Carl Richards started The Sketch Guy column in The New York Times from the hills of Utah, crafting clear, relatable insights about money with just card stock and a Sharpie. Since then, Carl has become a Certified Financial Planner™, built and sold a successful investment firm, and spoken at financial and investment events worldwide. His bestsellers, The Behavior Gap and The One-Page Financial Plan, have been translated into over ten languages and continue to resonate globally. Through his daily podcast, Behavior Gap Radio, which now has over 1,000 episodes and more than one million downloads, Carl shares new perspectives on aligning our resources with what truly matters. Carl also founded The Society of Advice, a community of financial planners dedicated to the craft of advice. His latest audio project, 50 Fires, backed by executive producers Chip and Joanna Gaines, explores the intersections of money and meaning with guests like Pete Holmes, David Whyte, Krista Tippett, and his favorite guest by far, his wife, Cori. Learn more about Carl’s work and background here.

In this episode, Carl leads an exploration of the intersection of money, identity, and self-actualization. By delving into the psychology behind how people define themselves, he explains how professionals and clients can adopt intentional “forcing functions” to align their behaviors with their aspirations. From investing with purpose to navigating misaligned, aspirational regret, Carl provides practical and philosophical wisdom on becoming the person you strive to be—both for your clients and yourself. He also shares ideas about his new book, Your Money: Reimagining Wealth Through Simple Sketches.

Here’s What You’ll Learn

• Introduction
• What Is a Financial Advisor’s Job in 2025?
• Using “And” in Helping Clients Find Purpose
• Creating a Statement of Financial Purpose
• Identify the Client’s Behavior That Actually Drives Results
• Understand the Relationship Between Money and Identity
• Learn to Use Positive Behavioral Redirects
• Behavioral Completion Rates Drive Success
• Help Clients by Eliminating Distractions

Resources Mentioned in This Episode

• Sketch Guy
• Morningstar
• The Behavior Gap: Simple Ways to Stop Doing Dumb Things with Money
• BAM Alliance
• New York Times
• Harvard Business Review
• NPR
• Financial Therapy Association Conference
• SEMA Designation
• George Kinder
• Bitcoin
• Steal Like an Artist
• Scott Barry Kaufman
• The Society of Advice
• CNBC
• Your Money: Reimagining Wealth Through Simple Sketches

Quotes

“I have made a mistake over the years, and I’ve been called out for it, and I really appreciate it, that I’ve maybe overemphasized. Sorry, that’s not the right word. I’ve de-emphasized the math side of the job. I’ve never meant to, but because of my super enthusiasm for the sort of heart side of the job, sometimes it comes across that I’m deemphasizing the head side. And I so I’m trying to do everything I can to make sure people understand. I think the math stuff is incredibly important. Right? And it’s table stakes at this point. Do you know what I mean? Like, you have to be a technical rock star, and everybody is, and the stuff’s available outside. And it’s so I think if we understand that context, the job to me is not your money or your life. It’s your money and your life. And I think understanding that if we don’t help people get clear about why, like, why are you doing these things in the first place?”

“Client shows up and says, I need five million dollars in a sailboat to retire.  You know, like one of those very memetic I saw Yeah. On Instagram goals that clients often have. And I’m exaggerating it because the sailboat’s so exaggerated. But five million dollars in a sailboat. And with the work we do, we sort of over maybe right up front, maybe over time, we unpack that a bit and we realize, like, what they really want is a sense of adventure and a place to involve other people in that sense of adventure. Right now, we’re much closer to a sense of purpose, a sense of adventure, probably really cool experiences with the people that they love. That’s much closer to a sense of a sense of purpose. Then we can layer on top. Well, turns out you don’t have to have five million in a sailboat to do that.  You could do it this way or this way. We get into a bit of like how George Kinder’s work helps with that. Right?  Like an expression of the value, an expression of the purpose rather than the thing itself.”

“My friend Jerry Colonna often asks the question, what is it about your behavior that is complicit in the results you’re getting? Like, the results your clients are getting. So if you’re getting, you know, for example, and I’m not saying you shouldn’t do this, but if we’re sending out quarterly performance reports and really emphasizing them with a quarterly performance review. Is that helpful? I’m not suggesting it’s not. I’m simply saying it’s an interesting question. Right? Like, we as an industry, we certainly did this to people. Like, woke up, nobody was born thinking they need to outperform a benchmark. Right? Like, nobody had that goal until we taught them that they should have that goal.”

“I think what you should just think about as a real financial planner, real financial advisors, is if you’re feeling pulled in one direction or the other, because it very well could be, hey. I’m really good at getting people to cry in my office side of this business. I kind of need to shore up my tactical acumen. Right? Like, I’m not like, somebody asked me how to calculate a mortgage payment or build an amortization or what would the balance of my mortgage be in seventeen and a half years? I don’t know how to do that. Right? Like, I do know how to do that. But if you’re feeling you don’t know how to do that and it’s important to you, well, then learn. You could say, I don’t know how to do that and I don’t really want to. Awesome. Find somebody who does. Right? Like, there’s so there’s all sorts of room. Like, become the thing.”

Full Transcript

Sasha: Welcome to the Heart of Advice Podcast presented by eMoney. I’m Sasha Grabenstetter.

Connor: And I’m Connor Sung. We’re your eMoney experts. Today’s guest has spent over twenty-five years helping people make better decisions, not necessarily by throwing around jargon or spreadsheets, but by having real conversations about the role money plays in all of our lives. For more than a decade, he was the New York Times Sketch Guy where his simple hand-drawn sketches helped millions of people see money differently. His work has been featured in the Harvard Business Review, Morningstar, and NPR, and his drawings have been taped to refrigerators and office walls around the world. He’s here to challenge how you think about money and maybe how you think about yourself. Please welcome Carl Richards. Carl, thanks for joining us.

Carl: Yeah, Connor. Super glad to be here. Thanks for having me.

Connor: Yeah. Of course. Well, I guess let’s start there. Can you just tell us about yourself, some of the moments that maybe shaped your views on financial planning and led to the Carl Richards that we have with us today?

