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Episode #561 - Think Smart, Retire Smarter: The Map vs The Territory

Roger: The show is a proud member of The Retirement Podcast Network.

The models we create are our best attempts to explain what we see. They are not the truth. 

Welcome to the show dedicated to helping you not just survive retirement but have the confidence to lean in and really rock it. 

Today on the show, we're going to continue our series on, developing our toolkit of mental models so we can improve our decision making, which will lead to rocking retirement. You see the connection there. Today we're going to talk about a little bit more nuanced one called the map versus the territory and how that applies to retirement planning. 

In addition to that, we're going to have Dr. Daniel Crosby, one of my good friends, on, to talk about his new book, the soul of wealth. It is a fantastic book. It just came out yesterday. I was able to receive an early copy. I get excited about books, but I get really excited about some books. It has a soul to it. It helps give us perspective.

I'm excited to dive into that with you and Dr. Crosby. He'll be coming into the rock retirement club to have a round table because it’s an important book related to creating a great life. Now, we share links to resources that we mentioned as well as a summary of the show every Saturday morning in our email, 6-Shot Saturday. If you like the show, you're going to love our weekly recap. That's our way of giving you a link to Dr. Crosby's book, a link to resources that we mentioned, perhaps, and answering a question. You can sign up for that at sixshotsaturday.com. 

Let's get started with the show and talk about the map versus the territory.

PRACTICAL PLANNING SEGMENT

GPS and maps can be a good abstraction to help us navigate things. About a month and a half ago when I was in Colorado, I wanted to go on an off-road adventure with my broncos. So, I used an app for off road mapping that has all these off-road trails. I wanted to go to a moderate trail called Aspen Ridge. I plugged it into my Onyx off-road app and it mapped out how to drive from my town home in Colorado to the trail. So, I turned on the GPS and I followed the left and right turn as the GPS map directed me to get to the trailhead. I get to a trailhead.

There are no signs for these trails and I start up the trailhead and I'm getting into some very technical stuff with big rocks. I had to get out a couple times and navigate him, like, oh, I think I can get over that. That took a lot longer than I expected for the first quarter or an eighth of the trail. Then it became more of what I was expecting on this Aspen Ridge trail. I didn't realize until afterwards that my GPS map actually directed me to a different trail, I believe it was called Dead Man's Gulch, which was a hard trail that connected to Aspen Ridge trail, the actual trail that I wanted to. I trusted the map, and the map didn't align with the actual territory. There wasn't a way of getting to the Aspen Ridge trail that would have saved me the hassle or the experience of going over Dead Man's Gulch trail. I trusted the map. That's the important concept here. 

When we think about a map, what is a map? A map is a model of reality. It's an abstraction. It simplifies things to reduce complexity so we can make decisions. That is a very helpful thing. GPS and maps are a good abstraction to help us navigate things, but it can be harmful or even dangerous to believe that the map is actually reality, that it's actually the territory that you're going into. It's only an abstraction. To have a map detailed enough, you would need to have a map and then a map of the map and a map, another map, and the map of the map. And it would get complex again, because reality is really complex. So, maps are very broad simplifications. 

When you're looking at maps, you have some questions that you need to ask yourself. How detailed does the map need to be to be useful? Can I just draw an A and B, or do I need to have elevation, et cetera? What is the process for updating the map? What's the feedback loop to improve the map? What are the values and limitations of the map creator? Because each creator of a map is going to have their own limitations and their values, et cetera, that will influence how they create a map. 

Here, for a second, is a real practical example of this concept. When we think of map versus territory, let's think of building a map. How detailed does it need to be? We had a healthy discussion in the rock retirement club recently about Monte Carlo scenarios and a mark, you know that type of stochastic modeling to figure out whether a plan is feasible is a form of a retirement plan. It is a map. It is a framework to simplify things, to map out a course. The question came within the club of, okay, great, it's randomizing market returns to give us a sense of the feasibility of a plan in order to execute on the plan, but what about inflation? 

