The author and advisor to financial advisors discusses some of his favorite money-related sketches, the ‘fake advice industry,’ and how to have better conversations about money.
Hi, and welcome to The Long View. I’m Christine Benz, director of personal finance and retirement planning for Morningstar. Today on the podcast we welcome back Carl Richards, who’s the author of a new book called Your Money: Reimagining Wealth in 101 Simple Sketches. His previous books, The Behavior Gap and The One-Page Financial Plan, were both bestsellers. Carl started the Sketch Guide column in The New York Times and it ran weekly for a decade. Carl is a certified financial planner, and he started the Society of Advice, which is a community of financial planners dedicated to the craft of advice. In addition, Carl is active on the podcast circuit. He hosts Behavior Gap Radio, as well as a podcast called 50 Fires: Money and Meaning with Carl Richards. Carl also co-hosts a podcast with Michael Kitces called Kitces & Carl - Real Talk for Real Financial Advisors.
50 Fires: A Podcast About Money and Meaning
Kitces & Carl – Real Talk for Real Financial Advisors
“Carl Richards: ‘Less Focus on Being a Little Less Wrong Tomorrow,’” The Long View podcast, Morningstar.com, May 13, 2020.
“Carl Richards: It Should Be OK to Relax Out Loud,” The Long View podcast, Morningstar.com, July 27, 2021.
Your Money: Reimagining Wealth in 101 Simple Sketches
The Behavior Gap: Simple Ways to Stop Doing Dumb Things With Money
The One-Page Financial Plan: A Simple Way to Be Smart About Your Money
“Visual Sketches as Conversation Starters to Help Clients Make Better Financial Decisions,” Kitces & Carl podcast, Episode 175, kitces.com, Oct. 16, 2025.
“Is There a Future of Financial Planning in the AI Era?” Kitces & Carl podcast, Episode 169, kitces.com, July 24, 2025.
“Brian Portnoy: Balancing Returns With Simplicity, Financial Independence, and Peace of Mind,” The Long View podcast, Morningstar.com, Sept. 29, 2020.
“Why We Spend the Way We Do With Gretchen Rubin,” 50 Fires podcast with Carl Richards, 50fires.com, May 28, 2025.
“Money, Family, and Meaningful Work With Jodi Kantor and Rob Lieber,” 50 Fires podcast with Carl Richards, 50fires.com, Sept. 18, 2024.
Zero to One: Notes on Startups, or How to Build the Future, by Peter Thiel
(Please stay tuned for important disclosure information at the conclusion of this episode.)
Christine Benz: Hi, and welcome to The Long View. I’m Christine Benz, director of personal finance and retirement planning for Morningstar. Today on the podcast we welcome back Carl Richards, who’s the author of a new book called Your Money: Reimagining Wealth in 101 Simple Sketches. His previous books, The Behavior Gap and The One Page Financial Plan, were both bestsellers. Carl started the Sketch Guide column in The New York Times and it ran weekly for a decade. Carl is a certified financial planner, and he started The Society of Advice, which is a community of financial planners dedicated to the craft of advice. In addition, Carl is active on the podcast circuit. He hosts Behavior Gap Radio, as well as a podcast called 50 Fires: Money and Meaning with Carl Richards. Carl also co-hosts a podcast with Michael Kitces called Kitces & Carl - Real Talk for Real Financial Advisors.
Carl, welcome back to The Long View.
Carl Richards: So excited to be here. Thanks for having me again.
Benz: Well, it’s great to have you here. I was thinking you’ve been one of our most frequent guests on the podcast, so thank you for doing it. We want to talk about the book, your new book, but before we dive into that, I saw something in your bio that made me smile, which is how you encountered the financial-services industry. There was a little bit of miscommunication. Can you talk about that?
Richards: Yeah, this is a true story.
Benz: OK.
Richards: Yeah, it is a true story. Just for context, I was an undeclared major, newest hire to landscaping company, going to school full time. So there’s a lot going on here, but I had no idea what I wanted to do with my life. And I came home one day, and my wife had recently graduated with a degree in finance, which did not sound that interesting to me at all. And she had opened the newspaper the help wanted ads. And she found a job that we both thought was a security guard job. And I wish I still had the ad, but I thought this would be great because I could work the graveyard shift or whatever and still go to school full time. And so I went to apply for it. And I was thinking like, mall cop or something. It’s really funny because the interview was held in the same building that I ended up working at later, like 10 years later at a bigger brokerage firm. But I remember being confused about halfway through the interview, just like, what? I don’t understand the questions. There’s nothing about self-defense or kung fu. And I was like, this is fascinating. I made it through the interview, which obviously tells you about the applicant pool.
And long story short, two weeks later, I ended up in the training center at Fidelity’s National Call Center. at the time it was in Salt Lake. The ad apparently said securities not security. And I didn’t know the difference at the time.
Benz: And now you do.
Richards: Yeah. That led to a series of—it wasn’t much later that Netscape went public a couple months later. And I remember, I could go on for 20 years about these sort of confusing surprises, like no plan. But just really quickly, I remember in the training room being like, kind of unmoored, like, OK, not a security guard. What is this? I was like, what is this? I remember asking myself, it’s a math job. I think this is math. This must be a math job. Because we’re training to get licenses and all that stuff, and there are spreadsheets and calculators everywhere. And then Netscape goes public. And that was the first time that we had been trained at least enough to handle a large spike in call volume. So they had kind of like little red flashing lights that if you were in the break room, you’re supposed to get back on the phones.
