Carl Richards: The Case for ‘Deeply Human’ Financial Advice

Summary

Podcast Summary: The Long View

Episode: Carl Richards: The Case for ‘Deeply Human’ Financial Advice
Date: October 21, 2025
Hosts: Christine Benz (Morningstar)
Guest: Carl Richards, Author, CFP, Founder of the Society of Advice

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Episode Overview

This episode welcomes Carl Richards, celebrated author and financial advisor, to discuss his new book “You’d: Reimagining Wealth in 101 Simple Sketches.” The conversation delves into the value of human-centered financial advice, how to foster more authentic, personal conversations about money, and the broader societal pressures that shape our financial fears and desires. Carl and Christine also explore practical ways to define “enough,” experiment with meaningful spending, combat comparison, and the role that technology and self-awareness play in modern advising.

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Key Discussion Points & Insights

1. Carl Richards’ Entry Into Financial Services

• Funny Beginnings: Carl shares how he mistakenly applied for a job in “securities” (investments), thinking it was for a “security” (guard) position, highlighting his unplanned entry into the finance world.
  • “The ad apparently said ‘securities,’ not ‘security.’ And I didn’t know the difference at the time.” (03:11, Carl Richards)
• Early Lessons: His early days were marked by confusion—thinking the job would be about math, only to realize it’s about humans and emotions (03:27–04:47).

2. The Society of Advice – Purpose and Philosophy

• Mission: A monthly gathering for real financial advisors focusing on the “craft of advice,” emphasizing human connection and trust rather than technical skills or product knowledge (05:13–07:33).
• Focus: The Society prioritizes understanding, presence, and facilitating client self-knowledge.
  • “You want to be a better financial planner or advisor—be a better human.” (07:52, Carl Richards)

3. The New Book: Conversation Grenades

• Purpose: The book is intended as a “conversation grenade”—provoking real, valuable dialogues around money and values, both among professionals and families (09:03–12:03).
  • “Could I put together a series of really short...conversation grenades?... My goal…is to start a million conversations around money.” (10:00 & 11:30, Carl Richards)
• Example: A family conversation about wealth prompted by his daughter’s unexpected definition.

4. Memorable Sketches and Ideas

• Magic Certainty Button (13:12):
  • Satirical sketch reflecting humans’ desire for certainty in finance, but the impossibility of ever achieving it.
  • “We so desperately want certainty as humans...But the problem is it’s impossible to deliver.” (13:56, Carl Richards)
• Range of Outcomes (15:19):
  • Based on Monte Carlo analysis, illustrating the unpredictability of financial outcomes and the need for comfort with uncertainty.
• Focus Where It Counts (17:00):
  • Venn diagram of “Things That Matter” and “Things I Can Control”—guiding focus to this intersection.

5. Thinking, Nature, and the Power of Stepping Back

• Reflection Techniques: Both guest and host discuss the value of physical activities (laundry, gardening, outdoor time) for mental clarity and emotional regulation (18:47–22:53).
  • “Knowledge work requires large chunks of unstructured time. It’s not a reward, it’s a prerequisite for continuing to do the work.” (21:26, Carl Richards)
• “Relaxing Out Loud”: Encouraging a workplace culture where taking breaks is visible and accepted for better wellbeing.

6. Defining 'Enough' and Combatting Social Comparison

• Envy and Comparison:
  • “What Envy Feels Like” sketch contrasts personal possessions with the inflated, curated world of others (especially through social media).
  • “We need to carefully cultivate our comparison set…We’re memetic creatures at heart.” (25:17–27:20, Carl Richards)
• Conversation on Experiences:
  • Cautions that even spending on experiences can become another arena for unhealthy comparison, urging true self-reflection (28:23–31:47).

7. Practical Approaches to “Enough”

• Action Over Analysis:
  • Recommends experiments and guesses—try new things, see what resonates, and iterate rather than endlessly planning (32:34–36:03).
    • “Run experiments, see what I notice…You’re running the experiment to find out if you [like it].” (35:24, Carl Richards)
• Testing Contentment:
  • Examples included “no spend” periods, staycations, or trying out luxury purchases in low-cost ways before committing.

8. Spending in Retirement and Overcoming Frugality

• Habits from Accumulation:
  • Many struggle to transition from saving to spending in retirement, as frugality becomes core to identity (36:38–39:56).
  • “The very habits and traits…that got you there—delayed gratification…Now you’re at the spot you’ve been waiting for. And it’s antithetical to your very identity [to spend].” (36:38, Carl Richards)
• Small Steps:
  • Practice enjoyable, purposeful spending in small increments to rewire habits and increase comfort.

9. Human Financial Advice vs. Algorithms

• The “Deeply Human” Difference:
  • Technology excels at analysis, but meaningful advice navigates complex, emotional human realities (40:37–43:30).
  • “Algorithms can answer, analyze patterns brilliantly. But...they can’t feel the anxiety of a major investment decision or the pride of achieving a financial goal or…the responsibility of providing for a family.” (42:51, Carl Richards)
• Self-Driving Money Metaphor:
  • Even the best automation requires humans to determine direction and purpose.
  • “The car still needs to know where to go. The self-driving money still needs to know where to go.” (45:51, Carl Richards)

10. Automation and the J-Curve of Learning

• Cold Start Problem:
  • Automate repetitive tasks, using AI as a tool to get started and save time—especially in communications or administration (46:34–49:02).

11. The Value of Being In Over Your Head

• Growth Through Challenge:
  • Regularly pursuing “stupid human tricks” (impossible tasks for current self) promotes personal growth—both in finance and life (49:20–52:20).
  • “You almost always find out you underestimated what you could pull off…We’re really bad at imagining that we can do it.” (51:47, Carl Richards)

12. Sources of Inspiration

• People Doing Their Own Thing:
  • Draws inspiration from those truly themselves—like poet David Whyte or even controversial figures like Peter Thiel—not for imitation, but as models of deep self-engagement (52:42–55:31).

