Speaker: [00:00:00] From Childfree Insights, this is Childfree Life By Design, the go-to resource for building the Childfree life you want. Every episode gives you practical guidance, clear direction, and meaningful conversations to help you live intentionally and design a future on your terms. This podcast is for educational and entertainment purposes only.
Please consult your advisor before implementing any ideas heard on this podcast.
Dr. Jay: So welcome to Childfree Life by Design. Today we’re talking about re-imagining life and financial planning and what it means for people who are building a Childfree life on their own terms. I’m Dr. Jay Zigmont, in this episode, we’re covering defining wealth beyond dollar signs, overcoming the behavioral gaps that sabotage our goals, and using simplicity to gain financial clarity.
If you’ve been wondering how to reimagine your wealth, this conversation will give you the practical tools to make intentional decisions that support the life you want.
Our guest today is Carl Richards, a [00:01:00] certified financial planner and the creator of the Sketch Guy column in the New York Times, where he crafted clear, relatable insights about money with just a Sharpie and card stock for a decade. Carl is the author of the Best Sellers the Behavioral Gap, and the one Page Financial Plan. His unique journey into the finance started with a slight misstep when he applied for what he thought would be a job as a security guard, only to find out the ad actually said securities. Sparked a lifelong dedication to reshaping how we think about money. His latest book, your Money, reimagining Wealth in 101 Simple Sketches came out in October, 2025. It’s a powerful collection of sketches and essays designed to spark real conversation about what truly matters. Carl’s also hosts the Behavioral Gap Radio, his daily podcast, and his latest audio project, 50 Fires explores the intersection of money and meaning. So welcome Carl Richards.
Carl Richards: Jay, thanks. I’m really looking forward to the conversation. Thanks for having me.
Dr. Jay: And if you’re listening to this, you probably wanna go to the YouTube and look at the video. ’cause we’re gonna use some images from the [00:02:00] book and we will explain them as best we can. A picture’s worth a thousand words, but you got the guy who drew the diagram, so you should probably go look at the video.
Alright, Carl, so the first image I’m gonna grab is actually one of those weird stories. I’ve been working on this project with one of my clients who happens to be a crew chief for Nascar, and I went into his Haller, which is their office, and saw this image sitting on the wall.
And I was like, how in the world do you know Carl?
And it’s amazing to me because I knew you didn’t draw this. Hey, how do you run a NASCAR race?
But this image I know you told me this has been everywhere. So talk a little about what this is and why it matters.
Carl Richards: Yeah. So for your listeners, let’s just call it a Venn diagram. And one circle in the Venn diagram is labeled things that matter, and the other circle is labeled Things I can Control. And then there’s a little overlap, and that overlap is what I try to focus on. So the things that matter, things I can control, I’m gonna try and focus on those.
[00:03:00] And yeah, that story’s fascinating because I have heard all sorts of stories like that. One of my favorite bike companies, they have it in their boardroom, and a venture capital private equity, a doctor. So, this is the only one of my sketches that my wife allows in the house.
Right. The rest have to live in the garage. I can tell you a quick story, this was generated when I was at a lacrosse game. I believe my son was maybe between eight and 12 years old. And if you’ve ever watched, let’s say 10-year-old boys playing lacrosse, it’s really just 10-year-old boys knocking each other down with sticks.
And my mom was coming to watch her grandson. And I could see from a hundred yards away when she showed up, I saw her walking across the field that something was wrong. And she sat down and I asked her, what’s wrong? And she said, what all mothers seem to say? Oh, nothing. And then I pressed a bit and she let out this long sigh and in our family, we never talked about money.
So to have a conversation about currency, [00:04:00] she’s let out, a big sign said, oh, the dollar. I’m just so worried. And I was just like, I’d been in the business maybe 10 or 11 years helping institutions make decisions about money. And even in my own work, I’d never had a conversation about currency. ’cause in the United States, we typically don’t talk about it.
Everybody else talk about it. It’s a whole nother story. But, she said, oh, the dollar. And I was like, what do you mean the dollar? First thing I wanted to say, what have you been reading? But I didn’t, I said, tell me more. And she said, well, it could collapse. And I said, okay, now I get the dollar and collapse in the same sentence.
