ACCORDING TO OXFORD Languages, the word invest means to “expend money with the expectation of achieving a profit.”
I like this definition better than some others because it includes the word “expectation,” which therefore should exclude casino gambling and sports betting. But what if you have an expectation of winning? Couldn’t casino gambling and sports betting both be considered investments? As Zach Galifianakis’s character said in The Hangover, “It’s not gambling if you know you’re going to win.”
How can one create this expectation?

I DREAD THOSE RED down votes on my HumbleDollar comments. Perhaps at times I come across as less than empathetic, but that’s not really me. I have sincere empathy for anyone who honestly struggles to make life decisions, including financial decisions. I also realize that adhering to good financial practices is made hard by the problems that arise with the ups and downs of daily life.

I spent my working life, which spanned nearly 50 years,

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.

I JUST FINISHED rereading a book every serious investor needs to reread: Moneyball: The Art of Winning an Unfair Game. It was written by Michael Lewis in 2003, but it’s still quite relevant to baseball—and to investing.
It’s the story of the Oakland A’s general manager, Billy Beane, and his struggle to create a competitive baseball team on a limited budget. How does this relate to personal finance? Well, first let me explain my connection to Moneyball.

I KNOW I’M NOT WISE. Still, I’ve picked up enough wisdom to realize I didn’t have much of it when I was younger. At the very least, 60 years of stubbed toes, slips and falls have shown me that some paths shouldn’t be trod, while a few are worth traveling.
I try to refrain from offering unsolicited advice. But I’ve lately had a growing desire to steer young adults toward choices that escaped my notice when I was their age—with a focus on three areas:
Think about who came before us.

I’M ONE OF THE 30 writers who contributed an essay to My Money Journey. As the book’s publication drew closer, I found myself worrying about how readers would react to my story.
Will they see me as someone who saved a lot of money because I was thrifty—or because I was cheap? As I mention in the book, I was embarrassed about my spartan lifestyle, including the crummy apartments I lived in and the cars I drove.

NEAR THE END OF 2019, just before a couple of coworkers and I headed out for lunch together, I said to them, “I’m 26% smarter than I was at the beginning of the year.”
“What are you babbling about now, Johnson?” one of them said.
“The mutual funds where I have my investments went up by 26% this year,” I said. “Clearly, I’m 26% smarter now than I was at the beginning of the year.”
“Guess you’re buying lunch then,” he said.

IMAGINE YOU TOOK a group of folks—mostly male, mostly older, mostly upper-middle class, mostly well-educated—and had them describe their financial journey. They’d all be pretty similar, right? You might be surprised. I was.
Next Tuesday marks the official publication of My Money Journey, which you can now order from Amazon and Barnes & Noble, as well as directly from Harriman House, the publisher. When I asked 29 writers for HumbleDollar to join me in contributing essays to the book,

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,

NETFLIX BEGAN AN experiment in 2003 that seemed crazy to management experts. It instituted a policy of unlimited vacation time for its employees. In the years since, a number of other companies have followed Netflix’s lead, offering employees unlimited paid time off.

The results have run counter to intuition: Employees who are offered unlimited vacation end up taking less time off than those working for companies with traditional vacation policies. Why? A common explanation is that people struggle when they lack clear guidelines.

“I DON’T LIKE BEING too much of an example for people who just want to make money. If you wrest a fortune from life by buying little pieces of paper, I don’t think that’s enough. I never consider it enough of a life to merely be shrewd at picking stocks. If you’re good at just investing your own money, I hope you’ll be good at something more.”
What Charlie Munger, the vice chairman of Berkshire Hathaway,

ABOUT A DECADE AGO, when I was in college, I lived in an off-campus apartment complex. The complex had an on-site property manager named Joni. She got to live in one of the apartments in exchange for managing leases. Joni was in her 60s and didn’t have any close family, so she was always eager to talk to whoever stopped by her apartment “office.”
Many of my fellow residents tried to minimize their interactions with Joni,

CAN WE REALLY EXPECT Americans to be financially literate and act prudently with their money—when they can’t even return a shopping cart to where it belongs, or stop dropping litter wherever they stand?

I was in the grocery store recently and came out to find a shopping cart pushed into the side of my car. I was parked eight feet from the cart corral. Meanwhile, on my last trip to an ATM, the ground was littered with receipts.

“IT DOESN’T MATTER IF our planned trips might jeopardize our retirement savings.” The word “jeopardize” was spoken with a sarcastic tone.
It was clear my two financial-planning clients didn’t appreciate my message. They were adamant. Their 10 pricey National Geographic trips, which would span the globe, must remain on their bucket list.
So began a challenging chat. Based on their excitement about their retirement wish list, it would have been easier to simply applaud their exotic plans.

I SPOKE RECENTLY with a fellow who had climbed Mount Everest. The first question I asked: What was it like at the top?
What I expected him to say was that the view was dramatic. Instead, he said, his time at the summit turned out to be less than he’d expected. For starters, it was 4:45 a.m., so there wasn’t a lot of visibility. In addition, it was minus 45 degrees. Because of that,