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Selected Notable Quotes

• On Human Advice:
  “You want to be a better financial planner or advisor—be a better human.” (07:52, Carl Richards)

• On Financial Certainty:
  “We so desperately want certainty as humans...But the problem is it’s impossible to deliver.” (13:56, Carl Richards)

• On Automation:
  “The car still needs to know where to go. The self-driving money still needs to know where to go.” (45:51, Carl Richards)

• On Enough:
  “Enough can’t be a number or else you never get there.” (34:05, Carl Richards)

• On Personal Experiments:
  “Run experiments, see what I notice.” (35:24, Carl Richards)

• On Growth:
  “You almost always find out you underestimated what you could pull off.” (51:47, Carl Richards)

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Timestamps for Key Segments

• Carl’s entry into finance: 01:59–04:47
• Society of Advice: 05:13–08:42
• Conversation grenade/book purpose: 09:03–12:03
• Favorite sketches: 12:17–17:00
• Nature and reflection: 18:47–22:53
• Envy and comparison: 25:17–31:47
• How to find “enough”: 32:34–36:03
• Spending in retirement: 36:38–39:56
• Human vs. algorithmic advice: 40:37–43:30
• Self-driving money metaphor: 44:02–46:11
• Automation/J-curve: 46:34–49:02
• Getting in over your head: 49:20–52:20
• Sources of inspiration: 52:42–55:31

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Tone & Language

The episode is conversational, candid, sometimes humorous, deeply reflective, and loaded with practical wisdom. Both host and guest are approachable, with Carl’s language often drawing on metaphor, story, and gently provocative questions.

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For Those Who Haven’t Listened

This episode is a wide-ranging exploration of what it means to give and receive “deeply human” financial advice in a world of uncertainty, comparison, and technological automation. Filled with stories, sketches, and actionable insights, it illustrates why good advice—and good money conversations—are ultimately about understanding yourself and others, embracing uncertainty, and having the courage to define your own version of “enough.”

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Transcript

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[Christine Benz]

Hi and welcome to the Longview. I'm Christine Benz, director of personal finance and retirement planning for Morningstar. Today on the podcast, we welcome back Carl Richards, who's the author of a new book called you'd Reimagining wealth in 101 Simple Sketches. His previous books, the Behavior Gap and the One Page Financial Plan, were both bestsellers. Carl started the Sketch Guide column in the New York Times and it ran weekly for a decade. Carl is a certified financial planner and he started the Society of Advice, which is a community of financial planners dedicated to the craft of advice. In addition, Carl is active on the podcast circuit. He hosts Behavior Gap Radio, as well as a podcast called 50 Money and Meaning with Carl Richards. Carl also co hosts a podcast with Michael Kitces called Kitces and Real Talk for Real Financial Advisors. Carl, welcome back to the Longview.

[Carl Richards]

So excited to be here. Thanks for having me again.

[Christine Benz]

Well, it's great to have you here. I was thinking you've been one of our most frequent guests on the podcast, so thank you for doing it. We wanna talk about the book, your new book. But before we dive into that, I saw something in your bio that made me smile, which is how you encountered the financial services industry. There was a little bit of miscommunication. Can you talk about that?

[Carl Richards]

Yeah. This is a true story.

[Christine Benz]

Okay.

[Carl Richards]

Yeah, it is a true story. Just for context, I was an undeclared major. Newest hired a landscaping company, going to school full time. So there's a lot going on here. But I had no idea what I wanted to do with my life. And I came home one day and my wife had recently graduated with a degree in finance, which did not sound that interesting to me at all. And she had opened the newspaper that sort of help wanted ads, and she found a job that we've sort of both thought that it was a security guard job. And I wish I still had the ad, but I thought this would be great because I could work the graveyard shift or whatever and still go to school full time. And so I went to apply for it, and I was thinking, like, Mall Cop or something. And it's really funny because the interview was held in the same building that I ended up working at later, like 10 years later at a bigger brokerage firm. But I remember being sort of confused about halfway through the interview, just, like, what? I don't understand the questions. There's nothing about self defense or kung fu. And I was like, this is fascinating. I made it through the interview, which obviously tells you about the applicant pool. And, you know, long story short, two weeks later, I ended up at the training center at Fidelity's National Call Center. At the time was in Salt Lake. The ad apparently said securities, not security. And I didn't know the difference at the time.

[Christine Benz]

And now you do?

[Carl Richards]

Yeah. I mean, that led to a series of. I mean, it wasn't much later that Netscape went public a couple months later. And I remember I could go on for 20 years about these sort of, like, confusing, like, surprises, like, no plan. But just real quickly, I remember in the training room being like, you know, kind of unmoored, like, okay, not a security guard. What is this? I was like, what is this? I remember asking myself, I was like, okay, it's a math job. I think this is a math. This must be a math, because, you know, we're training to get licenses, all that stuff, and their spreadsheets and calculators everywhere. And then Netscape goes public. And that was our first time that we had been trained at least enough to handle a large spike in call volume. So that, like, they had kind of like little red flashing lights. You know, if you were in the break room, you're supposed to get back on the phones. They pulled us out of the training room, and I remember walking onto the, you know, the kind of trading floor there and being completely shocked again by, like, what is this? Like, people, this is not math. People are yelling and people are excited. People are scared. This is not math. So it was just that went on and on and on for my whole career. And I think it has something to do with what we're going to talk about in terms of, like, money's role in our lives and how do we make sense of it.

[Christine Benz]

Yes. And that, of course, has been a key thrust in your work. Before we go to that, I wanted to talk about this endeavor. You have a lot of different things going on all the time, it seems, but one of the main things, things you've been working on over the past several years has been to create the society of advice which we actually have talked about on the podcast before. But can you refresh everyone's memory about what that is and what you're trying to do there?