I understand you’re a little worried about that, but we went on to have this conversation. Okay, let’s talk about would it matter to you? Then a more technical way to say that would be, what’s your exposure? If that did happen, are you exposed to that? Does it matter? And then the second thing is, can you control it?
Right. And she had no control over the dollar and I would argue that there, that day. It didn’t matter. And the next day when she was supposed to be at church, she was still spinning around the dollar and the next day she’s supposed to be on walk-on with friends, it [00:05:00] didn’t matter then either.
So that’s been really useful for me to get really clear about. And the good news in financial decision making, most of the things that actually matter at the end of the day, there’s a couple notable exceptions, but most of them you have some control over, or at least you have control over your exposure to them.
So that’s where that comes from.
Dr. Jay: Yeah, and I don’t know about you, but at least this year it seems like the political stuff is way too much of a topic. You wouldn’t expect it to be the middle of financial planning topics, but it has been for our clients, and we’ve had a lot of folks, well, maybe I wanna leave the US or whatever else.
I’m like, okay, cool. You can create a plan that if you think things are going so bad, you can leave. That doesn’t mean they actually leave, but if you have the plan, you feel like you have little bit of control because there’s so many things you cannot control. That at least having the financial independence to be able to choose to move or do whatever change your life, sometimes can help.
Does that make any sense?
Carl Richards: Yeah, totally. There’s two ways you can go with that, one is, where I thought you would go would be, [00:06:00] there’s so much noise that we have no control over. And to be honest, do it even matter. It doesn’t even matter. I had this great conversation with Morgan Housel recently where we talked about three or four things in the last decade, probably three or four things in the last 20 years of the United States economic history actually made a difference. And there’s hundreds of headlines every day.
And almost all, 99.9999% of them don’t matter. So I think getting more clear about that. But what you’re pointing to is when we feel a little outta control, when we feel a little scared, when we feel anxiety or nervous, it really helps to take some action to give you some locus of control. If I read the headlines about investing right now, and I get nervous, my default is to go clean the garage.
Go chop wood and carry water, and that sounds silly, but the little act of, oh, the garage is cleaner, gave me a [00:07:00] sense of control of my life. Allowed me to focus that my energy on that locus of control rather than the spinning ball over here that I have no control over,
it makes me feel better, and my even better default is a little bit of my hands in the dirt, something real, something tangible. That’s much better than what should I do with my stocks? And what you pointed to is like, Hey, maybe I should know that I have a plan. I’ve talked about my exposure to these things.
I’ve made myself more resilient if one of them shows up and now I can try to set it aside and the next time I get hit by one of those things. ’cause I can’t avoid the world, headlines, news, whatever I can say, I can notice it in my body and I can go, oh yeah, that’s right. I already talked with Jay about this.
I could set this aside. Go clean the garage.
Dr. Jay: Yeah, and I think the hard part is there are some things we just can’t control and we’ve gotta let ’em go. And I’m not good at that. So, maybe I can’t help my clients through that, but I’m like, Hey, let’s make a plan.
And that’s where this financial [00:08:00] planning thing comes in.
And we say, we try to make your finances simple, so your life can be amazing. You We’re planning for your life first, then your finances,
your diagram brings ’em together.
Carl Richards: So again, another Venn diagram’s, pretty simple one, one circle says your money. The other circle says Your life, so your money, your life. The overlap is labeled real financial planning. And sometimes this is painted as a choice. We have to choose between your money or your life.
I don’t think it’s a choice. I think money is often the current, we use this word, currency, the current that flows through much of our lives. Now we can argue about whether that’s good or bad, but it is reality. So I think the better approach is to say, how do I align my use of capital, my money, my time, my energy and my attention even?
So, four sources of capital, how do I align my money, with what’s important to me. In other words, my life. And I think it’s that alignment, that tension, and I wish that this diagram could, [00:09:00] and we do have a version of it that is animated because sometimes there’s a bigger overlap, sometimes there’s no overlap.
