A High IQ Alone Won’t Make You Happy : Part 1

Jeffrey Madoff: This is Jeffrey Madoff, and welcome to our podcast called Anything and Everything with my partner, Dan Sullivan. Dan, I had read this really interesting article by social psychologist Adam Mastroianni, and it challenges a lot about what we think and what we know about intelligence and happiness. And one of his primary findings is that there's essentially no correlation between IQ and happiness. And IQ scores have risen substantially over recent decades, to so-called Flynn effect, it's called in psychology. Yet by every measure, we're no happier than previous generations. So what Mastroianni argues is that IQ tests only measure one narrow type of intelligence, the ability to solve well-defined problems with clear rules and right answers. But life isn't a math test. The most important questions we face—how to build a meaningful business, how to be a good parent, when is enough is enough—these are all very poorly defined problems in our education system, our culture. Even our definition of smart has left us completely unprepared to solve. And so today I'd like us to explore what this means for entrepreneurs, how we build teams. Some of this directly relates to the book that we're doing, Casting Not Hiring, and for how we bring about success and ultimately how we live. Because if solving problems doesn't make you happy, once you've solved them, what does? So the first question I wanted to ask you, do you have any response so far?
 
Dan Sullivan: Yeah, well, the IQ is an indicator of, as I understand it, because we have in our screening people, we actually use a variation of an IQ test. And it's, to a certain extent, it's the ability to see patterns and connect patterns. And the other thing is that you can think in terms of abstractions. Some people, it has to be a concrete thing for them to think about it, but being good at comparing one idea with another idea requires a comfort with abstractions. But I've never had any indication—I mean, I think I had my first IQ test when I went into the Army in 1965. They tell you what your score is, and it was interesting, but it didn't really have anything to do with anything. So I've never related that people who score very high on an IQ test, that it has anything to do with whether they're happy or not. I think happiness is more related to a sense of agency than it is the ability to take a test.
 
Jeffrey Madoff: Well, yeah, it's funny. When you mentioned the IQ test many, many, many years ago, I was asked to join Mensa. And I said, if this truly measured intelligence, then you should be smart enough to know that I'm not interested. And I always thought that it was really weird. I guess in every pursuit, people look to somehow distinguish themselves, set themselves apart in terms of excellence and high achievement. But I always wondered, you know, so what's the value of that declaration? Other than it sounds obnoxious, you know? And I think there's an intelligence paradox that I'd like us to address first, that despite the higher IQ scores, smart people aren't necessarily happier. And in your experience coaching thousands of entrepreneurs, have you noticed this disconnect? I mean, what separates the successful entrepreneurs who seem to be genuinely happy from those that are successful but miserable? Because we know those people too.
 
Dan Sullivan: Yeah, I think that there's actually an ability to see an opportunity that others don't see. So there's a certain extent it's a kind of a visualization about the future where they can see where something's heading in a way that other people can't see where something's heading and they can create something out in front. There's a book of quotes, and this one was Coco Chanel, the French designer. And she said, you know, ever since I can remember, I've had an ability to kind of see what people will like wearing next year, and then to do something that was not really expensive, but was distinctive, and just get it out in front of them, you know. And so there's a certain ability that they're departing from what everybody's doing, because, you know, if the trend is in a particular direction, that means that there's probably going to be another trend that replaces that trend. Because trends don't last forever. Fashions don't last forever. And you're just having a sense of what might people like next that can't be seen yet. So I think that there's a foresightedness that entrepreneurs have. And I don't think that can be measured by an IQ test.
 
Jeffrey Madoff: Well, and it's interesting, like when you mentioned Chanel, every designer faces that dilemma because it's going to take some months to get a collection out there in front of the consumers. They have to make their commitments to the fabrics, to the contractors and labor and all of that. And I think in just about everything, going back to the phrase that I love, it's all guesses and bets, that trends by definition don't last, otherwise it wouldn't be a trend and it would be a reality. Everybody's still eating food, but now there's a trend within that, which is the Dubai chocolate.
 
Dan Sullivan: I haven't seen that.
 
Jeffrey Madoff: Oh, God, it's everywhere. It's unbelievable. It was like there was a light switch thrown, and everybody's, Dubai chocolate, and it's crazy. But anyhow, so I think that anybody selling something is, in most instances, looking for some kind of future demand for what it is that they're putting out there. So, you know, television, filmmakers, I mean, on and on, car manufacturers, they're all trying to come up with what people are going to want. And of course, the further out it is, the more difficult it is to achieve that, and it's never easy. But I think that the ability to solve well-defined problems, clear rules, measurable outcomes, and so on, is what people look at as smart. I remember that in physics class, and I remember that in science class in high school. But if you only have the ability to solve well-defined problems with those clear rules, but most of life is made up of very fuzzy boundaries and not-agreed-upon solutions, how does this distinction apply to entrepreneurship? Because most important business problems are the poorly defined ones.
 
