Carl Richards: Guarding Contentment – The Secret to Financial Life Planning?

March 12, 2019 | Episode #4

Whenever he flies, Carl Richards asks the pilots if they make a detailed flight plan. They say yes. He then asks how often they stick to that flight plan. They say never. Conditions always change mid-flight, and they too must adjust. Carl argues that the same sort of micro-adjustments are essential to living a life of deep peace and contentment. He also shows us how such thinking can help us avoid the handful of catastrophic mistakes that can, and often do, decimate financial futures.

“On the gap between our values and our actions—misalignment angularity, I would call it—there’s pain there. This is what it means to be a human. The process of real financial planning is to get those two circles closer, right?”


Announcer: The true WELLth Podcast is made possible with support from Brighton Jones, helping clients, colleagues, and the global community live a richer life. To learn more about how you can live a richer life, visit

Carl Richards: Certainly, the pursuit of happiness pulls you away from contentment, right? For some reason, I’m having this memory of a white Range Rover Sport driving around Park City. It actually had the bumper sticker that said “need less”. Which I was so struck by the image of the whole thing, and I think we now are competing and keeping up with the Joneses on mindfulness. “I’m more mindful than you.”

Manisha Thakor: Hello, and welcome to another episode of the true WELLth Podcast. My guest today is certified financial planner Carl Richards, author, artist, and speaker. For those of you who are regular readers of The New York Times, you may know Carl as the Sketch Guy, from his very popular weekly personal finance column. Others may know Carl from his two critically acclaimed books, The Behavior Gap and The One-Page Financial Plan. Carl also does keynote speeches around the world about a wide range of personal finance topics, and as you’ll soon hear, is an absolute delight to listen to. What I love about Carl is that both his work and his life embodies the concept of contentment management. His thesis is that, whether it’s your emotional wellbeing or your financial wellbeing, an ongoing iterative practice of making micro-adjustments in response to changing circumstances is the surest path to peace, balance, and contentment. Now, if what I just said sounded like a mish-mash of words and concepts, let’s break it down by hearing directly from Carl himself.

Manisha Thakor: Carl, so you’re a CFP, which stands for certified financial planner, and yet you are speaking to me today from New Zealand, which was not exactly where you expected your family to be living today. So tell us how this happened, and what role planning played in all of it.

Carl Richards: It’s such a fun story for us to reflect on now, and what’s so interesting, Manisha, about these stories is that, when we look back, we tend to make these stories up about … like it was all part of some grand plan, and the reality is, it’s really challenging to stick to the fact pattern, right? Versus the narrative that you’ve built afterwards. My wife and I have been married 23 years, so … I can’t do the math right now. I know when we were married, we were married in ’95, so 23. This year will be 24. 24 years. And from the beginning, there had been this sense of wanderlust. We spent a lot of time, and I bet your listeners will really … many of them will understand this tug of war between deep stability and roots in a sense of community, and this desire to see the world, right? So we always think of it as like fast and light lifestyle, and deeply rooted lifestyle, and there seems to be a little bit of a … at least in our minds, we felt this tug of war. So we talked about it nearly constantly. I mean, so early on, we were like, “Where should we live?”

Carl Richards: We always had this sense of like, “Where’s the place? Where should we go? What should we go see?”

Manisha Thakor: So what stopped you?

Carl Richards: I was on this track that I just unfortunately didn’t have enough foresight to see was just nothing more than a story I’d made up about finance track, right? I had this great job, and if I left this job, and blah blah blah … just, in hindsight, all garbage, right? Didn’t take the time to go do it. So, long story short, you fast-forward 20 years, and we have this deep sense of community. Living in Park City, and we’re both deeply involved in our community and our church, and heavily committed to some volunteer programs, and building a business, and I mean, everything … our kids are loving the school, we’ve got a dog, the whole thing. And yet, this story kept coming up. “Hey, are we going to spend some time overseas?”

Carl Richards: And then it got more specific, so we were like, “We should go to France.” So we actually took a couple trips to Chamonix, so we could be, again, in the mountains and skiing. So we had some friends who lived over there, we went and visited, we even went to a school. This was all looking great. And then we just had this feeling, and I think it’s just like doors weren’t opening. There was no tailwind. We made the commitment, “We’re going.” But there was sort of no tailwind behind it. It just didn’t seem to work.