Sometimes, I look at the way I’m using my capital, my money, my time, energy and attention. But for this sketch, your money. Sometimes I look at the way I’m using my money, I’m like, that doesn’t match at all with what’s really important to me. And that hurts a bit, but I can use that pain, that awareness, that inauthentic behavior to make some subtle changes.
I did this recently. I went and canceled some subscriptions. You know what I did, Jay? This was so fun, I took the actual dollar amount of those monthly subscriptions that I canceled and I upped the dollar amount going towards my mortgage. And I did another thing, which is interesting.
When I fly for speaking events, often there’s an allocation for you to sit in business class. I mean, I would never pay for business class in my own life. There was a recent trip where I was like, man, there’s a great seat in comfort [00:10:00] plus, I’ll probably get upgraded anyway, but I’ll buy that seat. I’ll take the difference. And I did it. I immediately did it. I took the difference and threw it at a really important project. And now when I get on that plane and I walk past business class and I sit in the comfort plus, I’ve got a bigger yes
screaming at me. And so I just think that idea of looking for subtle little ways, $20 subscription turns into $20 a month going into the Vanguard srp 500 or whatever, right? Or towards debt or towards something that’s really important. I’m trying to align my money in my life.
Dr. Jay: Yeah, and I think the hard part and why I like the drawing is people go like, your money drives your life. And I’m going, no, it gives you different options. Let’s be real, I mean, if you’re broke, you have less options than if you have financial independence. But, it’s not like one has to drive the other.
We try with our clients to start with a life first approach. What matters to you? What do you want your goals to be? And then circle back to how do we make your money match it? But it’s not even that clear. There’s this weird, squishy space in the [00:11:00] middle where they overlap. I understand how it’s the goal you want, your money ain’t gonna get you there. Do you wanna change your goals or do you wanna change your money? It’s not as clean of a line as it seems.
Carl Richards: I think you’re pointing at the real work of making good decisions about money, real financial planning and advice, is a never ending process of managing that tension. There are no solutions. There’s only trade-offs. And so, yeah, I think that’s the real work of managing that and realizing it’s gonna be squishy, it’s gonna be awkward, you don’t ever resolve it.
It’s a never ending process. Cause I always felt like, oh, I’ll solve that. Nope. Because as soon as we get clear about it, something changes, our station in life changes, something about what we find out that something we thought was really important to us no longer is. I thought I always wanted a sailboat, and then I went on one and I was like, yeah, I don’t even like this.
It never ends, which is beautiful. It’s not a burden, it’s beautiful.
Dr. Jay: [00:12:00] I gotta ask you this one, Carl. So we just had a prospect come in through the door and we’re doing our intro meeting, and I was doing a debrief of it, what my planner talked to them about. And at one point the prospect’s like, Hey, you’re asking a lot of questions about my life, what about my money? We always try to say, Hey, we try to figure out what you want out of it first. And it got to the end of the meeting. She’s like,
oh, I get now why you asking questions about life. But it’s really interesting when people reach out to us, our website says we do life and financial planning.
I think they skip over to Life Corner and then we ask these questions and they’re, why aren’t you asking about my savings rate or my investments?
Carl Richards: Yeah, that’s a real challenge with the work that we do and I understand why, our favorite humans that we call clients or perspective clients, I empathize deeply with that feeling. Because, we speaking really broadly, the financial services industry have taught them on the financial pornography network and [00:13:00] all the magazines and whatever else, that that’s what it means to make decisions about money is let’s talk about money, let’s talk about the markets, let’s talk about products, and we’ve also taught them most likely through unfortunate experience, that it’s gonna be a little bit adversarial.
It’s gonna be a little bit like a used car sales experience. I’ve gotta protect myself from this person and I completely get it. And a lot of that is actually true, right? The big financial service industry. But when you run into somebody who’s a real financial planner, somebody who cares deeply about the craft of financial advice, it’s a different conversation.
But you don’t know that going in. And so, yeah, you show up with presenting, the financial question you need solved. And suddenly you’re being asked about something else.
