Most people were never taught how to manage money. Yet they’re expected to navigate rising housing costs, student debt, investing, retirement planning, and an economy that often feels stacked against them.

In this episode of Career Sessions, Career Lessons, JR Lowry sits down with Carrie Joy Grimes, founder of WorkMoney and author of the USA Today bestselling book The Joy of Money, to explore why financial success has far more to do with psychology than spreadsheets.

Carrie explains why shame and avoidance keep so many people financially stuck, how small behavioral changes compound into long-term wealth, and why the biggest obstacle to financial security often isn’t a lack of knowledge—it’s the stories we tell ourselves about money.

They also discuss:

Why “I’m just bad with money” is one of the most damaging beliefs you can have

The surprising connection between money habits and career success

Why budgeting should create freedom—not guilt

How to overcome financial avoidance and build confidence one small step at a time

Why chasing the next hot investment rarely beats mastering the fundamentals

How to think about raises, retirement savings, and building wealth in today’s challenging economy

Whether you’re just starting your career or trying to gain greater financial confidence after years in the workforce, this conversation offers practical, encouraging advice that can help you take control of both your money and your future.

Subscribe to Career Sessions on YouTube and wherever you get your podcasts for weekly episodes like this.

Check out the full series of “Career Sessions, Career Lessons” podcasts here or visit pathwise.io/podcast/. A full written transcript of this episode is also available at https://pathwise.io/podcasts/carrie-joy-grimes/.

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Listen to the podcast here

Why Smart People Get Financially Stuck (And How To Break Free), With Carrie Joy Grimes

Even with a stock market near all-time highs as we record this episode, a lot of people are feeling pretty gloomy about the economy. The cost of living keeps going up, becoming a homeowner feels increasingly unreachable to many, and a lot of people feel financially stuck. Moreover, they feel financially insecure. It’s not necessarily related to how much they’ve scrolled away, but due to the sense that they’re not good at managing their money, as if they somehow missed out on a magical money gene that everybody else got.

Here’s the thing. Most people were never taught how to manage their finances, and then they get dropped into an economy that’s often designed to profit from their confusion, debt, and financial anxiety. That’s where my guest, Carrie Joy Grimes, comes into play. Carrie is the Founder of WorkMoney, a nonprofit with millions of members, nine million members, focused on helping everyday Americans build financial security.

In her new book, The Joy of Money, which made the USA Today bestseller list, she makes an argument that some people think sounds simple, but it’s pretty radical. You can be good at money, and you can learn to become good at money, even if you grew up in chaos, even if you avoid checking your bank account, made financial mistakes that you’re still trying to recover from, and shame has convinced you that everybody else out there somehow understands money better than you do.

The conversation that we’re going to have is much more than about budgeting tips or cutting back on gourmet coffee. What we’re going to be talking about is the psychology of money, why shame and avoidance keep people financially stuck, why traditional financial advice often fails ordinary people, and how building financial security is as much emotional as it is mathematical.

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Carrie Joy, thanks so much for being on the show with me.

Thanks for having me. I’m excited to be here.

We are going to talk about a very important topic, which is how you manage your money and build wealth, particularly in a very uncertain world and uncertain economy. A lot of people don’t see themselves as good with money. You have said you saw yourself as one of those people. What was the turning point for you that led you to realize that you could learn this stuff?

Shifting Your Money Story

This is going to maybe sound hokey, but it’s very true. I decided to let a choice I made change my life. I ended up backing into a lot of behavioral science about behavior and money. What happened is I had gotten myself into a little debt with my boss. I showed up on my first day of work at this job. It was my first big professional job. I was working poor at the time, so I didn’t have great shoes, and I couldn’t afford to eat out.

The team was going out for dinner that night, and it was one of those mandatory works that you had to go to. It was my very first job, and I hadn’t gotten my first paycheck yet. If you all can remember back in those days, I didn’t have the money for a big dinner out yet, and I didn’t have the money to upgrade my wardrobe. He said, “You got to go.”