[Carl Richards]

Yeah, it's really interesting because the essence of it is I just wanted to gather my friends for a really great conversation once a month that you wouldn't hear anywhere else. And the goal of the conversation was to make us all better at giving advice. And there's not much more to it, but I get this question a lot, like trying to make a worldwide organization. Because sometimes we joke, we're like, it's the worldwide chapter meeting of the Society of Advice. And for a while I called it the Secret society. And what that's pointing to is because, as you know, it's really hard for anybody to navigate the financial advice industry speaking broadly. Like, again, back to that earlier story. Like, it took me another three or four years to figure out the difference between people who worked at a bank and people who sold insurance and people who sold investments and stockbrokers at the time. And so I think from the public's perspective, and that's where this started, was I remember saying something like, and this was near like after Madoff, I remember being so kind of struck by all the news stories about Madoff and mini Madoff and all the people in our industry that were untrustworthy, et cetera, et cetera, et cetera. Struck by the difference between that and the work that I hoped I was doing, but I knew my colleagues were doing for people during 08 09, I really honestly felt like they were saving lives. You know what I mean? Like, really helping people make really important decisions in very scary times. And the difference between this kind of fake, speaking really broadly, and I wouldn't even know how to draw the boundary conditions around these ideas, but this sort of fake advice industry and real financial advisors, I remember being struck by that and thinking it's like, there's a secret society of real financial advisors. And what does that mean? Like somebody you could trust, somebody who's technically really professional, competent, like a rock star technically, and you can trust them. That's kind of. And I was like, why don't we just gather once a month? And that's how we started the Society. We just get together once a month for a 90 minute call with a really smart guest is the idea.

[Christine Benz]

And as far as I can tell, it's not so much about homing in on the technical aspects of doing financial planning. It's more about how to understand your clients, how to communicate with them, how to get them to understand what they're going for. Isn't that more the focus of the Society?

[Carl Richards]

Yeah, I think that's fair. I mean, somebody said recently if you want to get technical skills, and they named other programs if you want to be a better advisor. That's what the Society of Advice is about. I think of it as, you want to be a better financial planner or advisor, be a better human. And so a lot of the things we talk about are that, like, how can we see our own foibles? How can we get better at being present? How can we listen in better ways and then therefore get better at helping clients clarify the journey they're really on? Instead of sort of always, you know, endlessly debating the products we use or the tools we use, let's get clear about where we're going first. So that's a lot of our focus.

[Christine Benz]

So I want to switch over to talk about the book, which is called you'd Reimagining wealth in 101 simple sketches in the intro to the book you wrote. This is not a book that. It's a conversation grenade. So I'm hoping you can talk about who you're hoping will start talking after reading this book. And what do you hope they'll be talking about?

[Carl Richards]

Yeah, that's such a nice question. So I resisted doing another book. It's been 11 years, and not a month went by that somebody, publisher, agent, friend, didn't ask me what I was going to write another book. And a couple years ago, I was like, gosh, this just doesn't seem to be getting any better. The global anxiety around money doesn't seem to be getting any better. And I'm convinced that good financial advice and good financial decisions happen in conversation. That getting sort of clear about what it is you care about, where you're headed, that happens. I don't even know if it happens best. I think it happens almost only in conversation. And so that's kind of why I was like, man, could I put together a series of really short. And I use. Hugh McLeod first introduced me to this term conversation grenade, because I noticed advisors were using them that way. They'd print them and put them on their walls, and then they would email me stories that clients experience. Like, they would walk into the conference room and a client would be standing up, a couple would be standing up talking about one of the sketches. So my hope is that, look, advisors are, I believe, and we may even talk about this later. I still believe that the human advisor is the best positioned to facilitate these conversations and So I hope advisors will have them and they are. But I have a deeper goal. Right. Like I just, in my mind, I imagine a family sitting around the dinner table talking about what it means to be free or what, what wealth means. My daughter said this to me the other day on a bike ride. So my 20 year old daughter said, we're one of the wealthiest families I know. And I had this immediate reaction of like, no, you know, no, we're not. And I said, what about? And then I caught myself and said, help me understand. So this is the idea of a conversation. I said, help me understand what you mean by wealthy. He said, well, we really have been able. We sort of do what we want, you know, like we're living lives. And I was like, oh, okay, if that's your definition. So that's the kind of conversation out on a walk, on a road trip, sitting around by the lake, sitting at dinner table, what does it mean to have enough? How do we pay this bill? Can we talk about these things instead of saying that's none of your business or we don't talk about such things. So I'm hoping everyone, I mean, my goal, Christine, is to start a million conversations around money. And not the kind of conversations that are about what product, but more about what does it mean to us.

[Christine Benz]

Yeah, that's a good summary and I will say I enjoyed the book thoroughly. When you think about your favorite sketches in the book, does one stand out as your favorite or maybe a couple stand out as your favorite?

[Carl Richards]

I thought you would ask that question and so I even thought about it. It's a really hard question to answer. It depends on the day. The one that I'm thinking about today is there's this sketch called the Magic certainty button and it's just a square. I've done a lot of this art on the radio. So it's just a circle that looks like a button. I mean, it's my hand drawn version of a button that you'd press like on the wall, like a button. And above it it's lab magic certainty button with an arrow. Those words have an arrow pointing to the button, like, hey, this is the magic certainty button. Then under it in brackets, it says, I can't seem to find it. And I was just trying to get at this idea. And the reason it's sort of the one that came to mind was we so desperately want certainty as humans and I think as an industry we're at risk of becoming or being seen as sellers of certainty because certainty is so easy to sell. Because everybody wants it. But the problem is it's impossible to deliver. And so I think that's one of the reasons people get sort of frustrated, maybe with their experience, their interaction. Speaking very broadly here with the financial services industry, broadly is sometimes the language we use, we might actually explicitly be doing it, but sometimes even the best of us, the language we use might be overly precise. Like, here's a 30 year line. I'm going to show you what the next 30 years of your life looks like. And we're so technically good. We love big calculators and spreadsheets and we should draw the best line possible with all the assumptions really well thought out. But the dilemma is, of course, we know it'll never be that exact path. And so I kind of like that sketch of just sort of trying to be. My editor at the New York Times called my best work confrontational without being off putting. And so I was trying to be a little bit like cheeky about the absurdity of trying to find the magic certainty button.

[Christine Benz]

Yeah, I think sometimes there is this gravitational pull toward like faux precision. You see someone saying, like, stocks should return 8.6% over the next decade. And it's like, really? Where'd the 0.6 come from? I mean, it's like, wow.

