The Retire Ready Podcast

Episode 13: Talking Your Money with Carl Richards

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October 15, 2025
Retire Ready Podcast
Behavioural Finance

In today’s episode with talk with former financial advisor, author, and speakerCarl Richards to discuss his upcoming book release, Your Money. Carl describes YourMoney as being “not a personal finance book but a conversation grenade.” The book includes 101 of Carl’s sketches, some from his time writing for the New YorkTimes and many new ones as well. We talk about a few of my personal favouritesfrom the book.

Carl Richard Bio:

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. 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.

Through his daily podcast, Behavior Gap Radio, which now has over 1,000 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.

In 2025, Carl will release a new book that, true to form, will be unlike anything seen in the personal finance section—and you better believe there will be sketches (97 of them, to be exact).

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.

More about Carl: https://behaviorgap.com/about/

Link to Carl's new book: Indigo / Amazon

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Key Takeaways

Transcript

Scott: Welcome to TheRetire Podcast, the podcast that helps Canadians prepare for all thatretirement brings. I'm your host, Scott Sather, Founder, President, andCertified Financial Planner at Awaken Wealth Management and Portfolio Managerwith Awaken Investments of Aligned Capital Partners in Regina Saskatchewan.

In today's episode, we talk with former financial advisor,author, and speaker Carl Richards to discuss his upcoming book, release YourMoney. Carl describes your money as being not a personal finance book, but aconversation grenade.

The book includes 101 of Carl's sketches, including an essayfor each sketch, some from his time writing for the New York Times, and manynew ones as well. We talk about a few of my personal favorites from the book.You can find Carl's full bio as well as any resources mentioned in the shownotes@retirereadypodcast.com, episode 13, along with a link to purchase thebook.

So without any further ado, let's jump into the conversationwith Carl [00:01:00] Richards.

Carl Richards, welcome to the Retire Ready podcast. Great tohave you on,

Carl Richards: Scott.Thanks for having me. I'm looking forward to this conversation.

Scott: Absolutely.You have an upcoming book, uh, "Your Money" Re-Imagining Wealth inSimple Sketches. Tell me a little bit about that.

Carl Richards: Yeah,so I, I, um, I wanted to put together, I, I had noticed something happeningwith the sketches. People were printing them out and taping them to theirfridge or putting them, putting them up on the wall. Like, yeah, you have, andI kept getting these emails and none of the emails said. I put this on my wall.It's so visually striking.

Scott: Yeah.

Carl Richards: Whatthey said was, I put this on the wall and my son walked through and asked me aquestion about it. Mm. Or I put this on the wall and my clients wanted to talkabout it. Like what they said was, what they were pointing to is the [00:02:00] conversations that these sketches weregenerating.

Scott: Yes.

Carl Richards: And soI thought, man, I had kind of decided not to write any more books and justfocus on conversations, to be honest, like I just was, podcasts and audioprojects and video projects and. So I, I'm a, like, that's feels like my wholecareer right now. It's about conversation. So the idea behind the book was toput together a, a, there was something unique about the artifact of handing abook to somebody or having the book out on the coffee table, or, or having thebook, you know, taking the book with you on a road trip or something to justgenerate the conversation.

So that's really the goal is I, I care deeply about this book,getting into the world, but I care way, way, way more. About the conversationsit will generate. So that's what the book is. It's 101 and some of them aregreatest hits.

Scott: Mm-hmm.

Carl Richards: Um,some of them are brand new, um, but there's 101 sketches with 101 essays.

Some of the essays are two sentences and, but none of [00:03:00] them will take you more than three minutesto read.

Scott: Yeah.

Carl Richards: Soit's meant to be a series of conversation starters, journal prompts, that kindof thing.

Scott: That'sawesome. That's awesome. Yeah. I mean, this is book number three, right? That'sbeen published to the public? Yeah. Um, I would say different than the othertwo.

Carl Richards: Yeah,very different. So there's no sort of like kind of ongoing narrative. There'sno chapter format. It's literally, I mean, it is divided into 10 sections, butthose are even rather loose boundaries around the edges of those sections. So Ithink you could really, in fact, I talked to somebody this morning on a podcastthat said her favorite thing to do this last couple of days, she printed outthe, the copy of the book we sent her, and she just loves to flip to a randompage.

Scott: Yeah.

Carl Richards: Right.So you, any one of these stands in isolation. Um, so yeah, that's how it'sdifferent than the other books.

Scott: Yeah. That'svery cool. It's almost almost like a money devotional.

Carl Richards: Yeah.I, I, I was really like, even the way it's designed, the physical book, [00:04:00] it, uh, I had much more, and I thinkpeople will understand this when they see it. Much more in mind, like a a, abook of poetry. And I'm not calling this poetry, I'm just saying a, a poetrybook. It was much more the template than a personal finance book.

