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,

AS A TEENAGER, I wanted to be an architect. I took six years of mechanical drawing during junior and senior high school, and I was good at it, earning nearly all As.

At another time, in my 30s, I thought about becoming a lawyer. People told me I’d make a good one. A lawyer’s opinion seemed to carry more weight, even when the subject was unrelated to legal matters.

I also wanted to play a musical instrument.

MY AFFINITY FOR spreadsheets began in the late 1960s when I was a paperboy in Virginia Beach. I had a morning route for The Virginian-Pilot and an afternoon route for the now-defunct Ledger-Star. I used my Huffy bicycle with huge baskets front and back.
The business model was straightforward. I paid wholesale for the papers, and customers paid the retail price of 35 cents per week, or 55 cents if they also got the Sunday paper.

I SPENT NINE YEARS at English boarding schools. The food was beyond disgusting. The buildings were cold and drafty. I was constantly bullied. I would go as long as 14 weeks at a time without seeing my parents, who were based first in Bangladesh and then Washington, D.C.
But I also knew I was getting a good education, and I opted to stay when I had the chance to return home and go to the local U.S.

EVEN IN OUR consumer-driven society, some things are looked down upon if bought. One of those things is companionship.
I’ll leave the topic of sexual intimacy for another day. What I’m talking about here is paying—directly or indirectly—for social interaction. We might buy a younger colleague lunch simply to have somebody to dine with. We might continue therapy long after we’ve finished exploring the issues that prompted us to sign up. We all have a need to connect with others and thereby have our own existence validated.

IN OLD ENGLISH, to be “ready” for something meant to be well counseled. The English King Aethelred the Unready earned his nickname because he was ill-advised. His tumultuous reign ended with invasions and revolts, including one by his son.
When we feel we have “extra” money or even just a hankering to spend, there’s a host of outside voices to counsel us. Most try to influence our actions out of self-interest—for their commercial benefit.

HOW WE SPEND DEPENDS on how we feel about money.
To be sure, we’re supposed to spend according to our financial situation and needs. But life experiences can so badly distort our attitude toward money that our financial decisions end up being ruled by fear and insecurity rather than questions of affordability. Such is the case with an acquaintance—let’s call her Satee—whose money habits are at odds with her financial standing.
Satee grew up in a typical Indian family of four.

IN JANUARY 1987, I was an unmarried junior Coast Guard officer just beginning the flight stage of U.S. Navy flying training. I decided to see a financial advisor who’d been recommended by friends.
This wasn’t just any advisor, but rather a retired Air Force lieutenant colonel and fighter pilot. He worked for a firm whose advisors were comprised mostly of retired military officers, and they marketed their services primarily to military officers. If there was anyone I could trust,