Sometimes that takes 12 to 18 months of being a client, and you wake up one day and go, yes, the investment products matter. Yes, the plan matters. Yes, the calculator matters, but you know what matters way more? And the thing that I value way more is I’m not [00:14:00] worrying about it anymore.
So I think, that’s a really interesting experience that you had. I understand it. And I also understand the value of the work that real planners do.
Dr. Jay: Yeah, and I think that my challenge is, read whatever financial planning textbook you want, they’ll say something like, 80% of your success with finance has to do with your behaviors, your mental models, a
way of thinking, all of that. And 20% the actual numbers. So we as a firm try to spend 80% of our time
on that life and behavioral side, and people are like, oh. When we say we wanna make your finance as simple, so your life is amazing.
We spend all the time on an amazing life and making you comfortable with your body and understanding what you can do, but that’s not what they expect.
Carl Richards: It can be completely fair. The reason it’s not what they expect is because we, not you, but the broad finance reserve taught them that. We created this problem. I understand that feeling and it’s actually true that the thing they’re gonna get the most value for, they don’t even expect it.
And 18 months later, they’ll be like, oh my [00:15:00] gosh, that’s what it’s about.
Dr. Jay: Yeah, and let’s talk about mind shifts. So we often talk about the difference between the standard life script and the life Childfree people who are living.
So a standard life script is you go to school, you get married, you have kids. It’s the American dream, the house, the two and a half kids, the picket fence, and built into there are certain milestones of life, certain financial milestones, certain things you have to do. And to me, the hard part is helping our clients go, you are living a different life. You do not have to follow the script.
And when I was looking through your book, I found this one talking about herd mentality and I’m like, yeah, this is the point.
Carl Richards: Yeah, and I mean, you’re pointing to a very specific version of it, which I think is incredibly important than the work that you’re doing needs to be done. As far as I’m aware, there hasn’t been a place to go to work through this. There’s a lot of versions of that, the version of always the normal script. Look, the whole point of this is to help [00:16:00] clients be who they really are. And, nobody comes to a financial planner saying, Hey, will you help me be who I really am? I wanna sit on your couch and cry. But what’s the point? My favorite saying about this idea came from Stephen Covey, I’m just gonna paraphrase it.
The last thing you wanna do is spend your whole life building and climbing a ladder only to figure out, it’s leaning against the wrong wall. And getting clear about the wall you want your ladder leaning against why you’re climbing it, you’re gonna change walls. It’s tricky. And you’re pointing to a very specific thing around that, which is incredibly important.
So yeah, I think that’s really valuable to be like, wait, whose life is this? Am I living my mom’s life, my dad’s life, that life that they say in the newspaper? Or am I living my life? And then be generous with yourself on unfolding of that, right? And the ability to find it over time. So that’s how I think about that.
Dr. Jay: [00:17:00] And the image itself, is an actual Venn diagram. The other ones, we can have a whole debate on what’s a Venn diagram versus not. My wife will approve this one as a Venn diagram.
Carl Richards: I’m so glad I get long emails from the Venn Diagram police, so this is nothing new.
Dr. Jay: This is just poking at it’s intersection between the her of sheep investors and teenagers in the middle, is because everyone else is doing it. And my favorite example of this for Childfree folks is buying a house. The Share Life strip is, you gotta buy a house. Well, Childfree people move all the time. My wife and I sold our house two years ago. We rent and plan on renting for us our life. It’s not ’cause we can’t afford a house, but it’s because it doesn’t match our goals, our life. But so many things have said, you must do this. You can’t get ahead without buying a house.
Or if you rent, you are second class citizen, because everyone else says you need to buy a house. You need to buy a house. And I’m like,
Carl Richards: That’s a great example. You should have as much money as you can possibly handle in stocks. That’s a great example. I personally don’t want that. Somebody else, [00:18:00] great advice. I can build a spreadsheet that shows you why you should own a house
Dr. Jay: Yep.
Carl Richards: and it still doesn’t matter because it’s not your goal.