They pulled us out of the training room. And I remember walking on to the trading floor there and being completely shocked again by like, what is this? Like people are … this is not math. Like people are yelling and people are excited. People are scared. This is not math. So that went on and on and on for my whole career. And I think it has something to do with what we’re going to talk about in terms of money’s role in our lives and how do we make sense of it?
Benz: Yes. And that, of course, has been a key thrust in your work. Before we go to that, I wanted to talk about this endeavor. You have a lot of different things going on all the time, it seems. But one of the main things you’ve been working on over the past several years has been to create The Society of Advice, which we actually have talked about on the podcast before. But can you refresh everyone’s memory about what that is and what you’re trying to do there?
Richards: It’s really interesting because like the essence of it is I just wanted to gather my friends for a really great conversation once a month that you wouldn’t hear anywhere else. And the goal of the conversation was to make us all better at giving advice. And there’s not much more to it. But I get this question a lot, like trying to make a worldwide organization. Because sometimes we joke, we’re like, it’s the worldwide chapter meeting of The Society of Advice. And for a while I called it the secret society. And what that’s pointing to is because, as you know, it’s really hard for anybody to navigate the financial advice industry speaking broadly. Like again, back to that earlier story, it took me another three or four years to figure out the difference between people who worked at a bank, and people who sold insurance, and people who sold investments, and stockbrokers at the time.
And so I think from the public’s perspective, and that’s where this started, was I remember saying something like, and this was near like after Madoff, I remember being so struck by the all the news stories about Madoff and mini Madoff and all the people in our industry that were untrustworthy, et cetera, et cetera, struck by the difference between that and the work that I hoped I was doing, but I knew my colleagues were doing for people during ’08-’09. I really honestly felt like they were saving lives. Like really helping people make really important decisions in very scary times. And the difference between this fake speaking really broadly, and I wouldn’t even know how to draw the boundary conditions around these ideas, but the fake advice industry and real financial advisors, I remember being struck by that and thinking it’s like there’s a secret society of real financial advisors and what does that mean?
Like somebody you could trust, somebody who’s technically really professional, competent, like a rock star technically, and you can trust them. And I was like, why don’t we just gather once a month, and that’s how we started the society. We just get together once a month for a 90-minute call with a really smart guest is the idea.
Benz: And as far as I can tell, it’s not so much about homing in on the technical aspects of doing financial planning. It’s more about how to understand your clients, how to communicate with them, how to get them to understand what they’re going for. Isn’t that more the focus of the society?
Richards: Yeah, I think that’s fair. Somebody said recently, if you want to get technical skills, and they named other programs, if you want to be a better advisor, that’s what The Society of Advice is about. I think of it as, you want to be a better financial planner or advisor? Be a better human. And so a lot of the things we talk about are that, like how can we see our own foibles? How can we get better at being present? How can we listen in better ways? And then therefore get better at helping clients clarify the journey they’re really on instead of always endlessly debating the products we use or the tools we use. Let’s get clear about where we’re going first. So that’s a lot of our focus.
Benz: So I want to switch over to talk about the book, which is called Your Money: Reimagining Wealth in 101 Simple Sketches. In the intro to the book you wrote, this is not a book; it’s a conversation grenade. So I’m hoping you can talk about who you’re hoping will start talking after reading this book. And what do you hope they’ll be talking about?
Richards: Yeah, such a nice question. So I resisted doing another book. It’s been 11 years. Not a month went by that somebody—publisher, agent, friend—didn’t ask me when I was going to write another book. And a couple of years ago I was like, gosh, it just doesn’t seem to be getting any better. Like the global anxiety around money doesn’t seem to be getting any better. And I’m convinced that good financial advice and good financial decisions happen in conversation. Getting clear about what it is you care about, where you’re headed. That happens, I don’t even know if it happens best, I think it happens almost only in conversation. And so that’s kind of why I was like, man, can I put together a series of really short, and I used Huma Cloud first introduced me to this term conversation grenade. Because I’d noticed advisors were using them that way—they’d print them and put them on their walls and then they would email me stories that clients experienced, like they would walk in the conference room, and the client would be standing up.
A couple would be standing up talking about one of the sketches. So my hope is that, look, advisors are, I believe—and we may even talk about this later—I still believe that the human advisor is the best positioned to facilitate these conversations. And so I hope advisors will have them, and they are. And then, but I have a deeper goal. I just, in my mind, I imagine a family sitting around the dinner table talking about what it means to be free or what wealth means. My daughter said this to me the other day on a bike ride. So my 20-year-old daughter said, “We’re one of the wealthiest families I know.” And I had this immediate reaction of like, “No, we’re not.” And I said, “What about…,” and then I caught myself and said, “Help me understand.” So this is the idea of a conversation. I said, “Help me understand what you mean by wealthy.” She said, “Well, we really have been able, we sort of do what we want, like we’re living lives.” And I was like, “OK, if that’s your definition …” So that’s the kind of conversation—out on a walk, on a road trip, sitting around by the lake, sitting at the dinner table, what does it mean to have enough? How do we pay this bill? Can we talk about these things instead of saying that’s none of your business or we don’t talk about such things. So I’m hoping everyone—my goal, Christine, is to start a million conversations around money and not the kind of conversations that are about what product, but more about what does it mean to us?
