44. Carl Richards: A Conversation About Money and Mid-Life
“I want my future to be bigger than my past.”
Messy Middlescence is thrilled to share their conversation with Carl Richards.
Carl who? – you might ask.
Tina asked Tara that exact question when Tara – breathless with excitement – informed her over the summer that she had secured an interview with Carl. It turns out Tina did know of him through his 50 Fires podcast (which Tara often refers to here on Messy Middlescence) but was unaware of the VERY BIG DEAL that Carl Richards is in the world of finance/financial advising.
When you listen to the interview today, you will quickly understand why. This 27 minute interview is packed with an amazing amount of story-telling, practical advice, and interesting outlooks and ideas.
Carl Richards is the beloved “Sketch Guy” from The New York Times, a bestselling author, speaker, and host of Behavior Gap Radio and 50 Fires podcasts.
He is also smack in the middle of middle age which is the primary focus of this interview and differentiates our conversation from the many others he has done recently for his new book, Your Money: Reimagining Wealth in 101 Simple Sketches.
Tara and Tina discuss with Carl many of the complex yet common issues of mid-life which showcase his financial insights along with his creative (yet often simple) solutions. Carl has a unique perspective on most things which are guaranteed to make you think.
Some of the topics covered today include:
The most common question Carl receives from successful people as they progress through middle age
Carl’s “Project Half Life”; what it is and its value in Carl’s life
How those approaching retirement can help themselves feel less “stuck”
The concept of having your future (regardless of age) be bigger than your past
The importance of having interests/hobbies/connections beyond work before you retire
How his advice is often simple but not easy; that sometimes the most difficult part is giving yourself permission to think differently
The shifts that mid-life is bringing to Carl
The beauty in breaking things down and starting small regardless of the problem
The recommended first question to ask those close to you about money
And what it really means to live with tension — not trying to solve the mess, but learning to sit within it
With wisdom, humor, and humility, Carl reminds us that “money is just a door to meaning,” and that midlife isn’t an ending — it’s an invitation to start again, one small step at a time.
-
[00:22] Tara Bansal: Welcome to Messy Middlescence.
[00:24] This is a podcast where we talk honestly about the changes, change, challenges, connections, and gifts that come with midlife.
[00:32] Nothing too polished, just real conversations that remind us we're not alone.
[00:37] So let's dive in.
[00:40] Tara Bansal: A big welcome and hello, this is Tara Conti Bansal, and I am here with my sister, Christina Conti Donovan.
[00:49] And I can't tell you how thrilled we are to have for me, the Carl Richards with us today.
[00:58] If you.
[00:59] I feel like Carl's pretty famous and well known in the financial advisory space,
[01:07] but just in case you have not heard of him, he is a certified financial planner and a visual artist.
[01:15] Tina Donovan: Renowned.
[01:16] Tara Bansal: Renowned for his ability to simplify complex financial concepts and ideas through simple sketches.
[01:25] He had sketches in the New York Times for more than a decade and he's had two,
[01:34] I think, bestsellers, at least to me, they're bestsellers called the Behavior Gap and the One Page Financial Plan.
[01:41] He has several podcasts.
[01:45] If you've been listening to our show, you've heard me mention 50 fires is one that Carl does. He does another one with Michael Kittis that's more financial advisory focused and a daily podcast called Behavior Gap Radio.
[02:03] Carl lives out in Utah with his lovely and beautiful and smart wife, Corey. He has four children.
[02:11] What else? I know you love to be outside.
[02:14] What else would we share, Carl?
[02:16] Carl Richards: No, that's really kind of you. Thank you. I've got a new dog. Oh, yeah?
[02:22] Tara Bansal: What's the name of your dog?
[02:24] Carl Richards: Kenna. K E N A Kenna. Yeah. Yeah.
[02:28] Tara Bansal: And how new?
[02:29] Carl Richards: Well, she's seven. She's almost seven months.
[02:32] Tara Bansal: And when did you get her?