Most financial planning software uses a static amount of inflation in its retirement map in terms of the results it generates. The discussion was, well, shouldn't we randomize inflation as well? Because since 1970, last 50 years or so, the average inflation rate has been 2.7%, it's been as high as the mid-teens, and it's been as low as zero over that 50 plus years. So, there's a standard deviation around that. Shouldn't we randomize inflation as well? Will that improve the map? That is the question, and the answer is, we don't know. Does it add more complexity than is needed? Does it make it more useful, or does it create more noise? The answer isn't necessarily clear. So, we had a really good, healthy discussion around that, and I actually have an opinion about that, in that I don't know if it adds enough to the model or the map to make it useful. If you have an active feedback loop to keep improving your map as reality happens. 

The other part is that there is a problem with using maps. Let's go back to this Monte Carlo scenario related to retirement planning. Maps can be very useful in retirement planning, but they can also have limitations. A map cannot see everything, and if you don't understand this, it can become useless and dangerous. So, let's use a very practical example.

Let's talk about the case study with Rosie a year and a half ago, where she retired with a feasible map. The Monte Carlo scenario said, statistically, this is a feasible direction for her to go, but the map wasn't complete enough. It didn't make it resilient. So, when a bad market happened, her feasible plan, her map, suddenly became very treacherous, and it wasn't feasible, and it was dangerous in this case for Rosie, in that what she thought was a feasible plan became very unfeasible, and she was faced with a lot of very difficult decisions. This is where maps can be dangerous if we don't understand their limitations. So, some dangers to maps are they can lead us to think that we have all the answers. Because we are experts on map reading, we think we have the answers and that seemed to be the case with the advisor working with Rosie. They maybe knew the software really well, and they had a false sense of security in their guidance to Rosie, because they didn't know what they didn't know. It led to overconfidence, not really appreciating that the map is not actually the territory.

Another danger of being an expert in using a map without actually walking into the territory is it can lead us to create static rules based on the map. Because of the map, we fool ourselves and think the map is reality, and it's easy to create static rules within a mathematical model to come up with results, not realizing that it's not actually reality. The 4% rule is a good example of this. It is an excellent map, and if we use it as a map without acknowledging the territory, well, that's not reality at all. That's not the territory and that can give us a false sense of confidence. Now doing this may not cause us to run out of money in the case of the 4% rule, but it could cause us to die with too much money which would lead to regret because we could have done more. 

The other problem, or danger that comes with focusing too much on the map and having confidence in it, is that it reduces our ability to adapt. We have overconfidence because we're experts in the map. We create these static rules, and we execute the static rules, and we don't spend enough time letting what's actually happening in the territory change our plans. Maps can be very useful, but they can be very dangerous in retirement planning. 

In the context of retirement planning, the map is the plan, and it has a lot of limitations on the financial forecasts, of inflation, of investment returns, of sequence, of returns in terms of standard deviation. It also has major limitations in regard to projecting life expectancy because we're making the map using a guess of how long we're going to live, of what we're going to spend in different seasons of our life. 

Maps also have blind spots when it comes to accounting for taxes. If we don't have a constant feedback loop to improve the map, it could be very detrimental to our retirement and we could end up paying more taxes than we had to. 

Territory is the actual experience as you're using the map to take steps on the ground, the practical application. In our industry, we have a lot of experts that are experts on the map but they never actually go into the territory to do retirement planning. They're amazing map makers, but they have their biases because it's easy to trust too much in your maps and not actually go walk in the territory. 

Now, on the other extreme, and this is generally in the advisor crowd, not the academic crowd, we have people where all they do is live in the territory, and they don't do a lot of work in understanding maps and going up to the balcony to get perspective and look down on the route. They're just taking one step in front of the other without a reference point. 

Both of those extremes can be detrimental to your retirement. I think that a good, happy medium is having both great map makers and people on the ground to provide a feedback loop to continually improve the map, knowing that it's going to keep changing. 

Hence, in my world, I value an agile approach to retirement. That process mixes those two things in a healthy way so we don't get overconfident in the map, but we also don't get overconfident with whatever recently happened on the ground.