Benz: Yeah, that’s a good summary. And I will say, I enjoyed the book thoroughly. When you think about your favorite sketches in the book, does one stand out as your favorite or maybe a couple stand out as your favorite?
Richards: I thought you would ask that question. And so I even thought about it. It’s a really hard question to answer. It depends on the day. The one that I’m thinking about today is there’s this sketch called “The Magic Certainty Button.” And it’s just a square. I’ve done a lot of this art on the radio. So it’s just a circle that looks like a button. I mean, it’s my hand-drawn version of a button, that you press like on the wall, like a button. And above it, it’s labeled “The Magic Certainty Button” with an arrow. Those words have an arrow pointing at the button like, hey, this is the magic certainty button. And under it in brackets, it says, [I can’t seem to find it.] And I was just trying to get at this idea. And the reason that came to mind was, we so desperately want certainty as humans. And I think as an industry, we’re at risk of becoming or being seen as sellers of certainty. Because certainty is so easy to sell because everybody wants it. But the problem is it’s impossible to deliver.
And so I think that’s one of the reasons people get sort of frustrated maybe with their experience, their interactions—speaking very broadly here—with the financial-services industry broadly, is sometimes the language we use, we might actually explicitly be doing it, but sometimes even the best of us, the language we use might be overly precise. Like here’s a 30-year line. I’m going to show you what the next 30 years of your life looks like. And we’re so technically good, like we love big calculators and spreadsheets. And we should draw the best line possible with all the assumptions really well-thought-out. The dilemma is, of course, we know it’ll never be that exact path. And so I kind of like that sketch of just trying to be—my editor at The New York Times called my best work confrontational without being off-putting. And so I was trying to be a little bit cheeky about the absurdity of trying to find the magic certainty button.
Benz: Yeah, I think sometimes there is this gravitational pull toward like faux precision. You see someone saying like, “Stocks should return, 8.6% over the next decade.” And it’s like, really? Where did the 0.6 come from? I mean, it’s like, wow.
Richards: Yeah, I love it when you see Monte Carlo assumptions out to two decimal. I’m 98.27%. Easy, tiger. Easy.
Benz: Right. In terms of the ones, the sketches that you get the most feedback on, what are the ones that seem to stand out as readers’ favorites? Or what are the ones that you’ve heard from advisors that their clients have really reacted to?
Richards: Yeah, maybe just two really quick. I’ve heard a lot and it’s been really interesting. I care deeply about getting the book into the world. But what I care more about is getting conversations in the world. And so this has just been a giant excuse to have lots of conversations. So we’ve been having lots the last couple of weeks. And I’ve been surprised at how many people have asked about … All the sketches are numbered. Sketch 55, which is “Range of Outcomes.” And this is one of the things I work really hard at. I get it wrong most of the time, but sometimes I get it right, which is taking a very complex subject and trying to make it accessible. And I’ve been surprised at how many people have asked about “Range of Outcomes” simply because basically I’m trying to talk about Monte Carlo analysis. And so it’s just to describe it, on a piece of paper, imagine the left hand side label now, and there’s a point there with maybe looks like—I’m trying to count as we do this—maybe 10 lines, and they’re all squiggled in different ways. And some end up on the right-hand side. On the right-hand side of the paper, it’s labeled the future. And the lines, as you can imagine, there’s a potential range of outcomes, just like you’d see in a Monte Carlo analysis.
And I’ve been surprised at how many people that has resonated with, and the point of the essay was really that we need to be comfortable. We need to—back to our false sense of precision conversation—we need to understand that, yeah, there might be some paths that are more or less likely, but there’s a probability assigned to each path, but the path is still a random draw based on those probabilities. So the likelihood of you getting one exact scenario is still based on probability. Who knows what could show up. We saw that with, was it was it the NFL draft? No, the NBA drafts with the Mavericks getting the first pick, right? Like very low probability and it still showed up. So I love that one. That’s been asked a lot about. And then I’ll tell you really quickly, the only one—we do a lot of like art with these canvases—and the only one my wife is ever allowed in the house is number 22, “Focus Where It Counts.”
So that’s just, I call them circle sketches, Christine, because I don’t know if you know, but there’re a Venn diagram police out there. I think we may have talked about this before. And so it’s a Venn diagram. Don’t send me an email if you don’t believe that. In one circle it says, “things that matter.” The other circle says, “things I can control,” and the overlap is labeled “what I try to focus on.” And that seems to be the one that has the most universal, like I hear it from a lot of like mindfulness, meditation people, yoga studios, that have put that up as well as just sort of a touchstone.
Benz: I love the essays. You’re so well-known for your sketches, but the essays are really good. And I noticed kind of a through line in the essays is this idea of getting away to think better. And for you a lot of that happens in nature, this idea of putting some space between yourself and the thing that’s bothering you or nagging at you. Can you discuss that concept? Because it seemed to come up quite a lot, the importance of separating yourself from the thing that’s giving you angst and walking away and maybe letting your subconscious brain work on it. But maybe you can expand on that.
Richards: I’m actually quite curious. Tell me sort of your experience with that.
Benz: Well, I find that it works like a charm. And that’s one reason why...
Richards: What do you do? What do you do?