[02:35] Carl Richards: When she was 12 weeks. So. Yeah, when she was three or four months. Three, about three months. We've had her for four months.
[02:40] Tara Bansal: Okay.
[02:41] Carl Richards: Yeah, it's been. It's super fun because, of course, the kids have all moved out of the house. So we decided that we should make another 13 or 14 year commitment. So it was.
[02:52] It was a great idea.
[02:54] Tara Bansal: So I. Why? Yeah. How did you come about deciding to get a dog? We.
[03:00] Carl Richards: We have thought about it for years. The dog. We had a dog before we moved to New Zealand.
[03:05] And when we moved to New Zealand, the neighbors took him and so he comes over all the time. Like we were sort of.
[03:10] Tara Bansal: I got to meet your old dog.
[03:11] Carl Richards: When we were here. Yeah.
[03:12] Tara Bansal: Yeah.
[03:13] Carl Richards: And so we've wanted a dog forever and it's turned out to be an amazing, just amazing experience. I've met a whole new group of people.
[03:20] It's a hunting dog. I didn't Know, I wanted to hunt until we got the dog. And so it's been really, really fun. Given me another source of connection and community, which I think is really important at, at this point in my life.
[03:33] Tara Bansal: Which is a theme we have here on messy. The importance of connection and community.
[03:40] Carl Richards: Yeah.
[03:42] Tara Bansal: What. Well, just jumping in. What, what do you notice about how money conversations shift for people in midlife based on your experience?
[03:57] Carl Richards: Yeah, I,
[03:58] I,
[04:00] I've had, I've thought a lot about this because I would say probably five years ago when we got back from New Zealand, which has been about five years,
[04:12] I started increasingly having these conversations with people. And I would say it was like between 45 and 55 year old, it was largely men.
[04:25] And they would have read maybe something in the column or one of the books. And then they come to the town I live in. Lots of people come here for vacation in Park City, Utah.
[04:35] And I would get these emails that would say, hey, could we get together for coffee? And I, I kind of after the like, 10th one, I started to like,
[04:44] suspect a typical pattern. Cause what would happen is we would sit down,
[04:49] I'd either meet on a certain trail or meet at, I tried to meet at the same coffee shop on the, at the same table. Cause I was trying to embed the,
[04:56] the table with the emotional patina of these conversations.
[05:00] And I,
[05:01] I, what would happen was they would sort of look around to make sure nobody was listening.
[05:07] And then they would show me some evidence of having made it. You know, like, it was often just a, like I sold a business or I, you know, an income statement or balance sheet, although they didn't actually pull those out, but they would say something like that, I make a bunch of money,
[05:19] I made more money than I ever thought I would, or I sold a business.
[05:22] And then they'd look around to make sure no one was listening.
[05:26] And it was always some version of is this all it's for?
[05:32] Right? Is this like,
[05:34] what, Is this what I did it all for? Like,
[05:37] what, what now? And it was always very, it's a very,
[05:42] I don't know that sad's the exact word I'm looking for, but it's a very lonely sort of question,
[05:47] you know, is this what I did it all for?
[05:50] And so I've,
[05:52] I think there's this.
[05:54] Among people who have been fortunate enough to have things work out a little bit financially so they can at least afford to think this way at all,
[06:03] there's this,
[06:05] this sort of realization that I, I may have conquered,
[06:10] I don't love that language. But that's kind of the feeling out there,
[06:14] you know, Like, I figured out how to do a thing. I figured out how to build a business. I figured. But I haven't really gotten clear in here.
[06:21] And, and sometimes that's even like back in the house,
[06:25] you know, Like, I'm, I'm super, I'm a superhero out there,
[06:28] but here I'm a mess.
[06:31] And, and so I think there's a lot really. And the way this interacts with my work is that I think money is just a door to meaning.
[06:42] Right? It just gives us an interesting way to get into conversations about meaning. And so I think at that age, middle age, I actually call, like, I started celebrating Project Half Life when I turned 50,
[06:54] and he celebrated every year. That's the cool part about Project Half Life. So at 50, you have 50 more years.