Dr. Jay: And that’s what I tell people. If you don’t know your goals, it’s kind of that covey thing. You could get to the goal, Hey, I rang the bell, and they’re like, this is not what I want. We call it the Childfree midlife crisis. You hit your personal professional financial goals and then you’re like, now what? What’s the next 40 years of my life look like? And if you don’t know what your goals are, it doesn’t matter.
Carl Richards: Yeah. You’ve brought up another sketch here and it’s just a whole bunch of different size asterisks, if you will, and they all look very similar. Some are smaller, some are bigger, and the word on the sketch says the only goal that matters is yours. Now, I don’t mean that in a selfish way that nobody else’s goals, but to you in your financial decision making, the only goal that matters is yours.
I originally drew this because there was a period of time years ago when David Swenson at the Yale Endowment, [00:19:00] had become a rockstar ’cause the Yale Endowment had done so well. You would get clients who would call and say, Hey, should we invest like the Yale endowment? And that’s when I drew this was like, you’re not the Yale endowment for lots of reasons.
And so the answer is, I understand, let’s see what we can learn to apply to the investment process, of course. But the only real goal that matters with your decision making, your investment process, your spending, your saving is your goals.
I wanna really emphasize this, don’t be stressed or worried if you don’t know what they are. That would be normal. One of my least favorite questions is what are your goals? I hate it when people ask me, ’cause I can feel it right between my shoulder blades. Oh, smart people have goals. I should have a goal.
I don’t know what my goal. Don’t worry, we’re gonna learn what they are over time. I call that goal clarification over time, but that doesn’t change the point that the only thing that really matters is that we make every attempt we can over time to align [00:20:00] how you’re using your money with those goals that are yours.
Dr. Jay: Yeah, and I think this is one of the challenges for Childfree folks and people that reach out to us as prospects and they’re talking to other financial planners. I often tell ’em, go ask the financial planner how your plan is different ’cause you’re Childfree. And most times the answer is something dismissive like, oh, you’ll change your mind.
So we’re just playing like everybody else.
I’m like, no no no.
Carl Richards: Jay does that really happens.
Dr. Jay: Oh yeah. All the time. We could have a whole separate discussion, but the vast majority of the financial planning world doesn’t even realize Childfree people exist. They don’t understand how their goals change. And I’ll give you a concrete example of this, because when you go to a standard financial planner, you throw in the software, the thing they’re solving for is for you not to run outta money.
That’s
the Monte Carlo simulations. You got 97% chance of running money. The vast majority of Childfree people do not have a goal of passing out money to the next generation. If your goal is to die with zero, their math is wrong, the system is wrong, and there’s a built in conflict there. Because if they’re charging 1% on assets
[00:21:00] and they always want your money to go up and you want it to go down, I don’t know how you square that.
And the problem is they could be getting to a place where the goal doesn’t match you.
And we spend more time on our clients talking about spending money than saving money and really about getting what you want out of it to get to your goals. And the hard part is, if you work with the standard financial planning process, standard life script process, you are going to miss this opportunity to truly use your money in ways that enhance your life.
Carl Richards: This is a very specific example of a broader problem that is really hard to manage. I say this to financial planners, keep your values off other people’s plans. But it’s really hard to do, the fact that I’m in the room, I’ve gotta set of biases already based on my own life experience.
So you have to work really hard. What I meant when I asked you if that really happens was not necessarily that a financial planner may not know the unique planning challenges that [00:22:00] Childfree people face. I understand that. It is the dismissive nature of it. Like, oh, you’ll change your mind, or, that’s not important.
And, I’ve seen that. Be dismissive around like equity allocations or paying down your mortgage. Anything that doesn’t fit in a standard calculator can be often, easily dismissed. The real financial planners that you and I know, probably aren’t dismissive about it, but it’s a second layer problem of like, oh, what are the unique planning challenges you face?
Because, as you just brought up, there are some real unique financial planning challenges.
Dr. Jay: Yeah. And Carl, I’ll give you one example, you and I have gone to a lot of the same conferences and you see the
people talking, and there was somebody I’m not gonna name because I don’t wanna call ’em out. And they’re up there, you and I would recognize a person.