Benz: I’ll go down and fold some laundry. I mostly work remote now. So yeah, I’ll do stuff little things in the house just to kind of walk away and take care of a few things. Very short, but it does seem to help. Or getting outside, the shower thing really works, I find. Or even sometimes when I’ll be on the cusp of waking up in the morning, sometimes I’ll be like, oh yeah. And sometimes it’ll be a completely stupid idea, but sometimes it’ll actually be a good idea and a good way to address the thing that’s been bugging me. So walking away, I do think works.
Richards: I love that. I think it’s interesting just tangentially that I’ve been asked a lot lately in these conversations about what do you do when you’re scared? Like what do you do when it’s really uncertain? And I think that’s just sort of the nature of the current environment, which seems like we’ve been saying this for 10 years. But my new answer is, I go organize the garage. I think there’s something really interesting to that idea that you bring up laundry. There’s that old Zen saying like, before enlightenment, chop wood, carry water. After enlightenment, chop wood, carry water. Like if we’re feeling nervous about the market or nervous about our financial situation or nervous about anything, I’ve been surprised at how much, in fact, yeah, I did write another essay about this called “The Power of Order,” how much it helps to just go organize something and just put some sense of order, even like if I organize my desk, I feel better. But your question about getting out, and I wish I had been better at this.
It’s the one thing I wish I could tell my 25-year-old self. Finding a place to pause whatever it is in your activity. Before this, because I’m doing four or five of these today, before this, I had five minutes between the last one and this one. No, sorry, I had 15. I went out and sat with my feet in the dirt in the garden for five minutes. And like rather than trying to crush my email, because I know how thoughtful you are. Like I wanted to show up in a head space where I was prepared to be present and thoughtful. That is not the opposite of ambition. And I wish I could tell my 25-year-old self that—like, it’s not the opposite of hustle. Like you can still be up to something and be ambitious and not have it be heavy all the time. And not be like grinding. But now I know it’s an incredibly important part of my life where my best work, and I think this is really important for your audience, like we’re all knowledge workers. Knowledge work requires large chunks of unstructured time. It’s not a reward. It’s a prerequisite for continuing to do the work. So like my time in the mountains is not a reward.
I didn’t earn that as a reward. It’s a prerequisite for continuing to do this work. And I’ve just found that to be incredibly important. It’s my best thinking, because often I’m trying not to think at all, but the best ideas occur there. And then the other thing I’d say about it is like, if I’m nervous or worried or scared or feeling reactive at all, and I know what that feels like in my body now, like if I’m feeling reactive at all—a client said something to me, somebody wrote an email, the Venn diagram police wrote in, if I’m feeling reactive at all, I know now and I don’t always follow it. But every time I don’t, I regret it. I know now to pause, like go do the thing, go fold the laundry, go organize the garage, go on a bike ride before I respond. Because if I respond in that place, I will almost assuredly regret the response.
Benz: I remember you made the point when you were previously on our podcast about how we need to, the phrase you used was to “relax out loud,” to not feel like you need to furtively steal off to give yourself a little bit of space between your thoughts and your work. And I thought that was powerful.
Richards: Do you think we’ve got any better at that?
Benz: Maybe? Yeah. I guess having more confidence in my work and my place in the world has just made me feel like OK, not everything is an emergency all the time. So I’ve gotten a little better at that, I guess.
Richards: Do you think we generally—not you, but like the people you work around, or you see, or your listeners that write in—do you think we’re any better two or three years later?
Benz: I think covid actually was kind of healthy for workplaces. Even still, like I’ll be in a meeting or something and someone who you’d think would be there, someone will be like, “Oh, his son had a soccer game,” or whatever. Not that that wasn’t OK before, but now it just seems like there’s more flow to the workplace in a really nice way I think.
Richards: I love that.
Benz: Yeah. But it would be a shame if we forget all of—there were some positive side effects from covid. It would be a shame if we forgot all of them. And I think that’s a real possibility.
Richards: Yeah. And just continue to keep in mind that does not mean we need to be less ambitious.
Benz: Right.
Richards: It does not mean we need to be less productive or action oriented. It just means realizing that knowledge work is different than other types of work. And it requires you to treat your brain probably a little differently than maybe a system built around labor. So anyway, I think it’s important.
Benz: I wanted to ask about some of the themes in the book. And a recurrent theme in the book and in your work in general is this idea of enough and how societal pressures and especially social media get us feeling bad about what we’ve got and how it compares to other people. You have a wonderful sketch in the book that is titled “What Envy Feels Like.” I’m wondering if you can describe that one and discuss what you wanted it to illustrate?
Richards: So a small circle. So imagine a small circle drawn on a piece of paper that says, “my stuff” and then a much bigger, much, much bigger circle. And that one has room to put the words inside the circle. It’s so big. It says, “everyone else’s stuff.” And then the caption below is labeled “What Envy Feels Like.” And one of the things I was really trying to get across there is this idea of a comparison set. And I think what you’re pointing to, especially when we bring up social media, is this is a new problem. And the phrase I like to use is the idea that we need to carefully cultivate our comparison set is a new problem. Because it used to be that it was what your buddies had or your neighbors. And it used to be that everybody in your neighborhood, and it might still be true, this might still be true—but I remember growing up, we were all kind of generally the same. It was the same socioeconomic group in the neighborhood. And we all had—and I’ve told this story before—but we all had BMX bikes because we rode our little dirt bikes around in the mountains of Utah.
