THE ENGLISH POET Alfred Tennyson wrote that it is “better to have loved and lost than to have never loved at all.” When it comes to matters of the heart, maybe Tennyson was right. But when it comes to personal finance, I’m not sure that’s the case. If you’ve ever seen a gain slip through your fingers, you know the feeling of regret can be powerful.
Two conversations last week prompted me to take a closer look at this topic.

IN THE WEEKS BEFORE my annual physical, I made a concerted effort to lose a few pounds, drink more water, skip my evening glass of wine, eat more fiber, and avoid red meat, French fries and cheese. The happy result: My blood pressure was low. My weight was down slightly from my previous checkup. My cholesterol count was good. My A1C level suggests my prediabetic condition hasn’t got any worse. All in all, last month’s physical found that I had little reason to worry.

MEET THE LATEST feature added to HumbleDollar—as well as the website’s first calculator: the Two-Minute Checkup.
How does it work? All you need to do is input up to nine pieces of information, the sort of stuff most of us know off the top of our head. There’s no need to create an account or link to your brokerage firm or bank, and none of your information is saved on HumbleDollar or anywhere else. 

IF WE GO TO THE movies and buy a mega-tub of popcorn, we’ll eat a lot, probably too much. If, however, that same amount of popcorn is packaged into four bags, we won’t eat nearly so much.
Why? With the four bags, we keep arriving at a decision point—that moment when we have to ponder whether it’s worth opening a new bag. This is the insight of behavioral economist Dilip Soman of the University of Toronto’s Rotman School of Management,

I RECENTLY CHATTED with a clerk at an art supply store. We both complained about the Texas heat. Whenever I engage in small talk or meet new people, the weather is my safe, go-to topic. As the saying goes, “Everyone talks about the weather, but no one does anything about it.”
Changes in the weather affect us to varying degrees—pun intended. Some effects are minor, like rain interrupting our outdoor plans. Others are more serious.

ALMOST SEVEN MONTHS on, I’ve failed miserably with one of the New Year’s resolutions I wrote about for HumbleDollar—but I’ve done well with the other.
I’d like to take credit for my success in not obsessively checking my IRA, but the discouraging reality of the financial markets has a lot to do with it. This year, going online to view my account several times a day—which I’ve been known to do—would have left me feeling truly hopeless.

I WAS EDITING a fellow graduate student’s paper. She’s in her mid-20s, less than half my age. She’s bright and communicates well in class discussion, but her paper—frankly—was a mess. Great ideas, but she expressed them in overly pretentious language. One bloviated sentence was more than 60 words.
When I asked her why she did this, she said she wanted to “sound smart” by not using the same old words she normally uses. She worried that no one would take her seriously unless she adorned her ideas in the polysyllabic jargon of academia.

I THINK SERIES I savings bonds are a great place to stash money you’ll need to spend in five or six years, and yet I’ve resisted buying. I’ve seen credit cards that offer more cash back than the cards I currently carry, but I haven’t taken the bait. The reason: My goal is to have fewer financial accounts, not more, even if it means fewer dollars in my pocket.
As I discussed in an article earlier this year,

IT WAS JUNE 3, 2006, and I was in the starting lineup for the New York Yankees. We were in Baltimore, playing against the Orioles at Camden Yards. I went 1-for-4 in my major league debut.

A week later, I had the experience of a lifetime. June 10 was my first start at Yankee Stadium. It was a nationally broadcast Fox Saturday day game against the Oakland A’s. I hit my first major league home run.

INVESTING MAY BE simple, but it’s far from easy. Our mettle is tested during market extremes, whether it’s bubbles or bear markets. Today, both U.S. and international stocks are close to bear market territory. Amazingly, even major bond market segments are sporting double-digit losses, with Vanguard Total Bond Market ETF (symbol: BND) down almost 10% in 2022.
What makes years like this one so difficult is our deep aversion to losses. Successful investing is about balancing risk and reward.

THE HIGHEST expression of complexity is thoughtful simplicity. It’s like standing on a mountaintop after navigating the ascent.
The work of the mountain’s trailblazer is arduous. He or she must focus intently on the task at hand, glancing left and right, guessing what will come around each new bend. But from the pinnacle looking down, the perspective puts the most efficient path in clear view. It becomes possible to make a map to aid those who will come next.

WHAT ARE THE MOST important financial notions? For me, the answers are “compounding” and “financial independence.”
Albert Einstein purportedly called compounding the eighth wonder of the world. Warren Buffett has said that the power of compound interest played an important role in his success. But what I’ve learned is that compounding doesn’t just apply to our finances. It can also be used to improve our health, our relationships and our mastery of whatever topic we choose.

EVERY LEGITIMATE short list of history’s greatest basketball coaches includes Pat Summitt and John Wooden. I’m not even going to attempt to recount their myriad successes. Instead, I want to discuss why they were successful.

Many of the best to ever play basketball went to the University of Tennessee and to the University of California, Los Angeles, to work with these legendary coaches. When players like Candace Parker and Kareem Abdul-Jabbar (then Lew Alcindor) stepped onto the floor,

WHILE VISITING MY mother, I walked along my old paper route. It made me wonder: Which customer am I?
It helps to have a little background on these long-ago entrepreneurs. Paper carriers were independent contractors with the local newspaper. We were given a territory—the route. We purchased the papers from the newspaper company and then delivered them to our customers. Every other week, we would also go around to our customers and ask for payment for the preceding two weeks.

THERE ARE MANY virtues, but one of the rarest is persistence in following through. In our complicated world, often you can’t get something done on the first go. Instead, you have to revisit the task, sometimes more than once. This is true not just of financial decisions but also many other aspects of our lives.
In fact, if you’re trying to get folks to do something, often their first defense is to stall—because they know that,