Dan Sullivan: Yeah, well, the original definition, and it's fairly recent in history, 1804, French economist who is a fan of Adam Smith, famous in the 1700s for Wealth of Nations, you know, a major economic book. But he had another one called The Theory of Moral Sentiments that basically there's emerging sentiments about what people need. And it starts with an individual and then there's a shared feeling that we need something. And he said, there's an interesting combination. And he was talking, essentially, he didn't have the word yet because the word entrepreneur really didn't get coined until Jean-Baptiste Say did. And he said an entrepreneur is someone who takes a resource from a lower level of productivity to a higher level of productivity.
 
Jeffrey Madoff: Can you give an example of that?
 
Dan Sullivan: Yeah, records, recorded music. And Steve Jobs, when he was fired from Apple, went out and he experimented with a whole bunch of things that he actually liked. You know, he had some time on his hands. And one of them was music, and then he would hear some music and he would go to the record store and he would say, I'd like to get this song. And they said, well, it's on an album. And he began thinking, why in order to get one song do I have to buy ten other songs? So you have a resource called Recorded Music, but there's real friction to it because you're having to pay for more than one song, you're having to pay for a whole bunch of songs. And in your play personality at that time, it was two songs. You had to have a B-side. In order to get the A-side, you had to pay for the B-side, too, because the records had two sides. And he started putting together the fact that there was now an internet, and that music could be sent on the internet, and that a company named Napster had actually taken advantage of this and was stealing music off the internet and allowing people to download it, which was a good solution, but it was a crime. And it's not a good starting point for a long-term profitable business to start off with crime.
 
And then he had on the Apple, you could have apps on. And he started putting it together. So he took the fact that you could get ones on, but you could have an MP3 player, which Sony was the real big player with the Walkman. And so he put the Walkman, he put Napster, and the fact that you had apps on your computer, and he put them together. And he says, why don't we just have all music downloadable as single things on your computer, and you can put them on a Walkman? So the big thing was, he was taking a resource, he was taking a resource called the MP3 player, where you also had to go to the record store and get an album for your MP3 player. And then you had the internet, which was useful, but you couldn't do anything with it legally. And then you had computer platforms where you could put music on your platform. And he put it together and he created iTunes. And within two years, Apple was the largest distributor of music on the planet.
 
Jeffrey Madoff: I would say that when we were coming up in age, the 45 RPM, the A-side, B-side that you referenced, it's interesting because, you know, you didn't have to buy a whole album. Albums actually came later, because initially with first the Edison cylinders and then 78s, there wasn't that much time.
 
Dan Sullivan: Yeah, 33 and a third was the real breakthrough.
 
Jeffrey Madoff: The LP, that's right. The one playing record.
 
Dan Sullivan: Yeah, which was great.
 
Jeffrey Madoff: But before that, everything was basically singles. A record album was actually a literal album that had sleeves that would be, you know, six records that might be a symphony of some sort. But things were singles, essentially, when we were teenagers and that sort of thing, which is interesting. So, you know, I think that what Jobs did was adapt something to the rising digital marketplace. And Napster is the one that kind of showed, oh, this is a way to do it. I don't know if initially they were sued and I think it became illegal. I don't know if initially it was illegal because those things weren't covered in copyright law. That became later, which is also interesting. But do you agree that, and this is actually part of what our Casting Not Hiring is about, do you agree that there's an education entrepreneurship gap that our educational system trains people to solve well-defined problems through the standardized tests and clear answers? And does it actually prepare people poorly for entrepreneurship, because the most critical decisions don't have objectively correct answers?
 
Dan Sullivan: Yeah, well, I think there's been a real shift in my experience with education, what I've heard, because I really don't have any personal connection with it, except that you're hiring the products of education. And I think the big thing was that where you have education that you're training to the test—in other words, you're educating to the test—in other words, it's about getting the test right that indicates that you're educated. But it doesn't really involve any creativity. It requires memorization, probably. But it doesn't say anything about what's happening to the thinking abilities of the person being trained.
 
Jeffrey Madoff: Right. Bravo. There were substantial businesses like Kaplan and others that parents trying to give their kids any advantage possible in terms of getting into schools they wanted and so on, that exactly what you're saying, you'd train and study for the test. Not for what you learned, and nothing would be retained as a result. It was literally figuring out how to test better, not how to think better. but how to test them.
 
