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Why So Many Millionaires Feel Bad About Themselves - Dave Ramsey

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Dave Ramsey highlights a pervasive psychological error among millionaires and successful business owners: an internalized sense of guilt regarding their wealth, despite having done everything right to achieve it. Through his work with Entree Leadership coaching thousands of small businesses and conducting studies on the demographics of millionaires, Ramsey observes that many wealthy individuals suffer from damaged psyches due to what he terms "antisuccess" or anti-wealth movements. These negative narratives have stolen their pride and hope, causing them to question their morality even when they are objectively successful. Ramsey argues passionately that there is a lower percentage of bad people among the wealthy than in the general population; rather than being moral reprobates who got rich through wrongdoing, these individuals typically succeeded by serving more customers—whether selling chicken or pizza—and working harder than anyone else. The source of this negative sentiment is often traced back to communist college professors and a cultural shift that promotes envy over achievement, creating what Ramsey calls "hope stealers." This ideology suggests that equal wealth for unequal effort is fair, which Ramsey vehemently rejects as unjust; he insists that those who work sixty hours should earn more than those working six. He notes that this mindset has created an environment where success gets a bad name, fueled by movements like Occupy Wall Street and language from the 1960s American Dream era that promised upward mobility regardless of starting point but failed to deliver for many today. Consequently, even financially secure individuals in Generation Z and Millennials often feel disenfranchised because they compare their current standing unfavorably to their parents' generation or perceive systemic barriers like racism, sexism, and "baldism" as insurmountable injustices that excuse a lack of personal effort. Ramsey challenges the victim mentality by pointing out that while external factors like unfair stereotypes—such as southern accents being misinterpreted due to ignorance from shows like *The Beverly Hillbillies* or assumptions about footwear based on location—are real, they cannot be fixed by complaining. He recounts his own experiences facing prejudice and tax law changes in the 1980s that affected his real estate business, noting that while he was a victim of these circumstances, no one forced him to sign mortgages or take specific risks; those were acts of free will. Therefore, standing and screaming at "the machine" for forty years results only in a substandard life because it focuses on uncontrollables rather than solutions. He emphasizes that the only path to a higher quality life is controlling what can be controlled, acknowledging that while unfairness exists, one must choose resilience over entitlement or martyrdom myths. Ultimately, Ramsey concludes that avoiding pitfalls like gambling as an escape mechanism and rejecting a sense of entitlement are crucial for long-term success. He warns against looking up to role models who drink away their problems or use gambling to solve issues, noting that such behaviors indicate a value set that is not working because the "fruit" is absent. The discussion underscores that while society may be rife with prejudice and broken systems, focusing on these grievances does not change outcomes. Instead of succumbing to feelings of unfairness or believing the system itself is the sole issue rather than one's own meritocratic efforts, individuals must adopt a mindset of action over complaint. By outlasting stereotypes and controlling their controllable actions, successful people can maintain their integrity without feeling guilty for having achieved more through hard work and service than others have done.
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What are some of the biggest psychological errors that people make when it comes to thinking about wealth and business building? What are the the traps that people fall into? Uh, you know, one of the ones I've been working on a lot with our entree leadership clients, which we coach about 10,000 small businesses in under the brand Entree Leadership that this book is in. As a matter of fact, it's in that same brand. and the uh and then of course we work with uh people on the financial side and so I've been and you know I did the book millionaire uh baby steps millionaires and is number one again teaching people you know here's what these millionaires look like we did a huge study on millionaires here's what they really look like and so in both of those cases I'm spending time with the wealthy or I'm spending time with a successful small business person in either case I'm uh appalled at how much damage the uh antisuccess movement has done to their psyche. I'm appalled that they've actually too many of them. They're they're very successful on almost every front. But when I look at them and say you haven't done anything wrong, you did everything right is why you're successful. You are not a moral repbate for becoming wealthy or becoming successful. Quite the opposite. I'm proud of you. You have done good stuff, my son, my daughter. I And I'm amazed at somebody that's got a $5 million net worth and I look at them and say that and their body language changes. Their shoulders go back, their head comes up because this communist negative uh anti-wealth, antisuccess stuff that is floating around has had an impact on them and and impacted their spirit. the hope stealers, I call them, has stolen a lot of these people's pride, their hope. Uh and uh and I I've started getting quite frankly pretty angry about uh these people that are spreading this negative thing about successful people because I got to tell you man I know a lot of billionaires not just millionaires and the percentage of wealthy people that are bad people is lower than the percentage of the population. Now there is bad people among them. But they did not get there by doing something wrong. By and large they got there by doing more right than anybody else did. They served more chicken. They served more pizza. They served more business help. They served more something than you did. Shut up. you know, and uh man, but they it's amazing to me to sit with a guy's got a 15 or $20 million net worth and a guy like me from a redneck, a hillbilly can look at him and go, "Dude, I'm proud of you. You did good." And he goes, "You know, I did." But nobody says that to him. Everybody says, "You're a dog. You're an idiot. You're a crook. You must have done something wrong. The eat the rich and all this stupid 1enters and Operation Wall Street's language