wellbeing and happiness. But then how do you reconcile that with retirees with ultimate time freedom that are suffering from record-high depression and reduced happiness levels?

Daniel Crosby: Yeah. So, there’s a couple of things. One of the things, like everyone, you talk to basically anyone, you see someone at the store, at the ballpark, or whatever, you say, “Hey, how are you?” “Oh, busy, busy. Oh, so busy.” Well, we have more disposable time than any generation ever. I mean, we have more free time. Thanks to things like dishwashers and washing machines and shorter work weeks and more holidays. We have a lot of disposable time. But if you look at the gains that we’ve made in time over the last 50 years, and they’re considerable, it’s a couple hours a week, which is a lot. Like if you directed that in a good way, we have filled that time with one thing, like minute for minute, and I bet you can guess what it is. Got a guess?

Casey Weade: Screen time.

Daniel Crosby: Screens. Every minute that we have clawed back from the clutches of human misery and all the hard work we used to have to do as a society, we have now given over to watching TV and playing on our phones. So, it doesn’t feel substantive. It doesn’t feel substantive because we’re effectively squandering the time that we have. We had given it back minute for minute to screens. And so, one of the things that we have to do, one of the conversations that we have to have is how do we take those gains that come from nice things like technology and being able to eat out and do these things that save us time and how do we spend that time in a way that is personally fulfilling?

With respect to retirees, Chapter 1 of the book is worth the cost of admission, I think, because it basically gives the five facets of a happy life. In Chapter 1 of the book, I talk about, look, here’s the research. There’s five things that lead to a life of flourishing. And when you look at those five things, one of them is called positive experiences, which is basically shorthand for fun and leisure. Retirees have lots of time on average for fun and leisure. And when most people conceptualize retirement, that’s what they’re thinking of. Like, finally, I’ll be able to golf. Like, finally, I’ll be able to spend time with the grandkids. Finally, I’ll be able to go on long walks on the beach, right? Because you can’t do that when you’re working. That’s good. That’s important stuff. And it’s one facet of a life well lived.

But if I could just breeze through the other four real quickly, one is deep work, one is strong relational ties, one is meaning. So, working for something bigger than yourself, like as part of a team or part of a church or something like that. And then the last one is advancement, which is personal growth, learning new things, being better today than you were yesterday. If you think about work, work is good at all of those things except for fun and leisure. Work gives us engagement. It surrounds us with people, teammates. It helps us work on projects that are bigger and more enduring than ourselves and it has natural opportunities for advancement.

The average retiree is trading a work life where four of life’s five deepest needs are met for a retirement life where one of life’s five deepest needs are being met. And so, people need to be intentional about planning for their time and not just their leisure. Retirees need to be asking themselves questions, like, what am I going to do to connect with people? What am I going to do to stay sharp and continue to learn and grow? What am I going to do that’s bigger than me that’s spiritual or philanthropic or charitable or team oriented? These are the sort of questions we need to be asking, and people are way over-indexed on spending their time on fun and leisure, which gets old super fast.

Casey Weade: Yeah. I think there’s been times in my life when I’ve had nothing but fun and leisure for extended periods. I’m playing golf every day, hanging out with the family, going to church, just doing the things that are fun, spend time on vacation, going on the beach, all these things that you talk about. And what I often say is when I’m not stressed, I’m stressed. And I think, it feels to me that anytime that I am unhappy, I need to artificially manufacture some type of struggle in my life. I think the struggle creates meaning for me. And in retirement, does that hold true? Do we need struggle in our lives? And do we need to artificially engineer some of that struggle when we have all of this time freedom and we have all of the wealth that buys us the easy life?

Daniel Crosby: Hans Selye, the seminal stress researcher came up with something that’s called the inverted U-curve of stress. If you think about two plot lines, one is performance and one is stress level, the optimum performance or happiness or whatever you’re trying to measure occurs at a moderate level of stress. People who are stressed out of their minds don’t perform well, whether it’s an athlete or someone on the job or a parent or whatever it may be. There’s a crippling level of stress, there totally is, and it leads to poor performance and poor mood. But there’s also a crippling level of boredom or even a crippling level of leisure. And the complete absence of responsibility or absence of structure leads to outcomes that are as negative as crippling stress. And a lot of times, people don’t think about that, because, look, as I sit here today and I think about what I have on my calendar for the rest of the day and even the rest of the week and the month, it’s a lot. Like, it’s a lot. And so, I think most of us fall down much further on the side of too much stress than too little. And so, we sort of mistakenly long for just nothing to do in an empty calendar, but it’s just as bad. I mean, it’s just as bad for your mental health as too much.