And I remember wanting a slightly better BMX bike. But I didn’t know I was supposed to want a private jet. And now I do. Or a Swiss chalet. I didn’t know those things. And now we do. And so I think that’s the real challenge is we are mimetic creatures at heart. We don’t really actually know. It’s quite hard to figure out what we desire. We just mimic other people from the youngest age. First, we just mimic, what does mom want? Oh mom wants that, that must be desirable. Because mom wants that. And now that mimetic problem has gotten so big because we look around. And so getting clear about what is your goal, like what’s enough for you, not your mom, and not your sister-in-law, not your brother-in-law, and certainly not all the people on Instagram. And it doesn’t even, we’re not even going to talk about the fake problem. That like we all know half that stuff is not real anyway. I was so shocked to first learn that influencers, there was a place that you can go that has a jet there. And for $100, you can go take your pictures as if you were on that. Do you know what I mean? Like I was like, really?
Benz: I didn’t know that either.
Richards: One of my friends compares like thinking you can still know who you are in the face of that onslaught is like showing up to a gunfight with a knife. Like there’s 300 PhDs on the other side of that fight. So that’s what I was trying to emphasize here is can we get really careful about cultivating your comparison set? Because envy, it turns out, it seems like it was mentioned in the Bible. Like you know what I mean? It’s been around a while.
Benz: Relatedly, I think it was Brian Portnoy made an astute point, we have all heard about how if we’re going to spend our money, our best ROI is spending on experiences, especially with loved ones. But he made the point that now that we can all see everybody else’s experiences, is that going to diminish our own experiences somehow if now they can be weighed and measured alongside other people thanks to social media? What do you think about that point?
Richards: Yeah, I think it’s a huge problem. Because now it just becomes one more place we could compare and compete. And I think again, it really points to this need for intentional conversation around like what really matters to you. Gretchen Rubin was it, yeah it was—it was Gretchen Rubin on my podcast 50 Fires she talked about how she was at—this story was so great. She was at some event in New York as one does I guess, like a cocktail party or something, and somebody came up and Gretchen was just either coming back or on their way on a trip to the mountains to ski so I’m sure it was Colorado because the skiing is terrible in Utah, you shouldn’t come to Utah to ski. That’s just a joke. And this lady says to her, “Are you going to ski?” And Gretchen’s like, “No we don’t ski. We don’t like to ski; my husband doesn’t like to ski; we don’t like to ski.” And the lady really insists like, “You’ve got to ski! I didn’t like it either, and I’ve started skiing. You got to ski; it’s the best thing. You got to ski.” Gretchen is like “No, no we don’t ski, it’s fine.”
And the lady went away, and she came back, she came back sometime later, 15-20 minutes, 30 minutes, and said, “You know what I realized in talking to you? I don’t like skiing either. I’ve just been doing it because it was what you do.” And I was like that is so interesting. I have lots of stories about that for me. Like dinner and a movie with friends. My wife and I went through this time where we were like we want to build more connection with some close friends. So let’s systematically invite friends, let’s go every, whatever, like twice a month on Friday night. And what should we do? OK we’ll go to a movie and dinner because we want deeper connection with friends. And after like five times we were like wait if the goal was deeper connection, we were just in a noisy restaurant and a movie. So we’re like but that’s what everybody does so that’s of course what you should do. We don’t like movies, and we actually don’t love eating out. You know what we love doing? Let’s buy all the ingredients, come over, plan on two to three hours, we’ll make the meal, we’ll talk. We like that. And it turns out that was less expensive but that was not the point; it was a better expression of the value of connection. So I think what you’re pointing to makes this even more important. How do you get clear about your goals? And by the way that’s a practice that’s never done because you’ll be wrong. Your guesses will be wrong. Five million dollars on a sailboat—well have you ever been on a sailboat? Go try that first. So anyway that’s how I think about that sketch.
Benz: Well that’s something I want to delve into is—and we’ve talked about this with you before—but the idea of enough, finding your enough, finding what your values are. What are some key questions people should ask themselves to try to get to the bottom of that?
Richards: I really think that I have a heavy bias toward action for this experience. So start by some questions and some conversations around “make a guess.” And this is coming up a lot. I think it’s the age cohort of like 45 to 60 year old who’s been working, working, working, working because that’s what we all did. And is now saying—I just had this conversation with the chief creative at a public company everybody would recognize, the head of creative. And he’s like, “I don’t have any hobbies. I don’t know what I’m going to do five years from now. I need to figure it out.” So OK we start there, and we say let’s just guess, like just a guess like and some of the places you can look for hints: What podcasts do you listen to? If you were still getting magazine subscriptions, what magazines are arriving at your house? If Gun Dog Weekly or Gardening is arriving, you got some hints. What conversations are you interested in?
Then you could go back 20 or 30 years and be like, what did you used to like to do? OK, so we’ve got a guess. And then my bias toward action is go take the smallest experience you can with that. Go do it and see what shows up, because new information will show up. And this is the same thing with the concept of enough. Enough—we’ve talked about this, but enough can’t be a number or else you’ll never get there. So how do you define your enough? Well you start to test things, like what if—I was just having this conversation with Ron Lieber and Jodi Kantor were out here for 4th of July and we were talking about, and I can’t remember who it is, was it Paige Pritchard? It might have been Paige Pritchard that wrote about her no-spend year, no-spend month.