Manisha Thakor: I’ll stop us here for just a moment to emphasize something Carl just said. Quote, there was no tailwind behind it. Just didn’t seem to work.

Manisha Thakor: I literally wanted to jump out of my recording chair when I heard Carl say this, because it was a feeling I knew, personally and professionally, all too well. Like all humans, there are hopes, dreams, and plans that I’ve had at different points in time, diverse ones, that never came to fruition. And as I reflect back, the one constant amongst them was this feeling that I was swimming against the tide. There was struggling. In contrast, when I look back at some of my proudest moments, the one constant was a feeling of flowing forward with ease, as if I were being helped by an invisible tailwind.

Manisha Thakor: Carl, so you were swimming upstream, and the moving overseas thing, that just wasn’t happening for you and your family. What changed?

Carl Richards: We had another opportunity open up, just because of some sort of local circumstances, that we’re like, “Oh. Hey, maybe this is the door opening.”

Carl Richards: And my wife was a yoga instructor at the time, and she was at a class, and she said, “We’re thinking about moving to France.” And one of the people in the class, who was a friend, said, “No no no no. You guys should go to New Zealand.”

Carl Richards: Now, that was the first, like literally the first mention of New Zealand. It was that quick, that the person was like, “Hey, you should go to New Zealand, here’s where you should go,” and everything was just like da-da-da-da-da. Like the tailwind picked up behind us, doors opened, we had plane tickets, we were gone 60 days later. And we had never been here. The five of us arrived, 17 bags, sight unseen, and we’ve been here … for a year trip, it was a year trip, and we’ve now been up in here almost two and a half years.

Manisha Thakor: This rather dramatic life shift that Carl and his family went through brings up an interesting question about what role planning should play in our lives. From a young age, most of us are asked questions, like what do you want to be when you grow up? Where do you want to go to college? What do you want to study? Embedded in these seemingly harmless questions is the implicit notion that we should, and that we can, plan our futures. But is this true? Do we really have control? Here’s a thought to ponder: in the iconic book, Zen and the Art of Motorcycle Maintenance, Robert Pirsig says, “The pen may be mightier than the sword, but the pencil is mightier than the pen.”

Manisha Thakor: Carl, I’m fascinated by this concept of no plan, especially given both of us have this training and designation that have the word “planner” in them, i.e. certified financial planner. How did you make that shift into the place of feeling comfortable with this lack of planning?

Carl Richards: It’s really funny. I’ve been talking more and more about this inside the financial planning industry, and it’s really interesting how much it resonates with people. And then I find, talking to listeners like yours … humans, that’s how we refer to them, versus planners, like non-planners and non-advisors, when we would have these plans that have like 20 years worth of assumptions, and including … for your listeners, when you do the financial plan, you have all these what we call capital markets assumptions, where you have to assume inflation, tax rates … we have to assume all sorts of things about the returns you might get from different types of investments, three different variables we have to assume. And then, after we’re done with all of those what we call capital markets assumptions, we have to talk with you, listener, about your life, and we have to make a bunch of assumptions about your life. What date are you going to die? We have all this list, and then at the end of that, we would say we’re 97.235% confident you’re going to meet your goals. And what I found with plenty of people, but there was a stronger vein of it with female clients, was them saying, “Wait a second. Are you serious? Are you really trying to tell me what the next 25 years of my life is going to look like? And did you really carry out your confidence levels to three decimal points?”

Manisha Thakor: Yep, they nailed it. As I was taught about financial modeling in business school, garbage in, garbage out. So Carl, should we not plan, in life or with our money?

Carl Richards: What’s interesting about this is that I don’t think it gets rid of the need for a plan, but what it emphasizes is let’s base that plan in reality. So that’s what I’m calling it, reality-based planning. And maybe the best comparison would be a flight plan. Every pilot I meet, I ask, “Do you write a detailed flight plan for every flight?” And every pilot, with the exception of one, who I would never fly with, has told me, “Yes, I write a detailed flight plan.”

Carl Richards: And then the second question I ask is, “How often does your flight go according to the plan?” And the answer, unsurprisingly, is never. Right? “The wind is always a little different than we thought. The weight of the cargo, whatever. There’s some variable that we got wrong.”