and all that garbage that's out there. And it's having an impact on success is now getting a bad name, you know, and it didn't used to have a bad name in America. Yeah. Where do you think that's come from? Uh communist college professors. Okay. Yeah. Uh but if that's surely those communist college professors were were they in tenure when the people that you're speaking to were going through college? Yeah. Yeah. They've always been there. I mean honestly truthfully there's very little pe there's very few people that believe that communism is a better system than capitalism unless you're on a college campus. You can't find them. You can't even find them in communist countries that think it's better than capitalism. There's nothing more there's nothing more capitalistic than a good communist. Right. uh honestly. And so uh but this idea of equal wealth for unequal effort and call that fair, that's not fair. Guy works 60 hours, he should make more money, guy works six hours. That's not fair. You make the same money and you work. That's not fair. My kids used to say growing up, "Well, that that's not fair." I'm like, "Fair's where the Tilta World and the cotton candy is, kid." You know, you want some fair, go get some. Yeah, I I'm very grateful that where I'm from, the northeast of the UK, it's spit and sawdust, blue collar stuff. Yeah, there was no airs and graces. And in some ways for the British people that are listening and the Australians and maybe some of the Canadians and maybe the working-class Americans as well, uh that has some pains. Um because if you try and stray from the beaten path a lot of the time that's locked down on that's not exactly supported. You don't you're kind of in a role model desert a lot of the time. There's not that many people. I was having dinner with some Aussies and they said tall poppy syndrome. Correct. And uh I said well that's not an Aussie thing. That's an Aristotle thing. But okay. Yeah. Still it's a little older. It's a little older than Australia is. Yeah. Yeah. But still it's you know that poppy that you can't stick your head up. You must be cut down. Yes. And in envy and jealousy. Yeah. Yeah. Yeah. Yeah. Exactly. Um I I really didn't like that. But one of the things that it gave me was uh people like the sort of person I didn't want to be like. And avoiding pitfalls are almost as important as expediting successes. So, okay, I don't want his relationship with his wife. I don't want the way that he drinks his problems away. I don't want the fact that he seems to be using gambling as his get out of jail free card for all of the problems that he's got, etc., etc., etc. And uh it's not working. Your your your ideal your value set is not working. The fruit is not there. And you look at that and go, "Okay, I don't want to do that." Correct. But uh one of the things that it does give you is no hes or graces or expectations, no sense of um entitlement. Precisely correct. Precisely correct. There's no there's zero entitlement. What myth of martyrdom are you going to have? You weren't promised anything. And I think uh I wonder whether the anti- wealth movement in America is kind of like a bastard love child of the American dream from the 60s. That if you give people blue sky vision, white picket fence, this is the sort of world that you can get. It doesn't really matter where you started. You can ascend into the middle class and maybe even above. That's a big hope. And if you get to the stage where the world doesn't deliver the thing to you that you expected or that you hoped, uh even if by pretty much all metrics, Gen Z and millennials financially, even adjusted for inflation, are in a a pretty good spot, intergenerational competition theory, they compare themselves to where their parents were at their same age, their ability to access things like housing, and their uh level of comparison across the internet. Even if they are wealthy, they don't feel that wealthy. comparatively and that means well maybe there's something wrong with the world maybe this is unfair in some sort of way maybe the system is broken maybe work actually isn't the the solution to these problems maybe I shouldn't be resilient maybe the system is the issue as opposed to the meritocracy or my efforts that I've put in or the way that I've approached things yeah the I get the uh disenfranchised feeling I I understand that I've been there myself uh we were just talking about that but the um you know the mean old banks took Dave down, right? The mean old IRS took Dave down. The president changed the tax law and it affected the real estate business in the 80s big time. Shut down the entire SNL industry because of that. And so I was a victim. I was a victim. I was a victim of all these things. And uh and yet I was the one signed up for the trip. I no one made me sign those documents. No one made me sign those mortgages. No one made me do any of it. It was it was an act of my free stupid will. And so I had to kind of get through that. So if you're going to stand and scream at the machine, 40 years later, where are you? You're still standing there screaming at the machine and you've had 40 years of a substandard life. So it just doesn't work for me. It's it's impractical to me. the philosophy that philosophy is uh I'm gonna be a victim. I'm gonna scream about this. I deserve better. The the the system is broken. You can yell about all that if you want, but you're not controlling any of the controllables. Your only option to have a higher quality life is to control the controllables. And uh are are there is there racism? Yes. Is there sexism? Yes. Uh are people uh less likely to believe a guy that is bald than a guy who has a great head of hair? Yes. Uh there's baldism. And so uh there there's all kinds of things that can hold you back that are unfair. But I can't fix that since I choose not to have a hairpiece. I can't fix that. So I've get to do it anyway. I can stand and yell about how unfair it is that people that, you know, the people in the radio business thought because I was broadcasting from Nashville, I must not be wearing shoes and being a double wide because they had ignorant stereotypes of southern hillbillies, right? And they because they'd watched the Beverly Hillbillies when they were a child and thought that was real. And so, you know, ignorance ignorance is what all uh prejudice is based in. And and so are are those things real? Did I get did I get uh as I grew a 640 station network, did I get unfairly characterized as not being smart because I had a southern accent? Oh, like every day. And I can yell about that, but I don't think I'm going to change the stereotype of some Yankee in Cleveland, Ohio. The only thing I can do is go, you know, outlast him and then he ends up working for me later. 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