Casey Weade: Yeah. You mentioned that when it comes to our income levels or our wealth levels, that some of those studies can get it wrong. We get them thrown out the window because we inherit some of this unhappiness, especially when it comes around money. You talk in your book about financial scripts. I just want to talk about those a little deeper because I see this come up time and time again. This seems to be one of the most common themes that we see when we’re working with clients, especially on the scarcity side of things. So, they’re having trouble spending in retirement, having trouble taking risks, having trouble actually enjoying what they’ve worked so hard for. Let’s talk a little bit about inherited money scripts and how we can better understand our relationship with money through those scripts and ultimately make healthier decisions.

Daniel Crosby: Yeah. I think the first thing to understand here is that you do have a money script, right? You inherited this. And in the same way that a fish doesn’t know what water is, right? Like, a fish doesn’t know what it means to be wet because it’s so immersed in water, we are so immersed in typically our parents or our cultures or our society’s attitudes about money. These things are so pervasive that we don’t even know we have them until oftentimes, I think a lot of times, people’s first experience of understanding that other people see the financial world differently is having a romantic partner, getting married, living with someone, and understanding that, oh, like, this person views money very differently than I do.

In terms of the specific scripts, there’s a handful of them, but I did some research a few years ago where I interviewed married couples, hundreds, 400 and something married couples, and I asked them, what do you fight about when you fight about money? They were more elegant than that. That was effectively what it was. The number one answer was whether money is best used to enjoy today or to secure tomorrow. And if you think about this, most people grow up in households where one thing, one of those two considerations is emphasized to the exclusion of the other. And in almost like a very– in moderate way, like they’re kind of all one thing or all the other, but a happy financial life balances those realities.

And what we find is that people are very judgmental. People who are in the “enjoy today” camp, when they marry or they partner with someone who is in the “save for tomorrow” camp, they tend to think they’re lame and they’re no fun and they’re a stick in the mud. And then, conversely, people who are in the “save for tomorrow” camp, look at the “enjoy today” camp and they think they’re frivolous or they’re unserious or they’re irresponsible. And we get very judgmental about these things. The truth is that happiness is found like most things in life in moderation.

And we find this across different money scripts real quick, a couple of the others. There’s ones around communication, whether you direct or indirect in how you communicate about money. There’s ones on whether money is best used as a collective or an individualistic good. So, this one was interesting because it was gender linked and culture linked. So, we found that women on average, non-white, non-Western folks and women tended to be more collectivistic in their thinking. So, if my grandma needs her light bill paid, I’m going to help her because this is not my money. This is our money collectively, right? As a family.

Men and white folks and Western folks tended to be more individualistic, sort of put your own air mask on first to say, look, I’m going to take care of me, you take care of you, and that’s what we’re going to do. Like, we’re all going to be responsible for ourselves. If you think about these things, to a degree, they’re both positive, right? Being generous is a good thing. Being responsible is a good thing. Keeping your own house in order is a good thing. But true wealth is found in the synthesis. So, those are the two things that I would say. You have a money script. It’s only whether or not you are aware of it and how it’s at play in your life and driving your decisions subconsciously. And then the second thing is, once you become aware of that, if you’re far to the left or to the right on sort of a continuum of ideas about money, I think the job is to move toward the center.

Casey Weade: Let’s talk about the job. I grew up on that frugality side. The frugality addiction was something that I think was passed down to me and I’ve worked hard to adjust that and change that and focus on the things that really matter the most. Now, I think most of the families that we work with, they didn’t get wealthy because they were frivolous, right? They got to where they’re at today because they had some level of frugality and that was probably passed on from them just like it was for me. But now, it’s no longer serving them. They’ve already made it, right? How would you help them rewrite or help me rewrite that script using the A, B, C model that you lay out in the book, adversity, beliefs, consequences.

Daniel Crosby: Yeah, I love it. So, the first thing is, of course, to become what’s the old adage from like the 12-step program? The first step is admitting that you have a problem. I grew up in a household that sounds like similar to yours. My dad is still a financial advisor. And I grew up in a religious household where we couldn’t say bad words, and debt was considered a four-letter word, like all the others. I mean, my dad was so maniacal about paying off our house. I mean, we never went on a vacation. All that man, he was single-minded in trying to pay off our house and save for retirement. Never went anywhere, just cheapest of everything.

And then what happened is, at some point, his career as an advisor kind of took off. The kids were off and settled and on their own, and he had way more money than he needed. And at that time, my mom’s health had started to decline. My mom’s now in a wheelchair. So, when they were in the early days, they were save, save, save, no fun, no vacations, and now, they kind of made it, but now their health is gone. They didn’t do a good job of balancing that.