Carl Richards: So, in essence, the only thing we know about the flight plan, and I would say the only thing we know about your financial plan, the only thing we know for sure is that it’s wrong. We just don’t know how, or in what direction. And so, that doesn’t eliminate the need for the plan, but I just think we need to relax a bit about the false sense of precision that we all get on planning our lives, our businesses, and our finance. Let’s still put a stake in the ground, I think we’re headed that way. And then let’s take a step, and realize that was a guess. When we take a step, what new information comes to light, so that we can make a new better guess?

Manisha Thakor: You know, one of the things I’m semi-obsessed with at the moment is the concept of more versus enough. As we’re talking, it’s making me wonder, what is your current thinking about the role of those two words in your own life?

Carl Richards: What’s so tricky about those words, especially enough, is how insidious, how tricky, how slippery the narratives and the stories of the world we live in, not just your neighbors. It’s so simple to say, “Oh, you’re trying to keep up with the Joneses, right?” And then all of us adults, especially your listeners, smart intelligent people, would say, “I don’t do that, that’s silly. Peer pressure is for teenagers.”

Carl Richards: But then we just … this little, slippery, sneaky little thing happens, where your neighbor buys a new car. And you don’t find yourself thinking, “I’ve got to get a new car to one-up the neighbors,” but instead what happens is there’s just this subtle little element of permission, kind of dropped into your mind, like oh … and I don’t even think it’s conscious, I think we just think, “Oh, if it’s okay for them, it must be okay for us.”

Manisha Thakor: So Carl, another word that I’ve been ruminating on of late is contentment. When you hear the word contentment, what bubbles up for you?

Carl Richards: I’m actually really curious, why do you think you’re struck with it? Tell me more about that.

Manisha Thakor: Recently, I have had a number of conversations where people have been talking about happiness, and how it’s become such an overused word and such an overused movement in positive psychology, and blah blah blah. And that, perhaps, the real calling on my roots, the real nirvana state, is one of peace and contentment, which doesn’t necessarily mean that things are going well for you, but you’re just in this place of okay-ness. And I feel like we’re at some kind of zeitgeist of a moment where people are craving something different than just happiness.

Carl Richards: Think of it as this concept like contentment protection. The contentment protection plan, like how carefully we have to guard our own contentment, because as soon as you get that garden weeded and clean, and you walk inside, the wind drops another weed seed in there, and it’s going to grow tomorrow, right? And so, it’s so tricky because no-one … we all want someone to tell us, like I do, gosh, I would love it if somebody could just tell me what is enough for me, but the reality is, we have to figure that out on our own. And then we get so carefully caught up in these stories. Like Instagram, anyone? You know what I mean? It’s so hard to avoid.

Manisha Thakor: Shakespeare famously said, “There’s nothing either good or bad, but thinking makes it so.”

Manisha Thakor: Carl has a wonderful example from his own life, describing the differences between his childhood, growing up with a single mom struggling to make ends meet, and his wife’s experience growing up in an entrepreneurial household, and the impact that each of those experiences have on the way each of them viewed money. At least, until Carl’s wife Cori gave him a lesson of the power of subtle shifts in the spirit of Shakespeare.

Carl Richards: So, my mom finds herself, three kids and not an ideal financial situation. And I developed this sense of scarcity from it, and it was always like, “Are we going to have enough money?”

Carl Richards: We lived in a good neighborhood and my mom … my sense was, and I never actually asked her, but my sense was my mom worked really hard to keep us in that neighborhood. So that’s what I grew up with. Now, you go two miles, separate high school, my wife is growing up, two miles east. We didn’t know each other. And her dad was a real estate developer, who was very comfortable with risk. So he’s an entrepreneur in real estate, which makes him even more comfortable with a potential range of outcomes, right? So to them … for some reason, my wife developed, and again, I don’t think her parents actively taught this, it was just for whatever reason, a mix of the environment, my wife grew up with this sort of … money was kind of easy come, easy go. Right? If something didn’t go well, that’s okay, we’ll move into the apartment, we’ll rebuild, it’s all good. It’s an adventure, it’s fine. My wife actually says, “Making money is fun and easy.”

Carl Richards: So it was just maybe a couple of months ago, where I was coming home with this attitude that I’d had for 22 years, of the grind. “Oh, man, it’s so hard.” And my wife said to me, she’s like, “Hey Carl, you know it doesn’t have to be.”