Now, let me loop this back to the discussion about variability of inflation. The two ways I think of to deal with this is one, to introduce variability of inflation into the map making tool, the Monte Carlo engine. We could use the average inflation rate over the historical numbers. We could use the average standard deviation over the same time period and let that vary as well, which potentially could improve the model. 

The other way to deal with it, in the way that I've chosen as of now anyway, is rather than execute on variability of inflation into an already noisy map, is to recast the spending estimates in the plan each year to reflect what is happening from an inflation standpoint in spending. A couple of the reasons that I've chosen that is one is average inflation is what everyone has, right? That's just a statistical model. Some clients will have higher inflation based on their choices. In this latest period, some people will never stop buying filet mignon when they have steak. Other people will buy lower grades of beef when they experience inflation. I battle that in my house when my wife buys the filet, we're like, yes, this is so good, but many times she'll come home with lesser grades of steak that aren't as good because we're just too price sensitive. There's elasticity, if I can say that word correctly, for, each of us, on what we're willing to do. I would rather focus on the personal inflation rate of someone and recast their spending as they're actually doing it. Knowing that we have that system in place, I feel much more comfortable in not trying to improve the map with variability of inflation. 

My core point to you is all maps are wrong, and that's just the nature of any kind of planning. They're abstractions. There needs to be a natural feedback loop in order to improve those models. The question, though, that you also have to answer is, if they're all wrong, how wrong do they need to be for them not to be useful to me? The 4% rule would be an example of that for me. I believe it is so wrong that it's not useful to me. It doesn't help someone rock retirement. It may help them not run out of money and they will likely die with too much money. So, when you're looking at a model you want to understand, is it detailed enough to get the job done? What is my feedback loop for improving this map over time based off of what's actually happening in the territory? 

It can also help you in identifying people that are practitioners, and they may be walking the territory, but they don't have perspective. They're not using the value of the people creating the maps. Maybe I should avoid them, just like maybe I should avoid people that are too theoretical because they're overconfident in their maps, in creating these static rules that are based on an abstraction, not reality. A little bit more of a nuanced one. 

Next week, we're going to go back to one that's a little bit more basic, which is the circle of competence. This can really help us stay out of trouble as we apply this to ourselves, but also apply this to people in our life, advisors, CPAs, etcetera. But for now, let's get on to Dr. Daniel Crosby with his newly released book, The Soul of Wealth.

INTERVIEW WITH AUTHOR DR. DANIEL CROSBY

All right, we're here with Dr. Daniel Crosby, Chief Behavior Officer of Orion Advisor Services, author of The Soul of Wealth: 50 Reflections on Money and Meaning.

Dan, how are you doing, buddy?

Daniel Crosby: Hey. When I see a book marked up like that, I'm doing fantastic. No higher compliment. Great to be here.

Roger: Yeah, I just began, so you'll see, this will probably be one quarter of what actually happens. This is how I steal content. Daniel.

Daniel Crosby: Everything's a remix, Roger. I get it.

Roger: Everything’s remixed. I'm going to tell you, I remember when we had lunch near your house, you brought me a gift bag of your books. All of them. This is by far, not that I didn't like the other ones, this is by far my favorite one.

Daniel Crosby: It's by far the best. I'm proud of the other ones. This one's going to reach more people, do better, and it's better than the other ones. I mean, like most things in life, you get better with time and practice, hopefully, and I'm glad to hear you say it, because I'm totally with you.

Roger: I have one of my axes, and I have many axes, in financial planning, specifically retirement planning. It can become about the numbers more than about the life. I was thinking about this because we just ended the third quarter and I updated my net worth statement, which I do every quarter. There's something about updating your financials that gives you a scoreboard, right? We are driven by that. We started with that in school, right. Get an A, a B, or a C, and then get into a certain college and then get promotions. Life is gamified from a scoreboard perspective, and it's easy to make the scoreboard the thing rather than the vehicle. 

You use a phrase called soulful wealth to describe what makes life rich. I think that's what hits you. Can you define that for me?

Daniel Crosby: Yeah, loosely, because it's going to look a little different for every person. But, you know, when you talk about the soul of something, you're really talking about the essence of it, right? The bottom to the top, the most important thing. The essence of the thing. 