Dan Sullivan: Yeah. Well, you know, first of all, I don't think you can make someone into an entrepreneur. So I don't think that there's any educational process that turns someone into entrepreneur. My sense is that entrepreneurs, from what I've been able to tell, and I've had 50 years of working with them, is that it shows up quite early. Not necessarily going to be an entrepreneur per se. In other words, they're going to create an entrepreneurial company and be in the marketplace. But there's a certain divergence from the norm that shows up very early in somebody's life. And one of the things is a comfort of being by themselves and exploring something they're interested in, regardless of what other people are doing. And I think it shows up before teenage years, before adolescence, I think it shows up 8, 9, 10 years old. And it's that there's something that you're attracted to and you find very, very meaningful and you kind of focus on it and it's irrespective of what other people think about this.
 
And as you go deeper and deeper with your interests, you develop new kinds of thinking skills out of doing this. You're essentially creating your own self-school. You're creating a certain kind of self-schooling. Mine was really interesting. It was a combination of asking adults what their experiences were, having them talk about their experiences, major experiences like being in the First World War, going through the Roaring Twenties, being on their first airplane flight, remembering when electricity came into their house, radio, when they first heard radio. And then I would go to the encyclopedia and look up the actual historical facts. So I had this deep interest that people's experiences were actually very connected to realities out in the world, historical facts, and that this was a way of educating myself that bypassed what I was getting in school.
 
Jeffrey Madoff: Coupled with, since we have a history now of doing these podcasts together, you also got cookies and milk.
 
Dan Sullivan: I got cookies.
 
Jeffrey Madoff: Yeah. So you also were prompted by the award or reward you could get for doing it.
 
Dan Sullivan: Yeah. Yeah. Yeah. It was very interesting. Stephen Poulter, he's friends with both of us. He has three sons and the youngest, Sam, who's now first year in university when he was around 10, 12 years old, he came home one day and he says, I figured it all out, which prompted a question. You figured all of what out? Anything my teachers tell me, I go to YouTube, and I look at five videos on that subject, and tomorrow I know more than they do.
 
Jeffrey Madoff: Of course, assuming that that's the only thing that they knew and pursued.
 
Dan Sullivan: No, but what they were teaching was what they wanted the students to think. You know, whatever it was that they were teaching, they were teaching. And I find with AI right now a similar experience, that if I see an article, and I read The Wall Street Journal every day, and they have a very extensive editorial and comment section. And I read something, and then I go to Perplexity, my AI, I download the particular article, the particular comment, and so I say, I'm downloading this article, tell me ten things about this subject that the author doesn't mention. And bang, all the gun. And you see, they've just picked one thing to focus on, but they're trying to say that this is the most important thing. It may be the most important thing or it may not be the most important thing, depending on, you know, what it is. I sort of have this attitude, 10 reasons for anything. If somebody says, well, this is the reason why this is happening, and I said, yeah, but there's probably 10 others too.
 
Jeffrey Madoff: I think it's interesting because to me what that demonstrates is over the years you have gained the wisdom to know to look beyond those boundaries that are placed in front of you. So I think that, for instance, IQ tests don't give you wisdom. They don't test for wisdom. And there's no wisdom score, right? But in Strategic Coach, how do you help entrepreneurs measure progress on things that matter but can't be easily quantified, like quality of life or, you know, relationship depth or personal fulfillment or things like that?
 
Dan Sullivan: Yeah. Well, it's actually creating a structure where they can look at their own thinking and they can look at their own experience. Okay. So I introduced a new thinking tool last week and it's called You Simplify To Multiply. And so I said, throughout your entrepreneurial career, where did you get to a point where you weren't making progress and you realized that things had become too complicated? So you had to really simplify, especially in terms of how you were using your own time and what you were focused on. And then maybe you had to bring in other people to do things that would free you up. And the moment you got freed up from simplifying your role, all of a sudden the results started multiplying again. Okay, so they did two and a half minutes on simplifiers, and then two and a half minutes on multipliers, and then I had them pick the top three simplifiers in their entrepreneurial career, top three multipliers, and I said, okay, now put them together. Let's put the top simplifier, top multiplier, number two and two, number three and three, and let's see if there's some real opportunities in what you've already done that can be acted on during 2026. And the whole room went crazy. The whole room goes crazy because they didn't have a structure for thinking about their thinking. The moment you gave them the structure, they did new thinking about things that they were the expert on because it was their experience.
 
