SOME FOLKS SEEM HAPPY to tell the world how much they earn, how much they have in the bank and what their portfolio is worth. Not me.

If I were to share my income and net worth, I’d expect some serious consequences, and not just from local thieves. In fact, I’m so cautious I have a plan not to tell anyone, except my wife Connie, if I win the lottery.

To be sure, overt sharing often isn’t necessary.

I DIDN’T ALWAYS LIKE my retirement. After I quit my full-time job, I briefly went to work for another aerospace company. It seemed like the perfect arrangement for a retiree: just 16 hours a week, with the luxury of setting my own schedule.
But it was the same old pressure cooker environment that I’d wanted to get away from. Although I was working fewer hours, it didn’t feel like I was retired. Instead, it felt like the same old grind.

ROGER PENSKE STARTED as a race car driver, but soon found he’d be better off as a team owner. Penske’s holding company also has stakes in Penske Truck Leasing, among other businesses, as well as the Indianapolis Motor Speedway, home of the Indy 500.
One of Penske’s criteria when hiring race car drivers: select folks with a burning desire to win. Penske has said he can guide a driver’s thinking about the best way to pursue wins,

WHEN I WAS A KID, a popular expression was “same difference.” It meant that two choices were essentially interchangeable. It turns out the idea can be helpful in financial planning.
While some financial decisions are very important—and thus warrant careful analysis—others make far less of a difference. In those cases, additional analysis typically contributes little. According to one study, it can even be counterproductive. Below are several topics where extensive analysis is often less important than it might seem.

WE’RE ALL CAPTIVES of our own experiences. Want to behave more rationally? We should set aside our life’s anecdotal evidence and instead make decisions using the best information we can find. Yet our experiences—especially those during childhood and that involve family—tend to triumph, shaping our world view and potentially setting us up for costly financial mistakes.
What drives your behavior, financially and otherwise? A little introspection could help you better understand your financial choices—a crucial first step to behaving better.

LARRY BURKETT WAS one of my early financial influences. Burkett, who passed away from cancer in 2003 at age 64, had a daily program called Money Matters on our local Christian radio station. For years, it came on during my commute home from work, and I’d faithfully tune in.
Burkett was a prolific author, publishing more than 70 books. His final book, Wealth to Last, co-authored with Ron Blue,

THE FIRST TIME I GOT laid off, I was working in an insurance company’s training and development department. I’d been working in another department at the company when I saw a job posting for the position. The training department was looking for someone with subject matter expertise and experience in teaching.
At that point, I’d been working in property and casualty underwriting for 14 years. On top of that, I was a certified instructor for the Dale Carnegie course in public speaking.

ON OUR RECENT TRIP to Alaska, I was surprised by the number of solo women passengers. It turns out I shouldn’t have been.
According to a recent report from Road Scholar, a not-for-profit travel company geared toward those age 50 and older, a quarter of its travelers were single, with 85% of them women. That group included married folks traveling solo. It’s a growing trend. The Road Scholar study reported that 60% of the company’s solo travelers in 2022 were married.

IT’S BEEN MORE THAN 10 years since my retirement journey began at age 52. For almost 30 years, I’d worked hard, especially the last two decades, when my twin brother and I owned a landscaping company. Vacations were few and far between, and even on vacation I was always on call.
I was burned out and ready for a new chapter. Going into retirement, I was well-prepared financially. But how I’d fill my days was something of a mystery.

MY LATE FATHER SPENT his entire career, from the time he dropped out of college to marry my mother until the day he died at age 61, in the insurance business. My father was also a huge fan of the San Francisco 49ers, our hometown NFL team.
Last year, the 49ers cruised through the playoffs, led by the team’s dynamic young quarterback, Brock Purdy. But then, in the NFC Championship game against the Philadelphia Eagles,

FLAPJACKS IS LITERALLY on the other side of the tracks. The place is a throwback to the diners of the 1950s, when waitresses wore white aprons and took orders on little green pads, and where the red vinyl seats were cracked.
Charlie and me. I’ve been meeting Charlie at Flapjacks for weekly pancake breakfasts since I partially retired seven years ago. I spot him in our back booth and slide in across from him.

“WE CANNOT GET RICH doing dentistry, but we can get rich investing what we make in dentistry.” A nationally recognized lecturer on dental-practice management shared that piece of advice with me some 40 years ago.
I’d been out of dental school for a year when Dr. Dick Klein spoke at our local dental society’s annual meeting. The meeting’s organizer was a friend. He asked if my wife and I would take Klein and his wife out to dinner after his presentation.

BILLY JOEL WROTE a song that declares, “I love you just the way you are.” But as parents, sometimes it isn’t easy to say those words about our children.
We’re supposed to train them to succeed in life. We all probably think we’re excellent trainers, so—when our children don’t get it—it must be their fault. We did our part, so why don’t they learn?
For parents of special needs children, things are different, but also similar.

RETIRED HEDGE FUND manager Jim Cramer is the host of Mad Money, a staple of financial television. For years, critics have derided his investment recommendations—to the point where there’s now a fund designed specifically to bet against him: the Inverse Cramer Tracker exchange-traded fund (symbol: SJIM).
For investors who see Cramer as the P.T. Barnum of finance, this fund offers the ability to make bets that are precisely the opposite of what Cramer recommends.

MY FAMILY HAS BEEN regularly visiting a remote corner of southwest England since 1968, when I was five years old. My maternal grandparents retired to the area, and for a while my parents owned a holiday house nearby. It is, to me, the world’s most beautiful place.
Decades ago, while walking the country lanes, I came across the ruins of a church that was under the protection of a group called Friends of Friendless Churches,