As you suggested quite beautifully just a minute ago, we've taken a very one-dimensional view of wealth. I mean, you could make a case for wealth encompassing things such as your level of financial preparedness, but it could also include things like your relationships, your health, having meaningful work to do, working for something bigger than yourself. I mean, there are many facets and many dimensions to wealth that I cover in the book because I think it's been so roundly ignored because they're messier, they're harder to measure than your net worth statement, but they're also a lot more enduring and a lot more gratifying and frankly, a lot more important.

Roger: When you have highly successful people that are nearing retirement, which is generally the people that listen to this show, a lot of them are engineers or project managers. It's comforting and safe to quantify things. I have a sticker here that says, “Retirement is not a spreadsheet”, just to help remind people that this is a means to an end, not the end. 

For some people, it's difficult to get over that and get into uncomfortable conversations rather than just stay in their spreadsheet. How do you navigate that?

Daniel Crosby: Yeah, so, first of all, I would say that we're not trying to take away your spreadsheets. I think the dollars and cents, blocking and tackling the pieces of retirement preparedness is very important, and it facilitates a lot of these other things. It is sort of a vehicle for a lot of these other things to happen. So, I think that's an important distinction. Nobody is trying to take away you hitting your number, but once you have hit that number, what's a way that you can conceptualize that wealth and spin that wealth into something a little more fulfilling holistically. That's what I'm trying to broaden and deepen the conversation, not to take away the good that people are already doing.

 I think there are a couple of different ways that you can measure it, too. Right. Like, in the book, I introduce some of the work around positive psychology, and I give a model, the five-factor model for human flourishing. I cited some of them earlier.

Roger: Yeah, great work.

Daniel Crosby: Yeah, it's like, here's the five things that make life rich. Make a spreadsheet about that. I set goals in all of those areas every year, and I put a big poster board on the back of my door here, and I grid it out, and I work towards that, and I try and solidify those relational goals. It's always a little bit of a copy of a copy, because there's no blood test for whether or not my kids love me, or if I am a good parent, but I think that that's not a bad way. Take the good that you're already doing and apply greater richness and greater depth.

Roger: We may need to incorporate that model into our process. 

We start with establishing your top ten values right before the financial goal conversation, with the idea that if the top ten values are the beginning of the thread, you should be able to follow a thread from a financial standpoint all the way down to every individual investment and back up. Your values are established, your goals are how you express your values and so forth. Can we go over what your structure is really quickly so people understand that framework? 

Daniel Crosby: Sure. 

So, it is the PERMA model from Martin Seligman, he's the father of positive psychology. Just a quick little psychology history lesson. 

For many years, psychology was just about all the ways your parents screwed you up, right, and that was sort of all. All we talked about was why you were anxious, why you were sad, why you were depressed, and Seligman comes along and says, “Look, there's another side to this coin. Let's talk about what makes people thrive. Let's talk about what makes people great leaders or great partners or great parents, and he found that there were really these five elements to human flourishing, and they spell out PERMA. 

The P is for positive experiences. This is fun. This is leisure. This is going to the beach with your family. This is eating an ice cream cone. This is watching a movie. Money checks those boxes very nicely. The P in Perma is a lot of what the folks who are over indexed on just getting the number right are preparing for and it's also kind of sexy and easy to imagine. Like, I want a beach house, I want a lake house, I want a mountain house, I want a Porsche. All of that is P. It's positive experience, it's fun, and there's nothing wrong with that, but it's only the first dimension. 

The second dimension is E. This is for engagement, which is deep, meaningful work, right? We need deep work to be happy, according to science. We’ll talk in a minute about why retirement can kind of throw a lot of people into crisis. We need deep work to be happy. I think a lot of times that gets overlooked. People who retire, I mean, there's a good reason why death rates skyrocket hot on the heels of retirement, because people have lost their north star. They've lost this deep work. 

The R is relationships. If you just had to maximize, for one thing, this would be the one you'd choose. The science is pretty unequivocal here, that this is where we get the most benefit. The most uplift is through love, by loving others, by being loved, by giving and receiving. Love is the foundation of a happy life. 