Jeffrey Madoff: It's interesting. There again is a great example of you using wisdom that goes beyond the knowledge base to provoke thinking, which is very hard to test for, you know? And so when you were a kid or even with what you do with the people in Coach is you're bringing a certain wisdom to it from things that you have learned, certainly things you can't test for, but the wisdom that you are bringing to that helps in the problem solving and also helps them. And I wonder how many of those people who you have helped in that way understand the dynamic of it so they can do it themselves. I mean, I know the tools are to get them focused on thinking about their own thinking.
 
Dan Sullivan: Yeah, I think they do. You know, the whole thing is the test is very, very clear. It's productivity and profitability. You can test for their being clearer about how they're going to conduct themselves in the future. It's increased productivity and it's increased profitability. That is a test.
 
Jeffrey Madoff: Right. And it's measurable.
 
Dan Sullivan: It's measurable, yeah.
 
Jeffrey Madoff: But it's also, and I find this fascinating, that there's big problems like, you know, curing cancer. And you hear like that steadily over the decades IQ scores have gone up. Now I question the whole concept of IQ in the first place. To me, if there's constant improvement, it only means to me that possibly they're learning to test better. And again, as I said, there are those businesses that are dedicated to that. But do you see successful entrepreneurs falling into this trap, which is they think that the next revenue milestone or the next business achievement will finally make them happy, but it doesn't.
 
Dan Sullivan: I'm not sure they think it'll make them happy, but progress does make them happier. So we know that, for example, we have a model in Coach called The Gap And The Gain. And it has to do with how you measure your progress. So if you're a Gap person, your goal is to have the ideal result. You have an ideal. So you pick something that moves you towards what you think is your ideal. And it's a tangible goal, you can measure the progress. But when you reach the progress, and you measure it, you realize that you're no closer to the ideal, because the ideal actually doesn't exist. It's just a mental framework. It's like the horizon line. I don't care if you try to do it at night, or you try to increase your speed, you're not going to get to the horizon line, because it's a mental structure. It allows us to orient ourselves in space and I think the ideal is similar to the horizon line in the sense it allows us to orient ourselves in time. It's a time framework, I think the ideal is.
 
So, when you measure and you increase your progress and you achieve, and you measure against your ideal, you feel you haven't done anything, but people outside of you can very clearly see that you've made progress, but you can't accept that as real. And this is a huge jump in their thinking, is that you also set goals, but when you achieve your goal, you turn around and you measure from where you started. And that always makes people happier. So you have lots of people who are very successful from an external observer standpoint, and they win things. They win the Oscar in movie making, and they land on the moon, and they win the Olympic gold medal, and they make their first million. But because that doesn't satisfy their image of the ideal, that they don't get a positive result from the achievement.
 
Jeffrey Madoff: Meaning happy and satisfied. Yeah, they're not happy, yeah. So that's also very interesting because you would think if you define the problem of you want to hit a certain revenue number, that means you no longer have these financial issues. They aren't obstacles anymore. You've gone past that threshold. I think that you get there, they get there, and they don't, as you're saying, don't feel any closer to it. And I think by nature, entrepreneurs are strivers. And as a result, maybe the striving never ends as long as you're active in what you're doing and pursuing that.
 
Dan Sullivan: Yeah. I mean, use your own example. I can say that I'm always striving, but I've developed a way of feeling happy every day that I'm striving.
 
Jeffrey Madoff: In what way is that?
 
Dan Sullivan: This is because I've given some thought because we had mentioned that we might talk about this several podcasts ago. And I said that I think the first requirement for being happy is that you actually like who you are.
 
Jeffrey Madoff: Yeah, before any activity is defined.
 
Dan Sullivan: I mean, it's based on your experience so far. And one way of knowing you're happy with who you are is that you don't want to be someone else. Oscar Wilde had a great line, he said, be yourself, everyone else is taken. I've just got a memory, childhood onward, liking who I am. I got a good model.
 
Jeffrey Madoff: Yeah, I mean, liking who you are, a certain sense of self, is probably the hardest thing for most people to achieve. I mean, in your book, The Gap And The Gain, the interesting thing is it's kind of like a very sophisticated look into, is the glass half empty or half full? How are you actually measuring this? And I think unless you are an elite athlete or on the highest level of whatever, the main thing is, you know, so if you're gonna be entering a competition, you gotta be realistic about how fast you have to go with that competition. But for the most part, the vast majority of people, their only measurement in terms of achieving any happiness is going to be how far they have come compared to where they were.
 
