“SOME PEOPLE automatically sell the ‘winners’—stocks that go up—and hold on to their ‘losers’—stocks that go down—which is about as sensible as pulling out the flowers and watering the weeds,” argued Peter Lynch in his 1989 book One Up on Wall Street.
My father worked for Sears for 30 years, delivering washers, freezers and other appliances. Sears rewarded employees with stock, even delivery men like my dad. Over time, through splits and spin-offs,

HOW DO WE MEASURE societal wealth? And what triggered this thought?
I started pondering the issue early last year. I had a total left knee joint replacement in January 2023. Not long after, I was sitting in my living room with an ice pack on my knee, having just completed a strenuous set of stretches and exercises.
The room was being warmed by a modern gas fireplace, lit by a remote control. No wood to split,

IF YOU’VE READ MY articles, you know I don’t respond to readers’ comments very often. It’s not because I’m quiet or shy. Rather, it’s because I like to be thoughtful in my responses, rather than firing off a quick one- or two-sentence answer in the comments section.
That brings me to four comments that I’ve found myself pondering, often months or even years after the article appeared. Here’s my belated response to each.
Trading up.

FOR THE PAST FEW years, I’ve been on a Radiohead kick. For the uninitiated, Radiohead is an English rock band whose lead singer is Thom Yorke, known for his distinctive whining vocals—I mean that in a good way—and innovative songwriting.
As I read about Yorke, a quote from him leaped off the page: “When I was a kid, I always assumed that [fame] was going to answer something—fill a gap. And it does the absolute opposite.”
I immediately thought of the financial corollary.

THE FIRST ROCK concert I attended was The Byrds at Bowdoin College in Maine. We stayed nearby at a cabin in the woods. It was there that I had my first experience with marijuana. It was not a good experience—thank goodness. My drug days were short-lived.
One of the songs made famous by The Byrds is Turn! Turn! Turn! The song was written by Pete Seeger, who derived it from verses in the Bible.

IN TRYING TO FORETELL the economy’s direction, former Federal Reserve Chair Alan Greenspan has shown “a keen interest in men’s underwear,” according to CNN Business. “He sees underwear sales as a key economic predictor.”
This isn’t because Greenspan is preoccupied with nether garments. Rather, says an NPR reporter, he believes that “the garment that is most private is male underpants because nobody sees it except people like in the locker room.”
Yes, the men’s underwear index exists.

IN THEIR NEW BOOK The Missing Billionaires, Victor Haghani and James White make an interesting argument. Looking at the number of millionaires in the U.S. in 1900 and doing some math, they estimate that there should be many more billionaires today—thousands more, in fact—than there are. The question Haghani and White ask: Where did they go? Or, more specifically, where did their wealth go?
The authors consider possible explanations, including taxes—especially estate taxes—and the 1929 crash.

IN RECENT YEARS, I’ve confronted a choice: I could fund my solo Roth 401(k)—or I could use the dollars to cover the tax bill on a large Roth conversion. I wish I could do both. But after using my earned income to pay living expenses and make financial gifts, I don’t have the necessary cash.
My choice: Go for the big Roth conversion.
Why? In part, it’s because I’m focused on shrinking my traditional IRA before I turn age 75 and have to start taking required minimum distributions (RMDs),

MY ALL-TIME FAVORITE movie is the Coen brothers’ 2000 classic, O Brother, Where Art Thou? At one point, Holly Hunter’s character, Penelope, declares, “I’ve said my piece and I’ve counted to three.” Her estranged husband, played by George Clooney, understood from long experience that once she had “counted to three,” her mind couldn’t be changed.
Last summer, I wrote an article that explored the decisions my husband and I are working through about our retirement date and location.

YOU COULD CALL ME a 529 superfan. The college savings plans helped me put my two kids through college. Their state and federal tax advantages cut the exorbitant cost of college just enough so we didn’t have to borrow for our two kids’ education.
Which makes it surprising that I knew the man who created the 529 plan—but I didn’t realize he’d fathered them.
I covered Senator Bob Graham of Florida as a newspaper reporter in Washington in the 1990s,

HOW DO SOME INVESTORS end up in places they don’t belong? Where do they turn for information and guidance? Who do they talk to before making important financial decisions?
What follows are the results of my unscientific research, which was conducted in some of the finest and most respected centers of advanced learning anywhere.
Barroom seminars, your window on the world. Are we talking politics, investing, religion, world peace or other topics of paramount importance,

FOR MY BIRTHDAY this year, my wife gave me a card that declares, “Not Dead Yet.” That might sound morbid, but I laughed. The reason: My wife had misinterpreted something I used to say to colleagues at my final job.
When they saw me at the coffee machine, they’d often ask, “How are you doing, Dave?”
Instead of saying “fine,” I used to say, “I’m still breathing. Count your blessings. Blessing No. 1: I’m still breathing.”
In many cases,

MOM AND DAD WERE products of the Great Depression. I feel like it affected every single day of their lives. Despite their difficult upbringing, they made good financial decisions that allowed them to live comfortably. Part of it was because Dad worked for the same company for almost 42 years. His pension paid him more than I earned in my first job as an engineer.
When Mom died in August 2004, she was almost 84.

JANE IS A SINGLE woman in her 80s, sharp and friendly. She’s a former state employee with a solid retirement income. Unfortunately, she’s suffered some health issues in the past few years that have forced her to make serious changes.
I became aware of her issues when she came into the local AARP TaxAide site where I volunteer. She was the last client of the day, and the other scheduled client had rescheduled, so she got our full attention.

I HATE BEING IN DEBT. It makes me feel anxious and uncertain, as though my finances are out of my control. If I don’t pay all my bills in full every month, I feel trapped, and I’m endlessly restless until I get free.
I understand that other people manage their finances quite differently, and are happy to pay their bills in installments. Not me.
Years ago, I made a small bet on a minor thing.