Carl: Yeah. Such a, you know, it’s always tempting. I think it’s a human thing, but it’s certainly tempting to me to look backwards and make up really cute stories. Right? Like narratives about how all these things make sense and it was all part of a grand plan, but anybody who knows my story knows it wasn’t part of a grand plan. So I literally applied to be a security guard during college. I thought that’s what I was applying for. It turns out the ads had securities, not security, and I didn’t know the difference. So I got into the industry quite by accident, and that was right before the big tech bubble. And I had early experience of being like, wait. I’m not a security guard. What is this? Oh, it’s a math job. That’s I remember thinking like, oh, I’m in a room. We’re doing calculations. Like, this must be a math job. And then I walked into an early IPO. It was actually Netscape for anybody who remembers that. And I remember walking onto the trading floor at the big firm I worked at and realizing this is not math. Do you know what I mean? Like, there was so much, like, energy. And so I was like, okay. It’s not security guard. It’s not math. What is it? And that led to this quest that’s been going on for twenty-five years. Like, what is it? Like, how do we help people make better decisions with money? And the sketches happened really out of an act of desperation one day. I had clients. I was trying to explain a complex concept that I felt like they needed to know before they could make this decision. And I had never done this. I wasn’t a doodler in high school. I have no art background as should be obvious by looking at my work. And I stood up, they just got blank stares. Right? And they were smart, successful people. I remember who they were, a doctor and a technology sales rep. And I just out of an act of desperation, the first time ever stood up at a whiteboard that was in this shared conference room, drew a thing, and they were like, oh, I get it now. And I remember being just, like, sort of addicted to that feeling of, like, clarity, like something complex, something abstract, something intangible just became something somebody understood. And again, no grand plan with it. No grand realization. I just did it again. Right? And then I did it again. And then one day I put it on the early version of the Internet, and then for two or three years, nobody was paying attention except my mom and my sister. Right? And then one day I got an email from and I know how it happened, but again, it was just pure luck. A guy named Kent, an advisor named Kent, sent an email to the New York Times said, you guys might like this. And the Times said, would you do this for us? And I said, yes. And that was a week. At the end of the week, we were like, should we keep going? Yes. So it was just this series of kind of playing in traffic, and the Times led to the book, and the first book led to the second book, and here we are. Right? So the thread, the through thread to it was like, a, how do you increase your luck surface area? Right? Like, how do you play in traffic a lot? And b, this deep I didn’t know I had it, but I’ve just realized the last couple of years, like, this deep passion for helping people, like, live lives of meaning. Like and when you said twenty-five years helping people make better decisions, yeah, it’s better decisions of how to align our use of capital with what’s really important to us. And that’s been the through line of the work.

Sasha: It’s like, I really appreciate listening to your story. I’ve actually seen you before, Carl, and met you in person a very, very long time ago at the Financial Therapy Association Conference in twenty twelve, twenty You were the Yeah.

Carl: You were at the first event that I cried publicly at. That’s right.

Sasha: Oh, I don’t know if I remember that part of it. I just remember meeting you and getting your book, though.

Carl: Can I just tell you real quickly? Remember going into that thinking, here’s a room full of financial therapists. Or people who want to and I need lots of financial therapy, and I was like, I’m gonna go the whole way. And I was like, I’m gonna treat this sixty-minute keynote as a therapy session. So that was the first time where I just pulled the whole thing open and it was super beneficial.

Sasha: Carl, you often really remind advisors that their real work isn’t about crunching numbers, it’s about behavior and meaning. And so I want to ask, in your view, what’s the true job of a financial advisor?

What Is a Financial Advisor’s Job in 2025?

Carl: Yeah. Well, Sasha, that’s such a great question. And I have made a mistake over the years, and I’ve been called out for it, and I really appreciate it, that I’ve maybe overemphasized. Sorry, that’s not the right word. I’ve de-emphasized the math side of the job. I’ve never meant to, but because of my super enthusiasm for the sort of heart side of the job, sometimes it comes across that I’m deemphasizing the head side. And I so I’m trying to do everything I can to make sure people understand. I think the math stuff is incredibly important. Right? And it’s table stakes at this point. Do you know what I mean? Like, you have to be a technical rock star, and everybody is, and the stuff’s available outside. And it’s so I think if we understand that context, the job to me is not your money or your life. It’s your money and your life. And I think understanding that if we don’t help people get clear about why, like, why are you doing these things in the first place? Like, it’s such a funny thing to me, it’s such a funny thing that, like, somehow money has become this thing that sits over in this container that is called, you know, like spreadsheet or math over here, and it doesn’t have any impact with our what are you talking like, every single fear, desire, dream you have is unfortunately some funding with dollars. Like, maybe it just needs time. Well, time sometimes is bought with dollars. Like, there’s some element of the current underneath everything. And so what I think the job is to be a technical superstar, like, understand, like, if you know how to build an amortization table? Do you know what standard deviation is? Like, do you know what correlations and standard deviations and rates of return that need to go into a Monte Carlo analysis? Like, do you know that? Yes. And help people understand that if it’s not helping you towards your definition of a meaningful life, what’s the point? Right? What’s the point? So I think it’s both of those.

Connor: Which I completely agree with, and we talked about recently finding this true deep passion for helping people live lives of meaning and that this connectivity between your money and your life and the financial planning, I think, is in the crux of that as well as just advisors in there too. What led you to rethink how advisors were delivering advice and building trust? I feel like it’s everywhere now where, you know, it’s much more about the relationship, with the advancements of technology. But I feel like you’ve been on this soapbox for quite a long time now, kind of preaching connectivity between money and goals or money and values. Can you just talk a little bit about that?