[Carl Richards]

Yeah, I love it. When you see Monte Carlo assumptions out to two decimal, I'm 98.27%. You're like, no, easy tiger, easy.

[Christine Benz]

Right. In terms of the ones, the sketches that you get the most feedback on, what are the ones that seem to stand out as readers favorites or what. What are the ones that you've heard from advisors that their clients have really reacted to?

[Carl Richards]

Yeah, maybe just two real quick. I've heard a lot and it's been really interesting. I'm really just. I don't. I mean, I care deeply about getting the book into the world, but what I care more about is getting conversations in the world. And so this has just been a giant excuse to have lots of conversations. So we've been having lots the last couple of weeks and I've been surprised at how many people have asked about. All the sketches are numbered sketch 55, which is range of outcomes. And this is one of the things I work really hard at. I get it wrong most of the time, but sometimes I get it right, which is taking a very complex subject and trying to make it accessible. And I've been surprised how many people have asked about range of outcomes simply because it's basically, I'm trying to talk about Monte Carlo analysis. And so it's just to describe it. It's just now it's on a piece of paper. Imagine the left hand side label now and there's a there with maybe. It looks like, I'm trying to count as we do this, maybe 10 lines and they're all squiggled in different ways and some end up on the right hand side. On the right hand side of the paper, it's labeled the future. And the lines, as you can imagine, there's a potential range of outcomes, just like you'd see in a Monte Carlo analysis. And I've been surprised how many people that has resonated with. And the point of the essay was really that we need to be comfortable. We need to back to our false sense of precision conversation. We need to understand that, yeah, there might be some paths that are more or less likely, but there's a probability assigned to each path. But the path is still a random draw based on those probabilities. So the likelihood of you getting one exact scenario is still based on probability. Who knows what could show up? We saw that with was the NFL draft. No, the NBA draft with the Mavericks getting the first pick. Right. Like, very low probability. And it still showed up. So I love that one that's been asked a lot about and then I'll tell you real quickly. The only one, we do a lot of, like, art with these, like, canvases. And the only one my wife's ever allowed in the house is number 22, focus, where it counts. So that's just. I call them circle sketches. Christine. Because I don't know if you know, but there are Venn diagram police out there. Yeah. I think we may have talked about this before. And so it's a Venn diagram. Don't send me an email if you don't believe that. In one circle it says things that matter. The other circle says things I can control. And the overlap is labeled what I try to focus on. And that seems to be the one that has the most universal, like, I hear from a lot of, like, mindfulness meditation people, yoga studios that have put that up as just sort of a touchstone.

[Christine Benz]

Yeah, I love the essays. You're so well known for your sketches, but the essays are really good. And I noticed kind of a through line in the essays is this idea of kind of like getting a way to think better. And for you, a lot of that happens in nature. This idea of kind of putting some space between yourself and the thing that's bothering you or nagging at you. Can you discuss that concept? Because it seemed to come up quite a lot, the importance of separation, separating yourself from the thing that's giving you angst and kind of walking away and maybe letting your subconscious brain work on it. But maybe you can expand on that.

[Carl Richards]

I'm actually quite curious. Tell me sort of your experience with that.

[Christine Benz]

Well, I find that it works like a charm. And that's one reason why.

[Carl Richards]

What do you do? What do you do?

[Christine Benz]

Well, I'll go down and like fold some laundry. I mostly work remote now. So yeah, I'll do stuff, little things in the house, just to kind of walk away and take care of a few things. Very short. But it does seem to help. Or, you know, getting outside. The shower thing really works, I find. Or even sometimes when I'll be on the cusp of waking up in the morning, sometimes I'll be like, oh yeah. And sometimes it'll be a completely stupid idea, but sometimes it'll actually be a good idea and a good way to address the thing that's been bugging me. So walking away I do think works.

[Carl Richards]

I love that. I think it's interesting just tangentially that I've been asked a lot lately in these conversations about what do you do when you're scared? What do you do when it's really uncertain? And I think that's just sort of the nature of the current environment, which seems like we've been saying this for 10 years, but my new answer is I go organize the garage. I think there's something really interesting to that idea that you bring up laundry. There's that old Zen saying, before enlightenment, chop wood, carry water.

[Sam (possibly a producer or assistant)]

Water.

[Carl Richards]

After enlightenment, chop wood, carry water. If we're feeling nervous about the market or nervous about our financial situation, or nervous about anything, I've been surprised at how much. In fact, yeah, I did write another essay about this called the Power of Order. How much it helps to just go organize something and just put some sense of order. Even if I organize my desk, I feel better. But me too. To your question about getting out. And I wish I had been better at this. It's the one thing I wish I could tell my 25 year old self. Like finding a place to pause whatever it is in your activity. Like before this, because I'm doing, you know, four or five of these today. Before this, I had five minutes between the last one and this one. No, sorry, I had 15. I went out and sat down with my feet in the dirt in the garden for five minutes. And like, rather than trying to crush my email because I know how thoughtful you are, like, I wanted to show up in a headspace where I was like prepared to be present and thoughtful. That is not the opposite of ambition. And I wish I could tell my 25 year old self that, like, it's not the opposite of hustle. Like you can still be up to something and be ambitious and not have it be heavy all the time and not be grinding. But now I know it's an incredibly important part of my life where my best work and I think this is really important for your audience. We're all knowledge workers. Knowledge work requires large chunks of unstructured time. It's not a reward, it's a prerequisite for continuing to do the work. So, like, my time in the mountains is not a reward. I didn't earn that as a reward. It's a prerequisite for continuing to do this work. And I've just found that to be incredibly important. It's my best thinking because often I'm trying not to think at all, but the best ideas occur there. And then the other thing I'd say about it is, like, if I'm nervous or worried or scared or feeling reactive at all. And I know what that feels like in my body now, like, if I'm feeling reactive at all. A client said something to me. Somebody wrote an email that the Venn diagram police wrote in. Like, what if I'm feeling reactive at all? I know now and I don't always follow it, but every time I don't, I regret it. I know now to pause, like, go do the thing, go fold the laundry, go organize the garage, go on a bike ride before I respond, because if I respond in that place, I will almost assuredly regret the response.