Carl Richards: “What are you …” like I’d said before … normally when she’d said that, I was like, “Look, you don’t understand how hard this is, and it’s so tough, and I’m an entrepreneur. I own my own business and I’m the only one that understands,” and da-da-da. But this time, it hit me differently, where I realized, wait. One thought, if I could have a different thought around this idea of enough and abundance and think differently about it where I’m like, “Wait, it doesn’t have to be a grind, it could be an adventure.”

Carl Richards: There’s not much difference between those two words. And that changed … it’s so interesting, right? It’s not very dramatic, it was literally just a conversation were I thought, “Wait. I don’t know how to think that way. I’m not even sure how to think that way. Could you teach me how to think that way?” And it was just a function of changing thoughts around enough and abundance versus scarcity.

Manisha Thakor: Carl, will you say a little more about guarding contentment? It’s a very thought-provoking phrase.

Carl Richards: My wife’s a yoga instructor like I mentioned, and I remember one time walking out of yoga class. I will deny it to the death, but I’m incredibly competitive, and I remember walking out of yoga class and going to my wife, “I think I won.”

Carl Richards: And my wife was like, “What are you talking about?”

Carl Richards: And I said, “I won! I outstretched everybody!”

Carl Richards: And she goes, “Carl, I think you entirely missed the point.”

Carl Richards: So contentment, I think we think passive, like, “Oh, I’m relaxed, it just shows up.” No, I actually think you’ve got to actively practice being content, and I even think of guard rails, right? We’ve got to put guard … just pay attention. How do you feel? I’m sorry, the data’s clear about how you feel when you look at Instagram. The data’s clear! You do not feel content. And part of the problem with the statement I just made is you think, when I say “you”, you think I’m talking about someone else. We all do. So that would be one example. Maybe we should put some guard rails around that, because it steals contentment from you. All I’m saying is we can look, actively. There may be people in your work. You may be in a job that’s stealing contentment. Well, maybe you could make a plan. I’m not saying quit tomorrow, I’m just saying maybe you could make a plan to change that. I just think the word “guarding” or “protection” implies practice and active, versus sort of passive and sit.

Manisha Thakor: In our Western culture, the idea of actively managing and guarding our contentment can sound, well, odd. At the extreme end, one could interpret guarding contentment as synonymous with accepting mediocrity. Carl has a very thoughtful exercise to show us how guarding contentment is actually an active process that moves us closer to peace and contentment. If you have a pen and paper ready, I highly encourage you to pull it out and follow along.

Carl Richards: So, if you take out a piece of paper, and you draw … we’re going to draw a Venn diagram with no overlap. Draw a circle on the left-hand side, and just write in it, write “values”. And then, on the other side, with no overlap, with a gap between them, write “actions”. Draw another circle and write “actions”. Right? And values, we can just simply say, what I say is important to me. That’s what we mean when we say values, if you want to write that out, you can say what I say is important to me. And actions is like what I actually do. And I want you to notice that every time I’ve ever taken anyone through this exercise, there is a gap there, and that gap is often misalignment, angularity. I would call it … there’s pain there. But what I want people to understand, and what I’m still trying to understand myself, or really get clear about, is you could also label that gap, you could just write in that gap … I actually kind of want you to write in the gap, I want you to write “being human”.

Carl Richards: Right? This is what it means to be a human. Of course there’s a gap there. And the process, and I think this is the process, which is why I’m so gratified to hear that this is the kind of work you guys do which is the processes of real financial planning is to get those two circles closer, right? To get some overlap, and the overlap is often going to be temporary.

Carl Richards: This is what I sort of pointed at, like I can remember a couple Christmases ago, a Christmas Eve. The dog’s on the couch, everybody’s at home, we’ve had a wonderful meal, we’re sitting there watching some movie, and I looked around. I was like, “Whoa. These circles are perfectly … there is no two circle. They’re perfectly, complete overlap. Everything I say is important to me lines up perfectly with my actions right now.” Christmas Eve. And then, the next morning, we opened presents, and I’m like, “Who bought all these things? Why do we spend-” … and there was a gap again. So I think that, if we just give ourselves permission to be gentle about that gap, and learn that when we get information about that gap it normally is in-your-face-painful, so I would just say, look, that gap? Let’s give ourselves permission to gently explore that gap. I think that’s what I’m saying. Let’s just gently allow ourselves permission to explore that space and see if we can’t get those circles more overlapped, where our use of capital, our use of time and money, aligns with what we say is important.

