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.

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.

MY FAVORITE CLASS freshman year in college was introductory psychology. I found the lectures interesting, the textbook fascinating, and the course much less time-consuming than my engineering classes. Based on my positive experience, I decided I’d take a class called psychology of personality as an elective. What I didn’t realize was that many students considered the professor to be something of an oddball.
My first—and only—day in the class was surreal. The professor kept repeating that his class was “designed to be a real system.” Multiple times,

HEY GUYS, DO YOU carry a rifle like Clint Eastwood when you invest—or are you a vulnerable romantic like Hugh Grant? My contention: Most of us lean toward a traditionally masculine or feminine orientation when building our portfolio, similar to how we handle many other life choices, from career to sports preferences.
This gender orientation is, I believe, a pervasive bias when buying and selling mutual funds and exchange-traded funds (ETFs), not unlike the behavioral-finance biases you’ve likely read about,

REGULARLY CHANGING the oil is the most important step you can take to extend your car’s engine life. Oil is the engine’s life blood and changing it is one of the least costly maintenance steps. It’s also one of the dirtiest, crummiest, least pleasant jobs you can do.
Before I got married, I lived in a six-story apartment building in Brooklyn, with a parking garage in the basement. A friend of mine lived in the same building.

MY COLLEGE BUDDY Joe really looked forward to retirement. But in the weeks and months following his last day of work, he began to realize he didn’t have a core group of friends with whom to share his newfound freedom. Those he counted as friends were simply friendly workplace acquaintances. And several people who he thought might become deeper friends were still busy working and couldn’t “come out to play.”
So, after retiring two years ago,

I’VE SPENT MY ADULT life on a self-improvement journey. It’s kept me moving forward or, at least, trying to move forward. I take great pride in what I’ve accomplished and have no regrets about the goals I set.
But a funny thing happened. I retired. I’ve applied the brakes to my life, and now I’m reevaluating what I’ve done and what I want to do.
I’m not Catholic, but I’ve attended many a mass.

I DROPPED OFF OUR Honda Civic at the dealer for routine maintenance. A young Uber driver gave me a ride home in his new Tesla.
I was embarrassed when he picked me up, because I couldn’t figure out how to open the car door. I told the driver I owned a Honda Civic, not a luxury car. “Those Honda Civics are good cars,” he said. “That was the first car I owned.”
Our conversation seemed backward to me.

MY FAMILY ATTENDED the wedding of our neighbor’s daughter. I was seated next to a friend of my neighbor. My wife believes the seating chart was based on the fact that the family has special needs children. This has happened frequently over the years. It’s as if those of us with special needs children speak a different language.
During the course of the evening, the husband asked me if I had a pen. I knew I did,

DECADES AGO, WHEN I was trying to save consistently for retirement, I found that my impulse purchases were standing in my way. Like many, I wanted feel-good stuff or the latest gadget, and I was willing to spend money to get it.
Once, I saw an expensive jacket in a store and badly wanted it. I was about to buy it when reality struck. I said to myself, “Let me think it over for a day.

MANY YEARS AGO, a Wall Street Journal article quoted a source as saying, and I paraphrase, “Young-old age should last as long as possible, while old-old age should last 15 minutes.” Those of us who have visited nursing homes can all relate to this.
Public health initiatives and medical breakthroughs have extended lifespans significantly over the past 100 years. In his bestselling book Outlive: The Science and Art of Longevity, Peter Attia argues that we should focus not just on lifespan,

ON ONE OF OUR TRIPS to visit my in-laws in South Carolina, my mother-in-law asked me what I thought of her home in a 55-plus retirement community.
“It looks like a house,” I said sarcastically.
Her response gave me food for thought. She said, “I feel rich living here.”
My mother-in-law’s home was far from being a McMansion. It was a single-story two-bedroom house, but it had cathedral ceilings. I think it was the high ceilings that,

THE FIRST TIME I remember realizing that “time flies” was during my senior year of high school. One of my class periods each day involved working in the school’s main office. My primary duty was to walk the hallways, gathering attendance sheets from each classroom.
It was a highly repetitive task, each day a replica of the prior one, with the route through the hallways never changing. On one of those days, I recall thinking,

DECEMBER IS A BUSY month for everyone. But it seems especially busy for clergy and those who work with money.

If you work with money, there are important tasks to complete, such as planning for taxes, ensuring your investment allocations are where they should be, making charitable contributions, and getting ready for the new financial year.

Meanwhile, when I was serving a congregation as a minister, December was full of gatherings and services to celebrate the traditions and holidays that come this time of year.