To try to keep up with the 21st century, I recently started to use ChatGPT.
I have an excellent financial advisor, who is a Certified Financial Planner, and for over 40 years, I have also made a lot of investment decisions on a “do-it-yourself” basis. I have read the Humble Dollar for years as well.
An early request to ChatGPT was to develop a training plan for me to help me revive a long-neglected hobby. I was very pleased with the analysis and the specific suggestions that ChatGPT provided to me.

Our children know we are not your typical retirees when it comes to finances. I’m sure they figured that out from our funding eleven 529 plans, gifts and more often than not, picking up the check when families go out to eat, but that’s all they know. 
They have no idea of our income, no knowledge of our investments-what kind, or how much. They, of course, know we own two homes, but not our net worth. 

I don’t use Instagram. I drive a 21 year old car. Many of my clothes are from the charity shop. I really do spend most of life completely oblivious as to how I compare to others.
But my guilty pleasures are the “See the average net worth for Australians….” articles. It’s reassuring to think that you’re going better than average. That the hard work and moderate spending have actually led you to a healthy financial position.

I WAS RECENTLY asked about strategies that high earners can use to reduce their tax bill.
Most people know the usual options. They contribute to a 401(k), fund a health savings account or make a Roth IRA contribution through the backdoor method. Business owners may have additional opportunities through retirement plans and business structures.
But there’s another strategy worth knowing about: the Mega Backdoor Roth (MBDR).
The MBDR allows some workers to put far more money into Roth accounts than the usual contribution limits permit.

A WHILE BACK, I was speaking with a fellow who had recently retired. He shared this observation, only half-jokingly: “Working was easy,” he said. What he meant was that financial management during our working years is more straightforward than it is in retirement. We earn and save and hope that our savings grow. But when we get to retirement, it becomes more complicated to know exactly how to manage those savings.
In the 1950s,

In April 2025, I watched the movie Four Weddings and a Funeral for the umpteenth time. I found tears rolling down my cheeks as one of the characters read the poem “Funeral Blues,” written by W.H. Auden, at the memorial service for his partner. What sparked the tears? The poem tells of the emotional devastation of losing a loved one. But for me, it highlighted my distress at knowing that all that brings me happiness—Elaine,

Judging by all the buzz on social media—and the emails from the youngsters in my family—the SpaceX IPO appears to be the first investment in history with no downside.
The case seems straightforward:

Near-monopoly space launch provider.
Starlink.
Defense contracts in a tense world where every military is arming itself to the hilt.
AI somehow.
Mars.

Like flag pins and patriotic hats, accepting SpaceX’s invitation to participate in the IPO appears to be an American civic duty.

Over the years, Suzie and I have approached clothing from fundamentally different financial philosophies. The clearest indicator lives in our walk-in dressing room: 36 feet of hanging rails for her, approximately four feet for me. We also share two 12-drawer dressers. Four of those drawers are mine. I’m told this is generous.
Then there is one of three spare bedrooms, currently serving less as a guest room and more as a textile archive, complete with vacuum-packed clothing.

There are people who pass through our lives briefly, yet leave marks that time never erases. I briefly mentioned him in last week’s article, but his story deserves its own telling.
He was a teacher named Richard Hunter, though to nearly everyone at Bryanston School in Dorset, England, he was simply known as “Bunty.”
I arrived at boarding school at the age of ten. To some boys it may have been an adventure, but for others,

I have written before that I could look at your grocery cart and find money to save and invest. Some people thought I was joking, but I’m not. My point isn’t about groceries, it’s really about finding money to save and invest, even small amounts over time. Groceries are just one example. I suppose I am promoting a bit of frugality and financial discipline in very modest ways. 
Initially my conclusion about groceries was based on many hours of observation,

“The window to make advantaged Roth IRA conversions closes in 2028” was the hook my friend Sherry got from the salesman at the free steak dinner. Scheduling an appointment with him was Sherry being reeled in.  Sherry asked if I would go with her to a meeting with the guy to discuss the proposal.
The  first thing I had to do was figure out what an “advantaged Roth conversion” even was. Feel free to correct me if I am wrong,

I like to think of myself as a decent planner, and when I spend money I like to make sure I’m getting value. Both qualities were very much on display last August when I booked a trip to Valencia, Spain, to witness a total solar eclipse.
The planning had started years earlier. Solar eclipses are predictable to the minute centuries in advance, and I’d known about the Spanish eclipse long before it was on anyone else’s radar.

Do you know Peter Cancro? Peter is 69 years old and someone to be admired, someone who started out very ordinary and in one transaction became a new US billionaire, around $4.9 billion netted from selling his business. 
I greatly admire such people, I wish I was as ambitious, a risk taker and committed to success. Sure he had help along the way, notably his high school football coach who was also a banker, but he started this journey at age 14 and took the big risk at age 17. 

JONATHAN CLEMENTS’S final book was released this week. Titled Money and Me, it traces the arc of Jonathan’s nearly four-decade career as a personal finance columnist.
Money and Me starts with the story of a man named George Cope, who was a nineteenth century tobacco baron. At the time of his death in 1888, Cope was one of Britain’s richest men. But within just two generations, his fortune was gone.

WHEN I STARTED writing for HumbleDollar, Jonathan gave me some simple but important advice: “Don’t brag about your financial situation. You want readers to like you.” Perhaps that’s one of the reasons he named his financial site HumbleDollar.
I try to follow this advice not only regarding money, but in other aspects of my life. I know how fleeting things can be—especially when it comes to health. Life can change on a dime. It can humble you.