The M is for meaning. We need to work for something bigger than ourselves. It could be religion, spirituality, philanthropy, charity, yoga, like, whatever that is, you need to be working for something that's bigger than just your own success. 

The A is for advancement, which is, we are a growth-oriented species. We want to be better tomorrow than we are today and so we need goals, we need to be pulling towards something. We need to be growing, or we're dying. 

When you think about this in the context of retirement, we put so much emphasis on the P a lot of the time, and just prepare financially for the positive emotion stuff, which is great. But our work, that deep, meaningful work, if we're not careful, that goes away or is diminished. We have a lot of great relationships at work, often meaning we're working for something bigger than ourselves. We're part of a team or a corporate mission, and then achievement work does a very nice job of saying you did or you didn't do well, here's a promotion, here's a gold star, here's a raise, here's a spot bonus. That stuff is not baked into civilian life in the same way that it is into work life. So, there's a lot that needs to be prepared for from a retirement perspective if we're going to continue to flourish in a post work environment.

Roger: Let's hit on that for a second. 

When you hear those things, meaning deep work, in my experience, when you start talking about those, it's very easy to make them bigger than they need to be. Not everybody has to change the world. 

When we think of what my purpose is, we can make it so big, it's like, no, I just want to love my family. So, I want to confirm that, that it doesn't have to be intimidating. It can be literally just to be nice to people when I go to the grocery store in terms of interaction. It doesn't have to be big.

Daniel Crosby: That is 100% right. So, you know, I'm on a group chat with three of my college buddies, and it's hilarious. It's one of the best parts of my life, just getting to joke around and be goofy with these three guys. The conversation has moments of levity, and it has moments of, like, profundity. 

The other day, my friend sent this thing, and it was like this crypt had been, discovered of this king that was once one of the richest people on the earth, and no one had ever heard of this guy, and they had just discovered his tomb for the first time, and it led to this conversation of, like, this guy was the guy, you know, this guy was the guy for so long and to so many people, and now nobody knows his name, right? I mean, there's 8 billion people living in the world right now. We'll be reading about maybe five of them in the history books 100, 200 years from now. It's probably not you or me. 

The thing that really becomes meaning for most people is going to be something that profoundly impacts the lives of the handful of people in your immediate orbit. Being nice to people at the grocery store, If everyone just tried to be the best person they could be for the five people that they're closest to, the world would be flying cars and abundance for everyone. I mean, it would be incredible. These words can feel lofty, and we shouldn't let that get in the way of setting goals and trying to do something there. 

You spoke of engagement too. I'm looking at my guitars over here that are getting a little dusty, and I could imagine someone in retirement learning to play an instrument as their engagement, or woodworking, or getting in shape, or a hundred things. You just need to be working on something. It doesn't have to be PowerPoints for the man, you know? It could be a lot of things.

Roger:

I just finished Wendell Berry’s most recent book, where he explores racism in America. One thread that I pulled out of there that resonated with me that I think applies to this, is, it's easy to think of, well, racism, which is a very hot topic, and meaning and purpose similarly. 

We think of both as this large cloud that you can't really pin down. One of the things that he talked about is how you need to get that. Dr. Martin Feynman would say that you have to get very specific. If you can get very specific on what it means for you to have purpose in your life, you can think of wanting to take my grandchild to lunch once a week. The more specific you get, the more actionable it is and you feel like you have more agency to actually do something. Sometimes I think we can get into the clouds and it is hard to put clouds into practice.

Daniel Crosby: You know, you are one of the few people on earth that know this, but I'm undertaking a very serious study.

I've been a Viktor Frankl devotee for most of my adult life, and I'm undertaking a really detailed study of meaning and purpose in life. What I have found is what I call the three B's. 

At the risk of introducing too many models, people who have purpose in their lives have answered three questions.