They’re talking about estate planning and they said, quote, working with people without kids is the worst. And I was like, hold up, timeout. What do you mean? And of course you couldn’t stop the session, but you’re ready to lose your mind. What he really meant is it changes a lot about estate players, a lot [00:23:00] of issues about who’s gonna be a Power Attorney executor.
It’s why we actually created Traffic Trust. But his message was, these clients are the worst. And I’m like, that’s because you don’t understand them. You don’t understand the systems, your systems don’t fit. To be on a keynote stage and make that statement, I’m like, about to lose my mind.
Carl Richards: Right. I could see why. My generous take on that would be somebody pointing to a lot of work, right? It takes new creative thinking. It’s outside the box, maybe even different tools, right? I’ll just leave it at that. Try to be generous.
Dr. Jay: That’s fair.
So Carl, I’m gonna ask you one of the hardest questions and then I got a closer. But I’ve written a couple books. You’ve written books. If people pick up your book and they only take one thing away from it, what’s the one?
Carl Richards: Yeah, this recent book, the one thing would be, can I talk more about money? Can I have more conversations about money? That would be [00:24:00] the one thing. Can I use what I’ve learned to have some more conversations about money with the people I love.
Dr. Jay: That’s great. So we’ve reached our final segment of Childfree Life by Design called Deliberate Detail. It’s a segment where we share a small, intentional thing we’re doing to design an amazing life. We share what it is, why it matters, and what it costs. And Carl, I’m sure you have an answer to this, so what are you doing to reimagine your own wealth?
Carl Richards: Here’s a small, you used the word small, ’cause I’ve got two that have been on my mind lately, but one that I’m pretty surprised at the impact it’s had. We live in the mountains of Utah. We live literally out our property. You walk out the back gate of our property and you’re on
incredible trail system. That’s 420 miles of trails. So the trails play a daily role in my life. There’s this period twice a year that we call the mud season when the skiing isn’t good enough, but you can’t bike anymore ’cause the trails are wet and in the spring, [00:25:00] the trails aren’t dry enough. So there’s those two periods of time, the shoulder seasons. They’re beautiful times of year and I just suffer on the trails. ‘ cause I just wear my normal Hoka and my feet get cold and they’re mesh and I’ve always just been like, yeah, whatever.
Feet get wet when you run. That’s what you do. I bought some shoes. They’re made by Las Tiva, one of my favorite climbing companies. They have little gators on, my feet don’t get wet anymore. Snow doesn’t get in my shoes. They were on sale for $180. I was like, I’m not gonna spend $180 on shoes, but they were on sale from 2 64, so I was like, okay,
I can’t believe I’m doing this. I’ve worn them every day since I’ve owned them, which has only been 12 days. Every morning I come home and I’m like, this has materially changed the quality of my life. Why did I wait so long? You pointed to small. That’s one small thing that’s really changed my life.
Dr. Jay: It’s amazing ’cause sometimes, we’re all a little frugal in our own ways. I’m not gonna spend 180 bucks in shoes, but it’s life-changing shoes. ’cause you get to do what you [00:26:00] enjoy for 180 bucks.
Carl Richards: I bet nobody else listening to this is like, me too. And that’s fine. We talked about that. It’s incredibly important to me. And I can’t believe how much it’s changed my life. So are you per unit of fun? That’s the best investment I’ve ever made.
Dr. Jay: So thank you so much, Carl for sharing your insights today. Where can our listeners find you in your work?
Carl Richards: The easiest place for people to go is behavior gap.com and sign up for the week. I send out the shortest, most impactful email on the internet, and we’ve been doing it every week for 10 years. So it’s a sketch and as few words as possible.
Dr. Jay: Awesome. So that’s all for this episode of Childfree Life by Design. Remember, intentionally choosing to invest in moments of joy is just as important as investing in your future. Until next time, happy designing.
Speaker 2: You’ve been listening to Childfree Life by Design. Make sure you follow the show. Leave a rating or review and connect with us on social at Childfree Insights. For more [00:27:00] resources, guides or upcoming events, visit Childfree insights.com.