[07:00] At 51, you have 51 more years. At 52, you have 52 more years.
[07:05] So that's the cool thing about celebrating Project Half Life is you, it, it, you celebrate it every year. So I have found that to be a, a widespread question that people are asking, like, what is this for?
[07:20] Why am I doing this? How do I turn the success or this money or this freedom or this into meaning that actually makes sense to me.
[07:31] Tara Bansal: How, what do you do with your Project Half Life? What has that meant for you?
[07:37] Carl Richards: Yeah, I, I, I, Project Half Life is very specific for me. I, I pick a stupid, a stupid human trick every year.
[07:44] And I define a stupid human trick by something that I want to do.
[07:49] It's typically at least six months. So like, in the late summer, early fall,
[07:56] that I could not, in my current condition, there's no way I could do it.
[08:00] So that's kind of the definition of a stupid human trick. It's like in my current, like, this could be something as simple as the split. Not as simple, but, yeah, simple, not easy, but something as simple as the splits or a ring pull up, pull up, right?
[08:14] Like, or it could be run a half marathon or run it like, or write a book, like some,
[08:20] something that's going to act as a forcing function for me to become the kind of person who could pull that off.
[08:27] So I don't really,
[08:28] I mean, I don't tell my brain this when I'm making the goal. I don't really care about achieving the actual goal.
[08:33] What I care about is becoming the kind of person who could.
[08:38] And so that's how I celebrate Project Half Life every year. Like, what's a stupid human trick that would require me,
[08:44] like,
[08:45] you know, in really dramatic language. It would require the current version of me to go away and a new version of me to be born.
[08:52] And I want to keep doing those for.
[08:55] I just met somebody who is 90, 92, 92, 93 and just started his first venture capital fund and he's only making 25 year investments.
[09:08] Right. Like I want to hang out with that guy.
[09:11] You know what I mean? So that, that's how I think about Project Half Life.
[09:14] Tara Bansal: What, what was your project, Your stupid human trick for this year?
[09:19] Carl Richards: Yeah, this, the stupid human trick for this year. The stupid human trick for last year was big, a big objective in the mountains and it was hard and it involved out there and it involved scary scenarios and risky things that I've been doing my whole life.
[09:37] But,
[09:38] you know, making sure you put your foot in the right place. And,
[09:41] and my stupid human trick for this year was the opposite.
[09:45] Like, could I get comfortable here?
[09:47] Could I spend more time in the garden? Could I like. And so it revolved around more time, quiet. And to be honest, I haven't done a great job the past two months, but for a while I was doing really, really well.
[09:59] So more meditation.
[10:01] It was a, it was a, it was a journey into the, into the scariest terrain of all.
[10:07] Right. Like inside. Yeah, yeah.
[10:11] Tara Bansal: Pretty cool. We do talk about getting outside your comfort zone here on the show. And that's the theme for this.
[10:17] Carl Richards: There's no reason it has to stop.
[10:20] Tara Bansal: No, but I feel like it's common that it stops.
[10:24] Carl Richards: It does, it does. We start shutting things down.
[10:27] Which is why I pointed to that 92 year old. I'm like,
[10:30] I, I, I just want next year to be bigger. Whatever bigger means then I want my future to be bigger than my past. I don't want it to start getting, that's a Dan Sullivan idea.
[10:43] I don't want it to start getting smaller.
[10:46] And that, that does not mean,
[10:49] you know, more money or more fame or more, it could mean getting better at meditation.
[10:55] Like, whatever it is, I just want it to be, I want to feel like my future is expanding, not contracting.
[11:01] Tara Bansal: What do you tell the people at the coffee shop that keep asking, like, is this what it's for? What do you do?
[11:11] Carl Richards: Yeah, often. That's.
[11:14] I just had this conversation with the chief creative officer at a publicly traded company that everybody listening would know.
[11:22] And he is seven to eight years away from knowing that he'll be sort of forced out in terms of retirement.