The first is believing. Like, what do I believe about the world? People with purpose in their lives have some sort of intellectual, philosophical, moral, religious, spiritual scaffolding in their lives. They have a set of core assumptions and beliefs about the world. It could be Catholicism or Buddhism. It could be stoicism or existentialism. It could be a million things. But you need sort of some roadmap for making sense of the good and bad parts of life. That's very consistent. People who are religious are consistently happier than people who aren't. It's not like, again, this isn't a commentary on you should go be religious. It's because they have a map, right? It's because they have some sort of map. So, you do need that. 

The second B is belonging. You need a tribe, right? You need a tribe of people that are your people. It could be your family. It could be your bicycle club. It could be a thousand things, but you need a crew. Like, you need a group of people. 

Then the third B is becoming, you need a vision of the kind of person you want to be. You need growth goals, you need progress. So, if you want purpose in your life, right? What do you believe about the world? Who is going to walk with you on this journey and where are you going? 

Those questions, they're still big questions, but think of conceptualizing it that way. I can figure that out. What do I believe about life? Who do I want to walk with on that journey and where are we going? I think that's sort of the formula. It's not as grand as I think we make it out to be sometimes.

Roger: I was on stage Sunday introducing a speaker. We had our conference for our club and we had about 280 people that came to Grapevine, Texas for three days. I started saying what a mess I am. I had made a personal error where I felt really bad. I'm like, I'm a mess. I’m greedy. I’m mean. At times I'm forgetful. Then I looked at the people in the crowd and I said, “Well, so are you, but we're a glorious mess in that we're trying to be better. We're working on a mastery journey in different areas, and that makes it a glorious mess.” Having the tribe of everybody working on their own mastery journey is really fulfilling and empowering, and that's a little bit of what you're talking about.

Daniel Crosby: Yeah, the scariest person in the world is the one that doesn't know they're a mess. I think the people who have embraced their messiness are the ones you want to surround yourself with, and the people who feel like they're above the messiness you should probably run from, because that's a very scary way to live.

Roger: Part of that takes risk, right? I made notes as I was preparing for it, this is like on page 68. You had said, “It takes calculated risks and ambition to create the future you want to live. Go ahead, you can.”

Daniel Crosby: That's beautifully written. Who wrote that? That's gorgeous. Just kidding. Yes, I agree.

Roger: I’ve had well over a thousand conversations individually with people at or in retirement. I had office hours in the club for years, and they would come with questions like, should I do Roth conversions? Should I think about taxes? Or I want to do this vacation. They were presenting some issues that they wanted to talk about, and my observation, Dan, is 99% of the time, the issue wasn't the issue. What I identified as a thread through those thousand plus conversations is a crisis of confidence. They already knew what they wanted to do, but they somehow needed permission or affirmation that they could actually do the thing that they already desire.

What is it, especially around retirement, that creates this crisis of confidence with people

Daniel Crosby: It's a great point. One of the things that I see while writing this book and studying meaning, I set out to write a book around how it can help people discover their meaning, their north star in their lives and that's not the book that we need, or the book that I ended up with. Most people have a pretty good idea of what that looks like. The book that we need is, how do you have the courage to go after it. Just like you're saying. 

In terms of why are we this way? One reason, just to get a little dorky psychologist. Well, we're evolutionarily wired to be this way. We are wired to avoid risk. We have this asymmetry in the way that we even think about risk and reward where our fear of risk is two and a half times as bad as our desire for that anticipated reward. It keeps us kind of stuck. From an evolutionary perspective, you only get one bad day, right? If you take a big risk and it doesn't work out, then you're done, and you don't get to pass on your genes. We're in a very real sense, wired to play it safe. 

But then, as I talk about in the book, we arrive at the end of life and we look back over our lives and it looks very vanilla, then we get frustrated with ourselves for not having taken adequate risks. I think that at a primal, fundamental level, it's how we're wired. 

The second thing is there's a real crab in the bucket mentality. There's a real mentality that everyone is sort of head down. Well, most of the world is sort of head down, squeaking by doing the best they can, living a life of quiet desperation. So, if you want to go do something big and bold and grand and different, that threatens their complacency, because if they see that, they go, oh, gosh, if she can do it, that means that I can do it and my failure to do it makes me culpable. Because we want to blame everything, right? We want to blame the economy, you know, the budget and the kids and the spouse and everything, but our own timidity and our own lack of courage. You're never going to get chided on doing the safe thing. If you work yourself into an early grave at a lame job that you hate, that gives you benefits and an okay salary, no one will give you a hard time about that. But if you swing for the fences, there will probably be lots of people in your life that will chide you. We're social creatures. I think we get penalized for it.

