THERE ARE TWO TYPES of mistake I make: those that are unintentional and those where I should have known what would happen.
After an unintentional mistake, I’m perplexed by what went wrong. I might say to myself “I’ll never do that again” or perhaps “what the heck just happened?” These are genuine mistakes, and I try to learn from them.
By contrast, stupid mistakes are those that I should have known would occur. No matter how many college degrees we have or how many years on the job,

ONE SPRING DAY IN 2022, an elderly woman entered Paris’s Picasso Museum to see a new exhibit. Among the items on display was a decorative blue jacket, which was positioned on a wall next to a portrait of Picasso.
The woman liked the look of the jacket, so she took it down from its hook, put it in her bag and quietly walked out the front door. Only later did the museum discover the theft,

I’VE SPENT MUCH OF MY life trying to better understand the world, especially the financial world. But I wonder whether I should have spent more of that time trying to better understand myself.
Why do some financial situations scare us, while others leave us unperturbed? Why do we spend time and money in ways we later regret? Why do we find our bad habits so difficult to change? Why do we admire some folks,

LIKE OTHER FOLLOWERS of HumbleDollar, I look forward to Jonathan’s Saturday articles. I have to admit that my interest has been heightened by his cancer diagnosis. Not many folks would have the courage to write about what’s going through their mind when they’re fighting for their life. We don’t often get this kind of insight into someone’s life.
Jonathan has probably received a lot of advice about treatment plans and the doctors he should see.

WE’VE BEEN TAKING stock of our nomadic life. We’re quite happy living as we are. But we’re also conscious that things could change at any time for multiple reasons, and we’re ready to shift gears if needed.
We aren’t exactly “living the dream”—because being nomadic was never our dream. We hadn’t even thought about it until a few months before we started our travels. We officially uprooted ourselves—meaning we sold our Houston home—after we’d been away from the place for most of the first year of my retirement.

HUMANS HAVE ALWAYS celebrated the good times in their lives. These can be massive occasions, such as New Year’s Eve in New York City’s Times Square, or small and personal, such as birthdays. Celebrating is good. But what happens when it’s not?
Adults tend to celebrate with alcohol. For people like me, who lean toward shyness, alcohol can allow us to let loose. It feels good. We smile. People smile back. All is good.

IN THE FINANCIAL world, some topics are serious, others not so much. Since it’s the holiday season, it seems appropriate to look back at some of the past year’s lighter moments.
No joke. In 2019, artist Maurizio Cattelan unveiled a collection he called Comedian. The item that received the most attention: a sculpture that consisted only of a banana duct-taped to a wall. The banana gained fame when it sold at a Miami auction for $120,000.

IT’S SEVEN MONTHS since I received my terminal diagnosis. Cancer is now the reality that looms over each day, and it’s been a rocky road, though the latest abdomen scan suggests I’ll be around for a while longer.
Where’s my head at? Here are four questions I’ve been asking myself—questions, I suspect, that might also be interesting to those who aren’t facing a terminal diagnosis.
1. Am I afraid of dying? No,

WE SUFFER LOSSES throughout our life. During our youth, we might leave old chums behind when our family starts fresh in a new town or when we go away to college. Later, a job loss or a divorce could leave us drained both financially and emotionally. But for most of us, our senior years are when loss hits hardest.
Our body is often the first casualty, especially the face we see in the mirror each morning.

DURING A PROJECT meeting at my old employer, a member of our team was constantly raising questions without offering any solutions. Afterwards, the team leader commented, “This guy always thinks his cup is half empty. Nothing will ever satisfy him.”
We’ve all known such people. Is there anything wrong with their attitude? It depends. My boss told me during my first week, “Never be satisfied with the status quo. Find ways to improve everything.

I SPENT MANY HOURS reading articles and books about retirement before I actually retired. I knew I’d retire eventually because of how often I found myself out of work. Studying retirement became one more thing I needed to do so I could be successful.
Under the category of retirement, grandparenting was a frequent subject. This is understandable since many retirees are or soon become grandparents.
My situation is different. My special-needs son will not get married or have kids.

EARLY LAST WEEK, The Wall Street Journal ran an article with the headline “Why This Frothy Market Has Me Scared.” The author cited a number of indicators that have him worried, including a survey of investor optimism that’s at a 35-year high. Investors, the Journal said, are feeling “euphoric,” and that’s often a bad sign.
So, as we head into year-end, it’s worth taking stock of where things stand. The stock market has returned nearly 25% so far this year.

I’M WRAPPING UP MY final big investment. Going into it, I knew it would lose money, unleash unwanted disruption and chew up time when it’s never been more precious—and yet I still went ahead.
As readers might recall, last year, Elaine and I remodeled the kitchen in our Philadelphia home. This year, we decided we’d revamp the upstairs bathroom, despite my cancer diagnosis and the forecast that I might live just 12 more months.

AT LEAST ONCE A YEAR, I watch the hilarious short YouTube clip by personal-finance author JL Collins. If you aren’t around small children and can handle liberal use of America’s favorite four-letter word, check it out. Some may recognize it as a parody of actor John Goodman’s soliloquy from the film The Gambler starring Mark Wahlberg.
The clip, however, is more than just entertaining. Its content is what keeps me and, judging from the half-million views,

SIPPING MORNING coffee on the porch of my 40-year-old aluminum box in the Sonoran Desert, I’m pondering the cost of housing.
My affordable unit sits on cement piers at the end of a street within an age-restricted park, at the sparsely populated edge of Tucson. Few jobs exist nearby. Civic amenities are modest. Summer weather is challenging, with heat, thunderstorms and seasonal rattlesnakes. Still, these conditions have created a financially comfortable place for a retiree to live.