After dinner, he paid for my dinner, and then he gave me $100. He was like, “This is for some shoes.” That was the most mortifying thing to have a man that you work for give you money. He wasn’t wrong, but I did not want to have that feeling ever again in my life. I’ve been in debt before, but that felt serious. I ended up paying him back in a few weeks.

That experience where I could pay him back, I was like, “That was some good money behavior. What if I’m good at money?” I had been telling myself for years I was bad at money. Everything and every mistake I’d made was more evidence that I was bad at money. I had this intensive period where I said, “If I can do that with him, I could pay off this credit card.”

I took that same mindset, and I was pretty ruthless with myself. I had a whole new money story. I was like, “I can be good at money. I can do it.” I tried to catch myself doing something good. I worked it pretty hard. That process built the muscles and the neurology for me that I could. That changed my money life. It led to a whole bunch of different learnings and experiences. I got into the science around all of it, like, “Why did that work? What was different about that time?” That was my experience. I let a random plate of barbecue change my money life.

We’ve all collectively discovered behavioral science, whether we got it from Malcolm Gladwell, the Heath Brothers, or Daniel Kahneman, if you wanted to go deep into the Nobel laureate version of behavioral science. Since it’s so out there and it’s so entrenched, once you understand it, you realize how entrenched it is in the way that people market and advertise to us. That includes the way they market and advertise to us about how we save and spend our money. If you’re not tuned into it, at least at enough of a level, you’re going to get manipulated by it. That’s a key thing you’ve got to understand.

That’s super right. Many of us didn’t grow up with clear conversations or teaching about money. There are these financial literacy or education classes in high school, which are great, but the way we learn money is mostly through our families of origin and the culture around us. There’s not a lot of substantives, reliable, good information that people have access to as they’re growing into their money lives. There’s tons of information out there. You can hit the internet, but it’s hard to tell good from bad in some cases.

A lot of people I talk to have this vague sense that they’re doing something wrong, and they feel ashamed of themselves for it. Those two things, what you said, are so important. Those are the pain points that a lot of companies take advantage of to increase people’s spending or get them to use financial products that are probably not a good idea. Learning how you are with money is such a great first step to not only making better choices yourself, but being able to resist the pretty powerful forces of psychology and advertising that are pulling us in directions that aren’t always good for us.

That’s true. To your point, a lot of times, you get tricked, for lack of a nicer way of saying it, into believing that you need something that’s more complex than what you need. For most people, it’s to live within your budget, pay down your debt, and save a little bit each month. People think, “I’ve got to go invest in crypto.”

We could probably have a whole conversation about all the get-rich-quick schemes that are out there, whether it’s investing in AI, tech stocks, prediction markets, crypto, or whatever. There’s a lot of that that’s been going on over the last couple of years or so. In my coming-of-age era, if you weren’t working on a dot-com something, you were an idiot. I was working at McKinsey at the time because I needed a paycheck. Everybody believed that they were going to get rich. A few people did.

Most people ended up working in companies that were failing. It’s like having a cheat code. It’s like, “I want a cheat code that’s going to allow me to get fabulously rich without ever having to work at it.” It’s very harmful to people’s psyches. There’s a lot of that going on that makes people think in many of the wrong ways about how to think about their career and also how to think about their financial habits.

Mastering Personal Finance Basics

That’s such a good way to say it, too. What’s interesting about money is, you’re right. I say this thing all the time, which is that money is not rocket surgery. It’s not that hard. For most of us, the basics are the things to do to make us wealthy. The biggest problem most people have is they don’t make enough money. That is something that is dealt with through education and career advancement. There are lots of ways we can talk about how to get more coming in. That is the biggest problem most people have.

The next biggest problem is that when people do look at their money, it feels very confusing, and it feels like it’s unclear what to do. That one is a great problem because it’s very solvable. It is having a budget. It is getting out of high-interest debt. It’s having 3 to 6 months saved up so that you don’t have to borrow expensive money to solve problems. Everybody gets problems in their life. It’s maxing out your tax-advantaged retirement accounts.