Roger: Because we want to fit in. So, if we stick our head up, we don’t “fit in”, so to speak. I was going to ask how we get over that? I'm assuming it's somewhat mental work, but also surrounding yourself with people that are striving to stretch themselves. 

I'm guessing that's part of the solution. But what else might be?

Daniel Crosby: Yeah, I think first you have to have the eyes to see it, because I think for most people, the self-deception runs so deep that they would not tell themselves that, hey, I'm living a low agency, low meaning life. They would just say, I'm being practical, I'm being sensible.

I think the first thing you have to do is learn to call yourself out and know when you are placating yourself, lying to yourself, or deceiving yourself. Then when I think that self-deception becomes more obvious to you, it becomes harder to be complacent. But the first thing you have to do is to realize that you're fooling yourself. As Richard Feynman said, “The first principle is that you must not fool yourself and you are the easiest person to fool”. So, yeah, after that, I think you can move to more black belt stuff, like surrounding yourself with the right people. I write in the book about how deeply predictive that is of success, from everything, from weight loss to financial success, to promotions. Surrounding yourself with the right people is a very, very big deal, but I think the first thing you have got to do is achieve escape velocity from your own cloud of nonsense.

Roger: Yeah. One little buy-in that we use in the club and with clients is to get themselves comfortable enough to spend money on first class. M right. Which, assuming it's safe financially and everything else, is just so against their financial comfort level that it's like, just to get yourself to do it, especially on an overseas trip and once they do it once, there's no going back.

Daniel Crosby: Once you. There's no going back ever.

Roger: I need to make a first-class sticker. I need to make a first-class sticker.

The other thing that I wanted to ask you about in retirement is purpose of your money, and this is definitely true in retirement. It needs to be true more when you are focusing on de-cumulation. I have encountered, and again, I'm talking about very first world problems here. There is a subset of individuals that have over saved or between hard work and blessing and all sorts of reasons, have way more than they're ever going to need for whatever they can imagine. They're sitting there at age 60 and they're happy, they're content. They've hit a lot of those categories that you talked about, that Seligman talks about, but then you're also left with opportunity. The cost of it ends up being a lack of imagination of what you could do in life when you, for whatever reason, have way more than you're ever going to need. So, you just don't do anything. 

How do you start to imagine purposes for that excess resource that you've received?

Daniel Crosby: Yeah, so this is one of one thing that I talk about a lot and something that I bemoan in my own circles in the financial technology world. You know, it's potentially a high paid world. I have friends in this space who are sent to millionaires and I think a lot of times, they'll sell a company, they'll make more money than they can ever spend, and you go, what's next for you? They go, well, I'm going to start another business. Now if that is your heart’s desire, and for some of these folks, that is truly their heart's desire. They are creators. If that's you, God bless go do it. Go start ten companies, because they're helping a lot of people. They're doing good in the world. 

But there's another subset of people who should go be a soccer coach or a pastry chef or a flight attendant or a hundred different things. There is this lack of creativity. The first thing is, I think you have to work with someone. I think you have got to work with a professional. It is really hard to escape the noise in your own head. Go get a shrink, go get a career coach. Go get someone to help you sort of get out of your own head, because you have to play a new game and you have to measure with a different yardstick because, yes, obviously, if you want to go make more money, the thing to do is to start a company. But when you don't need money, it can be hard to switch that off, because for most of us, I'll speak for myself, right. The way that I have effectively made every career decision in my life has been what will pay me the most money. There will come a day when that should no longer be my guiding star. When that time it takes the help of a financial professional, probably a life coach, psychologist, career coach type.