Manisha Thakor: So Carl, at Brighton Jones, we’re pivoting from a traditional wealth management firm towards one that does all of that, and helps our clients move towards increased holistic wellbeing. So I have one last question for you. What personal practice most supports your wellbeing on a daily basis?

Carl Richards: So, Manisha, I have a long list of daily habits that I know if I did them, they would support my wellbeing, that I don’t regularly do. And so, high on those lists would be what all the cool kids do, right? Meditation, good sleep, food, all that stuff. But I’m not, I’m still … there’s still a big gap that I’m exploring gently with myself, and sometimes not so gently, to be honest. But if there was one that I do feel like I’m relatively consistent, that absolutely every single time I do it changes my whole life, it’s time outside.

Manisha Thakor: Carl, that was a truly delightful conversation. Thank you so much for joining us here today.

Manisha Thakor: When I reflect back on this conversation with Carl, I had both a personal and a professional take away, and in many respects, they blended together. On a personal level, the word that kept popping up for me is contentment. In particular, Carl’s point that contentment is a result of a deliberate active practice, just like a yoga practice, that you come back to again and again. I’m a fan of clear mental models, so in my mind, I boiled down Carl’s insights on how to have a contentment practice into these three steps:

Manisha Thakor: Number one: evaluate your current values and your current actions, and identify any gap between them.

Manisha Thakor: Number two: set a flight plan, to close that gap between your current values and actions, knowing, as Carl pointed out, that your flight plan will inevitably need all sorts of micro-adjustments along the way.

Manisha Thakor: And third, engage in what Carl calls contentment guarding: the very active process of routinely assessing what, if anything in your life, internally or externally, is draining your contentment and bleeding that out of your life.

Manisha Thakor: Professionally, I was struck by the similarities between money management and what I’ll call contentment management. The three things I took away here were:

Manisha Thakor: First, you can make the most detailed financial plan out there, but the results are only as good as the assumptions. Alas, as Carl pointed out, no-one on the planet will ever know in advance if all their initial assumptions will end up being correct. This is why financial advisors don’t give you a definitive single-point prediction about your financial future. Instead, they write what we call Monte Carlo analyses. In plain English, computer iterations on thousands of possible scenarios, to give you a range of possible outcomes that might happen.

Manisha Thakor: Number two: you need to periodically review your financial plan, to make sure that as the actual market economic saving and spending results materialize, you are making any new adjustments necessary. This is the financial planning equivalent of that pilot resetting their flight plan.

Manisha Thakor: Number three: it’s possible to experience the exact same situation in a dramatically different way with a simple but profound mindset shift. Carl talked about his shift from “Making money is so hard,” to “Making money is fun and easy!” Mindset shifts are where I see financial advisors adding tremendous value. A high quality advisor will help their client shift their view of market downturns as scary and a reason to sell stocks, to something that is inevitable and already baked into their plan. By implementing an investment plan rooted in a cash needs analysis, and explaining fully to the client what this means, clients will know that even when markets go down, they will have the cash flow necessary to keep living their lives. Thus, they will not be tempted to sell stocks in a down market. And, as I mentioned in the episode we did with Dr. Daniel Crosby, avoiding catastrophic mistakes like panic-selling in a downturn can make all the difference in your long-term financial success.

Manisha Thakor: In conclusion, going back to the wisdom of Zen and the Art of Motorcycle Maintenance quote, “You look at where you’re going and where you are, and it never makes sense. But then you look back at where you’ve been, and a pattern seems to emerge.”

Manisha Thakor: I’m Manisha Thakor, and that’s it for this episode of true WELLth.

Announcer: To learn more about Carl, be sure to head over to our show notes on, where you will find links to Carl’s New York Times column, personal website, and books. If you enjoyed this episode, all of us here at true WELLth would be absolutely grateful if you’d take just few minutes to rate and review us on iTunes, or wherever you get your podcasts.

Announcer: true WELLth is made possible by Brighton Jones, an innovative wealth management firm founded 20 years ago in Seattle. Today, Brighton Jones serves a nationwide client base, with the goal of helping clients, colleagues, and the global community to live a richer life. To learn more, visit

Announcer: The true WELLth podcast is edited and produced by Stan Hall, with support from Hallie O’Reilly, Michael Stubel, Marc Asmus, Chris Sylvester and John Dougherty. For more information on the show, visit


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