[Christine Benz]

I remember you made the point when you were previously on our podcast about how we need to. The phrase you used was to relax out loud, to not feel like you need to furtively steal off, to give yourself a little bit of space between your thoughts and your work. And I thought that was powerful.

[Carl Richards]

Do you think we've gotten any better at that? Maybe. Maybe, Maybe, exactly.

[Christine Benz]

Yeah, I guess, you know, having more confidence in my work and my place in the world has just made me feel like, okay, not everything is an emergency all the time. So I've gotten a little better at that, I guess.

[Carl Richards]

Do you think we generally not you, but like the people you work around or you see or your listeners that write in, do you think we're. Do you think we're any better two or three years later?

[Christine Benz]

I think Covid actually was kind of Healthy for workplaces even still, like, I'll be in a meeting or something, and someone who you'd think would be there would. Someone will be like, oh, you know, his son had a soccer game or whatever. Not that that wasn't okay before, but now it just seems like there's more flow to the workplace in a really nice way, I think.

[Carl Richards]

Yeah, I love that. Yeah.

[Christine Benz]

But it would be a shame if we forget all of, you know, there were some positive side effects from COVID It would be a shame if we forgot all of them. And I think that's a real possibility.

[Carl Richards]

Yeah. Yeah. And just continue to keep in mind that does not mean we need to be less ambitious. Right. It does not mean we need to be less, you know, productive or action oriented. It just means realizing that knowledge work is different than other types of work, and it requires you to treat your brain probably a little differently than maybe a system built around labor. So, anyway, I think it's important.

[Christine Benz]

I wanted to ask about some of the themes in the book. And a recurrent theme in the book and in your work in general is this idea of enough and how societal pressures and especially social media get us feeling bad about what we've got and how it compares to other people. You have a wonderful sketch in the book that is titled what Envy Feels Like. I'm wondering if you can describe that one and discuss what you wanted it to illustrate.

[Carl Richards]

Yeah. So a small circle. So imagine a small circle drawn on a piece of paper that says my stuff. And then a much bigger, much, much bigger circle. And that one has room to put the words inside the circle. It's so big, it says everyone else's stuff. And then the caption below is labeled what Envy Feels Like. And one of the things I was really trying to get across there is this idea of a comparison set. And I think what you're pointing to, especially when we bring up social media, is this is a new problem. And the phrase I like to use is the idea that we need to carefully cultivate our comparison set is a new problem. Because it used to be that it was what your buddies had or your neighbors. And it used to be that everybody in your neighborhood. And it might still be true. This might still be true. But I remember growing up, we were all kind of generally the same. It was the same socioeconomic group in the neighborhood, and we all had. I've told this story before, but we all had BMX bikes because we rode our little dirt bikes around in the mountains of Utah. And I remember wanting a slightly Better BMX bike. But I didn't know I was supposed to want a private jet, right? And now I do, right? Or a Swiss chalet. Like I didn't know those things. And now we do. And so I think that's the real challenge is we are memetic creatures at heart. Like, we don't really actually know. It's quite hard to figure out what we desire. We just mimic other people from the youngest age, right? Like first we just mimic, like, what does mom want? Oh, mom wants that. That must be desirable because mom wants that. And then now that mimetic problem has gotten so big because we look around and so getting clear about what is your goal? Like, what's enough for you, not your mom and not your sister in law or not your brother in law, and certainly not all the people on Instagra. It doesn't even. We're not even gonna talk about the fake problem. You know that, like, we all know half that stuff is not real anyway. I was so shocked to first learn that influencers. There was a place that you can go that has a jet there and for a hundred bucks you can go take your pictures as if you were on that. Do you know what I mean? Like, I was like, really?

[Christine Benz]

I didn't know that either.

[Carl Richards]

Yeah, like, we're losing like one of my friends compares. Like, thinking you can still know who you are in the face of that onslaught is like showing up to a gunfight with a knife. Like, there's 300 PhDs on the other side of that fight. So that's what I was trying to emphasize here is like, can we get really careful about cultivating your comparison set? Because envy, it turns out it seems like it was mentioned in the Bible. Like, you know what I mean? It's been around a while, right?

[Christine Benz]

You know, relatedly, I think it was Brian Portnoy made an astute point. We have all heard about how if we're going to spend our money, our best ROI is spending on experiences, especially with loved ones. But he made the point that now that we can all see everybody else's experiences, is that going to diminish our own experiences somehow if now they can be weighed and measured alongside other people's thanks to social media. What do you think about that point?

[Carl Richards]

Yeah, I think it's a huge problem. I think it. Because now it just becomes one more place we could compare and compete.

[Christine Benz]

Right.

[Carl Richards]

And I think again, it really points to this need for intentional conversation around, like, what really matters to you. Oh, Gretchen Rubin, was it? Yeah, it was it was Gretchen Rubin on my podcast 50 Fires. She talked about how she was at. This story is so great. She was at. At some event in New York, as one does, I guess, like a cocktail party or something, and somebody came up, and they were. Gretchen was just, like, either coming back or on their way on a trip to the mountains to ski. So I'm sure it was Colorado, because the skiing's terrible in Utah. You shouldn't come to Utah to ski. That's just a joke. And this lady says to her, are you gonna ski? And Gresham's like, no, we don't ski. We don't like to ski. My husband doesn't like to ski. We don't like to ski. And. And the lady was like, no. You got so, like, really insistent, like, you gotta ski. Like, I didn't like it either. And I've started skiing. Like, you gotta ski. It's the best thing. You gotta ski. Chris is like, no, no, we don't ski. It's fine. And the lady went away, and she came back. She came back, like, sometime later, 15, 20 minutes, 30 minutes, and said, you know what I realized in talking to you? I don't like skiing either.

[Christine Benz]

Wow.