Scott: Yeah, ahundred percent. Um, there's a couple of them that kind of stood out to me. I'dlove to hear a little bit more from you on them, if that's

Carl Richards: Yeah.Yeah.

Scott: The first onewas outside the lines, number 8.

Carl Richards: Yeah.

Scott: The squarewhere money won't stay inside the lines.

Carl Richards: Yeah,that's, I, I, I really enjoyed this one. 'cause I was literally like, you know,I, I remember having a conversation about sort of like, money won't fit in thebox, or money doesn't stay inside the lines, or money doesn't stay inside theboundaries.

And in my mind, this was back during the New York Times column,so I was always thinking of like, well, how am I gonna visualize that?

Scott: Mm-hmm.

Carl Richards: Andsometimes I would hear things described like somebody would say like. The [00:05:00] line between this and that is very fine. Iwould literally, in my mind be like, oh, the line between, and this was anotherone of those, like, money won't stay inside the lines.

And I was like, oh. So it's just a, a, a, yeah, a, a box withthe words money won't stay inside the lines. And the, those words are outsideof the box. The box is nice and clean, but the words are going outside of it.And I, I think about this like, um, you know. If we're taught anything aboutmoney, we're taught that it's a math problem, that it will fit into aspreadsheet.

Scott: Mm-hmm.

Carl Richards: Youknow, we have really clean, you know, accounting ways of organizing a balance,a balance sheet, or an income statement. But you know, I, I've been sayinglately like two plus two always equals four, but two plus two never equals envyor greed.

Scott: Mm-hmm.

Carl Richards: And soI, I, I think it's like we [00:06:00] thinkwe're talking about something that should fit in the spreadsheet and then, andsome of it does.

Part of it does, it's an important part of it that it fits in aspreadsheet. Yeah. But then there's this feeling piece that suddenly like,we're like, wait a second, that doesn't fit in a spreadsheet. So that, that waswhat I was trying to capture with that sketch is, you know, money doesn't fitinside the lines and we should probably stop expecting it to.

Scott: Yeah it, itties in very well to one of your other sketches. The money equals feelings.Right. That,

Carl Richards: Yeah.

Scott: It's not alogical thing, there's a lot of feeling that comes in with money.

Carl Richards: That'sactually the first sketch in the whole book is the just money equals signs,feelings.

Scott: Yeah

Carl Richards:Because I just wanted to set the tone of the idea that like. Hey, this is notabout spreadsheets and calculators.

Scott: Mm-hmm.

Carl Richards: Thisis about this interesting relationship we have with money, which indeedinvolves spreadsheets and calculators, but it's not all about that. It's aboutthe feelings. We have greed, fear, dreams, worries, freedom, security, likethose are all feelings.

Scott: Yeah.

Carl Richards: Notnumbers.

Scott: The next onethat caught my eye, and on [00:07:00] this one,I liked it so much. I went out and bought the sketch number 37, Spend theMoney.

Carl Richards:Mm-hmm.

Scott: This one, uh,yeah. Is a newer one, right.

Carl Richards: That'sone that hasn't really appeared in very many places, um, and it's justsometimes I, I, you can think of this as a Venn diagram.

Scott: Mm-hmm.

Carl Richards: Andone circle says, uh, people you love and the other circle says, experiences. Sopeople you love and experiences and there's an overlap and that overlap. So theoverlap of people you love with experiences. The overlap is labeled, spend themoney and there should be an exclamation mark on there.

There's not, but that's so I feel like I'm saying like spendthe money to myself and to everybody else. And I, I think it's just interestingthat like, it's pretty subtle doctrine at this point. At the end of our lives,we won't regret, you know, we won't regret things. We tried and failed. Wewon't regret spending money. We will regret the things we didn't try. Right?The [00:08:00] things we didn't do, the time wedidn't spend. And so much of that is tied up in money. Like Will, will regret.How do you put a price tag on an experience, like a new experience that you'vehad, uh, like something that strikes you with awe.

With a grandson or a, or a, a, a best friend or a spouse thatyou're standing there watching, you know, the sunrise or a sunset or eating ata restaurant you've always thought about in Norway, or, you know, and thesethings, by the way, they don't have to cost a lot of money. Like, it could justbe, you know, skipping rocks with your granddaughter on a calm day in the lake.

Scott: Yep.

Carl Richards: Andthat involves just having the space and time to do it. So I, I think whateverit is, experiences are far more valuable than money in a bank and far morevaluable than useless plastic crap, you know?

Scott: Yeah. Thestory of people on their deathbed, right, they're not thinking about all of the[00:09:00] money that they have in the bankaccount. They're thinking back to those memories that they had with family andfriends and those experiences.

Carl Richards: Forsure. For sure.

Scott: Yeah. We'llswitch over seeing as I am a financial planner, The Big Mistake, which isanother one of those more popular ones you have, right?