The money that people can make by maxing out their 401(k), their 403(b), or their IRA is so much more money than they’re going to make by taking risks with different individual stock investments. I’m a stock picker. I don’t do very much other than target date funds and put a lot of my money into index funds. Frankly, this is Warren Buffett’s advice. Warren Buffett is the only person to run a fund that beats the overall stock market for many years, except in the last couple of years.

Warren Buffett did not beat the stock market himself. In his will, when he passes away, he leaves his money to his wife. Ninety percent of his money is directed in the will to go into an S&P 500 tracking fund, an index fund that tracks parts of the market. I don’t think of myself as being a better investor than Warren Buffett. I don’t think most people in the world are better investors than Warren Buffett.

I always say that if you have special knowledge in an industry, or you understand a product or a service in a way that gives you an advantage, that’s one thing. If you’re like most of us and you’re trying to figure out, “How do I build wealth? How do I get myself to a good retirement?” The answer is pretty clear. It’s budgeting. It is taking a 401(k) match if you get one from your employer. It’s getting out of high-interest debt. It is saving up 3 to 6 months in an emergency fund. Finally, it is figuring out how to max out all of your tax and retirement accounts. After that, that’s when individual investment choices become clear.

The number of folks I talk to don’t understand how much more you make because of the tax benefits. They’re like, “Why shouldn’t I go after this stock or that one?” I say, “Have you done the basic, like maxing out your 401(k)?” They’re like, “No.” I’m like, “Let’s put your money there first.” Especially folks who are professionals who are figuring out their careers, I don’t know about you, but I remember all the paperwork, the HR lady telling me about all the things, and being like, “I don’t know how much to take out of my paycheck.” It is worth figuring that out first and checking the boxes.

Especially if you get a match from your 401(k) employer, it’s free money that you don’t otherwise get unless you opt into that. You’re never going to have a chance to get that free money again if you don’t opt into it year after year.

It’s part of your paycheck. Not taking it is like voluntarily taking a pay cut. This is so crazy. I did the math on this. There are some financial people out there who will say, “You should eat rice and beans and pay down your credit card debt. You should have no joy in your life. You should treat yourself like a prisoner in your own house.” I’m a big believer in getting out of high-interest credit card debt. Let me be very clear. The math on this is fascinating.

Maximizing Employer Matches

If you get an employer match, if you take that free money, and you put that free money into your 401(k), you are going to make more money than you would save by paying down your credit card debt. It’s one of the few things I tell people that they should be doing before they tackle the high-interest debt because you end up with more at the end of the process than you went right to debt. Folks who are professional people who work in businesses where your employer offers a match, the benefits of it are not that understood by most people. The compounding interest effects of that are so powerful that they beat what you end up owing the credit card company, which is crazy.

I will share an example. I’ve shared this with my kids and my wife before we were married. If you put $2,000 into an IRA many years ago, that’s now worth over $100,000. It was not invested in crypto. It was not invested in tech stocks. It was invested in a large-cap growth fund. It rolled. This is the power of compounding. It’s worth 50 times what it was before.

When people talk about the importance of saving a bit in your 20s, if you’re doing that in your 20s, you get 10 years of that compounding that you don’t get if you don’t start until you’re near your 30s. All of this, to your point, is not rocket science. It takes a bit of discipline. If you try to throw too much discipline on yourself, it’s not going to work because it’s a starvation diet.

Removing Guilt From Your Budget

I remember there was a study a while back that said that one glass of red wine is not the end of the world for your health. Everybody was drinking red wine all the time. A new study came out and was like, “Alcohol might be worse than we thought.” This is going to sound like that because it’s going to sound like I’m giving people permission, but the behavioral science on this has been repeated many times. Folks are much more likely to stick to a budget if there’s a little bit of joy in it or a little bit of a reason that that’s what the money is for.