Those are really interesting exercises of like well what if I didn’t buy any more running gear this year and I just used what I had, is that enough? What if we went on a—I was just talking to another friend who this year decided to do a staycation in somebody else’s house is what he called it. So they drove to a rental place in the countryside of Virginia. They didn’t spend any other real money. They ate at the house, the house had a pool, they went on lots of walks, like what if that was enough? We didn’t have to fly somewhere. How was that? So just start testing, running little experiments. Morgan Housel famously says that he’s supposed to be a car guy because he was a valet when he was 18 in Los Angeles. And everybody tells him he should be a car guy, and he could afford to be a car guy.
Well an experiment he runs is when he goes to the Hertz counter—he said that once every couple years he has to run this experiment. He’ll just be like, you know what, it’s an extra $200, give me the Porsche. And he said he doesn’t even have to drive; he doesn’t even get off the lot before he’s saying to himself, “I admire this. The craftsmanship is amazing, but it’s just not something I need.” Well that’s a that’s a very cheap way to learn that versus buying the car so that’s kind of how I would run experiments, see what I notice; run experiments, see what I notice. And one of the things you got to keep in your mind is like everybody else loves this; well you’re running an experiment to find out if you do.
Benz: I wanted to ask about older adults. I’ve been spending a lot of time talking and thinking about retirement planning and it seems that many folks at that life stage truly do struggle giving themselves permission to spend what they could spend. How can people at that life stage get more comfortable with the spending they do and maybe even do some lifetime giving to their loved ones versus leaving it as a bequest when they’re gone? Can you talk about planning to spend at that life stage?
Richards: Yeah, this is another surprise to me, the number of times this topic—I’ve run into it lots in my own planning work when I was running my own firm. I hear a lot about it from financial advisors but tall these conversations I’m having lately this has come up so often it’s so fascinating to me. And it’s easy to understand, like the reason—if you’re in a position where you’ve been successful, which a lot of the listeners of this show either are or advise people that are in that position. The very habits and traits and characteristics that got you there delayed gratification. You’re really good at that.
You might even be good at being frugal, but certainly delaying gratification, investing for the future, waiting, and now you’re at the spot you’ve been waiting for. And like you’ve been waiting for this thing, you’ve been successful, you waited for this thing. So what do you do now? And it’s antithetical to your very identity and so I think you practice. The same thing we do, you just practice. Look, the research is clear, but you don’t need another lecture about the research. This behavior is perfectly rational, but now the situation you’re in, it’s slightly irrational to be at the spot where you could put the golf shoes on and refuse to do it. Or maybe even more interestingly, wouldn’t it be fun to spend a little bit of time with the grandkids doing things they love? Oh man I have this one grandkid that really wants to learn to sail and his parents are busy, and they don’t have—can I go spend a week at a sailing camp? And I could kind of be on the shore or even sail with them? That’s going to cost some money. The research is pretty clear that, and you pointed to Brian’s work and many other people about this funded contentment.
So practice, and like anything you’d practice, start small. This is funny, Christine and I are asking you to go spend some money. Tomorrow, I want you to find something and ideally find something small that you’ve always just wanted. You don’t even need it; you just wanted to do it. It’s small, it’s $25, it’s $100, it’s $5. Maybe it’s even to the point of you bought into the latte thing; you didn’t buy coffee out because you were saving, but you love coffee out. Go tomorrow morning to your favorite coffee shop. Feel the whole way through it, buy your favorite thing; it’s going to be $12. Sit in your favorite seat with the book that you’ve been reading and enjoy it and feel the enjoyment of it. And it’s a $12 rep, a $12 practice. And I think that’s what you do, you rewire it until you get to the point where you’re like, you know what I’m going to pay for my grandson’s entire education, because I’m so excited about the fact that he wants to become an electrician. I’m going to fund a scholarship for women who are getting into biomedical engineering. I think the way you get there is you practice.
Benz: I wanted to ask about financial advice. You spend a lot of time talking to advisors and advising advisors, and you have some sketches in the book that address that. One of your sketches illustrates that financial advice is inherently human. And I’m wondering if you can talk about that sketch—it’s the algorithm is a straight line, and real life is this curly ball of squiggles. Maybe you can talk us through that and how you see financial advice evolving and how it seems like you don’t think that good advisors can ever be fully replaced by technology but maybe talk us through that.
Richards: This is super interesting to me because I drew that sketch probably 10 years ago, and I was actually quite curious if it was still right. And so I asked both Claude and Chat, is this still right? And I said I’m worried I think this might not still be right. And I told them it was for an upcoming book, and I put the essay in there because the sketch doesn’t mean a whole lot to them. But I put the essay in there, and the advice I got back from AI was this is more important than it’s ever been. And to get this right, because it’s getting clear that even the stuff we thought was uniquely human—I just read this fascinating study about people were more willing I think it was, I’m hesitant to cite who it was from. I’m hesitant because I’m not exactly sure I can pull it up really quick.