Carl: Yeah. Thanks, Connor. And preaching on soapbox is a nice word. I would have used, like, ranting and yelling into the wind. So, it’s been you know what it really was? Is it all started with the behavior gap. So, it all started with seeing this really interesting behavior with investments. Like, it was a very, very small segment. It’s like, well, that’s interesting. We often buy high and sell low. That’s super interesting. And I remember, like, I had the best training. I thought I had the best training in the industry. You know, CFP, I had the SEMA designation. I was at a firm that provided fantastic training, and I couldn’t get people to behave. Right? Like, I and I wasn’t even sure I could behave myself. Like, I my SEMA designation, right, I could do manager search and selection, and I figured out after a cycle or two, probably eighteen months or so without telling you the whole long story, but I figured out after eighteen months or so that I had built a very complex, really disciplined way to buy high and sell low and charge people money for it. Right? I had the best training in the world. So, I was ready to quit and go to law school because that’s what my grandpa did. Right? And then I stumbled upon some of this research that was like, it wasn’t just kids from the hills in Utah making this mistake. Right? This and, you and, you know, the early Dalbar research think what you want of it. But, like, the Morningstar’s later research that shows that this is a persistent problem, you know? And I don’t care if it’s half a percent or seven percent. I don’t think it’s seven, but I think it’s closer to Morningstar’s number. Right? And so then I was like, okay. Well, how do you solve that? Well, then as you probably know about that time, this revolution came along where we were gonna actually introduce portfolio design. You know? Nobel Prize winning research where we’re at instead of have a hunch buy a bunch, we’re gonna consider each individual component of the portfolio. Then that that was helpful but didn’t solve the problem. Then we had this crazy idea as an industry and a profession to tie the portfolio to goals. Goal based planning shows up. Right? Like, oh, okay. This is getting better. The whole time, I was just like, this is getting better. And then and then I was like, man, I noticed this interesting thing with clients where humans, me too. Where if you’re scared enough, you’ll just change your goals to give your permission to bail out in a scary market. Right? If you’re just if you’re scared enough, oh, you never mind. I don’t care about that. Just get me out. Wow. That’s fascinating. So I started thinking a lot about what’s under goals. What was under goals? And we had some early work done by a whole bunch of really, you know, fantastic financial planners around values, like, getting clear about values. And I actually really loved them and taking this, I think, a slight step further to purpose, this idea of purpose. So once you get down to purpose, suddenly you’re at, like, oh, what’s the purpose of like, we wanna link your portfolio to your definition of the purpose of life. You know? And now we’re talking, you know? And I again, why? I’ve found that it’s easier to help people make to say no to bad behavior if they have a much, much deeper and bigger yes. And the much deeper and bigger yes to me is the purpose of life. If I can help you say, wait. Wait. Wait. Wait. You’re doing this so that you can spend time with your family mainly outside and serve in your community, and then I can walk you from there to the planning process. I can walk you from the planning process to the investment specific investment process, and I can walk you from the investment process to our specific portfolio choices and say these are all linked. Do you see now? Then you’re more likely to say, okay. Okay. I got it. I got it. Not foolproof, but more likely. That’s how it happened.

Sasha: I have a follow-up question.

Carl: Please.

Sasha: I am curious how you define purpose. I think our advisors would love to hear it.

Using “And” in Helping Clients Find Purpose

Carl: Yeah. It’s such a good question. I remember, and I’ve been meaning to go back and do more of this work, get into the academic work around purpose. Because I remember where I was walking through. We moved to New Zealand for what was supposed to be a year, turned out to be four. And I remember the exact place I was in a forest in New Zealand listening to a podcast, and I’m blanking on all of the names right now, of Scott Barry Kaufman. Scott Barry Kaufman’s podcast. Back then, I think it was called Positive Psychology. And the guy he was interviewing was talking about purpose, and his whole academic career was around purpose. So my definition is that it’s something a little more enduring. It’s an active statement. I can give you statement examples. I remember Jerry telling me that he doesn’t want to be a burden to the kids, and he wants to make a contribution to his community. That gives you a sense of purpose. I’ve got a friend who is deeply engaged with the backcountry skiing sport called skimo. It’s where you race up the hill and down the hill. I’ve got a friend whose sense of purpose is linked to the contribution he’s making in the skimo community. You could say mountain bike community or trail running community, but it’s not that. If you talk to them, it’s actually, “I just love passing stuff on to the kids in my community who love spending time in the mountains.” But it’s not even that. It’s deeper than that. It’s like, “I have a passion for the mountains. These places have changed my life, and I want to be involved with making sure that continues.” And then you move up from there, like, “Oh, okay. I’ll coach.” If I have that purpose, what’s the kind of person who has that as their purpose? What would they do? And you pick a thing as a forcing function. It’s not that you care about riding a mountain bike really fast. What you care about is the enjoyment of the mountains. So that’s kind of the work that I think we do. Let me give you another example. Client shows up and says, I need five million dollars in a sailboat to retire.  You know, like one of those very memetic I saw Yeah. On Instagram goals that clients often have. And I’m exaggerating it because the sailboat’s so exaggerated. But five million dollars in a sailboat. And with the work we do, we sort of over maybe right up front, maybe over time, we unpack that a bit and we realize, like, what they really want is a sense of adventure and a place to involve other people in that sense of adventure. Right now, we’re much closer to a sense of purpose, a sense of adventure, probably really cool experiences with the people that they love. That’s much closer to a sense of a sense of purpose. Then we can layer on top. Well, turns out you don’t have to have five million in a sailboat to do that.  You could do it this way or this way. We get into a bit of like how George Kinder‘s work helps with that. Right?  Like an expression of the value, an expression of the purpose rather than the thing itself. Is that is that helpful?

Sasha: No. I think definitely for sure. And I also like the example that you gave, the first one of not wanting to be a burden, like knowing what you don’t want, but also what you do want. I think, obviously, you went a little deeper underneath that, but I think even just knowing that first top level that you talked about is helpful for advisors to help their clients.

Carl: Can I just make one more comment on this?

Sasha: Yes, of course.

Creating a Statement of Financial Purpose

Carl: I think for everybody listening, don’t be too anxious. And I’ve caused part of this problem, and I acknowledge that publicly, by saying, I’ve said, you know, the goal of my first meeting with somebody was going to cry and it wasn’t going to be me. And so, you know, and I that sort of as a joke, but not really. And I actually still operate that way because it’s how I’m wired. But I realize many people aren’t wired that way. And so you don’t have to be too anxious to get to this perfect thing you call purpose. I call it a statement of financial purpose. You don’t have to, like, this could take eighteen months with somebody could say, sell about five million dollars of Zillow, and you’d just be like, okay. Cool. You know? Like, let’s work on that. And then maybe the next meeting, you’re like, hey. You know what? I’ve been thinking about it. Tell me a little bit more about that. Why is that important? What would happen if you had it? What then? Right? Like, you slowly and maybe that takes not one meeting. Maybe that takes eighteen months. And I think sometimes I get so fired up about it. There’s this sense of urgency and this preciousness around it. I think it’s the other way of thinking about this is just like we want to help clients get clear about what they really care about because it turns out they don’t none of us humans know, especially with Instagram, right, as a metaphor. None of us humans really know what we want anymore. So goal clarification and purpose clarification over time is a massively valuable thing, and by the way, it will change. My friend who’s very specific about his coaching, I promise you in ten years, probably won’t be doing the same thing. But he’ll probably still have that same purpose underneath it, but he might be doing it in a different way.