I always say to people, “Treat yourself reasonably. Have something that you can afford that makes life a little bit more enjoyable within the bounds of reason.” That’s not because people should live good lives, although I do think that, but it’s also because the science on this is pretty clear. You’re more likely to stick to something if you’ve got a little bit of a reason to keep going.

It’s interesting because there are a couple of things I say that are not popular with other financial experts because they don’t follow the shame-based advice trail of like, “You’re the problem if you’ve got problems. It’s you. You are the problem. You should be punishing yourself for doing these impossible-to-continue behaviors.” When you don’t succeed, you have to go back to those financial people for more help.

There’s this cycle of a lack of success that breeds more engagement with financial experts that is a disincentive for people to succeed. It’s part of why I wrote the book. It’s because I got so frustrated by what was out there. I run a big organization of nine million members. It’s about how people do better with their money. It’s a nonprofit. It’s like the AARP, but about money for people. You can be any age. We don’t send you an envelope when you turn 50. That makes you feel old. It’s a little different.

My daughter started college. She finished her first year. She’s becoming an adult. I had this moment as a mom where I realized this economy is even harder than the economies that we’ve all been in. I’m Gen X. It wasn’t easy for me, but it certainly was not this volatile. I had this moment where I realized I wanted her to have something that would give her a roadmap.

Over the last few years of talking to nine million people, where we text, email, and call people weekly, I’ve had so many conversations where, over and over again, it was the same stuff. I was like, “It’s time to put it down on paper or a source where people can trust that the person writing it has their interests at heart.” That’s why I wrote the book. It’s not that complicated. It’s not always easy, but it’s not complicated. People have the right to understand how they can build wealth.

Your book is not called the Masochism of Money. It’s called the Joy of Money. You’re clearly trying to play more of the upside. It coincidentally gives you an opportunity to throw your middle name in there. I saw what you did there.

I see you see me.

Talk a little bit about what you lay out in the book. You’ve got a number of lessons you want people to learn as you progress through there. Give us a quick fly-by.

There are four big quick fly-bys. The first one is that your mental framework is fundamental to your financial success. I don’t mean Stuart Smiley, for those who know what that is from Saturday Night Live. I’m not saying that you can magic yourself into a bunch of money skills. It does take work, and it takes trying things. I do mean that if you don’t think you can hit the ball, you are not going to hit the ball.

The first thing everyone should be doing if they want to get their money life in order is deciding how they want to imagine themselves as successful and how they get there. I don’t mean a bubble bath and some nice music in the background. I mean you say to yourself, “I can be good at money.” It’s like an athlete. Figuring out the story that you want to talk about yourself and how you’re going to reinforce that over time is important.

The second big lesson for me that resonates with a lot of folks is that money is math, and it’s also feelings. The math part is evident. We all know the right thing to do or the best thing to do, but a lot of times, we aren’t doing it. It’s not because we’re crazy, lazy, or stupid. It’s because there’s another driver in the car, which is feelings.

You’ve had a hard week, and your budget has been cut to the bone. You don’t have ordering out in your budget, but you do it anyway, because shouldn’t life have one good thing in it? All your friends are taking a vacation. You don’t have the money for that, so you put it on the credit card because you don’t want to feel left out. These are normal human decisions.

I always say that it’s not that you should figure out what those feelings are so that you can kick them out of the room. It’s knowing what those feelings are, how you feel about money, what might come up that’s going to be meaningful to you, and building your budget as best you can, including those moments and those feelings. I would argue it’s way better to have all of you in the conversation and the plan than it is to try to be a robot about it. That’s both my personal preference, but also, it doesn’t work long-term to ignore the needs and wants that come with being a human being. Figuring that out is an important part.

I think about the stories I’ve heard from people who say, “I grew up without a lot of money, but we always went out on Saturday nights. It was a simple meal. We didn’t go anywhere fancy, but we went out to eat. We knew that that was something that was a big spend for our parents, but they were committed to it. We did it consistently.”