Roger: Well, I'm even thinking about it because I have a number of cases or people that are in this vein. I mean, we're talking big numbers, but not the kind of numbers you were talking about of, hey, I'm 65. This is what I need to live on. I have twice as much money as that. It will last me the rest of my life, but I can't think of anything to do with it. Essentially, you're deciding that you're going to die with it, will just go off into whatever estate plan. But there's an opportunity there. This is the thing I try to point out, there's an opportunity there. How can you use this money as a tool while you're living either for more experiences? It's not just about spending money, but into creating memories, speaking into other people's lives. There's an opportunity cost to the world and your family if you operate from fear that, well, I might need it later, how is it just the same process of getting out of our heads?

Daniel Crosby: In the book, one of the chapters talks about fulfilling ways to spend money, and you just touched on a couple of them there, but one of them that is consistently fulfilling and that people routinely get wrong is giving it away. 

Like when you ask people like, hey, I'm going to give you $100, and then you'll be assigned into a group where you either have to give it away or spend it on yourself. Then you say, “Which will make you happier?”. 90 percent or more of people say, well, I'll be happier if I get assigned to the spend it on myself group, right? That is exactly wrong. Better than 90% of the people are happier when they're assigned to the give it to others group. So, giving that money away, we know from the science, is one of the purest, straightest lines to happiness. 

There is another thing that we can do that might expose us to this greater creativity, one of the least effective ways you can spend money is in ways that lead to habituation. Habituation is just the human process of getting used to stuff. If I go buy a new Bentley or whatever fancy new car I want, and I'm driving that around, it's really awesome for like two weeks, and then quickly that falls off and it just becomes my car, right? Things, like a car or a house, even a really nice one, quickly become the backdrop against which we live our lives. But experiences that give us newness or novelty or break us out of sort of our sleepwalking stance, bring us happiness, and they tend to stay with us. If I fly to Japan and have food I've never tried and hear language I've never heard and meet people I'll never meet again, that gets better with time. That doesn't get habituated, that memory gets better with time. So, using some of that money to break out of the habituation cycle, to go try new people, new food, new experiences, new sites, new vistas, all of that has the immediate impact of giving you a boost of happiness. Then it potentially has the secondary impact of helping you discover this thing you're talking about. That's a creative act, too.

Roger: The Soul of Wealth. I love the way that it's written. I think what I love about this book is that it shows Dr, Crosby, but also the man, Dan Crosby, and that is much more meaningful. Let me see if I can hold it in the right direction. It's a great book, and we rarely have authors on just to talk about their books, but you are a friend and you are a kind man, and I think this is something that's important. Thanks for sharing it, Dan.

Daniel Crosby: No, I appreciate the help, sir. You're doing wonderful, soulful things with money, and you're a voice for reason in the wilderness. I'm appreciative that you'd have me on.

Roger: Yeah, we're excited to have you in the Rock Retirement Club here in the next few months.

Daniel Crosby: Love it. Thanks.

TODAY’S SMART SPRINT SEGMENT

Roger: On your marks, get set, and now we're off to set a little baby step we can take in the next seven days to not just rock retirement, but rock life.

All right. 

In the next seven days, I want you to evaluate whatever retirement plan you have in place and identify specifically what the feedback loop is to improve that plan on a consistent basis. That could be a six-month meeting, it could be an annual meeting. But what is the specific way you're going to revisit the plan, update the assumptions, and improve the model? 

For extra credit, I would put on the calendar a meeting date to actually do that in a structured way and if you have an advisor, get that meeting on that calendar so you can hold yourself and them accountable to continually improve the map so you can rock retirement. There are some people in this world that I just really love. I love how they think. I love how active their minds are. Dr. Daniel Crosby is one of them, and he has agreed, I think we're going to be able to make it happen, that we're going to have him on the show periodically to discuss one of the chapters of his book, the soul of wealth. They're written in essay style and so they're confined concepts that I think we can apply to improve our saw in order to rock retirement. 

I'm so jazzed to be able to walk this journey with you. I hope you have a great day. 

The opinions voiced in this podcast are for general information only and not intended to provide specific advice or I recommendations for any individual. All, performance reference is historical and does not guarantee future results. All indices are unmanaged and cannot be invested in directly. Make sure you consult your legal, tax, or financial advisor before making any decisions.