Connor: Yeah. It’s really cool. It is an amazing suggestion for advisors to continue to advance their thought process and how to actually help clients. Circling back to the actual how, which I think is kind of the basis of the behavior gap. As I’m thinking about kind of where we’re heading and you talked about values, maybe it was the next step towards bettering people. And then now this level of purpose, what do you think that advisors can do to continue to evolve to try and help clients drive towards that? You talked a bit more about continuing discovery, asking probably better questions to get to that level of purpose or understand that purpose. But what else can they do to try and help their clients?

Identify the Client’s Behavior That Actually Drives Results

Carl: Yeah. That’s a great I love that. My friend Jerry Colonna often asks the question, what is it about your behavior that is complicit in the results you’re getting? Like, the results your clients are getting. So if you’re getting, you know, for example, and I’m not saying you shouldn’t do this, but if we’re sending out quarterly performance reports and really emphasizing them with a quarterly performance review. Is that helpful? I’m not suggesting it’s not. I’m simply saying it’s an interesting question. Right? Like, we as an industry, we certainly did this to people. Like, woke up, nobody was born thinking they need to outperform a benchmark. Right? Like, nobody had that goal until we taught them that they should have that goal. And so again, I think that one, that example is probably less prevalent inside this thing we call the profession, but nobody else out there in the world, they don’t know the difference between a real advisor and a fake one. Right? So, I would just start looking at things. Like, what are the things on your, uh, what are the things in your background on your Zoom calls? Are they stock certificates? Is it the chart? What’s in your office? What’s on the coffee table? Is it, you know, Money magazine? But what is it on the table? Is CNBC on in the waiting room or the foyer? Like, don’t let me catch you doing that because then I anyway. So, like, those are simple places we could be thinking. Like, when we send out a monthly newsletter, do we send out market commentary and economic data? I again, I’m not saying it’s a bad idea. I’m just saying maybe we should deemphasize it a bit, tone it down a bit, and put more about living a meaningful life and maybe even some examples of good behavior? Like, should we look at everything we’re doing and say, how can I reinforce the kind of conversations, the kind of behavior I want clients to be having versus encouraging it? That’s one simple example. And then I think the other thing that we need to be aware of to me and, again, I’m not in any way predicting anything. I’m simply saying it’s been a long time since we’ve had something super scary in the markets. Like, there’s lots of scary news. It feels incredibly uncertain, but the markets have been well behaved. Like, we haven’t had anything prolonged. You know? Like, if so, it leads me to believe that it’s always a good time. I don’t think now is a better time or worse time, but it’s always a good time to be slipping in little conversations around risk. Because remember, risk is an arbitrary concept until you experience it. Right? And like talking about getting punched in the nose is completely different than actually getting punched in the nose, and it helps to talk a bit about it. And how would you talk about that? You talk about it in the context of goals and purpose and values. Right? Remember, our portfolio was built this way to help give you the best opportunity, the highest likelihood of realizing these goals with the lowest risk. Remember, that’s why we built this portfolio. And by the way, we know there’s going to be prolonged downturns. We just don’t know when. Right? They’ll be a surprise to us too, but it won’t be a surprise they happened. It will just be a surprise when and why. Like, we’re starting to blend that language in. To me, I think it’s really, really important now and probably always, actually. Which leads me to a follow-up question, which is, like, we are the change that we need to affect. Right? Like, I think a lot of clients come to financial advisors still, even real financial advisors, and that is the expectation or the experience is that they just want returns because that’s what their peers said is, I’m, you know, I got x amount of alpha. They don’t even know what alpha means, but they got it. Right? And then you want it. Right? So what do you think clients actually want from their advisor, and how does that differ from what we feel like we’re offering as advisors? Yeah. Look, Conor, you’re pointing to a real, real problematic paradox here. And the problem is nobody shows up in your office asking to cry on your couch. Right? Like, no advisor has ever had anybody show up and say, help me live a meaningful life. As far as I’m aware, it’s never happened. Even the ones that have branded and marketed themselves that way, like, gone full life planning, like, I still don’t think I can’t imagine. I have never heard. Maybe it’s happened. I’ve never heard of people showing up like, hey. So they typically show up with a presenting problem, and that presenting problem is often acute. And I sometimes compare it to an arrow in their arm. You show up at the emergency room with an arrow in your arm, and the doctor wants to talk to you about ankle flexion or your diet. Like, you’re gonna be like, bro, get the arrow out of my arm. You know? So I think what we can realize is that when advisors greet those presenting problems, they should do so with empathy. This was really hard for me at first. I just remember thinking, why in the world are we having this stupid conversation? And I think I could go toe-to-toe with anybody around investment performance. Like, again, back to our head thing, I felt you put me in any room, any institutional consulting room, and I can go toe-to-toe about investment performance with the investment process that I used. And I was aware that it didn’t matter at all if we couldn’t fix the behavioral problem, which leads us all the way down to purpose, like we talked about. So I think what we have to do is greet it with empathy. Like, hey, Connor, I get it why performance would be important to you and why you’d be nervous right now. Or I get it why performance, like, you show up, the guy next door, the guy I ride my bike with told me about this. I get it why that’s important to you. And it’s actually really important to us too. It’s a key driver in your overall success. Performance. Investment performance is a driver of your overall success, and it’ll be incredibly important. Right? Would it be okay if we back up first? Right? And then we slowly move back to whatever your questions are on why this matters and how we build. If it’s a client who’s coming in complaining about performance, like, hey. Why is my portfolio just doing, you know, only did seventeen percent this year because my buddy got forty-two. Then, like, we’ve got some, I call it vitamin C problems. Like, we haven’t done the work in advance to help them understand. But sometimes we have to say, look, I get it, man. When I hear those stories too, I wonder. In fact, at least once a week, our whole investment committee probably hears a story like this, and we go check it out. Like, so you’re implying here that you take it seriously. Would it be helpful if I walk you through why–what you’re hearing from your and then we have to have really good stories. Not stories, but examples, data around, a, we don’t even know if that guy really got forty-five percent. Did he get it on his whole portfolio? Did he get it on ten bucks that he lent his buddy to Sports Bet? Like, we don’t know. And b), it doesn’t matter anyway because here’s what we’re after with you. And we take them from so I’ll wrap this up right here. Like, I call this the scary markets conversation, but it can be the greedy markets conversation too. It enters at the product level. Top of a pyramid is what I’m pointing to for those of you who can see. This is one of my sketches. The top of the pyramid is sort of product market economy news. Almost all those phone calls come in at the top of the pyramid. But what we don’t realize is that that’s the least important, incredibly important part, but least important part of the pyramid. Like, as we move down, we’ve got investment process or planning process. We move down, we’ve got the plan. We move down, we’ve got purpose. So what we want to do is, with deep empathy, greet them at this phone call because they’ve been spinning around it for two weeks. You know what I mean? Like, they knew what you were gonna say. They didn’t wanna call you because they knew they were gonna get this tad little bit of a lecture. But if you greet them with empathy there and say, hey, get it. Could we back up real quick? And then you pull back out. Let me go grab my file. I call this the please hold method. So greet with empathy, step one. Number two, please hold. It’s just creating space between the stimulus and response. Hey, can you hold on a sec? Like, I hear you, Connor. I understand. Can you hold on a second? Let me go grab my file. Grab the file. What do you do when you have the file? You say, hey. Before we get to that, can I just check in on something? You told me time with your family, mainly outside and service in your community and your church is really important to you. I just want to check before we move on, is that still true? So we’re trying to pull them out of the branches where the wind is blowing to the roots. Then we can move up from purpose to plan, plan to investment process, all the way up to the product.