The people who tell me these kinds of stories who’ve grown up in those kinds of environments where there was that thing that they got, to your point, it wasn’t all about taking. There was something that they did give themselves in the scheme of their financial situation. It helps make it more tolerable and sustainable rather than being the pure guilt, shame, and masochism that a lot of people feel like they have to go through, which is why they get into complete denial. Somebody may be on this call who got a puppy instead of facing her 401(k) rollover.

I don’t know who you’re talking about, but it might be me. This is a true story. I had to rollover a 401(k) from a job I’d had. I’m doing very well financially by this point. I know how to do money. I know I’m not afraid of it. I have moved from saying, “I can be good at money,” to, “I am good at money,” but my old pal, money avoidance, shows up years into my success.

I have to roll this 401(k) over, but the paperwork was complicated, and I didn’t know what to do. I go to Google, and Google gives me all these adorable pictures of puppies. No kidding, I ended up buying a dog. This is how I have my delightful dog. I shook it off a few weeks after getting through the potty-training phase with my dog. I did manage to get my rollover done. It wasn’t that hard. I had to call people and fill out some forms.

That money avoidance comes from, for me and for a lot of people, shame. It’s like, “I don’t know what to do. I should know what to do.” I feel ashamed, and I look away. That’s a super normal, biological human thing. We don’t want to do things that make us uncomfortable. Way back, that was probably danger. That was a good safety response. If somebody feels uncomfortable or scary, we peace out. We avoid it.

One of the four things I often talk about with folks is figuring out how to identify shame and how to transmute it into something different and, hopefully, reduce it. Shame mostly creates avoidance, or sometimes even doubling down on bad money behaviors. We’re like, “Why bother? I shouldn’t even bother trying because I’m so bad.”

Separating Shame From Guilt

The difference between shame and guilt is important. Guilt says, “I did a wrong thing. I spent past my monthly budget for eating out.” That’s guilt. Shame is, “I am a wrong thing. I am bad at money.” The reason that this is important is that guilt, “I did something wrong,” is fixable. Shame, “I am something wrong,” is not fixable. That’s why it’s so limiting. I don’t like shame because I don’t like shame, but I also don’t like shame because it is the most limiting factor for most people in changing their money lives.

In the book, I spend a little bit of time at the beginning talking about how to stitch up someone’s mental game, like, “Get your mental game right. Get your mind right.” Part of that is being able to identify when you are taking yourself down a shame path and getting yourself out of that place. We all know that that’s where money mistakes happen more frequently.

You’re hitting on why Carol Dweck’s work on growth mindset is so important. That, in part, is talking about the difference between, “I made a mistake,” versus,” I am the mistake.” We also know that shame is prevalent because otherwise, Brené Brown wouldn’t be as monumentally famous as she is. She is the woman who made it okay for grown men to cry about their shame. There’s a lot of shame out there, and there is a lot of avoidance. You also talk about the fear of the thing is worse than the thing.

That’s a super ripoff from Buddhists. If you know, you know. The fear of the thing is worse than the thing. There are a couple of different things about shame and fear. One is creating the conditions to feel those things less. That makes it easier to succeed. If I feel guilty versus ashamed, that’s better. I have a whole bunch of practices in the book about how to deal with yourself when you do feel shame in the moment. You’re trying to create the conditions where you feel less shame. There’s what you do when you feel that fear, anxiety, or shame, like how to do it.

I’m going to say it out loud. There is an element of putting one foot in front of the other and doing something anyway. In those moments, what I would tell myself is, “I know that the fear of this is worse than doing it. I know that.” It turns out to be true. One of the things I often encourage people to do is whatever envelope you’ve been avoiding opening or whatever account you’ve been avoiding logging into, do it. Take five minutes. Set a timer. Go get the envelope. Go get that website up. Log in. You don’t have to do anything with it. Look at it, breathe, and then go do something else.

