AS I READ ARTICLES and comments on HumbleDollar, I see concerns about taxes, Medicare, Social Security, health care costs, college, inflation, investing—and the anxiety caused by the complexity of it all. I also see very different views on what’s earned and deserved. In some ways, it’s about what we consider fair.

I suspect the HumbleDollar community is more aware and more involved in their overall financial life than the majority of Americans,

I’M DOING RELATIVELY well—and therein lies the problem. No, it isn’t the “doing well” part that’s the issue. Rather, the problem lies with that all-corrupting word “relatively.”
We’re constantly reminded of how we stack up against others. Early in life, that can be useful. If we aren’t cut out to be professional athletes, effective leaders, academic stars or market-beating investors—this last one would include almost all of us—it’s good to find that out, so we don’t spend countless years pursuing goals we’re unlikely to achieve.

WORD ON THE STREET is that, if you want to use money to make yourself happy, you should buy experiences rather than things.
In principle, I couldn’t agree more.
There is, however, one kind of experience that I see touted both in the media and on social media that I don’t think reflects money well spent: the expensive family vacation to a distant destination. This status-symbol experience, complete with selfies at ritzy hotels, is supposedly designed to create priceless memories.

SMART GUYS CAN DO some really dumb things. Those dumb things include behavior that seems logical, but is often a sign of addiction.
The Merriam-Webster dictionary defines addiction as “a compulsive, chronic, physiological or psychological need for a habit-forming substance, behavior, or activity having harmful physical, psychological, or social effects.” Addictions come in many flavors. Some are benign, some more malignant. Many involve repeating a pattern or behavior in hopes of achieving a different outcome.

SAMURAI WERE EMPLOYED by feudal lords in Japan. They were skilled in the art of combat and highly trained—the best of the best.
A ronin—meaning a “drifter” or “wanderer”—was a samurai who’d left his clan, usually when his master died. Upon leaving, he was free to use his skills to seek similar employment elsewhere or even to choose a completely different profession. A ronin then relied entirely on himself and his skills to get by.

MY FATHER RAISED ME to think that, if I set my mind to it, I could do just about anything. He said that concentrated focus and drive would allow me to reach my dreams, and that there was rarely a time when I should settle for average.
Maybe it’s no great surprise, then, that I hate being average. I’m above average in smarts, the kind that gets you a side order of noogies as a second grader.

OPPOSITES MAY ATTRACT—but that doesn’t always make for a happy financial relationship. For instance, tightwads and spendthrifts often marry, each hoping the other will change his or her ways or perhaps provide needed balance.
But that, of course, can lead to conflict—and couples may struggle to negotiate their differences. They wind up having the same argument over and over, and nothing’s accomplished until they listen to each other and try to find common ground.

I’D PLANNED CAREFULLY. All I needed was to get from the Oslo airport to an Airbnb about eight miles away. It was 12 minutes by bus, the host firmly proclaimed.
I’d disembarked from a ship early that morning in Kirkenes, near the Russian border. I’d paid about $20 for a bus ride to the nearest airport, and then flown 850 miles to Oslo. Now, I was ready for the local bus and that 12-minute ride to the Airbnb.

THE CENTRAL Intelligence Agency knows a thing or two about gathering information. That’s why a CIA publication titled The Psychology of Intelligence Analysis is, in my opinion, a valuable resource for investors.
Of particular note is a section titled, “Do You Really Need More Information?” It offers this counterintuitive finding: To make sound judgments, some amount of information is necessary. But beyond a certain point, gathering more data doesn’t always lead to better decisions.

I WROTE AN ARTICLE in 2019 titled Mercedes and Me. It was about my 52-year quest to fulfill a promise to my father—one I’m sure he never even remembered. My promise: to buy a Mercedes, a vehicle my father sold for many years but could never afford, even at dealer cost.

In 2014, after 10 years of diligent saving, I achieved my goal. I paid $60,000 in cash to make good on my promise and to fulfill my dream.

I WROTE RECENTLY about my wife’s lifelong love of traveling, and of my resolve to get in step with her as she resumes her rambles. To that end, earlier this summer, I drove our family to Charleston, South Carolina, to attend the retirement ceremony for my cousin Chris, and to see a bit of the city, to boot.
As our departure time approached, we learned that the original schedule for retirement day had been altered.

WHAT’S THE PURPOSE of life? Is it to die with as much money as possible or, as magazine publisher Malcolm Forbes was quoted as saying, “He who dies with the most toys, wins”? An intriguing and provocative book, Die With Zero, says no.
The book’s author is Bill Perkins, a successful energy trader. In it, he argues that the purpose of life is to accumulate as many fulfilling experiences as possible,

MY WIFE HAS PLANS for retirement. Travel plans. For too many years, she’s lived a mostly travel-free life. We’ve logged just a few short excursions to hither and yon.
Yes, there have been reasons for this dearth of travel that were largely beyond our control. But her biggest obstacle has been—and continues to be—me. I’m mostly a homebody, and I’ve been reluctant to change my ways.
My wife didn’t choose to love traveling. Rather,

IN THE WORLD OF personal finance, there’s no shortage of formulas and frameworks for making financial decisions. But it’s also important, I think, to see these as guidelines rather than as rules. Consider the textbook view of money and happiness.
What the research says is that, all else being equal, we should opt to spend money on experiences rather than things. Let’s say the choice is between spending $1,000 on a new watch or on a weekend away.

A TIDAL WAVE OF workers quit the corporate world in recent years, starting an earlier-than-planned retirement. I can relate—because I did the same thing.
One reason these people left: Their psychological needs and values weren’t being met at work. We all want a sense that we’re accomplishing something important. We want to feel valued and respected by the company we work for, and we want a sense of autonomy and control.
What we don’t want is to work for bad bosses in a toxic environment.