COULD HUMBLEDOLLAR be replaced by a website chock-full of articles created using artificial intelligence? The short answer: It would be remarkably easy—and I fear readers wouldn’t object, especially if they didn’t know how the articles were generated.
To show what’s possible, I requested eight personal-finance articles from three freely available artificial intelligence (AI) tools, ChatGPT, Google’s Gemini and Microsoft’s Copilot. The first of those articles is published today, with the other seven appearing over the next four days.

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.

IN MY EARLY 50s, when retirement began looking like a viable option, I started thinking seriously about what my life might look like after I stopped working as an engineer at a nearby nuclear power plant. Earlier in my career, I’d imagined living off my pension and not working at all. But by my 50s, I wasn’t so sure. I felt retirement could be a time to explore other work opportunities.
My favorite hardware store is less than a mile from my house.

MY GRANDFATHER FALLS into the category of folks who are “not long remembered.” He died more than 75 years ago. None of his children or their spouses is alive. The one grandchild alive at the time of his death was only a few months old. It’s safe to say his memory has been all but erased, and yet his story offers a glimpse into what working life was like in the first half of the 1900s.

CALL IT THE GREAT unretirement. Hit by rising living costs and unexpected feelings of boredom, one out of eight retirees plan to return to work this year, according to a recent survey.
I’m one of them. Two and a half years after retiring from the corporate world, I’m headed back to work. I’ve accepted a position as lead writer for the CEO of a Fortune 200 technology company. I’ll be writing the CEO’s speeches,

MARCH MADNESS HAS descended on my family. I’m not just referring to the hoopla surrounding the annual NCAA college basketball tournament that runs from late March through early April. I mean the reckoning for our 36-year-old son, and his decision to switch careers and pursue his dream of becoming a professional sports bettor.   
For the 10 years after college graduation, Ryan taught high school math and coached basketball. But in between planning lectures,

MY HUSBAND SAYS I’LL never retire. He’s right. Now in my 78th year, I have no intention of stopping work altogether to devote myself to round-the-clock leisure. That sounds unappealing, especially since I plan to live well into my 90s, just like my great-grandmother.
Most of my friends opted to retire in their 60s. That includes my husband, Charlie. He retired at age 61 after 38 years as a nuclear engineer, all that time with the same company.

THIS ISN’T ANOTHER article about dreaming of retirement. Rather, it’s about dreaming in retirement.
I retired in 2017 after practicing criminal law in central Texas for almost four decades. It could be stressful at times. Before that, there were long years in college and law school.
College was relatively easygoing and enjoyable in the laid-back Austin of the 1970s, plus my major was sociology—a world apart from those in pre-med,

I LED A RETIREMENT seminar some years ago at a large manufacturing company. During the question-and-answer session that followed my presentation, a 60-something welder told the group he’d never retire. I asked why. His response: All his friends who’d retired before him were already dead, and he didn’t want to follow in their footsteps.
What he said resonated with me—because I knew someone who suffered a similar fate. Gino was a client back in my banking days.

THE FIRST TIME I GOT laid off, I was working in an insurance company’s training and development department. I’d been working in another department at the company when I saw a job posting for the position. The training department was looking for someone with subject matter expertise and experience in teaching.
At that point, I’d been working in property and casualty underwriting for 14 years. On top of that, I was a certified instructor for the Dale Carnegie course in public speaking.

FLAPJACKS IS LITERALLY on the other side of the tracks. The place is a throwback to the diners of the 1950s, when waitresses wore white aprons and took orders on little green pads, and where the red vinyl seats were cracked.
Charlie and me. I’ve been meeting Charlie at Flapjacks for weekly pancake breakfasts since I partially retired seven years ago. I spot him in our back booth and slide in across from him.

“WE CANNOT GET RICH doing dentistry, but we can get rich investing what we make in dentistry.” A nationally recognized lecturer on dental-practice management shared that piece of advice with me some 40 years ago.
I’d been out of dental school for a year when Dr. Dick Klein spoke at our local dental society’s annual meeting. The meeting’s organizer was a friend. He asked if my wife and I would take Klein and his wife out to dinner after his presentation.

CAN IT REALLY BE TWO years since I wrote about sending my twins off to college? One is a chemistry major, midway through her junior year. Meanwhile, for her twin sister, the artist, there have been big changes in her college trajectory.
My initial criteria for college selections included published statistics on cost, likelihood of admission, timely graduation and low rates of loan default. I took this last stat as a reasonable proxy for post-college success.

SIX YEARS AGO, I MADE a big life decision: I opted to scale back my work week with an eye to easing into early retirement.
I stayed in the same role, but reduced my hours and responsibilities, took a proportional pay cut, and bid farewell to potential future promotions. Essentially, my human capital shifted from a growth investment to an immediate-fixed annuity for the remainder of my part-time employment.
The change turned out to be far more fulfilling than I’d anticipated.

AFTER MY COLLEGE freshman year in engineering, I was hired for a part-time summer job by a civil engineering firm in my home town. The office was in an upscale building where a lot of respectable businesses were headquartered. The company had an impressive name. But after starting, I discovered it was just a one-man show. Mr. Jones was the owner. I became his sole employee.
Jones was probably in his mid-70s. He’d headed up his own company for decades.