You’ll find out that you survived. Lions did not come out of the walls to eat you. You’re okay. Building our tolerance for discomfort, which is not danger, is another core part of money. It’s two different things for a lot of people. It’s figuring out what the money is for, like what the things you want are or what the life you might want to look like is, and then also figuring out how to give yourself enough practice at building the muscles to take a look at what is, so you can figure out how to get more to what you want it to be.

We were talking a little bit about this before we started recording. This is a career-focused show. You have your focus on financials. I was saying to you that they are very related. Listening to the way you’re describing this, so many of these same behavioral things apply in the way that people think about their money and the way they think about their careers.

They avoid making the big decisions. They feel a lot of shame about things. They don’t have that growth mentality. Therefore, they lose out on opportunities because they’re not willing to consider them. In the same way, a lot of these same behaviors lead people to do less optimal things with their financial situations as well. If you can get one right, you could probably get the other one right with half the effort. That’s the overlap between our two topics.

Connecting Finances To Career Growth

That’s such a good way to think about it. One of the things I spend a lot of time talking to folks about is how to ask for a raise. For a lot of people, the biggest way they can change their money life is to make more money, especially when you’re earlier in your career. The culture of learning how and when to ask for a raise is the same mental muscle as it is to call your credit card company and ask for a lower interest rate, or call your cell phone company and ask for a better cell phone plan. It’s the same stuff. It’s the same mechanics. It’s the same prep. In my book, I have a whole section on, “Here’s how to ask for a raise at work.”

Money is a Rorschach test for what matters to us in our lives. How we choose that is one of the things we have control over. For example, a lot of people experience their budget as limiting and painful. Nobody likes to look at it because it’s evidence of how you didn’t make good choices. All that’s understandable. I am not saying to imagine a better thing, and then magically, you have more money and things get better. I get aggravated when people are like, “You can candle and crystal your way to a better money situation.”

To stop buying lattes. I know you hate that.

You’re trying to get me all riled up. That latte celibacy will not save us. It makes people poorer because then they hate their budget. It’s exactly what you said. I think of a budget. This was a mental shift for me, too. Not that I didn’t experience all these things before. I did, which is part of why I wanted to write the book. I’m not naturally gifted at money.

My husband has one of those calculator brains. He understands crypto and Polymarket. I could, but I choose not to. I think those are pretty unhealthy for wealth-building in our society. He can navigate all that stuff. I’m not like that. I’m a simple woman of simple pleasures. If I can figure out money, anybody can figure out money. I don’t want to take us on a road of banging on cryptocurrency, Polymarket, and policy embedding, so I’m curious if you have opinions on any of that that you want to talk about.

A lot of these things tap into the same things that all the lotteries tap into. It’s this idea that there’s a magic fix for this. My wife used to work with somebody. Every Wednesday night and Friday night when he would leave the office, he would say, “Have a nice life.” He was trying to tell you he was going to win the lottery the next time. It did not happen, for the record.

There are so many things that people believe and do that are ultimately unhealthy. If you step back and think about it, when you ask them to stop doing some of those things, you’re not asking them to give up eating. You’re asking them to give up having an entire bag of potato chips while sitting in front of the TV at 10:00 at night.

There are things in the extreme that ultimately hit you in terms of your health, your money, your career, or whatever that you can get rid of that aren’t going to kill you by doing it. It doesn’t mean you have to systematically dismantle your entire life. “I can get the most benefit that I want to get out of it for way less effort,” is the way to be thinking about a lot of this stuff because behaviorally, you’re more likely to sustain that.

That’s a great way to think about it. My mental shift around my budget was, “I feel so bad every time I look at it. I don’t have enough money. I see how I blew past these budget lines. I feel bad.” What I chose to do with my budget was to say, “This is how I’m making choices with my money.” I have one hour a month where I look at my money, and I choose. It’s like, “I get to decide. A budget is how I decide what I want to do with my money.”

It became for me a practice of feeling like I had more agency and control over what was happening with my money, which is often what I hear from people. They don’t use all those words all the time, but people say, “I feel out of control. I don’t know what to do.” People feel out of control because A) It’s hard to succeed in this society, and B) We don’t all have access to simple, easy information that helps us choose. Also, the feeling of looking at money makes us feel bad.

