Jonathan Clements

MAY WAS AN ECLECTIC month for HumbleDollar, with a wide array of articles published. But judging by the 10 most popular pieces, readers were intrigued:

When interest rates headed higher in 2022, Tony Wilson moved almost all his portfolio into money market funds. He plans to leave the money there—until there’s a major market correction.
Planning your estate? Adam Grossman lists five key issues to consider before you commit to any complicated estate-planning strategies.

IF 20-SOMETHINGS ASK me for financial advice, I suggest getting a job right out of college and saving like crazy, so they quickly get themselves on the fast track to financial freedom.
If 60-somethings ask me for advice, I advocate a phased retirement, seeking part-time work in their initial retirement years and, if they enjoy it, perhaps keeping it up into their 70s.
Yeah, I know, I sound like a real killjoy. My advice raises an obvious question: Is there ever a time when we should cut ourselves some slack and not have a job?

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.

OUR RETIREMENT INCOME is built on a slew of financial products and strategies. But we should think less about the gory details of each—and more about the role they play in our overall retirement finances.
The fact is, while each of us comes to retirement with different levels of wealth and different desires, we all want both a sense of financial security today and confidence about our financial future. How can we best meet those twin goals?

IN RECENT YEARS, I’ve confronted a choice: I could fund my solo Roth 401(k)—or I could use the dollars to cover the tax bill on a large Roth conversion. I wish I could do both. But after using my earned income to pay living expenses and make financial gifts, I don’t have the necessary cash.
My choice: Go for the big Roth conversion.
Why? In part, it’s because I’m focused on shrinking my traditional IRA before I turn age 75 and have to start taking required minimum distributions (RMDs),

SUPPOSE YOU KNEW you’d live until at least age 90. How would that change your thinking about retirement?
It seems most of us focus less on the possibility of a long life and more on the risk of an early death. This grim view is buttressed by endless anecdotal evidence—celebrities who pass away in their 40s and 50s, terrible accidents that take multiple lives, old classmates and colleagues who die at tragically young ages.

I HAVE NO IDEA HOW stocks will perform this year or next. But I have full confidence that a globally diversified stock portfolio will fare just fine over the decades ahead.
My optimism, it seems, isn’t shared by many HumbleDollar readers, who fear we’re facing some rough years for the economy and the stock market. How do I justify my optimism about the long term? Here are five reasons.
1. Heads I win,

IF YOU THINK IT’S irritating to debate an issue with folks who have already made up their mind, there’s one situation that’s even worse: debating an issue with those who have not only made up their mind, but also gone ahead and acted on their decision—especially if that decision is irreversible.
And, yes, many retirement decisions are irreversible.
Take issues such as when to claim Social Security, whether to take pension payments or a lump sum,

I HAVE ONLY A VAGUE idea of how much I spend. I figured it was time to find out.
I’ve never budgeted because I’ve never seen the need. From my early 20s until three-plus years ago, I kept an iron grip on my wallet, spending with the utmost care and saving great heaps of money. Over those 35 years of fierce frugality, I don’t feel like I deprived myself, but I do feel like I thought about money far too much—and tracking my spending would only have made that worse.

WHEN WE SPEND MONEY, we’re looking to get something in return. But what? Forget classic budgeting categories like housing, food, utilities, insurance and entertainment. Instead, suppose we used a completely different classification system—one that reflected the physical, social and emotional benefits we garner.
The list below is, I suspect, far from complete, especially when I compare it to the 16 basic desires developed by psychologist Steven Reiss. Moreover, as you’ll see, while an expenditure might fall predominantly into one category,

LET’S START WITH a contention that’ll get nods of agreement from the vast majority of HumbleDollar readers: Your portfolio’s core holdings should be total market index funds.
But which funds?
Frankly, the differences among the most popular total market index funds are modest and perhaps not worth worrying about. Still, worry we do. As I see it, which ones you choose depend on what you’re most focused on. Here are four key considerations:
Low cost.

HUMBLEDOLLAR HELD its inaugural meetup on March 4 in Philadelphia. I initially expected half-a-dozen attendees. We had 25. One couple came all the way from Virginia, while another gentleman traveled down from Long Island, New York.
Lots of pizza, beer and wine were consumed, and folks seemed to enjoy meeting their fellow readers. I spent a little time with everybody in attendance and, by the end, was hoarse after three hours of talking.

HAVE YOU EVER HAD one of those debates where you come up with the winning argument—hours later, long after everybody has gone home?
Among the many financial topics that cause confusion, extra-principal payments on a mortgage deserve a special mention. For decades, I feel like I’ve been trying to stamp out the nonsense that’s spouted on this topic, and I think I finally have the answer. Maybe.
The chief reason for all the confusion is a mortgage’s shifting mix of principal and interest.

WHAT’S THE BETTER choice? This is the perennial question for all of us, as we ponder how best to use our time, how to invest our savings and how to get the most out of the dollars we spend.
Want to lead a more thoughtful financial life? As I try to make better choices, here are five questions I find particularly useful.
1. Why would I stray from the global stock market’s weights?

INVESTING IS MESSY. Get used to it.
In the financial markets, you’ll typically pay a high price for certainty. That price is paid in lower investment returns, and sometimes also in greater financial hassles. Yet I see investors paying that price again and again.
Consider equity-indexed annuities. Investors imagine they’re getting stock market returns without any downside risk. But in truth, what they’re buying is an overhyped investment that captures only a portion of the stock market’s gain,