[Carl Richards]

I've just been doing it because it was what you do. And I was like, that is so interesting. Like, how. I have lots of stories about that. For me, like, dinner and a movie with friends. My wife and I went through this time where we were like, we want to build more connection with some close friends. And so let's systematically invite friends. Like, let's go every. Whatever. Like, you know, twice a month on Friday night. And what should we do? Okay, we'll go to a movie and dinner because we want deeper connection with friends. And after, like, five times, we were like, wait, if the goal was deeper connection, we were just in a noisy restaurant and a movie. Like, we never. So we're like. But that's what everybody does, so that's, of course, what you should do. Like, we don't like movies, and we actually don't love eating out. You know what we love doing? Let's buy all the ingredients, come over, plan on two to three hours. We'll make the meal, we'll talk. Like, we like that. And, you know, turns out that was less expensive. But that was not the point. It was a better expression of the value of connection. And so I think what you're pointing to makes this even more important. Like, how do you get clear about your goals? And, by the way, that's a practice that's never Done. Because you'll be wrong. Your guesses will be 5 million in a sailboat. Like, well, have you ever been on a sailboat? Like, go try that first. So anyway, that's, that's how I think about that sketch.

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[Christine Benz]

Want to delve into is, and we've talked about this with you before, but the idea of enough finding your, enough finding what your values are. What are some key questions people should ask themselves to try to get to the bottom of that?

[Carl Richards]

Yeah, I, I really think that I have a heavy bias towards action for this experience. So start by some questions and some conversations around make a guess. And this is coming up a lot. I think it's the age cohort of like 45 to 60 year old who's been working, working, working, working, because that's what we all did and is now saying, I just had this conversation with the, the chief creative at a public a company. Everybody would recognize the head of creative and he's like, I don't have any hobbies. I don't know what I'm going to do five years from now. I need to figure it out. So, okay, we start there and we say let's just guess, just a guess. And some of the places you can look for hints. What podcasts do you listen to if you were still getting magazine subscriptions, what magazines are arriving at your house? Gundog Weekly or Gardening is arriving. You got some hints. What conversations are you interested in? Then you could go back 20 or 30 years and be like, what did you used to like to do? Okay, so we've got a guess. And then my bias towards action is go take the smallest experience you can with that. Like go do it and see what shows up because new information will show up. And this is the same thing with the concept of enough. Like, enough, we've talked about this, but enough can't be a number or else never get there.

[Christine Benz]

Right.

[Carl Richards]

So how do you define your enough? Well, you start to test things like, what if I, I was just having this conversation with Ron Lieber and Jodi Cantor were out here for fourth of July. And we were talking about. And I can't remember who it is. Is it Ann Pritchard? It might have been Ann Pritchard that wrote about her. No spend year, no spend month. Those are really interesting exercises of like, well, what if I didn't buy any more running gear this year and I just used what I had? Is that enough? What if we went on a. I was just talking to another friend who this year decided to do a staycation in somebody else's house is what he called it. So they drove to a rental place in the countryside of Virginia. They didn't spend any other real money. They ate at the house, the house had a pool, they went on lots of walks. Like, what if that was enough? We didn't have to fly somewhere. How was that? So just start testing, running little experiments. Morgan Housel famously says that he's supposed to be a car guy because he was a valet when he was 18 in Los Angeles. And everybody tells him he should be a car guy. And he could afford to be a car guy, he should be a car guy. Well, an experiment he runs is when he goes to the Hertz counter. He said once every couple years he has to run this experiment. He'll just be like, you know what? It's an extra $200, give me the Porsche. And he said, he doesn't even have to drive. He doesn't even get off the lot before he's saying to himself, I admire this, the craftsmanship's amazing, but it's just not something I need. Well, that's a very cheap way to learn that versus buying the car. So that's kind of how I would. I would run experiments, see what I notice, run experiments, see what I notice. And one of the things you gotta keep in your mind is like, everybody else loves this. Well, you're running the experiment to find out if you do.

[Christine Benz]

I wanted to ask about older adults. I've been spending a lot of time talking and thinking about retirement planning. And it seems that many folks at that life stage truly do struggle giving themselves permission to spend what they could spend. So how can people at that life stage get more comfortable with the spending they do and maybe even do some lifetime giving to their loved ones versus leaving it as a bequest when they're gone. Can you talk about planning to spend at that life stage?

[Carl Richards]

Yeah. This is another surprise to me, the number of times this topic. I mean, I've run into it lots in my own planning work when I was running my own firm. I hear A lot about it from financial advisors. But all these conversations I'm having lately, this has come up so often. It's so fascinating to me. It's easy to understand the reason. If you're in a position where you've been successful, which a lot of the listeners of this show either are, or advise people that are in that position, the very habits and traits and characteristics that got you there, delayed gratification. You're really good at that. You might even be good at being frugal, but certainly at delaying gratification, Investing for the future, waiting. And now you're at the spot you've been waiting for. You've been waiting for this thing. Whether that, like, you've been successful, you waited for this thing. So what do you do now? And it's antithetical to your very identity. And so I think you practice, right? The same thing we do. You just practice. Like, pick one. Look, the research is clear, but you don't need another lecture about the research, right? This behavior is perfectly rational. But now the situation you're in, it's slightly irrational to be at the spot where you could put the golf shoes on and refuse to do it. Or maybe even more interestingly, like, man, wouldn't it be fun to spend a little bit of time with the grandkids doing things they love? Like, oh, man, I have one. This one grandkid that really wants to learn to sail, and his parents are busy, and they don't have to be like, could I go spend a week, you know, at a sailing camp and I could kind of be on the shore or even sail with them? Like, yeah, that's gonna cost some money. Oh, I don't like. The research is pretty clear that. And you pointed to Brian's work and many other people about this funded contentment, right? So practice. And like anything good practice, start small. Like, this is funny. Christine and I are asking you, go spend some money. Like, tomorrow. I want you to find something. And ideally, find something small that you've always just wanted. You don't even need it. You just wanted to do it. It's small. It's $25, it's $100, it's $5. Like, maybe it's even to the point of, like, you bought into the latte thing. You didn't buy coffee out because you were saving, but you love coffee out. Go tomorrow morning to your favorite coffee shop. Feel the whole way through it. Buy your favorite thing. It's going to be $12. Sit in your favorite seat with the book that you've been reading and enjoy it and feel the enjoyment of it. And it's a $12 rep, a $12 practice. And I think that's what you do. You rewire it until you get to the point where you're like, you know what, Saying, I'm to pay for my grandson's entire education because I'm so excited about the fact that he wants to become an electrician. I'm going to fund a scholarship for women who are getting into biomedical engineering. That's, I think, the way you get there as you practice.