So, working with my dad, who is of course my advisor, one of the things that he has helped me do is to try and shake that tendency to be my father’s son and to be so maniacal about saving and investing and trying to square away certain milestones in life. And I think the only way to do that is to have a yes, like a purpose, or a why that’s bigger than the no of your fear, right? So, if you think about the no of your fear, what’s the fear that undergirds like intense saving behavior, right, that you’re not going to have enough, that you’re going to be caught unprepared, that you’re not going to be ready, that you’re going to eat cat food in retirement, whatever.

You have to figure out your yes that’s bigger than that. And for me, that yes has been time with family. It’s been an acute awareness. I have a 16-year-old daughter and it’s like, look, I got two years with her. You spend 95% of the time you’ll ever spend with a child in the first 18 years of their life. And I’ve got two more years left with her at home, and then she’s going to be off to college and jobs and marriage and kids and her own stuff. And so, yeah, we’re spending a lot of money on travel this year and next year and the year after because it’s important to me to make memories with her and her siblings. And it’s more important to me to make memories than it is to have the incremental $10,000, $20,000, $30,000 in savings. So, I think the first thing is to recognize that you have a problem, or not even a problem, just an opinion that you have a tendency, and then to help you find a why or a purpose that’s more important to you than what that tendency is protecting against.

Casey Weade: Yeah. I see the way you’re living today really reflects a LinkedIn post that you had a few days ago. You said you think about death every day, and I don’t find it morbid. I find it motivating. You said that death can actually save your life, right? You had this health scare. And so, you have ended up in this place, this memento mori place, right, where you’re remembering death. What would you do differently if and how would you embed that earlier? It seems like most people only experience this and get to live in the moment and do the things that you’re doing, focus on these things, and think about death when they’ve actually had this kind of fear, they’ve had this kind of scare. What would you tell others about their death and remembering that could help them live a bigger life today?

Daniel Crosby: Yeah. So, I actually just recently took it off because it was scratching up my watch, but I have this bracelet, this memento mori bracelet that I wear, that I love to wear. And it’s just this basically remember that you’re going to die. And that can feel morbid to people, but we’ll talk about that in a moment, but even beyond that, I think the larger call is to remember the fleetingness of life and opportunity.

Go back to what I talked about with my daughter and I have three kids, the oldest is 16, but that time is passing and if you treat your time with your children like an unlimited good, then you don’t take advantage of it or treat it very preciously when you realize that there will be a “death” of their time at home or the death of any time or season that you find yourself in professionally or personally. When you realize the fleeting nature, the finitude of that thing, then you start to treat it more preciously. And that’s what I was saying about life there.

I feel lucky, I’m named after my grandfather who died on the day I was born, two years before I was born. I was born on the two-year anniversary of his death. And I look just like him. We have the same interests, we have the same name. I was born on the anniversary of his death. And so, like growing up in the shadow of my grandpa, who was a very successful businessman and a very smart guy, he died when he was 42. I mean I’ve already gotten more years on earth than my grandpa ever did.

But growing up, hearing about him and how much I was like him and how much I look like him and sort of having this special connection, impressed on me at a very early age that we don’t always get 83.7 years or whatever the actuarial tables tell us we get. And so, you have to live that life with urgency and you have to be aware of these, we’ll call them tiny deaths in your life. Whether it’s the end of a season of living in a certain place, the end of a season of a child at home, whatever that may be, it’s not depressing. It just gives life its savor and its urgency so you can take advantage of it, too, to fullest effect.

Casey Weade: Yeah. I’m curious, in the Standard Deviations podcast, you said this is the year of meaningful living. I have to assume that given that this is the year of meaningful living for you, then maybe you’ve implemented some daily practices or some unusual, unique practices into your daily life to ensure that this truly is a year of meaningful living for you.

Daniel Crosby: One of the things that we find in behavioral finance and psychology broadly is that there are certain things that are so simple and they’re so powerful, but they become easy to overlook because of their simplicity. In the book, I call these River Jordan problems. There’s a story in the Bible of a guy named Naaman, right, who is a powerful centurion, powerful warrior, powerful community leader, but he has leprosy. And so, he goes to the local holy man, and he says, “Hey, I need to be cured of my leprosy.” And the holy man doesn’t even come out. He just like sends a servant out and he goes, “Yeah, hey, tell him to go bathe in the River Jordan.” And the servant comes back to Naaman and says, “Hey, the holy man says go bathe in the River Jordan.” He sent a servant out to say it. And this powerful rich guy becomes kind of pissed off because he’s like, “What?” There’s a hundred better rivers, that River Jordan sucks. Like, the River Jordan’s not nice. He couldn’t even come tell me himself. Like, he’s sort of offended by this. And his servant says, “Look, master, if he had asked you to do something hard, you would do it. So, why don’t you just do this small easy thing?” And so, Naaman goes and washes in the River Jordan and he’s cured, right?