[11:32] And he's like, I don't have any hobbies,
[11:36] you know, I, I don't Really? I love work, love work, work on the weekends. Love it, because it's just creative. It's just my favorite thing ever.
[11:43] And therefore, I don't know my kids,
[11:46] and I'm not sure about my relationship with my wife.
[11:50] And so that's a very common, like, place. And so what do you do?
[11:54] You do the same thing you would do with anything that you're not good at is you start really, really small and you practice.
[12:05] Right. And so you just. You just make a.
[12:08] Like,
[12:09] with him, I had to say,
[12:11] well,
[12:12] you have no hobbies, like, nothing you're interested in? He's like, no. I mean, it's just been so. So we have to go back. Like, let's just guess,
[12:19] like when you hear something on a podcast or you see something on a TV show and you're like, that looks interesting. Like, what's the last one of those? And we had.
[12:27] It took us. It took us a while. Like, it was like a 15 minute sort of exploration idea. And we came up with paddle boarding. It's like, I've always kind of thought that was cool.
[12:37] I was like, okay, that's enough,
[12:39] like, to kind of think that's cool. You live in an area. He lives.
[12:44] Yeah, he lives in California, right near the ocean.
[12:47] You live in an area where people do it. Like, what would be the smallest version of that? It's like, oh, I could rent a paddle board. I could. I was like, smaller.
[12:56] Like, I could go out. I could sign up for a lesson,
[12:59] a group lesson. I'm like, no, smaller. Like a. A one on one lesson.
[13:03] Yeah, a one on one lesson in the bay,
[13:06] you know, so that's what you do. You practice, like, anything that you're out of practice at and you make guesses. I kind of. Man. I heard somebody talk about fly fishing,
[13:15] you know, or I've always wanted to write something.
[13:19] Or I love watercolor. You know, like, you just try to find something that you can guess, and then you go do the smallest thing and you see what shows up, and then you try again.
[13:28] And then you try again.
[13:29] You just practice.
[13:32] Tara Bansal: It's good advice.
[13:34] Carl Richards: Yeah.
[13:36] Tara Bansal: Yeah.
[13:36] Tina Donovan: I think one of the things in my circles, we all have lots of things we want to do,
[13:42] but not the. We're not ready to retire yet because of the financial situation. I hear this from my husband, my husband's friends. My friends,
[13:54] I guess.
[13:55] What do you say to people in midlife that feel like they're either behind in the sense of financially being ready to retire or maybe just even stuck financially in midlife because of all the obligations, I guess is the word I would use.
[14:19] Carl Richards: Yeah, Tina, I guess the first question I'd ask is, how do you know?
[14:24] Do. Do you. Is this an assumption that you're not,
[14:29] like, you're not on track financially to retire, or is it like, no, we're completely aware.
[14:35] Tina Donovan: I think it's.
[14:38] We know.
[14:39] At least with my other friends, I hear this constant thing about,
[14:43] I'd like to retire now, but I need five more years or six more years of income based on either college tuition or taking care of an elderly parent or. I don't know.
[14:56] I mean, there's a whole mix of things. So, yeah, it's people that I think are aware of their financial situation but feel stuck because they want to start doing their hobbies or the things that they love, but financially, they aren't ready yet.
[15:10] Carl Richards: I think there's two pieces of that. One is, I would double check the financial plan, quote, unquote. Like, just make sure. Like, maybe things. Maybe there's some creative ways to think about.
[15:20] Let me. Let me give you an idea. This comes up all the time.
[15:23] People are like,
[15:24] man, I. Oh, I really don't like my job, but I just. If I just keep working, I gotta keep working for. Till I'm 62,
[15:32] because that's. And.
[15:33] And I'm 55 now. And I mean, that's only seven more years. I just had this conversation with somebody. He's like, I have only seven more years to retirement. I hate every day,
[15:41] like, well, there's a bunch of things you can do to. And this. To me, I had this conversation more than any other around retirement, which was like, well,
[15:54] what if you got a different job that didn't pay as much, but you really liked it?
[16:00] And let's say.