Once you get your mind right, once you have a budget that lets you make the choices that you want to make, and you have time that you dedicate so that you are thinking about money, what became true for me was that it helped me understand how to look at things like my 401(k) versus meme stock, bets, or prediction market betting. It made me understand the math around that stuff.

The math is clear that it doesn’t make everyday people richer. The lifetime analysis of this is so mathematically not arguable that you will make the most money by putting your money into a tax-advantaged retirement account and putting it into a target date fund that has a standard mix of things and is largely invested in index funds. It’s so clear about this.

The reason that people get seduced into what feel like easier, bigger money opportunities is that the feeling that we can succeed the normal way feels much harder for people. They’re not crazy. The cost of education, healthcare, housing, and childcare has gone up so much farther than wages. The median first-time homeowner age has passed 40.

The idea used to be that you go to college and get a good job. It wasn’t always this way for everybody, but the theory was college gets you a good job. That job gets you a good salary. That salary gets you a house and maybe a family. Two incomes are required, but it felt more doable. As time has gone on, it’s harder to navigate. It’s harder to afford all of that. What we’re seeing is people turn to places that aren’t going to work for them in the hopes that this can solve what feels like an unsolvable problem.

I often say to folks, “I’m not asking you to give something up. I’m asking you to replace it with a different behavior, which is checking in with your money and making choices that are more likely to make you more money. We could talk about how you also increase your income.” For most people, that’s the limiting factor. I have empathy for the folks who are like, “I got to try to do anything. I got to go try to get that lottery ticket,” but I feel compelled to say, “There’s a better way to build financial security for yourself.

Talk a little bit about your organization.

I run a nonprofit called WorkMoney. We are building an America where everybody can afford to live a good life. We help people raise their incomes. We help folks lower their costs. We have coupons and discounts. We do a lot of work with folks on how to understand what you can do individually with your money. I have a very clear point of view on this. The math and science are pretty clear on this.

You must play the individual hand of cards you are dealt. There’s no getting out of your responsibility. It is also true that some of us have worse cards than others. That doesn’t, however, get you out of having to play those cards. Even if your cards are worse, you still have to do everything you can, put one foot in front of the other, learn to get back up when you fall, and do what you can to improve your circumstances.

Leveraging Collective Consumer Power

We have a lot of power as a group. We can get together as consumers and bargain for cheaper stuff and things. Who among us is not having a love affair with Costco? That’s a great example of group buying. Imagine if we could apply that kind of thinking to health insurance and cell phone plans. Imagine 50 million people in an organization using their strength in numbers to bargain and put ourselves in the market as players in the market. This is my ideal for WorkMoney. We’re about nine million. We’re trying to get much bigger.

We also have a lot of power as constituents. The economy is not a mysterious weather event that we must endure. It is a set of choices made by people whose companies we buy things from, invest in, or work for. It’s also made by people we elect and policymakers that they appoint. We do have levers. We need successful companies. That’s how we have jobs. That’s how our economy runs.

I’m a very pro-successful-company person. I’m pro people getting wealthy. I think all that’s great for the economy. It needs to be happening in a way that isn’t at the expense of the majority of humans who live in this country. We’ve done this before. We’ve seen versions of America where more people could succeed, and people had access to education. We know how to do this. This is not new news.

My vision for WorkMoney is an organization that helps people use that strength in numbers to lower prices through bargaining in the market and making sure that politicians and business leaders of any party, any stripe, and any size understand what we expect from them. I love this idea. Many of us can build the businesses that we want to exist in this world. I love the idea of WorkMoney seeing and backing entrepreneurs who want to bring good stuff into people’s lives, especially financial products and services.

