MY DAYS WRITING for HumbleDollar may be numbered. I recently started playing with Google’s Bard, OpenAI’s ChatGPT and Microsoft’s version of the ChatGPT artificial intelligence (AI) platform, and was curious to see how they might perform in providing basic financial guidance. Their answers were generally sensible and aligned with HumbleDollar’s approach—though also occasionally flawed.
You might think that AI can’t possibly replace articles penned by contributors, since the charm of HumbleDollar is the contributors’ personal stories.

IN THE SHORT TIME I’ve been writing for HumbleDollar, I’ve noticed that most readers and writers are either on the cusp of retirement or not too far along in retirement. Some have expressed a desire to find new careers, perhaps part-time and preferably more challenging than being a Walmart greeter or Home Depot helper. As they say, 60 is the new 40—still time for new ventures.
Life coaching is a profession that’s become more mainstream and,

I’M ABOUT TO MOVE OUT of my home for four or five months. Yeah, this takes some explaining.
In February 2020, when I was planning my move to Philadelphia, I wrote down 10 criteria I’d use to pick my new home. I recently re-read the article—and realized I broke the final two rules I’d laid down for myself.
To be sure, the home search didn’t go quite the way I planned. For starters, there was this little hiccup called the pandemic.

EVERY TIME I HEAR the sage advice to pay off a mortgage before retirement, I wince. Not only will I have a mortgage in retirement, but also I won’t even make my first payment until after I retire—just as my salary plummets to zero.
I hate going against the conventional wisdom. But I really have no choice. As an active duty military officer who, for the past 20-plus years, has had to move every few years,

MY HUSBAND AND I WERE late bloomers when it came to estate planning. Though we took care of the basics when we became parents, such as purchasing term life insurance and naming a guardian, we never had a professionally executed will and trust until 2016, when we were in our late 50s.
Observing my in-laws, now in their 80s, made us realize how important it was to get our own estate-planning house in order.

A RECENT CNBC SURVEY found that more than half of Americans don’t have an emergency fund to handle life’s financial curveballs. The survey also found that seniors are more likely to have an emergency fund than younger adults, and men are more likely to maintain a rainy-day fund than women.

I don’t know how I’d manage if I didn’t have an emergency fund. Now that I’m retired from fulltime work, I try to keep to a fixed budget,

SPRING TURNS A MAN’S fancy to… wait for it… outdoor power tools. Every April, I’d haul out the gas mower to prep it for the summer season. That meant a trip to the hardware store for oil, a spark plug and an air filter. Then I drove to the gas station for some new fuel.
For an hour, I would pretend that I understood the manly art of maintaining an internal combustion engine. I would gap and change the spark plug,

I GREW UP IN ENGLAND, with health-care coverage provided by the National Health Service, so I’m extremely sympathetic to people calling for “Medicare for All.” Still, I do wonder whether they realize that Medicare is neither cheap nor simple. My medical costs in 2021 were more than $10,000, with half of that for a single drug. And it would have been even more without the $3,000 a year kicked in by my former employer.

SELLING A HOUSE should be easy. Hire a realtor, find a buyer, the realtor takes a percentage and it’s a done deal. If only.

Try this version instead. Before we could sell our house in 2020, we had to fix a list of defects, including power washing the roof, having a dead tree removed, digging up an already drained oil tank and tearing up the pavers in the driveway to get at the tank.

I ONCE DABBLED IN the world of sales. I wasn’t very good at it. In 1997, I got a job at Schwan’s, driving one of those yellow trucks you see in neighborhoods all over the U.S. selling frozen treats, ice cream and a variety of food. I thought it would be a delivery and service job. But I found out during the orientation and training that there was an element of sales.

I read the books of motivational speaker Zig Ziglar in my free time and got some basic training in sales from the company.

A LONG TIME AGO, when I bought gas for my car, the attendant gave me a miniature jar of grape jelly. In fact, every time I’d fill up, I’d receive a little jar of jelly or a juice glass—back in 1964.

If I didn’t get jelly, I’d get a faux tiger’s tail, which I dangled from my gas tank. When that tiger tail was stolen, I hung its replacement from my rearview mirror. Yes,

AS A FAMILY MEDICINE physician associate, I frequently meet with patients early in the new year who are upset. The reason: They just learned their medications are no longer covered by their insurance or will cost significantly more than before. Many times, the insurance company will send them a letter providing other options to consider. I work with patients to find a generic substitute that isn’t as costly.
Several years ago, I had an elderly gentleman in our office one morning complaining that he was having difficulty urinating.

MY WIFE AND I VISITED Italy this year. We flew to Venice, where we stayed three days, and then hopped a train to Florence, where we spent the next five days. After that, we rented a car for three days and toured the Tuscany countryside, before catching a train to Rome for our final six days.
I learned a lot about Italy, but I also learned some things about myself. Here are 11 takeaways from our trip:
1.

LESS THAN HALF of Americans—46%—have tried to calculate how much they need to save to live comfortably in retirement, according to a 2022 survey by the Employee Benefit Research Institute. I often meet extremely bright people—doctors, residents, PhD students and professors—who say with a sheepish smile that they don’t understand the intricacies of their retirement plans.
For some, this lack of understanding is a choice. People who sense they haven’t saved enough, or any money at all,

WE HAVE A MEDICAL profession apparently wedded to the notion that quantity trumps quality. That’s why, although I have no problem with being dead, I have serious concerns about the process of becoming dead. I have no wish to linger for months attached to tubes, or to disappear for years into the mists of dementia.

I have few childhood memories, and I wouldn’t swear to the accuracy of those I have. Still, one from my teens has remained with me.