Sasha: But what is really the relationship between money and identity? And does adjusting one impact the other? And let me also emphasize, I feel like you’ve done a lot of really deep work with both. And so I think you come from a place, this is gonna, you come from a place of experience to tell advisors, hey. You know, I’ve done this for years, it’s easy. And you do make it sound very easy, but I feel like for them, maybe it might be harder. So, again, the question is what’s the relationship between money and identity? And does adjusting one impact the other?

Understand the Relationship Between Money and Identity

Carl: That’s such a beautiful question. Thank you. And thanks for the, you know, explicit and implied compliment. And I just want to be super clear. Like, I’m a mess. Right? And, like, I’m trying to figure this all out. Like, all my work really is an adventure journal. It’s not meant to be prescriptive or advice in any way. It’s just meant to be like; I’ve been walking on this path. I found this spring. It was really hot. If you happen to be hot and you happen to be walking past the spring, there’s water there. And so money and identity to me is one of the coolest subjects. Identity is so amazing, such an amazing discussion. So I think that we are often more interested in being seen as the type of person. So, for example, we’re more often more interested in being seen as contrarian, for example, than we are as actually being contrarian. Right? We’re more, uh, and I’ll circle this back to your question, but we’re more interested in being seen as creative than we are interested in actually being creative. Right? And I think this shows up with clients. Like, we’re more clients in our own work. Like, we’re more interested in and you find this as you slowly uncover this sense of purpose. You find that, like, sometimes we’re more interested in being seen as the person that owned Bitcoin, right, than actually doing the hard work. We’re more interested in being seen as a disciplined budget person than we are actually being. We’re more interested in owning the wake surfing boat. Sorry. We’re more interested in the idea of something. The idea of second homes. This really hits with second homes. Right? How many clients have bought second homes and then a year or two later been like, man, that thing’s an anchor. Like, we that thing drives me like, I hear that more with second homes than maybe anything else other than boats. Boats are the other thing that people are like. It’s much better to have a friend that has a boat than actually have a boat. So I think when we start to, uh, like, when we start to unpack, I was in this fascinating conversation on my podcast fifty fires with Austin Kleon, who wrote Steal Like an Artist. And he said like, Austin’s done really well, um, really, really well for himself, and he lives very frugally. And he said, you know, you’re talking to the guy who still drives a twenty-five-year-old Honda, and sometimes my feet get wet when it rains when I’m driving the car. Like but he said, I’m the person. I’m the type of person who drives a twenty-five-year-old car. And we spent a bunch of time on like, okay, this is so interesting. What do you mean? What does it mean to be the type of person? And so I think all of that’s preamble for the idea of if we get more clear about our own self-belief as advisors of our own identity, it turns out you can kind of just decide that if you want for instance, if you want to do more work in public, whether that’s have a newsletter, write a book, do a podcast, like, whatever, you can kind of just decide, I’m the kind of person who I don’t know which one comes first, identity or behavior. They’re a circular function to me. Because if I behave a certain way, I start to identify as that kind of person. If I identify as that kind of person, I start to behave a certain way. So, like, what do writers do? I’m a writer. What do writers do? They write. Why are you producing a podcast every morning? Because that’s what a podcaster, in my definition of a podcaster, does. Why are you investing on the fifteenth of every month? Why do you invest on the I just invested yesterday. Why? Well, because it was the fifteenth. Because I’m the type of person who is disciplined. What does the type of person who’s a disciplined investor do? They set up an automatic investment on the fifteenth. Like, I that’s a bunch of different examples of I’m not sure if it’s the behavior or the identity, but I also love last bit on this. I love the idea of picking forcing functions, uh, of a forcing function that will force you to become the kind of person that you want to be. Let me give you an example. I’ve got a friend at age forty-nine, sold a tech company, did decent for himself, but he realized his intention was totally fragmented, and he didn’t like that. And so he said, I want to be the kind of person who can think deeply about a single problem for a long period of time. That was his goal. That was a sense of purpose, if you will. And he said, what would the kind where do those kind of people hang out? What do they do? He’s like, well, know what? One thing they do is the type of person who can think deeply about a single problem for a long time often gets a PhD. So he got a PhD. He doesn’t care about the PhD. He cares about what it did to the old version of him had to die, and a new version had to be born to become that thing. So I love working with clients, man, I’d love to spend more time with my kids. Ah, what would be something we could enroll ourselves in? Like, I love that word. Enroll yourself in to become that kind of person. Well, my kids love soccer. God. What if you signed up to be the soccer coach or the assistant coach? You don’t have any skills, so you’d just be the assistant coach. Then you have to drive them to the thing, you have to be at the practice, you have to go to all the games. It’s a forcing function to become — do you care about being the assistant coach? No. You cared about time with your kids. So I love designing those sorts of things with clients and ourselves to become the kind of people we want. Talk about — sorry about this rant. Bain. Bain on their pyramid of value? This is crazy. Bain is like this, I thought this was just patchouli oil and drum circle stuff. Bain is as buttoned down as they get. The top of their pyramid of value for our profession is self-actualization. You can find this. Just search Bain’s Pyramid of Value. You’ll see self-actualization. That’s the job of an advisor. Now, at the base of the pyramid is all the stuff we all think we have to do, and we do have to do it. But the whole reason we’re doing it is to get to the point where we can help people become the type of person that they have the identity that they want and that’s going to change, and we’re going to keep doing it in a new version, a new version. And they’re going to wake up and just be like, are you kidding me? You know? Are you kidding me? That’s what my advisor does. Good luck cold calling against that. Right? Plug that into your little algorithm and see how that works.