People were more willing to interact with a computer named Ellie about trauma than a human therapist, and it was largely the metric was judgment because that’s what they kept citing—like felt less judged. And there was a super-interesting study about clients being more engaged on Zoom calls when the advisors’ camera was off, just because they couldn’t see the eyes of judgment. The AI doctor being ranked higher in bed side manner, wow that’s, I mean I thought it would maybe get diagnosis correct but I didn’t think it would be ranked higher in bedside manner. So all of those are super interesting to me and something we need to be thinking about, but I think there’s still this room deep to the human side. So that sketch—as often my sketches are—it doesn’t capture all the nuance in the edge case. It’s an opinion that by the nature of simplifying something that’s complex you’re going to leave some stuff out. And it’s an oversimplification for sure but it’s just to make the point that there’s still room, and I think it’s the answer is be deeply human because here’s my favorite bit about this is life and markets and money are messy. Algorithms can answer, analyze patterns brilliantly but here’s the key: They can’t feel the anxiety of a major investment decision or the pride of achieving a financial goal, or—and this one was really important to me—the responsibility of providing for a family. So I think that’s still there. And I don’t know how that’s replaced and maybe I’m wrong, but at least right now it’s still there.
Benz: You had a really wonderful discussion with Michael Kitces. I listened to it yesterday. I would urge people to check it out on the podcast that you do with him. You had this great metaphor where you’re talking about financial advice like there are aspects of it that can be a self-driving car, that technology can completely take care of them. But the car is still going to have to know where it’s going. Can you talk us through that? Because I found that really helpful in thinking about the role of human financial advisors going forward.
Richards: Yeah, I like I want self-driving money.
Benz: Right.
Richards: And we’re already getting closer. I got fired by my financial planner and my wife fired me from those meetings. They were like you’re the last person that needs to be here. So I’m creating self-driving. We’ve got a bookkeeper for the business, and to the degree that it just takes care of itself in the background. I think most of us would love that. I mean there are some of us that just love doing it. So I want self-driving money, and I don’t think we’re going to be far off. If you can have a self-driving car, if you can create a self-driving airplane? How can we not be very far off? But here’s the key thing—and I was in one of those Waymos recently in Los Angeles and it was amazing I actually felt safer.
Benz: Well I think they are safer on the data, aren’t they?
Richards: Yeah than my Uber experience right before it, I’m telling you right now, it felt better. So I’m excited about that, but here’s the thing: The Waymo car needed to be told where to go, and so there’s that. And that’s not as easy—most of our conversation to this point has been about how hard it is to figure out where you want to go. It starts out easy, $5 million and a sailboat, of course, because I saw that on Instagram, of course. And then you start breaking it down. You’re like, well wait, I don’t know, where did the $5 million come from and where’s the sailboat? It turns out figuring out who you are and going the whole way takes a lot of skill and conversation. And I still think that is the domain of skilled facilitators—people who know how to ask good questions and then people who know how to overlay the tools for getting there, the self-driving money on top of what you just described. So I think that that’s been really helpful to me. The car still needs to know where to go, the self-driving money still needs to know where to go.
Benz: You made the point in that podcast—it’s sort of apart from financial advice—in terms of guiding our activities, if we find ourselves doing a thing more than once you could maybe step back and think about how to automate that. Can you talk about that? Because it was something I hadn’t really thought about before, but it makes a lot of sense.
Richards: Somebody introduced me to the—maybe I’m late to the party—but somebody introduced me to the idea of a J curve. And you can think of this even when you hire somebody and you’re trying to delegate to them. Kids too, like if you want help doing the dishes it is almost always easier just to do them yourself than it is to get the kids to help you. And I think the same thing is true with AI. We start into any activity, and I would actually use as my like signal anything I have to do more than once. If I have to do it more than once is there a way to make this system—if I invest a little bit of my time and energy and maybe even a little bit of capital can I make the system better so that investment ends up paying off? Now that J curve ends up being a little bit like if you think of it as total cost like time, energy, money, attention to that process, you’re on the left side of the J. As you are starting to teach the kids to do the dishes or you’re starting to train AI to do the thing, it actually is costing you more than just doing it yourself.
And it cost you more and it cost you more and it cost you more and then it gets to the bottom of the J. And it starts to go up, and after a little while you’re back to where you were. To me, maybe the most useful one has been the cold-start problem. The cold-start problem to me is the most frequent interaction I have with a cold-start problem is in email. How many of us have opened an email, you read it—because there’s this asymmetry around email. Somebody can ask you a question, and they might be very thoughtful, they might be unthoughtful in asking their question. It took them 10 seconds to ask you the question, it might take you five minutes to reply.
So the cold-start problem in email to me is, you open an email you’re like gosh, I don’t even know how to start the reply to this. Maybe it’s emotionally challenging, who knows what the reason is. I can’t even imagine if you added up the hours of my life that have been spent thinking about how to reply. Now I just take that email, I copy it into a project inside your favorite AI tool, and I say, “Please—based on all our previous interactions and this editorial guide that I’ve written, part of the J curve—please write a first-draft response to this email.” I copy and paste that back into my email and then I work on it. And sometimes it’s 80%, sometimes it’s 10% but at least it got me through the cold-start problem. So that’s how I think about that—anything I have to do twice I may as well think about how I could get some help.
Benz: In the book you have a sketch and essay about getting in over your head, and you recommend it. Do you recommend what a lot of us would think of as being in over our head? Why? And you say that it’s been a great thing for you in your life to find yourself in those situations.