Dan Sullivan: And I think that that is uniform. Because first of all, because athletes, compared to a lifetime, their athletic careers are very short. And, you know, I've had clients who were athletes at a high level, professional football. They were in the National Football League and baseball, not basketball, I don't … we have height restrictions, so you can't. But they hit a point in their thirties where they're not good enough anymore. But their entire life, certainly in the United States, the athletes who end up in the National Football League, they're spotted when they're six years old. And a coaching system came along and picked them up and moved them along. I mean, there's exceptions to the rule, but the majority is they get a great deal of early support and a great deal of early focusing and their life is put into a structure where all they have to do is keep progressing within a certain skill area and they're going to end up as a professional athlete, tennis players, same thing. I mean there are certain tests for eye-hand coordination, for speed, for balance, and for agility that can be tested in a child very early. Then the other thing is, do they like the activity? They're passionate about the activity. But then they reach a certain point, and sports, I think, is probably the most brutal of the things, is that your career, as far as that activity has gone, is over before you're 40 years old.
 
Jeffrey Madoff: The thing that's interesting about the idea of, especially for sports, but it's also true in chess. It's true in …
 
Dan Sullivan: The younger beats older?
 
Jeffrey Madoff: No, no. What I was going to say is that parental involvement is essential because, you know, you got to take your kids to the soccer games, got to take your kid to the music lessons, you know. And then the question is, does the child have the passion for what that is, or is the parent trying to live through the child, and that's a whole other thing. And so, you know, ‘cause I'm sure that there are certain kids that are just, whatever that talent is, their drive to improve that is something more difficult to understand. ‘Cause how did they know that at that age? You know, a piano prodigy, whatever, because it does require a lot of parental support just logistically, you know, and then does your happiness come from the activity itself, or does the happiness come from pleasing the parent?
 
Dan Sullivan: Yeah, yeah, yeah. And I think that this is especially true in the educational field. We started off, you know, with IQ tests and the heavy emphasis on early learning. There wasn't kindergarten when I started, but then kindergarten came in about 10 years into our school, basically after I was a first grader. Now they've got preschool, and what I see is their life becomes very structured and very supervised at a very early age. And you realize that at a certain point that it really isn't very good for them. But it's very crucial for the parents that they achieve at this level and achieve at that level and achieve at that level and achieve at that level. But that's not the child's ambition. That's the parent's ambition.
 
Jeffrey Madoff: Yeah. And you know, you made a comment some time ago, I remember we were talking about Elon Musk, and obviously he has achieved a tremendous amount. But as you said, even if you make it to the moon, Mars, or, well, can you please say your comment?
 
Dan Sullivan: That was just a comment I made to somebody. And I said, you know, I think a lot of the drive, this is imaginary on my part, I'm just making something up when I observed that Peter Diamandis has known him for 25 years. So he goes back to when he was at the PayPal, you know, he was just, you know, he was a hustler in Silicon Valley, like there's a lot of hustlers, and he knew him. And he said, you know, all the stuff that he does to make money and to become well known is to have the leverage and the resources to go to Mars. He wants to walk on Mars. And I said, I think he will. But I know a little bit about his history, too. He had a very, very uneasy relationship with his father. And I said, and when he gets to Mars, he'll say, then daddy will love me. And I said, no, he won't, but we will have benefited enormously from his attempt.
 
Jeffrey Madoff: Yeah, you know, I think that that's huge. I mean, he's an extreme example of both achievement and, you know, success in certain areas. But also, I think that comment you made is not a joke. I mean, it's for real. And that impacts an awful lot of people. And, you know, it's the old looking for love in all the wrong places. You know, and it's kind of like, this won't mean anything to any of you listening until you've read our book when it comes out, Casting Not Hiring, plugging ourselves. But you had set up as a result of, you know, I started with Shakespeare and his entrepreneurial drive and so on. And then you picked up in your part, which was great, is the fact that theater has been around for thousands of years. And it was, I'll phrase it this way, it was ancient wisdom versus modern optimization. And because of ancient thinkers, Socrates, Buddha, whoever, they focused obsessively on how to live. But we've largely abandoned that pursuit. But it's interesting because Strategic Coach, and this isn't a plug for you, this is just what I've come to know over our years of talking and so on, is, in a way, you are telling them how to live. Take free time. Where did that come from? Because that's another separation, I think, from the coaches out there. And I'm curious as to how did you arrive at the point to include that as part of it? Did you see that certain level of self-satisfaction or seeking happiness, yet they paid no attention to their personal lives? They trashed their relationships. They did all of that. How did you look at that?
 
Dan Sullivan: That really comes from Babs, my partner.
 
Jeffrey Madoff: I should have guessed that.
 
