MY WIFE IS OUT OF town for a while, so I have a lot of free time on my hands. I asked Carl, an old schoolmate, if he’d like to have lunch. I thought it would be a chance to give Carl a couple of copies of the HumbleDollar book, My Money Journey.
I didn’t think Carl would actually read the essay I wrote, let alone the whole book.

AROUND 2,800 YEARS ago, Homer’s Odysseus decided that the whole Trojan war enterprise, in which all of Greece would go to war and destroy an entire city because a woman ran off with a guy she liked, was crazy, so he tried to get out of going by pretending to be crazy himself. The Greek allies were suspicious that their cleverest leader was really crazy, so they sent an emissary to find out.
When the emissary arrived at Odysseus’s small city state,

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 GREW UP IN A SMALL three-bedroom home, the youngest of 14 children. I was always sharing a bed with one older brother or another. My father drove a garbage truck for the county and my mom washed dishes in the school cafeteria.
Money was hard to come by and, when it was in hand, it needed to be spent wisely. My parents engrained in me the importance of education, although neither had a high school diploma.

IN GRADE SCHOOL, when my mother asked me what I wanted to be when I grew up, I recall saying “entrepreneur.” I’m sure she would rather I’d said “doctor” or “lawyer.” But the thrill of building something new and providing something of value to others has always appealed to me.

My first entrepreneurial memory was selling Entenmann’s donuts and coffee to captive motorists waiting on long gas lines during the energy crisis of the 1970s.

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,

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’VE BEEN AN IMPOSTER all my life. In high school, I drove my silver Corvette Stingray into the teachers’ parking lot, revving the engine to announce my arrival. But once I came out from under my shades and joined the throng of students converging on the entrance, I reverted to the shy introvert walking tentatively with his head down.
From time to time, we all take on the role of great pretender to hide our fears of failure and humiliation,

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.

HOW WOULD YOU DEFINE financial freedom? That’s the intriguing question I’ve been asked twice in recent weeks by journalists curious about the new HumbleDollar book, My Money Journey: How 30 People Found Financial Freedom—And You Can Too.
Financial freedom is something that pretty much everybody wants, and yet there’s no agreed-upon definition. Still, I think most folks would focus on two key elements: time and money. But I don’t think it’s a simple matter of having lots of dollars and lots of free time.

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.

A FEW YEARS BACK, I related a story about the comedian Joan Rivers. Her daughter, Melissa, likes to joke that her mother was always very consistent. Wherever she was, she would always drive at 40 miles per hour, whether it was on the highway, in a school zone or in the driveway.
This is funny, but it also illustrates a key challenge for investors. On the one hand, it’s important to be consistent. But at the same time,

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,

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.