[Christine Benz]

I wanted to ask about financial advice. You spend a lot of time talking to advisors and advising advisors, and you have some sketches in the book that address that. 1 I of your sketches illustrates that financial advice is sort of inherently human. And I'm wondering if you can kind of talk about that sketch. It's. The algorithm is a straight line, and real life is this curly ball of squiggles. Maybe you can talk us through that and how you see financial advice evolving and how it seems like you don't think that good advisors can ever be fully replaced by technology, but maybe talk us through that.

[Carl Richards]

Yeah. This is super interesting to me because I drew that sketch probably 10 years ago, and I was actually quite curious if it was still right. And so I asked both Claude and Chat, is this still right? And I said, I'm worried. I think this might not still be right. And I told him it was for an upcoming book. And I. I put the essay in there because the sketch doesn't mean a whole lot to them. But I put the essay in there. And the advice I got back from AI was this is more important than it's ever been. And to get this right, because it's getting clear that even the stuff we thought was uniquely human. I just read this fasting study about people were more willing, I think it was. I'm hesitant to cite who it was from. I'm hesitant because I'm not exactly sure I can pull it up real quick. But people were more willing to interact with a computer named Ellie about trauma than a human therapist. And it was largely the metric was judgment, because that's what they kept citing like, felt less judged. And there was a super interesting study about clients being more engaged on zoom calls when the advisor's camera was off just because they couldn't see the eyes of judgment. The AI doctor being ranked higher in bedside manner. Wow, that's fast. I mean, I thought it would maybe get diagnosis correct, but I didn't think it would be ranked higher. In bedside manner. So all of those are super interesting to me and something we need to be thinking about. But I think there's still this room deep to the human side. So that sketch, as often my sketches are, it doesn't capture all the nuance in the edge case. It's an opinion that by the nature of simplifying something that's complex, you're going to leave some stuff out. And it's an oversimplification for sure, but it's just to make the point that there's still room. And I think the answer is be deeply human. Because here's my favorite bit about this is life and markets and money are messy. Algorithms can answer, analyze patterns brilliantly. But here's the key. They can't feel the anxiety of a major investment decision or the pride of achieving a financial goal or and this one was really important to me, the responsibility of providing for a family. So I think that's still there. Right. And I don't know how that's replaced and maybe I'm wrong, but at least right now it's still there.

[Christine Benz]

You had a really wonderful discussion with Michael Kitces. I listened to it yesterday. I would urge people to check it out on the podcast that you do with him. You had this great metaphor where you're talking about financial advice. Like there are aspects of it that can be a self driving car, that technology can completely take care of them, but the car is still going to have to know where it's going. Can you talk us through that? Because I found that really helpful in thinking about the role of human financial advisors going forward.

[Carl Richards]

Yeah, like I want self driving money. Right, right. Like, and we're getting, we're already getting closer. I got fired by my financial planner and my wife fired me from those meetings. They were like, you're the last person that needs to be here. You're such a problem. So I'm creating self driving. Like we've a bookkeeper and we, we for the business and to the degree that it just takes care of itself in the background, isn't that like, I think most of us would love that. I mean there are some of us that just love the doing it. So I want self driving money. Right. And I don't think we're going to be far off. Like if you can have a self driving car, if you can create a self driving airplane, how can we not be very far off from like my finance now? But here's the key thing. I was in one of those waymos recently in Los Angeles and it was amazing. I actually felt safer.

[Christine Benz]

Well, I think they are safer on the data, aren't they?

[Carl Richards]

I mean, yeah. Than my Uber experience right before it. I'm telling you right now, it. It felt better. So I'm, I'm excited about that. But here's the thing. The Waymo car needed to be told where to go. Right? And so there's that. And it. That's not as easy. Like, most of our conversation to this point has been about how hard it is to figure out where you want to go. Right. Like, it starts out easy. 5 million in a sailboat. Of course, because I saw that on Instagram, of course. And then you start breaking it down. You're like, well, wait, I don't know, where did the 5 million come from and where's the sailboat? Like, it turns out figuring out who you are and going the whole way takes a lot of skill and conversation. And I still think that that is the domain of skilled facilitators, people who know how to ask good questions and then people who know how to overlay the tools for getting there. The self driving money on top of what you just described. So I think that's been really helpful to me. The car still needs to know where to go. The self driving money still needs to know where to go.

[Christine Benz]

You made the point in that podcast that sort of, apart from financial advice, in terms of guiding our activities, if we find ourselves doing a thing more than once, you could maybe step back and think about how to automate that. Can you talk about that? Because it was something I hadn't really thought about before, but it makes a lot of sense.

[Carl Richards]

Yeah, somebody introduced me to the. Maybe I'm late to the party, but somebody introduced me to the idea of a J curve. You know, it's like. And you can think of this even when you, if you hire somebody and you're trying to delegate to them, and kids too, like, if you want help doing the dishes, it is almost always easier just to do them to yourself than it is to get the kids to help you. And I think the same thing is true with AI. Like, we start into any activity and I would actually use as my signal anything I have to do more than once. If I have to do it more than once. Is there a way to make the this system? If I invest a little bit of my time and energy and maybe even a little bit of capital, can I make the system better so that that investment ends up paying off? Now that J curve ends up being a little bit like, if you think of it as total cost, like time, energy, money, attention to that process. You're on the left side of the J as you are starting to teach the kids to do the dishes or you're starting to train AI to do a thing, it actually is costing you more than just doing it yourself. And it costs you more, and it costs you more, and it costs you more. And then it gets to the bottom of the J and it starts to go up. And after a little while, you're back to where you were. And so I think anytime, here's to me, maybe the most useful one has been the cold start problem. The cold start problem to me is the most frequent interaction I have with the cold start problem is in email. How many of us have opened an email? You read it because there's this asymmetry around email. Like somebody can ask you a question and they might be very thoughtful, they might be unthoughtful in asking their question. It took them 10 seconds to ask you the question. It might take you five minutes to reply. So the cold start problem in email to me is like, you open an email and you're like, gosh, I don't even know how to start the reply to this. Maybe it's emotionally challenging, maybe it's fact. Who knows what the reason is? I've spent. I can't even imagine if you added up the hours of my life that have been spent thinking about how to reply. Now I just take that email, I copy it into a project inside your favorite AI tool, and I say, please, Based on all our previous interactions in this editorial guide that I've written, part of the J Curve, please write a response to this. Write a first draft response to this email.

