A reader in their 70s wrote to MarketWatch's money-advice column with a question that a lot of Americans over a certain age have probably asked themselves: why do people keep making the same avoidable financial mistakes?
The reader specifically cited two examples: accumulating credit-card debt and failing to plan for retirement. The column's answer centered on a simple test that the television judge Judy Sheindlin uses in nearly every episode of her courtroom show. The advice: before you lend money or take on a financial obligation, ask whether you could afford to lose it. If you could not, do not do it. The column framed the principle as a way to avoid the kinds of decisions people regret later, and pointed readers toward watching Judge Judy as a practical education in human behavior around money.
The reader's question landed during a period when household finances are under visible strain. Credit-card debt in the United States has been climbing, and the Federal Reserve's elevated interest rates since 2022 have made carrying a balance far more expensive than it was during the low-rate years of the previous decade. For a household carrying a balance, the annual percentage rate on many cards has been running above 20 percent, which means a few thousand dollars of revolving debt can cost hundreds of dollars a year in interest alone. Retirement planning has its own pressures: the shift from pensions to 401(k)s over the past several decades put the burden of saving on workers, and many households reach their 50s and 60s with less set aside than they expected.
None of that is new. What the MarketWatch letter illustrates is a frustration that runs in both directions. Older Americans who saved carefully look at younger relatives and see decisions they consider obviously unwise. Younger Americans look at housing costs, student loans and wages that have not kept pace with prices and see a game that changed the rules on them. The column's advice, though, does not require either side to win that argument. It asks a single question about whether a person can absorb a loss before they take a risk.
Judge Judy's courtroom is one of the most-watched programs on American television, and its cases are almost always small-dollar disputes between people who lent money, co-signed loans or made handshake deals that went bad. The judge's recurring line in those cases is to ask whether the person could afford to lose what they handed over. It is not sophisticated financial planning, and the advice column does not present it as such. It is a filter that catches the decisions people make when they are being generous, optimistic or pressured, and it catches them before the money is gone.
The letter also points at something the financial-advice industry does not always like to admit: most personal finance failures are not complicated. They are credit-card balances that were not paid off, emergency funds that were never built, and retirement accounts that were never opened. The fixes are boring and require discipline over years, which is why the mistakes repeat. A reader in their 70s who watched a generation of relatives make those mistakes has seen the pattern up close, and the column's response treats the question as a reasonable one rather than a complaint.
MarketWatch has published a long run of reader letters on retirement, debt and family money, and its advice column regularly fields questions from people dealing with the consequences of financial decisions made by spouses, adult children and aging parents. Wednesday's letter is in that tradition. The advice it produced is short enough to write on an index card, and the source it cites is on television most afternoons.
Our Take
There is a reason a courtroom show built on small-claims disputes has been on the air for decades, and it is not the bailiff. Judge Judy works because the cases are recognizable. Every viewer has a cousin who co-signed a car loan, a neighbor who ran up a card on a vacation, or a friend who promised to pay back a loan and then stopped answering the phone. The show is a weekly reminder that most financial disasters are not caused by Wall Street or the Federal Reserve or a once-in-a-century crisis. They are caused by people deciding in a moment that the money does not matter, and then discovering that it does.
The reader who wrote to MarketWatch is asking why the lesson does not stick. Part of the answer is that the country's financial culture has spent decades telling people to buy now and figure it out later. Credit is marketed as a convenience and a reward, not as a loan with a clock on it. Retirement is sold as something that will work itself out. And when the bill comes due, the people who warned about it get asked why they are being negative.
Here is the part that should frustrate every American who saved: the same institutions that profit from the mistakes then get bailed out when the system wobbles, while the household that carried the balance eats the interest. The advice in Wednesday's column is not going to fix that. But it will keep a family out of court, and these days that is worth something. The question for readers is simple: what is the one decision in your own finances that you would make differently if you asked the Judge Judy question first?