WorkMoney has a startup called MoneyFinder, where we’re negotiating to lower people’s cable, cell phone, and internet bills. I love this idea because it’s backed by a nonprofit. You can trust it. We’re not trying to extract. It’s also going to help people with their money. Finally, I’ll say that some of what you do is part of the answer. We’re also pretty powerful as an audience and as creators. We can make the content that we want to see. WorkMoney is a big nonprofit. My idea is that we use the strength of a lot of people to make the economy that we want to live in.

Thank you for doing what you do with your nine million members. Hopefully, that number will continue to grow. I hope the book has had success so far in its launch. I wish you well.

Thank you. I’m supposed to brag. The Joy of Money, which is the book I wrote, made the USA Today bestseller list.

Congratulations.

Thank you. I’m so excited. I love what you’re doing, too. Navigating careers is such an important part of people building financial security. I love recommending your show to other people. Thanks a lot. I appreciate your time.

I appreciate that. It’s great having you on the show. It’s good to get to know you.

Thanks a lot. I appreciate you. Take good care.

You too.

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That was a terrific conversation with Carrie Joy. Let’s talk about some of the key takeaways. First, being good with money may come more easily to some people than to others, but Carrie Joy’s core argument is that financial security and good money habits are learnable. A related point, one of the most important ideas in the conversation and her book, is that money isn’t math, but it’s also emotional.

You have to understand both parts of that equation to understand how to manage your own money and how to deal with it in the emotional context that works for you. Until we understand those stories and feelings that are driving our behavior, it’s hard to have a healthy relationship with money or to make lasting financial change.

Second, avoiding money problems almost always makes them worse. Carrie talked a lot about shame, avoidance, and what she calls the fear of the thing. Whether it’s debt, checking account balances, savings levels, or even asking for a raise, the anxiety around confronting these topics is often more damaging than the actual problem itself. That’s one of the most hopeful parts of her message. Progress doesn’t require perfection. It requires small, consistent actions that compound over time. She talked an awful lot about compounding, not just financially, but emotionally and psychologically as well.

Finally, the conversation challenged the idea that personal finance is purely an individual responsibility problem. Although we didn’t talk so much about this in our conversation, Carrie Joy makes the case that two things can be true at the same time. We are responsible for our financial choices, and the modern economy has become genuinely harder for us to navigate. Rising housing costs, healthcare, student debt, job insecurity, and wage stagnation are real forces that are shaping people’s lives.

What makes her perspective different is that she refuses to reduce financial struggle to either personal failure or systemic failure alone. She asks people to build skills, confidence, and agency, while also recognizing the broader economic realities that they’re operating inside. There’s a huge parallel here with the way that I think about career management. We have to have ownership for it. Even if the society around us is doing things that make having a sustainable career tough, we still have to make it work for ourselves. Avoiding that is only going to leave us feeling worse and being worse.

Ultimately, the conversation we had is about something deeper than money. It’s about dignity, stability, and freedom. It’s about the belief that your financial future is not already decided for you. Thanks again to Carrie Joy for joining me. I invite you to subscribe to the show on Apple Podcasts, Spotify, YouTube, or wherever you tune in. If you found this discussion enlightening, sign up for my membership community, which is called PathWise, and our newsletter, PathWisdom. Thanks.

Important Links

• Carrie Joy Grimes on Instagram
• Carrie Joy Grimes on YouTube
• WorkMoney
• The Joy of Money
• MoneyFinder
• Career Session, Career Lessons on Apple Podcasts
• Career Session, Career Lessons on Spotify
• Career Session, Career Lessons on YouTube
• PathWisdom Newsletter
• PathWise on LinkedIn
• PathWise on Facebook
• PathWise on YouTube
• PathWise on Instagram
• PathWise on TikTok
• PathWise on Twitter

About Carrie Joy Grimes

Carrie Joy Grimes is the founder and CEO of WorkMoney, a national nonprofit building an America where hardworking people can afford a good life. A former union organizer who helped win higher wages and better benefits for millions, Carrie Joy now channels that same people-first energy into practical money advice and strategies to raise incomes and trim costs for millions of everyday Americans. She lives in the Pacific Northwest.