[Sam (possibly a producer or assistant)]

Email.

[Carl Richards]

I copy and paste that back into my email and then I work on it. And sometimes it's 80%, sometimes it's 10%, but at least it got me through the cold start problem. So that's how I think about that. Yeah, that's how I think about that. Anything I have to do twice, I may as well think about how I could get some help.

[Christine Benz]

Yeah. In the book, you have a sketch and essay about getting in over your head and you recommend it. Do you recommend what a lot of us would think of as being in over our heads? Why? And you say that it's been a great thing for you in your life to find yourself in those situations.

[Carl Richards]

Yeah, I actually remember where that concept first came from. Somebody asked me, like, how come you keep doing projects? And my answer was that idea of like, I just love the Feeling of, how would you do that? Right. And I love the idea. And I do this very intentionally. Every year or so, I'll pick what my friend Rob calls a stupid human trick. I'll pick something that I know in my current state is impossible. And these often involve moving through the mountains or maybe a long mountain bike race or something like that. But they also involve work projects. Like, I thought the book's an example. I thought I was like, I don't know if I can pull this off. So I love the idea of, like, pick a stupid human trick that you know in your current state you will not be able to do. To do that will require you to become a different person, a better version of yourself. I have a buddy who did this with his PhD. He's like, I want to become a person who thinks deeply about a single problem.

[Sam (possibly a producer or assistant)]

Problem.

[Carl Richards]

Who can think deeply about. I'm pretty adhd. I want to become the kind of person that can think deeply about a single problem. He was in his late 40s. He's like, okay, what would be a forcing function? Who are the people? What would they do? Well, you know what, getting your PhD would require you to be that kind of person. So he's like, I don't really care about the PhD. I care about what it made me do. And I think that's this idea of getting in a little bit and over your head. I'm not necessarily. The story I shared here from my friends Chris and Amy was about money. You know, the mortgage. They were going to buy their first home, and they weren't sure that they could pull it off. Now they carefully ran the numbers, like carefully double. I just want to not be misinterpreted. They carefully double checked, but it still felt like a bit of a stretch. And most of us, us reflecting on buying our first home, that's not uncommon. And so that's why I love. The reason I love getting in over your head is because you almost always find out you underestimated what you could pull off. And we're notoriously bad at that. We're notoriously good as humans at getting into a situation that we don't know how to handle and figuring it out, like MacGyver style with bubble gum and duct tape. We're really good when we have to do it. We're really bad at imagining that we can do it.

[Christine Benz]

Last question for you, Carl, is about who you turn to for inspiration. It seems like you're an avid consumer. I know you're always talking to people through your various audio projects. And your other work. But who are your go tos for your work or your life? People you read or listen to regularly.

[Carl Richards]

So I'm a big fan of. There's an old quote that's attributed to Lao Tzu that says be who you really are and go the whole way. And I'm a big fan of people who appear to have done that like that are who they really are. So they don't pay attention. So like David White, the poet is an example of what David does in person. Nobody does like, it's not. It's uniquely David White. And so I'm a big fan of that. You know, a controversial one that I always find myself whenever I listen to him talk or read anything he's written, I always find myself for some odd reason wanting to be better, wanting to do. And it's Peter Thiel, which sounds really odd, but it's. And again, I want to be clear, like none of this is any statement about whether I agree or disagree and which is pointing to something really interesting like you don't have to love. One quick story about that. We were on a backpacking trip in New Zealand. When we lived there, we were out in the middle of the bush, like a long ways away. And there's these huts there that you can stay in that that department of Recreation had put up. And there was these kids there, like teenagers, 17, 18 year old kids. And they had their badminton rackets with them. And I don't even know what this means but they were like hitting, isn't it? I think it's called the birdie. Like they were like playing badminton out on the like field. They were so into it. And I found myself enthralled, like I don't know anything about. I could care less about badminton, but I was so enthralled by them. And it turns out they were on the national team of whatever country they'd come from. I can't remember what country it was. It was somewhere in Europe. And they were so enthralled. And I just. That was when I first realized like I'm just way into people who are doing their thing. I'm thing agnostic. And so I realized Peter Thiel might be a controversial idea. But I find listening to him every once in a while, like once or twice a year I run across something or reading books. 0 to 1 I walk away wanting to do my thing. Not his, but my thing more. And then one last one, I've got this friend Steve who founded a company called Volobach. And every time I'M around Steve. Steve's wild and crazy with his ideas and he's always way up in the clouds. So I don't want to make clothing like Volobak does. I want to do my thing. And so those are the kind of people that I get inspired by is people who've been, whether we know them or not, but have been deeply engaged in doing their thing.

[Christine Benz]

Well, Carl, I would say that describes you very well. I always learn from talking to you and I sure love the book. So thank you so much for taking time out of your schedule to be with us today.

[Carl Richards]

Thank you. It's always like such a lovely, fun, insightful conversation. So thanks for doing it.

[Christine Benz]

Thank you. Thank you for joining us on the Longview. If you could please take a moment to subscribe to and rate the podcast on Apple, Spotify or wherever you get your podcasts, you can follow me on social media hristinebenz on X oristinebenz on LinkedIn. George Cassidy is our engineer for the podcast and Carrie Gretchik produces the show Notes each week. Finally, we'd love to get your feedback. If you have a comment or a guest idea, please email [e-mail] until next time. Thanks for joining us.

[Podcast Disclaimer Narrator]

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[Sam (possibly a producer or assistant)]

Sam.