Dan Sullivan: But she grew up in a family where they took lots of vacations together, and I didn't. It was work, work, work, work. My father was always working, and I just got into, you know, and started doing entrepreneurism, I just got into the point where the more you work, the better things were going to be. And she let me know very early in our relationship that if I wanted to have a relationship with her, there was going to be lots more free time than I was used to, or there wasn't going to be a relationship. And it was tough for the first year, but then I began to realize I was becoming much more productive as a result of taking time away. And my life was less complicated. The things that you thought were urgent before you went off on Free Days, when you came back, if you thought 10 things were urgent and you came back, you realize that maybe one thing was, and you don't even remember why five of them were even on the list, because you had just become all about work. And I don't think life being just about anything is very good for you, but work is sort of the respectable addiction.
 
Jeffrey Madoff: Right, right.
 
Dan Sullivan: Yeah, boy, you can say anything you want about him, but boy, can he work, you know? I mean, you don't say that you can say anything about him, but boy, can he drink?
 
Jeffrey Madoff: It doesn't have the same respectability about it.
 
Dan Sullivan: Well, he can hold his liquor. You can't even tell.
 
Jeffrey Madoff: Until he projectile vomits on you, you can't even tell.
 
Dan Sullivan: You know, and it goes back to our common interest, I began to realize that entrepreneurism was not a junior edition of being a corporate executive. The model for entrepreneurism is actually the entertainment world, not the corporate world. It's not a factory you're trying to become, because entrepreneurs make their money in very short periods of time and very specific situations. There's an event that produces a year's worth of money, you know, compared. I mean, I'll have a workshop on Tuesday and there's four of them in the year. So that's four days of the year where my income for those four days is easily 50 times more than my first year in business. Just a function of building teamwork around me and systems and taking the size check you get from your clientele kind of comes in. I said, this is tremendous progress over the period that I've been working. But the big thing, going back to my first principle, you know, of what makes me happy, is the fact I really like the person I'm living my life inside of. Even where I've had failure, I like the way that I handled it. You know, I look back and I said, you know, I did a good job of handling my divorce, handling bankruptcy. I've been bankrupt twice. And I said, you know, I really handled that really, really well. I didn't blame other people. I didn't go into a funk. I said, okay, you've got to do something different. You've got to approach this differently.
 
Jeffrey Madoff: Which is a way of taking agency.
 
Dan Sullivan: Yeah, yeah. I see things in trilogies, you know, that it's not one thing, it's three things. The second one is a feeling of daily progress, and I measure on a daily basis. My measurements are really on daily, that when I get to nighttime, I turn around and say, what were the three best things that I achieved today? You know, that moves things forward. And the third thing is usefulness to other people. You know, what I'm creating is more and more useful to check writers.
 
Jeffrey Madoff: Which is good for your business, that's right.
 
Dan Sullivan: Yeah, but there's appreciation on their part that goes along with it. Yeah, that was really helpful, that was really useful, you know. That's applause.
 
Jeffrey Madoff: Yeah, that's right. Yeah, being acknowledged and appreciated for what you've done, that's right.
 
Dan Sullivan: Recognized, yeah.
 
Jeffrey Madoff: Oh, absolutely, absolutely. You know, so, we all know smart people who make some really dumb decisions or believe in some really out there crazy things. And you were at a crossroads with Babs.
 
Dan Sullivan: Well, I was not at a crossroads, but she laid down the rules pretty quickly.
 
Jeffrey Madoff: Right. But there are a lot of people that would have said, too demanding, I got to be who I'm going to be. You had—you know, it's certainly proved out over the years—you had, I don't know if it was wisdom, need, whatever it was, but you realized that there was something far more valuable and far harder to replace if you lost that, which was your relationship. And why is it? Because I'm sure you have seen people who are very successful in their business make terrible decisions about their lives. And do you ever think, or can you address the question, why some really smart, successful, in terms of their business, people make such terrible decisions in their personal lives?
 
Dan Sullivan: Yeah, well, smart isn't a wraparound concept. First of all, I think they have a talent in a particular area. You know, I think people are born with a particular talent. That's why I don't think you can take someone who's not an entrepreneur and turn them into an entrepreneur. It takes a certain pre-existing talent. And I think it's a comfort with, we could go into this a little bit more deeply on another podcast, but I think they have a tolerance for ambiguity and a tolerance for uncertainty that other people just couldn't sustain. They have to have certainty. They have to make sure that the paycheck is guaranteed, that the paycheck is certain, and entrepreneurs, for the sake of much bigger paychecks, are willing to pay with being uncertain about where the paycheck is going to come from in a way that most people can't tolerate.
 