Richards: I actually remember where that concept first came from was somebody asked me how come you keep doing projects? And my answer was that idea, I just love the feeling of how would you do that? I love the idea, and I do this very intentionally every year or so, I’ll pick what my friend Rob calls a stupid human trick. I’ll pick something that I know in my current state is impossible, and these often involved moving through the mountains or maybe a long mountain bike race or something like that. But they also involve work projects. The book is an example—I thought like I don’t know if I can pull this off. So I love the idea of pick a stupid human trick that you know in your current state you will not be able to do. To do that will require you to become a different person, a better version of yourself.
I have a buddy who did this with his PhD. He was like, “I want to become a person who thinks deeply about a single problem. I’m pretty ADHD; I want to become the kind of person that can think deeply about a single problem.” He’s in his late 40s. He’s like OK, “What would be a forcing function? Who are the people, like what would they do?” You know what? Getting your PhD would require you to be that kind of person. So he’s like, “I don’t really care about the PhD; I care about what it made me do.” And I think that’s this idea of getting in a little bit in over your head. I’m not necessarily the story I shared here from my friends Chris and Amy was about money. The mortgage; they were going to buy their first home, and they weren’t sure that they could pull it off. Now they carefully ran the numbers, carefully. I just want to not be misinterpreted; they carefully double-checked. But it still felt like a bit of a stretch, and most of us reflect on buying our first home, that’s not uncommon. And the reason I love getting in over your head is because you almost always find out you underestimated what you could pull off. We’re notoriously bad at that. We’re notoriously good as humans, at getting into a situation that we don’t know how to handle and figuring it out, like MacGyver style with bubblegum and duct tape. We’re really good when we have to do it; we’re really bad at imagining that we can do it.
Benz: Last question for you Carl is about who you turn to for inspiration. It seems like you’re an avid consumer. I know you’re always talking to people through your various audio projects and your other work, but who are your go-tos for your work, or your life, people you read or listen to regularly?
Richards: So there’s an old quote that’s attributed to Lao Tzu. It says: Be who you really are and go the whole way. And I’m a big fan of people who appear to have done that, who they really are. So David Whyte the poet is an example. What David does in person, nobody does. It’s uniquely David Whyte, and so I’m a big fan of that. A controversial one that I always find myself whenever I listen to him talk or read anything he’s written, I always find myself for some odd reason wanting to be better. And it’s Peter Thiel, which sounds really odd, and again, I want to be clear—none of this is any statement about whether I agree or disagree, which is pointing to something really interesting. One quick story about that.
We were on a backpacking trip in New Zealand when we lived there. We’re out in the middle of the bush, like a long ways away, and there were these huts there that you can stay in that the department of recreation had put up. And there were these kids there, like teenagers 17-, 18-year-old kids. And they had their badminton rackets with them. I don’t even know what this means. But they were hitting, I think it’s called the birdie? They were playing badminton out on the field, and they were so into it. And I found myself enthralled. I don’t know anything about, I could care less about badminton. But I was so enthralled by them, and it turns out they were on the national team of whatever country they’d come from; I can’t remember what country it was, it was somewhere in Europe.
And they were so enthralled. And that was when I first realized, I’m just way into people who are doing their thing. I’m thing-agnostic. I realize Peter Thiel might be a controversial idea, but I find listening to him every once in a while. Like once or twice a year, I run across something or reading his book, Zero to One, I walk away wanting to do my thing—not his—but my thing, more. And then one last one. I’ve got this friend Steve who founded a company called Vollebak. And every time I’m around Steve, Steve’s wild and crazy with his ideas and he’s always way up in the clouds. So I don’t want to make clothing like Vollebak does. I want to do my thing. And so those are the kind of people that I get inspired by, is people who’ve been whether we know them or not but have been deeply engaged in doing their thing.
Benz: Well Carl, I would say that describes you very well. I always learn from talking to you and I sure loved the book. So thank you so much for taking time out of your schedule to be with us today.
Richards: Thank you. It’s always like such a lovely, fun, insightful conversation, so thanks for doing it.
Benz: Thank you. Thank you for joining us on The Long View. If you could, please take a moment to subscribe to and rate the podcast on Apple, Spotify, or wherever you get your podcasts.
You can follow me on social media at @Christine_Benz on X or Christine Benz on LinkedIn. George Castady is our engineer for the podcast and Kari Greczek produces the show notes each week.
Finally, we’d love to get your feedback. If you have a comment or a guest idea, please email us at TheLongView@Morningstar.com. Until next time, thanks for joining us.
(Disclaimer: This recording is for informational purposes only and should not be considered investment advice. Opinions expressed are as of the date of recording and are subject to change without notice. The views and opinions of guests on this program are not necessarily those of Morningstar, Inc. and its affiliates, which together be referred to as Morningstar. Morningstar is not affiliated with guests or their business affiliates, unless otherwise stated. Morningstar does not guarantee the accuracy, or the completeness of the data presented herein. This recording is for informational purposes only and the information, data, analysis or opinion it includes, or their use should not be considered investment or tax advice and therefore, is not an offer to buy or sell a security. Morningstar shall not be responsible for any trading decisions, damages or other losses resulting from or related to the information, data, analysis, or opinions, or their use. Past performance is not a guarantee of future results. All investments are subject to investment risk, including possible loss of principal. Individuals should seriously consider if an investment is suitable for them by referencing their own financial position, investment objectives and risk profile before making any investment decision. Please consult a tax and/or a financial professional for advice specific to your individual circumstances.)