November 25, 2025

Nine Mistakes Wealthy People Make

8 minutes

Episode 359 – A few weeks ago we took an in-depth look at some of the things wealthy people understand that the rest of us tend to miss. Today, we’ll take a look at the opposite: some financial mistakes that even wealthy people tend to make, and how we can help avoid them.

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Transcript of Podcast Episode 359

Hello, this is Bill Rainaldi, with another edition of Security Mutual’s SML Planning Minute. In today’s episode: nine mistakes wealthy people make.

A few weeks ago, we took an in-depth look at some of the things affluent people understand that the rest of us seem to miss. But even successful, well-educated people do some dumb things. Today, we’ll cover the exact opposite of what we did before: some financial mistakes that even wealthy people tend to make. Here are nine of them:

Putting too much money into a single investment. Diversification is one of the cardinal rules of investing, but many wealthy people tend to break it. And it’s understandable why. So many of the ultra-rich became that way by starting, or investing in, just one or a handful of companies. Elon Musk and Jeff Bezos are great examples of this. At some point, putting too much money into a single investment just creates unnecessary risk. Some employees at companies like Enron and Lehman Brothers put all their retirement savings in their company stock. It worked spectacularly—for a while—but it eventually became almost worthless in a very short time. [1] Very few investors enjoy the measure of success that Musk and Bezos experienced.

They can be underinsured. It doesn’t really matter how wealthy you are, people make mistakes with their insurance across the board. If you don’t have enough homeowner’s insurance, it could end up costing you millions if you live in a valuable home.[2] And if you’re concerned about your children and grandchildren, life insurance can be an important and efficient way to transfer your wealth to future generations.

They have too much personal real estate. Some wealthy people tend to have too many expensive homes in remote places that they rarely visit. And they can be a significant cash drain. If you don’t use the place frequently, it may not be worth holding onto it. If you want to vacation in some unusual places, sometimes it may be better to rent.[3] Or if you insist on keeping the place, maybe you should consider renting it out when you’re not using it.

Trying to keep up with their peers. It’s human nature, and the wealthy aren’t exempt from keeping up with the Joneses. When we see our friends living it up, it tends to make us want to do the same. And if we’re not careful, it could mean significantly less savings and too much debt.[4]

Lack of liquidity. Private equity is all the rage these days, but there’s a downside. Some people tend to be too optimistic when they buy into illiquid assets. The fact is that for a variety of reasons, most of them don’t work out, even if it seems like a great idea. And if it doesn’t work out, it can be a drag on your finances for years.[5]

Fear of missing out, or “FOMO.” It seems that no one is exempt from this. Believe it or not, a recent study suggested that the wealthy are actually among the worst offenders.[6] Rich people may think they know better than the average investor. But they can be just as susceptible to media hype and/or greed. It pays to keep a long-term perspective and remember the fundamentals.

Neglecting estate planning. What do Howard Hughes, Prince, Sonny Bono and Pablo Picasso have in common? They all died with a lot of money but without a will.[7] It seems that the wealthy should all have done at least some rudimentary estate planning. But that’s not always the case.Whether you have a lot of money or not, you probably want to make sure it goes to the people or charitable organizations you care the most about. But if you don’t have an estate plan, you give up your right to decide these things. And it’s not just a will. It can be a succession plan for your business or an advance medical directive.[8]

Lifestyle creep. There is a tendency among the wealthy: the more you make, the more you end up spending on things like travel, fancy meals and transportation. There are so many examples of people—such as Michael Jackson or Lindsay Lohan—who overdid it and paid the price later on. The truth is that it’s easy to increase your lifestyle, but once you’re there, it’s much harder to bring it back down. If you’re not careful, spending habits can become unsustainable for just about anybody.[9]

Not understanding that wealth is about more than money. Newsflash: some of the richest people in the world are terribly unhappy. In the words of author Riley Clendenin, “True financial success isn’t just about accumulating wealth—it’s about using money as a tool to build a meaningful, balanced life. The smartest investors understand that their financial portfolio is only one part of their overall wealth, and they invest just as much in their health, personal growth, and happiness as they do in their bank accounts.”[10]

The ultra-wealthy certainly have the benefit of a bigger cushion when they make a financial error. And they all make mistakes, some big, some little. But the rest of us can also learn something from the errors that wealthy people tend to make, and how to avoid them.

[1] Clendenin, Riley. “Millionaire Blunders—13 Costly Mistakes Even Wealthy Investors Make.” Msn.com. https://www.msn.com/en-us/money/investment/millionaire-blunders-13-costly-mistakes-even-wealthy-investors-make/ss-AA1BaDTO#image=3 (accessed October 22, 2025).

[2] Maranjian, Selena. “7 Financial and Retirement Mistakes Even the Wealthy Make.” fool.com. https://www.fool.com/retirement/2024/04/28/7-financial-mistakes-even-the-wealthy-make/ (accessed October 22, 2025).

[3] Sergeant, Jacqueline. “The Mistakes Rich People Make–And How To Avoid Them.” www.fa-mag.com. https://www.fa-mag.com/news/how-to-avoid-these-common-mistakes-of-the-wealthy-83682.html (accessed October 22, 2025).

[4] Maranjian, Selena. “7 Financial and Retirement Mistakes Even the Wealthy Make.” fool.com. https://www.fool.com/retirement/2024/04/28/7-financial-mistakes-even-the-wealthy-make/ (accessed October 22, 2025).

[5] Sergeant, Jacqueline. “The Mistakes Rich People Make–And How To Avoid Them.” fa-mag.com. https://www.fa-mag.com/news/how-to-avoid-these-common-mistakes-of-the-wealthy-83682.html (accessed October 22, 2025).

[6] Clendenin, Riley. “Millionaire Blunders—13 Costly Mistakes Even Wealthy Investors Make.” Msn.com. https://www.msn.com/en-us/money/investment/millionaire-blunders-13-costly-mistakes-even-wealthy-investors-make/ss-AA1BaDTO#image=3 (accessed October 22, 2025).

[7] Phillips Erb, Kelly. “17 Famous People Who Died Without A Will.” Forbes.com. https://www.forbes.com/sites/kellyphillipserb/2016/04/27/17-famous-people-who-died-without-a-will/ accessed October 22, 2025).

[8] Maranjian, Selena. “7 Financial and Retirement Mistakes Even the Wealthy Make.” fool.com. https://www.fool.com/retirement/2024/04/28/7-financial-mistakes-even-the-wealthy-make/ (accessed October 22, 2025).

[9] Sergeant, Jacqueline. “The Mistakes Rich People Make–And How To Avoid Them.” fa-mag.com. https://www.fa-mag.com/news/how-to-avoid-these-common-mistakes-of-the-wealthy-83682.html (accessed October 22, 2025).

[10] Clendenin, Riley. “Millionaire Blunders—13 Costly Mistakes Even Wealthy Investors Make.” Msn.com. https://www.msn.com/en-us/money/investment/millionaire-blunders-13-costly-mistakes-even-wealthy-investors-make/ss-AA1BaDTO#image=3 (accessed October 22, 2025).

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