Carl Richards:Mm-hmm.

Scott: A lot of, alot of clients, and a lot of people think that an advisor's value is in pickinginvestments, , you know, even building the plan, whereas this one really speaksto, I would say, the biggest value an advisor has, right? Why don't you. Tellus a little bit more about the, the big mistake.

Carl Richards: Yeah,so this was originally drawn about me, like, as most of these are, and it, itused less kind language when it was about me. It said it's it, so it said me onthe left hand side of the page. Then there's a square in the middle, sort ofalmost like a barricade or a barrier.

Scott: Yeah, yeah.

Carl Richards: And,and the, the, the barrier was labeled my advisor. And the other side of thebarrier was dumb, dumb. So I had said like, I need something. [00:10:00] I had said this to my financial planner. Iwas like, I need something between me and dumb. I need something between me anddumb. And you heard that thing.

And, um, so I, I have permission to, to use that language withmyself, but I didn't really think it was fair to use it with other people. Sothat's when I changed it to you and the big mistake and I think, you know, wedon't hire, we don't hire. Uh, advisors, planners, we, frankly, we don't hiresurgeons or landscapers either because we couldn't do it ourselves if we didn'thave the, if we had the time inclination and skill to do it ourselves. , And soyou don't hire an advisor because you're dumb. You hire an advisor becausethey're not you.

Scott: Yeah.

Carl Richards: Andbecause they're not you, they can see your blind spots. Like that's why we'vehired a financial planner is because she can see my blind spots and sheactually has no problem pointing them out to me, which I've, I've, I've givenher [00:11:00] express permission to do that.Like, I want you to be partially a drill sergeant. I want you to tell me whenI'm thinking about doing something dumb, I want you to remind me and you don'tneed to do it gently. So that's, that's what that was about, is. Um, you know,it only takes one or two big mistakes. Really. You almost only get one adecade.

You know, like if you were to sell at the bottom of the marketin 2008 when things were super scary. Mm-hmm. You know, it, you may as wellhave been in certificates to deposit or had your money in the mattress duringthat decade.

Scott: Yeah.

Carl Richards: Soit's worth it, right?

Scott: Yeah.

Carl Richards: Sothat, that's how I think about the big mistake.

Scott: Yeah, that'scool. A lot of them talk about that real financial advice. The one I'm kind ofthinking of right now is the number 10, Life Meets Money. But I mean, so yourlife, the markets and where they intersect real financial advice. But so manyof the slides talk about real financial advice. What is real financial advice?

Carl Richards: Yeah,it's such a fair question. I, I, and who [00:12:00]am I to define it? So I'm just like defining my version of it and to me, realfinancial advice is when we understand this ongoing process of aligning our useof capital. And I actually think capital has an asterisk by it. It's, it's notjust money. It's money. Energy, time, and attention. I think those are the foursources of capital, so aligning our use of money, energy, time, and attentionwith what's important to us. That to me is real financial advice, and that'sgonna be a never ending prob. There are times in our lives when if those were aVenn diagram, you know, our use of capital, what's important to us, there aretimes in our lives where there's a gap between them.

There's no overlap. Yeah. Yeah. Like I, you know, I can thinkof lots of times in my life when the way I was using my money, energy, time,and attention did not line up with what I would tell you was time, outside timewith my family, mainly outside was the most important thing.

Scott: Yeah

Carl Richards: It'dbeen two weeks since [00:13:00] I, I've beensaying no to my daughter for going on a mountain bike ride. Well, okay, that'sthat. That's just called being human and how can I get there's some overlapagain, and there's gonna be other times in our lives when those two circles,your use of capital, what's important to you are look like one circle.

Scott: Yeah.

Carl Richards: Right.And there's a perfect overlap.

Scott: Yeah, yeah.

Carl Richards: Youknow, and, and then that's gonna change again.

Scott: Yeah.

Carl Richards: So Ithink real financial planning is the never ending process of aligning our useof capital with what's important to us.

Scott: Yeah. That's,that's good. Well said. I think I have one last one. I mean, there's lots ofthem. Um, yeah. But this is a big one that, you know, we work with a lot offolks that are before retirement, in retirement, you know, they have more thanthey'll ever need , but figuring out the enough question.

Mm-hmm. What, you know, you have the, the Enough one- what doesthat talk to?

Carl Richards: Yeah. [00:14:00] It's a real, um, we're kind of hardwiredfor more. Yeah. And that's, that goes back a long ways, right? Like if there'sfood around, I don't know when I'm gonna see food again. I should eat as muchas I can.

You know, it goes back a long ways and it's one of thosebehaviors that was really important to keep us alive as a species, but is nowmaladaptive in, in where we live now. Like in a a non scarcity basedenvironment like we have, most of us, most people listening to this at leastare not at risk of running out anytime soon in terms of food.