[16:02] And you'd have to sort of run the numbers in the financial plan to see if this works. But I saw this happen a lot where,
[16:08] let's say that it doesn't pay as much,
[16:11] but you really like it.
[16:12] And the difference in pay,
[16:14] like, let's say you no longer had to. You didn't fund your retirement accounts anymore,
[16:18] so that made up the difference in pay.
[16:20] But this allowed you to work, you know, till you were 65 or 66, because you were contributing and it was meaningful. I don't know that retirement's a good idea for most people, to be honest.
[16:29] Like, the. The definition of retirement, I think, is good for really hard manual labor. That's like, physically, I just can't do this anymore.
[16:37] But to be. To have a sense of purpose and Meaning in your life built around work,
[16:44] or even just a thing that you had to go to every day and then have it be gone doesn't really drive the kind of fulfillment most people think it will.
[16:52] It's much better to think,
[16:54] you know, could I. Could I do something that I could consider myself, that I would never want to retire from?
[17:00] And maybe I make a little bit less money, but I. Maybe I make up for that by keeping my benefits not touching my retirement account,
[17:08] because I can live off the income I'm making. And now I could keep working till I'm 70.
[17:12] Cause I like it.
[17:14] So that's. Step one is like, start rethinking this idea of, like, full gas,
[17:20] stop.
[17:20] You know, like,
[17:22] maybe start thinking a little bit differently because work.
[17:26] The hours you spend at work can be replaced with hours you spend at meaning. But it's most likely. There's still plenty of ways to find a way to get paid for that.
[17:35] Then the second thing I would do is, like, why are we waiting for hobbies?
[17:38] You know, like, even if I do, I. Okay, fine. I have to work. I don't like it. I'm gonna retire in seven years.
[17:44] Can we just start inserting a little bit of the hobbies before? Cause like, my friend, the chief creative officer guy,
[17:52] if you go very long,
[17:54] you're way out of practice. It's much harder to start again.
[17:57] So I would just find one thing, like, hey, on Thursday nights, could we go to the bridge club,
[18:02] you know, or could we start playing pickleball with our friends? Like, could we just do one thing?
[18:07] So that's. That's the two ways I would approach that.
[18:10] Tara Bansal: It sounds. I don't know. I feel like it's harder than it sounds. I don't know if that much of that is internal fear versus.
[18:21] Carl Richards: Yeah, I want to be really clear. Plenty of this stuff is simple but not easy. Yeah,
[18:25] right. Like, just to acknowledge that. Yeah, yeah. And. And. And. But I think the hard part of it is not, like, it's not. It's not like I'm incapable physically or I can't make.
[18:38] It's. It's just giving yourself permission to think a little differently. That's the hard part. Like most of your neighbors, most of your friends,
[18:47] you know, you might even get into. We in New Zealand, we call it. It was called the tall poppy syndrome. Like, anytime the. You know, the flower got a little bit taller than everybody else, it would get trimmed off.
[18:56] So sometimes you'll get the feeling of, like, who does that?
[18:59] That's not the way it's done. That's not the way my family's done it. I think it's really just,
[19:04] you know,
[19:06] a lot of the things you guys are both pointing to are systemic problems, problems with the system itself.
[19:11] And anytime you try to live a little bit different than the system,
[19:15] you've got a little bit of a challenge. It's scary,
[19:18] right?
[19:19] You have no path to follow.
[19:22] But I think just giving yourself permission to dream a little bit again in really small edges,
[19:26] around the edges.
[19:28] Can I do one? Hey, can we play pickleball Thursday night?
[19:31] Right? Could we?
[19:33] Yeah, pickleball, please. I've had enough of pickleball.
[19:36] But,
[19:37] you know, like, could, could I find a job that I like at the local nursery?
[19:42] Like, garden nursery, like, and they provide, we have one here, actually, that provides great benefits for I, I know people who enjoy being baristas at Starbucks.
[19:52] Right. So can I just give myself permission to dream a little bit? Ask questions like, well, what if?