Jeffrey Madoff: Well, and I also think we need to change the definition of certainty in those markets, job market and so on, because what we grew up with in terms of certainty, whether it was you could, in Akron, where I'm from, you could work at one of the rubber companies, or you could be a teacher, or whatever, and you had a lifelong career, that essentially doesn't exist anymore. And there is no certainty, because one day you may have a position, and the next day, tons of people are laid off.
 
Dan Sullivan: Yep, yep. Yeah, and I think the more the belief was that this is a safe, like the professions, you know, I think. You know, if you become a lawyer or an accountant or, you know, any of the ones where you have to study and perform for a long time before you get a credential to do something, I think that that was seen as the safest approach to the future. But those very, very professions are what are being threatened by AI right now, because there are a set of structured rules that you have to know, and AI is good at structured rules. I have a real estate investor, and he's gotten better and better at doing multi-state real estate deals, where you're dealing with a variety of different regulatory systems, you know, different communities, different states, and different financing structures. And over the years, with having his own lawyers, his own accountants, his own financial advisors in his network or within his company, he's been able to pull these out.
 
And when AI first came along, the task that you're doing is that you have all the final paperwork that's all legal. It's all makes financial sense. And all the paperwork, you know, it might be as thick as a binder of everything that would be need for a particular project. And he found out one afternoon that AI could do everything that would take three months for his network to do, he could do in three hours. And he said, I've seen the future and it's scary. But on the other hand, he's just made AI part of his team now. And he won't have a lawyer or an accountant or a financial advisor who's not good with AI. But that's an entrepreneur who's used to adjusting to uncertainty and sudden changes and everything. He's got a lifetime of, certainty is good for maybe two months.
 
Jeffrey Madoff: Yeah, well, the only thing that I think you can be certain about is that things will be uncertain. Yeah. I think that is true. And there is something I want to dive into with you about AI, but I wanted to put a cap on the question of the smart, successful people making stupid decisions that negatively impact their lives. And I'm sure, I mean, you and I know people who have done that. They've been very successful in business, but is it self-sabotage? Is it not paying attention?
 
Dan Sullivan: I mean, you know, it could be self-sabotage, where one reason that when they get everything they want, they still don't feel they deserve it. And that's a form of self-sabotage. You know, but the other thing is mostly it's a lack of context. They don't understand the overall, yeah, you can be successful here, but if you're not doing a good job over here, this is going to come back to bite you. They don't have that context. You have people who, you know, first of all, the factor of popularity, the factor of success, popularity, fame, celebrity, are drugs in themselves, and you can get very, very addicted to those things. And meanwhile, you can exhaust those resources. You get to the point where what made you really successful, well, that's not the way the world is anymore. And you kind of went to sleep while you were enjoying a previous success, but you didn't set up your next success.
 
Jeffrey Madoff: So let me ask you, when Babs said to you, look, we need to have more of this time together if we're going to be together, what kept you in that as opposed to saying, look, this is who I am, this is what I do, you don't like it, I'm sorry. You know, because a lot of people bomb their own relationships. And, you know, I think by all objective tests, you made a really smart decision. And it was both business, but primarily personal. What was the question you posed to yourself?
 
Dan Sullivan: Well, it wasn't so much a question. It was that I realized that my business that had gone bankrupt in 1978, 50% of the reason was I was living with someone who hated that I was a business person. So that divorce was because it just became impossible to be in that marriage and to be focused enough to be successful. So one of the lessons I got out of it, I will get into another marriage, but it has to be 100% support for what I'm doing. So Babs, right from the beginning, was 100% behind what I was doing. She was saying, you can't do what you're doing if you don't take free time.
 
Jeffrey Madoff: Because?
 
Dan Sullivan: She wasn't going to be in the relationship. I needed the relationship and so I had to do some mindset and habit adjustment.
 
Jeffrey Madoff: Yeah. And how many people have you seen in generally speaking that same position and it tanked their marriage because they made the wrong decision?
 
Dan Sullivan: I wouldn't say a lot, but I've seen it happen. You know, I mean, I would say if you did a survey, we did a major survey about five years ago when it was 80% response rate from around 2,500, so we got 2,000 responses. that marriage was very, very important, children were very, very important, community involvement was very, very important, health, other aspects. And it's interesting, for most entrepreneurs, the biggest thing that's lacking in their lives is a lack of a supportive community where they can grow and succeed and the members of their community reward them with applause and real interest in what they're doing. They can talk about their success. I would say most entrepreneurs live in a very lonely life, that they're way more successful than the family they grew up in. They're way more successful than the early friends they had in life. They're way more successful than a lot of people, and they can't talk about it.
 