Carl: Let’s ask the hard questions. Let’s do it. Let’s do it. Yeah.

Sasha: But, you know, I think a lot of clients, people, humans in general, really live their life kind of programmed. So what you’re asking essentially is to, like, flip the program, flip the switch. But that’s what you’re asking, though. Like, you’re asking them to sit down and really get to know who they are so that they can help others. Like, that’s a whole different ballgame.

Learn to Use Positive Behavioral Redirects

Carl: I think look, again, let’s back up for everybody listening. Be gentle with yourself. Be patient. Like, you don’t have to like, you maybe this isn’t what you want to do, and it’s not the job you signed up for, and I think you’re going to be fine. Right? Like, just help people have goals, build great portfolios, have plans. You can get your kicks elsewhere. Like, go do something after work. It’s all totally fine. But for the people for whom this resonates with and you feel sort of this, like, weird little I sometimes call it dancing with dragons, this weird little feeling inside where you’re like, that’s what I’ve always wanted to do. Just start practicing. Because you’re right. It’s nobody signs up for this. What’s so fascinating to me is I’ve done this, I don’t know, hundreds of times now. When you talk to clients because I do a lot of speaking engagements for, like, client appreciation events or gatherings of small family offices or small family meetings or whatever. I’ve talked to lots of your clients, and then I’ve gotten thousands of emails because of the weekly column. What they will tell me, the clients who’ve been with you for some period of time. I find it to be about eighteen months. The clients who’ve been around a while, when I ask them why do you like Julie as your advisor? They never tell me the things we all they never tell me what they came for. Right? When they showed up at your door, they don’t tell me those words. Oh, man. She picked the best investments. Oh, my gosh. Her performance is so great. Oh, my gosh. This financial plan. I mean, this thirty-year line is incredible. And they never tell me that. They tell me things like, I don’t worry about this anymore. They tell me, like, I used to be worried that I was going to end up like my dad. And Julie’s helped me realize, like, I don’t have to think about that anymore. They tell me things like, I spend quality time with my kids every summer because we’ve set aside this time, and they made that — they tell me things like this. Uh, we bought the ranch, but my family’s always wanted to move to a ranch and get back because that was what my grandpa did, and we did it this year because Julie helped us. That’s what they tell me. So you’ve got this really weird flipping of the switch thing that happens, and I think, to me, my approach has been to show up as what they’re expecting. Right? Because I understand you can do this differently. You can be like; I am this person who’s going to change your life and give you meaning and I’m going to use money. And people do that successfully and I applaud them. I’m a huge fan of those people. I know a bunch of them. But I think it works better for more of us to show up as they’re expecting you to and then slowly pull a series of righteous tricks. I call them righteous tricks, not bait and switch. They’re in service of the client. Slowly pull a series of righteous tricks in front of them to help them realize they’re going to wake up eighteen months later and go, oh my gosh. Like, they wouldn’t even be able to tell their this is why referrals are sometimes a problem. Like, they don’t even know how to tell their friends what you did. Right? They don’t even know how to talk about it. That to me is the approach. Like, yes, you’re flipping the switch. For me, I often show up the way they want, and five minutes later, I’m pulling the huge racist trick. It’s a giant punch in the nose and a deep empathetic hug, and everything’s going to change. Probably not a good idea. Like, probably the better idea is to slowly pull a series of righteous tricks to help them wake up one day and go, oh my gosh. I don’t even worry about that anymore. Hey. Can you believe that? Like, we have a financial planner. I’m sorry to get emotional about this, but we have a financial planner who we dared last week tell a dream that we haven’t dared tell anybody, and she stopped the Zoom meeting, looked my wife in the eyes, and said, so are we messing around, or are we going to do this? And the feeling was sort of like, are you she’s like, because if you’re going to do this, I know how to help you do it. And to even open that possibility for us, I mean, how do I tell? Like, I can’t like, what are you talking about when you send me a text message saying that you’ve got a great portfolio? Like, I don’t even know what to do with that. Sorry. So, anyway, is that hopefully, that’s helpful.

Sasha: I love your vulnerability, and I really appreciate it. I’m going to let Connor chime in.

Connor: Yeah. It is endearing, the transparency and the openness. It brings me to another question, which I think we’ve talked about quite a bit, but the real financial advisors, I think, are often not just the mathematician or the spreadsheet guy, but they’re part planner, part coach, sometimes therapist. How do you see all of those different roles complement each other? And, you know, what mindsets do advisors need to continue to move towards to continue to thrive, learn, evolve in order to help their clients to get to that level?