[19:59] Or why not? Like, I mean, just play. Like, no pressure, just play.
[20:04] Tara Bansal: And I like your, Just a little step almost. Yeah.
[20:08] Carl Richards: Yeah, for sure. Always. It's always, if it feels scary or hard or daunting, just make it smaller. Make it smaller.
[20:21] Tara Bansal: When you think of your own midlife, Carl, what's one shift you're making or one conversation that you're having that feels meaningful right now?
[20:33] Carl Richards: Yeah, it's more time.
[20:41] It's not always alone, but more time.
[20:45] I think actually there is a piece of it that's important is alone too.
[20:48] Like, I spend more time walking in the mountains alone than I used to spend. Like, it always was a hoop and holler and. Yeah, like, on the mountain bike and so excited and high fives.
[20:59] There's more of it now that's just quiet.
[21:03] And I, I, I, I think David White's my,
[21:07] I, I started saying that he was my favorite poet, and one of my daughters was like,
[21:12] at what point did you have a favorite poet? And who's number two? I was like, okay, fine. It's the only poet I know. It's fine, it's fine.
[21:19] Anyway,
[21:20] I love how she called you out. Oh, she for sure did. She was like, at what point did you get a favorite poet? And who's the second one on the list?
[21:26] I was like, no, you smarty pants.
[21:28] So I, I,
[21:30] he talks a lot about the need, and I don't know,
[21:33] he's talking about it specifically for himself. He just, he said, I, you know, I find that in middle age,
[21:40] I'm, I'm noticing a bunch of my male friends Needing an increasing amounts of solitude and quiet. Now, I don't know if that's the same because I only have my experience.
[21:50] So I'm. I'm not making it a gender thing. I'm just saying that's what David said, and that's been my experience. So more time, quiet.
[21:58] I'm finding my desire to, like, sit,
[22:02] do fun things with my kids, but I'm also loving the moments where we're just, like, sitting and having a conversation.
[22:07] Like, why do we always have to be going.
[22:09] We've got one daughter who's just.
[22:12] And I mean, we created this monster, but just a, like, mountain fanatic, you know? And every time,
[22:19] she's the one that lives closest to us right now. And she's just all the time like, dad, can we go run 20 miles? Dad, can we go climb this mountain?
[22:24] Dad? And I. And I have one goal is to never say no to her.
[22:27] And I'm getting pretty close where I'm like, I'm gonna have to start saying no. Cause it's just so much.
[22:32] But I often say to her, like, could we just sit for a bit?
[22:35] You know, so that's. That's one change I'm noticing.
[22:39] Tara Bansal: What's one you're all about conversations around money. What's one conversation you feel like our midlife listeners could start with that would make the most difference?
[22:57] Carl Richards: You know, what's been fascinating to me is, especially with a.
[23:01] A,
[23:02] A spouse or partner or a good friend.
[23:06] I've been kind of surprised at how few people have ever been asked what their first memory of money is.
[23:14] Right. And. And. And I think that's, like, you use the word I, it's gonna go a different direction. I was gonna go around, like, what's it all for? And what's.
[23:21] Why is money important and what the mean? But as soon as you use the word start with,
[23:26] I'm like, look, the simplest way to start practicing having conversations about these, like, meaningful conversations about money is.
[23:35] Yeah, like a spouse or part. I was shocked. I had never had this conversation with my wife. We've been married 30 years.
[23:41] I think I had her on the podcast three, two or three years ago.
[23:45] That's the first time I'd asked her that question,
[23:47] and I didn't know the answer. I was shocked. I didn't know the answer for my kids.
[23:52] So I think just simply asking, next time you're on a walk or a road trip or a quiet dinner, like, hey, and you can blame it on me, right? Like, I heard this crazy guy on the podcast and he's like, I'm sort of curious.
[24:04] What. What's your earliest memory of money?
[24:07] And then just ask more. Like, what was that? Like,
[24:09] you know. Oh, I remember it being very stressful. How did you know how? Like, is that in retrospect? Or do you remember how you knew it was stressful? Oh, my mom used to say this, or my dad did this.