Jeffrey Madoff: It's fascinating. I don't know that you could have made the same decision without a bad marriage, without going through what you went through, and realizing and acquiring the wisdom that you realized you had something you didn't want to lose.
 
Dan Sullivan: Yeah. And the other thing is that it actually happened on the same day in 1978, August 15th. It was just happenstance. It wasn't like I arranged it or anything, but the divorce was in the morning and the bankruptcy was in the afternoon. You know, it just happened. It was two report cards on the same day, you know.
 
Jeffrey Madoff: That's a bad day.
 
Dan Sullivan: Well, it's really interesting because, you know, it was the height of summer and it was warm. And the next day I went to a favorite restaurant for breakfast and I was walking. It was about a half hour walk. And people were on the street and nobody seemed to be bothered by my divorce and bankruptcy. So when I got to breakfast, I said, maybe this is all my deal. It's not like people invite you over for a special party where you get to talk about your divorce and bankruptcy. Dan, we were just putting together 20, 30 people, and we wonder if you'd just come over and spend the evening talking about your bankruptcy. People are very polite. They don't bother you, they leave you. So I just came to this realization that if I took 100% of the responsibility for both of them, it would be easier to correct things. And some of it, I was just stupid. You know, I mean, there's just a question of inexperience and not enough knowledge and stupidity and not doing the right things at the right time. And what I committed to, I committed myself that I wasn't telling myself what I wanted. You know, I was expecting that if I got married, the other person would sort of work out a number of things, you know, would psychically understand me and would give me what I wanted in a business situation.
 
So I set myself a goal that I would do a journal for 25 years. This was at the end of 1978. And every day I would write in the journal, I want this, okay? But I want it, but not because. Not because. I just want it, and I did this. Missed 12 days in 25 years. Took me up to 2003, and I became a really good wanter. And it had to do with, what kind of relationship do I want next? Not who the person had to be, but what the nature of the relationship had to be. And my first thing that I wanted about the relationship was that it was a relationship that you didn't have to work at. It was just a relationship that worked. And the moment I met Babs, I felt this incredible ease. You know, it wasn't some fall-in-love romantic thing. It was just sort of a friendship that got deeper and deeper over about two years. But we weren't together, so the whole question of if I was working all the time really didn't matter. I mean, I would take time to be with her, but I wasn't taking any other time. I was just taking time with her. But without Babs, nothing else that I've done could have been possible.
 
Jeffrey Madoff: Yeah, it's very interesting.
 
Dan Sullivan: And I think most relationships that are great lifetime relationships have a similar quality to them.
 
Jeffrey Madoff: That quality being?
 
Dan Sullivan: Well, it can be her or it can be someone else. It can't be her or somebody else. It can be her. And that I was willing to change my behavior to make it work.
 
Jeffrey Madoff: Mm-hmm. Mm-hmm. Well, thanks for sharing that. It's really interesting. I think that something else that you and I may have in common is that we're always our own guinea pigs.
 
Dan Sullivan: Nobody else wanted to be. Well, I'm thinking that we're at a point in this discussion where I
 
Jeffrey Madoff: Well, I'm thinking that we're at a point in this discussion where I think we might benefit from doing part two, because I want us to bridge into what we've been talking about for the past several minutes now has been, these are unique human problems, unique human issues and challenges. And I think it would be really interesting for us to get into AI and human uniqueness. You know, if AI will eventually beat us at all the well-defined problems in things that we've talked about in the past, but humans will always be needed for the poorly defined things. What does this mean for the future of work? Should we be training people to get better at that human stuff rather than competing with machines on the defined stuff? And how do we then look at the future of work and so on? And I think we can get into some really interesting things, again, all relating to happiness, and I think might be a good time to break and to do that.
 
Dan Sullivan: Yeah. Well, thanks. I got a lot out of this.
 
Jeffrey Madoff: Me too. Me too. I think it was really good.
 
Dan Sullivan: Yeah. But it's the one thing that just became clear to me, and it's not recently, it was a long time ago, was that happiness is not a destination. Happiness is a way of being throughout the entire journey.
 
Jeffrey Madoff: Yeah. Yeah, I mean, that's something that I have always gone for. And yeah, I think this has been really good and I'm looking forward to part two. Thanks for joining us today on our show, Anything and Everything. If you enjoyed it, please share it with a friend. For more about me and my work, visit acreativecareer.com and madoffproductions.com. To learn more about Dan and Strategic Coach, visit strategiccoach.com.