Carl: Yeah. Yeah. It’s a great question. I think there’s room for all of us. Do you know what I mean? Like, I and, again, I’m trying to emphasize that I get so fired up about one aspect, and I don’t want that to come across as it’s the only way. I don’t who am I? I don’t know. I think there’s room for all of us. And so I think what you should just think about as a real financial planner, real financial advisors, is if you’re feeling pulled in one direction or the other, because it very well could be, hey. I’m really good at getting people to cry in my office side of this business. I kinda need to shore up my tactical acumen. Right? Like, I’m not like, somebody asked me how to calculate a mortgage payment or build an amortization or what would the balance of my mortgage be in seventeen and a half years? I don’t know how to do that. Right? Like, I do know how to do that. But if you’re feeling you don’t know how to do that and it’s important to you, well, then learn. You could say, I don’t know how to do that and I don’t really want to. Awesome. Find somebody who does. Right? Like, there’s so there’s all sorts of room. Like, become the thing. My personal thought is to go all the way with the thing you’re really good at and find people to complement around you the things that you’re not. That’s my personal belief, but I’m not saying it’s the right choice. So, like, what that could look like is, let’s say you’re the opposite. You man, give me a calculator. I’ll run circles around anybody. I can explain the investment process, but I have to leave I don’t know what to do when somebody shares a vulnerable story with me. You know, somebody will tell me about their spouse passing away and I’ll be like, well, so is the will in the right place? You know, like, you know what I mean? Like, and that’s a real example, and I have deep empathy for that. It’s not my problem, but I can understand. I’ve talked with so many people. So that’s their problem. So you have a choice. Intentionally practice what you’re bad at, get better at EQ, practice it. You can do it with your spouse, your kids, your friends. Look for opportunities when there’s a chance to go, hey, can I ask you about that? How did that feel? Or, you know, that must have been hard. Look for chances to practice or find somebody who’s really good at that to complement what you’re not good at. And I think any of those options, there’s like that’s the whole range of options. And I just wanna repeat, I’m a big fan. If I was a hardcore analytical guy and didn’t have an emotional bone in my body, I would probably go all the way with that. Right? And if I was who, what I’ve been trying to get clear about is who am I? Who you really are and go the whole way is my preference. So that’s how I’d answer that question.

Connor: Well, as a current learner of “The Society,” can you just explain to our audience a little bit about The Society of Advice? I do think that’s a huge opportunity for folks to continue to expand their horizons and get to some breadth and depth of new topic areas.

Behavioral Completion Rates Drive Success

Carl: Sorry. I can’t talk about it. I’m just kidding. That’s actually here’s what’s funny about this Society of Advice is I don’t really know how to talk about it. So this like, I’ve been accused of being sort of like secret or maybe even like exclusive, and it’s not that at all. I literally don’t know how to explain it. So let me try though because we’ve been working on this. I think there’s a lot of really good people in our industry teaching tactical stuff, you know, tactical workshops, tactical courses, programs, right, year-long programs, month-long programs. Like, I have a bunch of names popping into my head right now. We all it’s not hard to find them. Marketing, how to have a good first meeting, you know, email marketing, like, really good people. And I don’t they’re doing a great job, and I don’t feel like that’s my unique contribution. And so what I feel like my unique contribution is how many places do you know where you can go and be in a space where you can be quiet and hear a thoughtful conversation that will spark insight. And here’s the problem I was trying to solve. We built some of those tactical workshops, and everybody bought them. Like, we built online courses back when it was before it was cool. And everybody bought them. We had a great business around it. But I noticed after six to twelve months of doing it that no one did anything with it. So I wondered, again, sort of like the behavior problem, is it just a problem for kids in the hills of Utah? Like, I must be doing something wrong? And then I looked. Like, the completion rate is in the single digits of online courses generally. In fact, most people, more than fifty percent, don’t even open them. Right? Don’t even start them, let alone completion rates. I was a bit frustrated with that. We had a great business, though. So I was like, oh, no. What do you do? And I didn’t care. We blew the whole thing up, and we said, I want to talk so if you are listening to this and you recognize this feeling of, like, you bought a thing, you didn’t do it, you bought a thing, you didn’t do it, you bought a like, welcome, like, deep empathy to you. I’m the same way. I wanted to create a place where we were more interested in the part of all of us that already has the tactics or knows where to find them and is still not doing them. Right? What’s that about? A place where you get more in connection with who you really are, align what you wanna do next with that because you’re more likely to do it. Like, because I want a group of people who are gonna change the world. Well, the only way we’re gonna change the world is if we stop hiding. You know, like, these places that hide, we’re also good at it. We call it research. That’s what we all call it, research. It’s just a like, if I could just look if I could just watch one more video about how to deadlift, I don’t have to go to the gym and deadlift. If I can just watch one more video about how to 10x my business, I don’t actually have to do anything to 1x my business. You know? So I we’ve created a place where we’re not worried about any of that stuff. What we’re worried about is like so here’s how it shows up once a month. We have we create a space. There’s no chat, there’s no forum, there’s no email newsletter. This is all on these are not flaws. These are features. There’s no there’s no archive, there’s no homework. You show up once a month for ninety minutes. Get quiet and listen to a conversation between me and somebody amazing. There are always people amazing. Some of them you’ve all heard of and some of none of you have heard of. And then you pay attention because this is my last bit about this. You pay attention because what will occur to you will be different. You know? Like, you two could be sitting next to each other on Zoom among two hundred other people on the call, and what will occur to Connor will be different than what occurs with Sasha. So you two could be sitting next to each other on the Zoom meeting with two hundred other people, and what occurs to Connor will be completely different than what occurs to Sasha. Right? And all I wanna do is create the space where those insights will occur. That’s what this is saying. So we do that every month. Thanks for asking.

Sasha: Of course. Yeah. I have this question, and it really goes back to kind of where you started being the sketch guy. And I heard a little earlier when you said, you know, like, it gave you, like, almost like a dopamine hit is what it sounded like to me is saying, like, “hey, I got them to understand this concept because I drew it out.” So when you sit down with the cardstock and a Sharpie, how do you take this really complex idea and distill it down into, like, this one simple powerful drawing? And as you think about describing the process, what can advisors take from it to bring that same clarity and connection to their clients?