[24:20] And then you can just be like,
[24:22] we just had a conversation about money. We didn't fight. And like, just make your way out. Like, oh, great, what do you want to do for dinner?
[24:28] And just like, count it as a win.
[24:30] And then try to build on that a little bit, right. Until you're having conversations. Like, my wife and I literally just over lunch just talked about, like, what are we doing all this for?
[24:41] Like, why should we just maybe, like, make things a little simpler,
[24:45] scale back a little bit? Like, not always have to be doing more things. Like, we were just. But. And the question was around, like,
[24:54] again, let's remind ourselves what the goal is. What does this all for?
[24:58] So that's how I would start.
[25:00] Tina Donovan: I've never asked anybody that question. And I'm. As you're talking, I'm going through my mind of all the people I know and I don't know anybody's earliest memory. Like, I don't know my sisters.
[25:12] Carl Richards: It'd be so. It's so fun.
[25:14] Tina Donovan: Like, I. Yeah, now I'm really curious.
[25:17] Tara Bansal: Well, Tina and I can share ours another time, because I definitely have done that.
[25:21] Carl Richards: But yeah, that, that. Like, so. And like,
[25:25] you know, people, you don't really don't know the answer for. Cause you don't know their background. Not your sister, but, like, in. In junior high, were you one of the rich kids or the poor kids?
[25:35] You know? And often the stories you'll hear with that one are pretty remarkable because they'll tell you and then you can say, well, how did you know? And they'll tell you stories about having one pair of jeans or, you know, like, whatever the stories are.
[25:46] It's really remarkable.
[25:49] Tara Bansal: We are approaching the end of our time. 1 like, our podcast is Messy Middlescence. What in your life feels messy right now? Is there anything. I guess.
[26:01] Carl Richards: Yeah. When you told me the name of the podcast, I literally was like, what a beautiful. Like, I think Pema Chodron, who wrote When Things Fall Apart, her teacher said, treat chaos as extremely good news.
[26:15] And as soon. And I. Like, that's a bit far for me. But as soon as I heard the word messy, I was like, oh, I'm such a fan of tension,
[26:22] because tension keeps bridges up. You know what I mean? Like, and I, I think the idea of just like, living in the messy,
[26:29] just being like, oh, it's okay.
[26:31] And I think that maybe comes with middle age of being like, I don't have to solve it. I can just live in this trade off, in this tension. And,
[26:39] and I think the trade off for me always is do more, have a bigger impact,
[26:46] be quiet, scale back.
[26:48] Right? That's. That feels very messy and very, like, fraught with emotion. Like, how much of this is for ego?
[26:54] How much of this is a cute story I'm telling myself about making impact, but I really just want people to have me on their podcasts. Like, like, how do I get to explore that stuff is super, super fun.
[27:06] So thanks for having me.
[27:07] Tara Bansal: Thank you so much for being here, Carl. It was a joy, as always.
[27:11] Tina Donovan: Very interesting. Thank you.
[27:13] Carl Richards: Thanks, Tina. Thanks, Tara. We'll see you soon.
[27:15] Tina Donovan: Bye.
[27:16] Carl Richards: Okay, bye.
[27:17] Tina Donovan: Before we wrap up, we wanted to invite you to do this week's Connection Challenge.
[27:23] One of the things Carl recommended was his question,
[27:27] what's your earliest memory of money? It's such a simple question,
[27:32] but wow, what a doorway it opens.
[27:34] Carl mentioned that even after 30 years of marriage, he had never asked his wife that question until recently on his podcast.
[27:43] When he finally did, he was surprised by her answer and by what he learned about her.
[27:49] So this week, we invite you to do the same.
[27:52] Ask someone close to you. Your partner, your sibling, your parent,
[27:57] or a friend.
[27:58] What's your earliest memory of money?
[28:01] Then just listen.
[28:03] No advice, no fixing, no judgment.
[28:06] Just curiosity.
[28:08] Tara Bansal: We hope you'll share your own story, too.