But he almost didn’t do it because it seemed too unspectacular. I say that because one of the things that I have started doing this year is counting one blessing, like being grateful for one thing at the end of each day. Sometimes that’s prayer, sometimes that’s writing it in a journal. At certain points this year, it’s been by writing a thank you letter. There’s research that shows that people who explicitly call out one thing they’re grateful for in the day, see a boost in their mood by up to 10%, which is equivalent to taking psychiatric medication. I mean, that’s like an enormous– that’s like a Prozac level boost off of just being, saying, “Hey, this is what I’m thankful for today.” And people will fail to do it because it’s a River Jordan problem. It seems too easy that there’s no way I could have a 10% boost in my mood just by being grateful for one thing, but you can.

The other thing the research shows that I talked about in The Soul of Wealth is writing a handwritten letter. And I’ve done this three times this year, just three times in whatever, five or six months, but it’s so powerful, writing a handwritten letter to someone who made a positive impact on your life, but you never told them. So, I wrote, this is, hopefully my wife will forgive this story. I wrote a letter to, and I had to hunt her down, to a girl in sixth grade. I changed schools in sixth grade and I went from being like big man on campus to like dorky kid nobody knows and whatever.

So, I changed schools in sixth grade, which is a very hard time to be a lonely kid. And I went to this school dance at my new school and I knew no one and no one was dancing with me. And it was just the worst day of my life. Right at the end, this woman– oh, well, now she’s a woman. This girl comes and says, “Hey, do you want to dance?” And I got my one dance that night. And we never really spoke again. I mean, we were like casual acquaintances through high school and stuff, but we know it was never anything, never a big deal. But it was such a big deal to me. And so, I wrote her earlier this year and I was like, “Look, I know this meant nothing to you. You forgot that this happened. But on the worst day of the hardest time of middle school, when I was as lonely and as unseen as a person can be, you bailed me out. And that means a lot to me.”

And it was really sweet. Like, it was really nice. I mean, she probably thought I was a serial killer, but it was great. It was a great moment to be able to say we’ve all had these experiences of someone who did us a kindness that put us on a good path or helped our lives in ways that probably didn’t register for them at the time. And so, taking that moment to thank them also leads to up to a one-month boost in happiness. So, for me, the year of meaningful living has been trying to be about being more grateful and more gracious with people who’ve been good to me.

Casey Weade: Oh, that’s beautiful. So, I asked you this question five years ago, and I can just see that so much has changed you. You seem like a different person today than you were five years ago, and I love seeing that. And I’m curious how you might answer this differently. I’ll have to go back and now listen again to the very end and we’ll have to compare answers. But you’re on the Retire with Purpose podcast, so I have to ask you, what does it mean to you to retire with purpose?

Daniel Crosby: So, as I’ve done, I’m writing this book which is on the hunt for a publisher, right, my next, next book, that’s all about finding a life purpose. And when I told people I was writing, they’re like, “What’s your next book going to be on?” I say, “Well, the meaning of life, like the purpose of life.” And people kind of get nervous and laugh and like, “Huh, what?” Like, that’s sort of too big of a thing to get your arms around.

But when I got into the research, I found that there’s three things that lead to a life of purpose and it’s really quite practical. And I hope this framework means as much to your listeners as it does to me, because for me, it was believing, belonging, and becoming were sort of the three things. So, what do those mean? Believing, we find that people who have a purpose in life have some sort of a playbook, right? It’s a personal philosophy, a personal credo, religion, spirituality. They have some sort of map for making sense of the world they have something they believe in.

The second thing is belonging, mattering to someone and having people who matter to you. Having a tribe, a family, a spouse. Giving and receiving love is the belonging piece. And the third piece is becoming, having a bright sense of the kind of person you want to be. Having a vision for your own growth and a sense of who you want to become. So, if you’ve got those three things, a personal roadmap for living rules you subscribe to, people who you love and who love you in return, and a vision for the kind of person you could grow into, that’s about as good as it gets. That’s what purpose is in the most practical way that I can tell you.

Casey Weade: Love that. I already wrote that down for myself. And I’ll be thinking about that the rest of the day. I’m sure I’m going to share that with my wife here on date night. And if you’re listening, you say, “I really want to create better connections between wealth and meaning,” then take advantage of our partnership here with Daniel. We’re giving away free copies of his book. All you have to do is write an honest rating and review over on iTunes. Shoot us a text. We’ll verify your iTunes username. We’ll send you a link to get your book. All you have to do is text the word “Book” to 888-599-4491.

Daniel, this has been awesome. I thought our first interview was fantastic. I think you one-upped yourself here and I’m sure it’s going to be even better. Hopefully, we don’t wait another five years, but I look forward to our next conversation.

Daniel Crosby: This was such a soulful conversation, man. Thank you for all your preparation. This was great.

Casey Weade: Thanks, Daniel.

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