Help Clients by Eliminating Distractions

Carl: Yeah. Well, having just sort of talked about my deep allergy to tactics, let me give you some specific tactics about this because this is one area that I do like to talk a bit about. Um, so, uh, the process of taking something that seems relatively complex and making it simpler, that’s probably the most common email I got from Times readers was, will you please tell the advisors to speak in a language I can understand? Some version of that. Please make it simpler. So here’s a couple things you can do. If you have a piece, let’s just say you have, like, an educational brochure or a marketing piece or even the about page on your entire website. Like, take your entire website and just for a minute largely, we’ve given these things, these marketing brochures, educational brochures, websites, email news, anything we produce, we’ve given them too many jobs. Like, I feel bad for these poor websites. They’re like beasts of burden, and they are always disappointing us because they can’t do that many jobs. So what is the one job you want this thing to do? You can do this in speaking or visuals. Let’s just stick with visuals because you’ve got a visual in one of your educational pieces that you hand out to clients. Look at the visual and think and you can do this with anything, but we’re gonna stick with visuals. What’s the one thing you want people to remember from it? You only get one. Like, I know you want two or three, but you only get one. These are single idea. It’s all they can do to move out of visuals from it. Imagine you’re gonna give a talk to you got invited to speak to a dentist conference. Like, they only get one thing they’re gonna remember. And so the way I visualize that is if you hand that graphic or that marketing piece or that educational piece to a hundred people, they all read it. And as they’re you have them all in a room, they’re quietly reading it, and they one by one start filing out the door. And if you were standing at the door and said, what’s the one thing you remember? What’s the one thing you hope they would all say? Okay. So if you can get that in your head, then you go back to the piece and say, okay, let’s remove everything that doesn’t reinforce that one thing. Now this editing and distillation process is really hard. It often is opinionated. Right? It’s like you have an opinion that you’re gonna say, I think I can remove that. Sometimes I get this wrong all the time. Sometimes I remove the wrong thing, and then I get feedback real quickly. Like, if you were standing at the door and fifty people told you that you were like, what? That’s not even I had no idea you’d take that. Okay. You got it wrong. Great. Now you know. Go back to the thing and say, wait, how do I fix that? I’ve had single words like, for instance, anything that distracts from the one point, remove it. I find this is a pretty general rule. I find that any number on the page will distract. You’ll look at my sketches. There’s no numbers on any of them, I don’t think. Any number will distract. People want to debate the number, and they’ll miss the point. So remove numbers, generally speaking. Remove any reference in a marketing piece to gender unless gender is the point. I have no problem writing something where gender is the point. But if it’s not the point, remove it. If politics is not the point, remove it. If religion is not the point, remove it. Anything that would distract people, you remove it. And then just think, perfection’s not this is, um, the little prince, I think. Um, perfection is not achieved when there’s nothing left to add, but when there’s nothing left to take away. So take stuff out and see like, on a written piece, I literally copy, um, a sentence, and I’ll remove it and see if I lost anything. Like, what happens if I pull that out? What happens? So that’s the process that I go through. Sometimes that’s literally like fifty back when it was cardstock and Sharpie, it was just, like, over my shoulder, shoulder, you know, like fifty to a hundred pieces of it. It’s a lot of work. I have things I’ve recently removed. There are words in some of the sketches. There’s one word. I can think of one specific example that I was thinking about for ten years. It wasn’t quite right. Just wasn’t quite right. I removed it and it was like, oh, that’s right. That’s right. So between ten minutes and ten years, just whatever you wanna spend to, like, work on what’s the point, what are you trying to get across. I know you wanna cram everything into that graph. It it’s not gonna work. Have multiple graphs if you need to, but it will not work. Your clients will just go, I don’t know what’s on here. I don’t know.

Sasha: That kind of leads me into my next question because I know your new book is coming out, Your Money: Reimagining Wealth Through Simple Sketches. I would love for our audience to hear just a little bit about it and how advisors can use it to work with their clients.

Carl: Yeah. I’ve been kind of resisting writing a new book for, I think, ten or eleven years since the last book came out. Mainly because I wanted to make sure it has a real purpose. I got really focused on conversations. My work has really become largely about conversations. Then I noticed something over the years people were using, and you mentioned in the intro, these sketches are taped up on refrigerators and conference room walls all over the world. What I found interesting was the emails I get. I never get emails saying it’s visually impactful. Instead, I get emails saying, “I had this on the wall, and my client saw it, and they asked about it.” I get hundreds of those emails describing the conversations that got started. So I started thinking of them using my friend Hugh MacLeod’s term: conversation grenades. It’s like you toss them into a room, and conversations break out. So then I thought, “Well, I don’t really care about a book. I care about conversations.” But over the years, I got convinced that if we could design it right—and this was really important to me—the book could be an artifact. It could be a thing that got passed around and generated conversations. I had this humble goal of starting a million meaningful conversations about money. So that’s what the book is. It’s 101 conversation grenades: 101 sketches and 101 short essays. Some of them are two sentences, but none take more than three minutes to read. The design of it was crucial. I wouldn’t do it unless I could find a publisher that would let me design it the way I wanted. There’s lots of white space. The physical piece, I think, will be the most valuable version of it for advisors. The digital version will be cool, and the audio version—which I’m working on now—will be great because I describe all the sketches, which is really fun. But I think the physical book will be the most valuable. It’s seven by seven, so it feels like an approachable coffee table book. It’s softcover—not paperback but softcover—so it feels approachable, like something you’d actually use. It’s much closer to a book of poetry than it is to personal finance. There’s lots of white space, lots of questions, and very few answers. We’ve been overwhelmed by the number of bulk orders happening because people want to use it as a client tool. That’s what I wrote it for—to compound conversations. It’s called Your Money: Reimagining Wealth Through 101 Simple Sketches, and you can get it now. My favorite suggestion is to buy a copy at Amazon and a copy at your local bookstore.

Sasha: It is amazing to—

Connor: See how much thought you put into even just the covering of the book.

Carl: Can I tell you one more thing?

Sasha: Of course.

Carl: Here’s the level of thought. You know all that front matter in a book? The copyright stuff and the legal disclaimers and all of that? I thought, “Does that serve the reader? Does any reader want that?” No reader wants that. I thought there was no way my publisher would let me move it, but I asked anyway. I said, “In service of the reader, could we move this to the back?” And they said, “We’ve never been asked that. We’ve never considered it. But yes.” So that’s the level of detail. Every single piece of this book was thought to be in service of the conversations I hope will happen around dinner tables, on road trips, and in coffee shops across the country.

Connor: Well, I guess just to wrap us up, our final question—which we ask all of our guests—is, how would you define the heart of advice when it comes to financial planning?

Carl: To the degree that each of us is comfortable doing it: helping people align their use of capital with what’s important to them.

Connor: Nice and succinct.

Carl: Yeah. I worked on that for a long time.

Connor: Yeah. So, Carl—

Carl: Thanks for this conversation.

Connor: Yeah. It’s been amazing. Thank you again for joining us. Number one, I’m glad that you didn’t end up becoming a security guard. We’ll start with that.

To listen to this episode and other full episodes of the Heart of Advice Podcast, visit our YouTube or our Spotify channels.

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