[28:10] Tina Donovan: You might be amazed by what it reveals. Not just about money, but about what.
[28:17] Tara Bansal: Makes you feel safe, free, or cared for.
[28:21] Tina Donovan: Carl Richards has a new book out called you'd Reimagining wealth in 101 Simple Sketches.
[28:30] We never got to talk about it on the show, but both Tina and I read it.
[28:35] And on one page, there's one of Carl's simple, hand drawn sketches. And on the facing page,
[28:43] a short reflection or a few questions to think about or discuss.
[28:48] Carl wants this book to be,
[28:50] quote, a conversation grenade.
[28:53] Something you can leave on a coffee table or kitchen counter that invites real, honest,
[28:58] sometimes uncomfortable conversations about money and meaning.
[29:03] That's exactly what this question does. It starts small, but it opens the door.
[29:09] So your challenge for this week is ask someone you care about what's your earliest memory of money.
[29:15] Have the conversation be curious and let it connect you in a deeper way.
[29:21] And if you do we'd love to hear what you discover.
[29:25] You can share your reflections with us via email or through our website.
[29:29] So go have that conversation and we'll.
[29:32] Tara Bansal: See you next time.
[29:33] We're so glad and appreciative that you spent this time with us here on Messy Middlescence.
[29:39] Midlife can be messy, but these conversations remind us that we're not alone.
[29:45] If you liked this episode, please share it with a friend. Subscribe or leave a review.
[29:51] We'll be back soon with more. Wishing you the best.
-
Carl Richards’ New Book: Your Money: Reimagining Wealth in 101 Simple Sketches
Behavior Gap Radio – Carl’s daily podcast
50 Fires Audio Project — conversations on creativity, meaning, and freedom
The Behavior Gap (book) – practical insights on the gap between what we should do and what we actually do
The One-Page Financial Plan (book) – how to simplify financial decision-making
The Sketch Guy Archive – The New York Times – Carl’s decade-long column on money and meaning
David Whyte – poet Carl quotes on the need for quiet and solitude in midlife
Pema Chödrön’s book, When Things Fall Apart– on treating chaos as good news
Tara’s previous podcast interview with Carl Richards for Her Life, Her Practice, Her Way - Noticing what Matters: Carl Richards on Life, Money, and Meaning
-
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 cardstock and a Sharpie. The column ran weekly for a decade. This journey began when Carl applied for what he thought was a job as a “security guard,” only to find out the ad actually said “securities.” That slight misstep sparked a lifelong dedication to reshaping how we think about money.
Since then, Carl has become a Certified Financial Planner™, built and sold a successful investment firm, and spoken at financial and investment events worldwide—from Australia to South Africa, the UK, and major economic centers across Europe, Canada, and the United States. His bestsellers, The Behavior Gap and The One-Page Financial Plan, have been translated into over ten languages and continue to resonate globally.His latest book, Your Money: Reimagining Wealth in 101 Simple Sketches, came out in October 2025. It’s a collection of 101 sketches and essays, designed to spark real conversations about money.
Through his daily podcast, Behavior Gap Radio, which now has over 1,300 episodes and over one million downloads, Carl shares new perspectives on aligning our resources with what truly matters. 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.Carl founded The Society of Advice, a community of financial planners dedicated to the craft of advice. They gather for a monthly online workshop and frequent retreats in Park City, Utah.
When he’s not exploring ideas about money, Carl, a Wilderness First Responder, can be found navigating Utah’s high mountain ridges on foot, skis, or bike. Married to Cori since 1995, they have four kids, whom they consider their best friends. -
In our conversation with Carl Richards, he shared one simple but powerful question that can open the door to a deeper understanding of ourselves and each other.
Ask someone you care about — your spouse, parent, child, or a close friend —
“What’s your earliest memory of money?”
Have the conversation. Be curious. Listen without judgment. You might be surprised by what you learn — not just about money, but about meaning, safety, and love.
And when you do, we’d love to hear how it goes.
Share your story with us here at messymiddlescence.com.