So in that environment, if we think about like, historicallywhat is enough, it's always like a little bit more.

Scott: Mm-hmm.

Carl Richards: Youknow, and so we, we kind of lose the plot a bit sometimes when we. Start torealize like, man, I'm, I'm still [00:15:00]working as if it's all gonna go away tomorrow and my kids don't even know myname. You know, like how much is enough and who gets to define it? And it turnsout if, if enough can't be a number. Because if it's a number you'll never getthere because as soon as you get to that number, you'll move it a little bit.

Scott: Yeah.

Carl Richards: Enoughcan't be a destination Enough is something you are, and so, and, and I can kindof like almost, I mean, I can at least anecdotally prove that like I know, Iknow people with more money than they, or any form of their posterity forever,will ever need.

Who are super insecure and it's not enough. And then I knowother people with almost nothing who seem to have enough.

Scott: Yeah.

Carl Richards: Soenough isn't a number it's a mindset, right? And once we do that work, [00:16:00] maybe a certain amount of money helpscreate the conditions under which we can feel like we have enough, but not ifwe haven't done that other work, whatever that other work is.

Scott: Yeah.

Carl Richards: Butit, it doesn't involve getting more money.

Scott: Yeah. Do yousee that as kind of a constant, like, a constant, I wanna say battle offiguring when, you know, even if you are at that point, there's always gonna besomething that's going to maybe challenge is this enough?

Carl Richards: Yeah,I do think particularly in the day and age we live in where, you know, it usedto be much easier if, if, like in growing up. I mean, I kind of, I rememberwhen I was seven or eight, all my buddies, we all had the same kind of bicycle.Mm-hmm. And I may have wanted a slightly nicer BMX bike, like a red lineinstead of a mongoose or whatever, but, but I didn't know that I was supposedto want a private jet. Right. And now I call that cultivating your comparisonset. Like our comparison [00:17:00] sets.Because of Instagram, you know, as a metaphor, Instagram has, we really losttrack of what actually matters to us. So it's a, it is a constant, I I thinkit's a constant, process of cultivating that comparison set. Like what are youcomparing yourself against? It's constantly weed weeding that guard. You'regonna be fine. And then you're gonna wake up one day and the neighbor justbought a new wake surfing boat and you'll just have this, it's like often it'sjust a little insidious it's like a little sneaky little thought.

Scott: Yeah.

Carl Richards: Justlike, oh, that, that's cool. Like that could be the beginning of it, right?Yeah. And then like, eh, man, if, if they can get one, why? You know? And maybethe kids say something. Mm-hmm. Oh man, I wish we had a boat. Yeah. Right. Andthen all of a sudden you're thinking about $120,000 wake surfing boat. Youknow, and, and maybe that's important, I don't know, but just we have to be,um, I think just carefully cultivate the comparison set.

Yeah. A hundred percent. [00:18:00]That's awesome. This was great, appreciate it so much. Getting some of thoseinsights. , Looking forward to the book coming out. When is it? Out foreveryone to pick up, Carl?

Well, it's available for presale now.

Scott: Okay.

Carl Richards: And myfavorite suggestion is buy order one from Amazon and one from your localbookstore. Yeah. Um, but it will actually come out August, sorry, October.October 21st.

Scott: October 21st.Awesome.

Carl Richards: ThanksScott.

Scott: Thank you forjoining us.

Carl Richards: Yeah.cheers..

Scott: Okay, thanksagain to Carl for joining me today. I hope you found our conversation of value.For more information on the topics and links discussed, please visit ourwebsite@retirereadypodcast.com and go to the episode 13 page. There you'll findthe show notes and resources for this episode. If you have any questions orwould like any retirement related topics discussed on future podcast episodes.

Please reach out to hello@retirereadypodcast.com. Be sure tocheck back in two weeks for our next episode. Thanks again for joining ustoday, and I look forward to seeing you back for the next one.

Julie: Thank you forlistening [00:19:00] to the Retire ReadyPodcast. Subscribe to this podcast or to learn more, please head on over toawakenwealth.ca/retirereadypodcast. Investment services are provided throughAwaken Investments of Aligned Capital Partners Inc. an approved trade name ofAligned Capital Partners Inc / ACPI.

Only investment related products and services are offeredthrough ACPI or Awaken Investments of ACPI and covered by the Canadian InvestorProtection Fund. Tax planning, financial planning and insurance services areprovided through Awaken Wealth Management Ltd.. Awaken Wealth is an independentcompany, separate and distinct from ACPI or Awaken Investments of ACPI AwakenWealth are not licensed tax professionals and you should consult with your taxadvisor before acting on any recommendations. Investments and investingstrategy should be evaluated based on your own objectives. Listeners of thispodcast should use your best judgment and consult a financial expert prior tomaking any investment decisions [00:20:00]based on the information found in this podcast.

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