HOW DO YOU COMPETE in an investment contest when you’re a firm believer that investors can’t consistently beat the market averages? That was my dilemma several years ago.
A school not far from where I taught was given money by an alumnus to endow the St. Louis Area Collegiate Investment Contest. All colleges and universities in the area are invited to participate in the competition, which is held regularly. Each is given a hypothetical $1 million and asked to select 20 value stocks.

WHEN I WAS NINE years old, I managed a diversified portfolio—and yet I knew nothing of stocks and bonds. My primary asset classes matched those of my peers: coins, baseball cards and stamps.
Rather than a brokerage firm, we had the Koin Korner, a fairly large store in our nearby shopping mall that sold coins, stamps and a few other collectibles. And instead of following the gyrations of the stock market in The Wall Street Journal,

“I ALWAYS MADE EVERY team I tried out for,” lamented a college freshman after failing to make the lacrosse team.
I tried to make him feel better. “I never made any teams,” I said.
His reply: “You’re used to failing. I’m not.”
That response took me by surprise. But I thought about it, and realized he was right. I had struggled all my life in academics, sports, socializing and with the opposite sex. I was getting used to others around me always being better.

A KEY CONUNDRUM FOR investors: On the one hand, the data on tactical trading are clear. Frequent portfolio shifts are a bad idea and can damage returns. On the other hand, we shouldn’t be so wedded to the status quo that we’re unwilling to ever make a change.
With this conundrum in mind, it was notable when investor and author Howard Marks declared a “sea change” in the investment landscape and recommended that investors revamp their portfolios.

I’VE LONG THOUGHT that my life has gotten better as I’ve grown older. At age 72, I can honestly say the past few years have been the best time of my life. I’ve never been this happy.
But I’m beginning to believe that my best years may soon be behind me. Maybe from here on things will trend in the other direction—because what makes me happy might be hard to hold on to as I age.

MY FIRST ACT IN retirement was to turn off my phone at night. The second was to change my socks. More about the socks in a moment.
I’m an Episcopal priest. My decades of fulltime active service were spent leading several parishes. Upon retirement, turning off my phone at night meant I was no longer readying myself for emergencies and crises. My wife—and our children in the early years—would no longer have me leaving suddenly because something awful was unfolding in the lives of others.

“AMORTIZATION, STEVIE, amortization. When I make a mortgage payment, part goes to the bank, the rest comes back to us.” My father’s cigar flailed as he patted his back pocket. “Listen to a man who worked his way up through the college of hard knocks. Don’t be a jerked-up kid.”
Wearing a sharkskin suit, charcoal shirt and wide red tie that preceded The Godfather’s Michael Corleone, my father confused talking about himself with teaching me.

WHEN I GRADUATED high school in the 1950s, I was age 17—and totally directionless. But living in New York City offered many opportunities, some of them right outside my front door.
At the time, the larger banks and insurance companies sent letters to recent graduates offering job interviews. I chose to accept an invitation from American Surety Co. I had no idea what a surety company did.
The venerable old company was housed in the second largest skyscraper in Manhattan—the American Surety Building at 100 Broadway in lower Manhattan,

I’M THINKING ABOUT retirement—again. But this time, it isn’t my retirement, but rather my wife’s. I earn our family’s primary paycheck, so I’m usually the focus of our discussions when we sit down to scrutinize the numbers and comb through the calendar, looking for a date when we should each hang up our physical therapist’s goniometer.
Even though I earn the bigger income, my wife has diligently worked just as long as I have,

WORK ON A HOUSING development began in early 2000 about a mile from where we lived. This was right around the time that my wife Lisa and I were starting to feel like we wanted some more room for our family. In addition, we were concerned about our current backyard. There was a swale—a shallow ditch—that ran the length of the yard, parallel to the house.
When we bought the house, there was grass in the base of the swale and nothing looked unusual.

MANY FOLKS—ESPECIALLY those still working—think retirement is “living the good life.” The truth is, unless you develop a solid plan for how to enjoy your newly available time, life after retirement can be filled with bouts of boredom, anxiety and even depression. My objective: Forewarn recent and soon-to-be retirees of the emotional dangers that lie ahead—and to suggest a road to a successful retirement.

Retirement isn’t a destination but a journey with three key stops.

THE TOPIC OF TRAVEL pops up occasionally on HumbleDollar, and I’ve even written about my own travels. The reasons for not traveling go from “can’t afford” to “no interest.” I can understand “can’t afford.” But the “no interest” is a mystery to me. The only budget we have in retirement is for travel. It’s funded with our Social Security checks.

When I was in school decades ago, my favorite subject was history.

WHEN I LAST REPORTED on our retirement journey, we’d decided to put our search for a second home on hold. Well, in the immortal words of Saturday Night Live’s Emily Litella, “Never mind.”
We looked at many properties in several communities earlier this year, but we didn’t find anything we wanted to purchase. We decided on a cooling-off period, while we pondered what our next step should be. We kept a casual eye on properties coming up for sale,

WHAT’S THE STATE of America’s family finances? The Federal Reserve just released its once-every-three-year look, in the guise of the 2022 Survey of Consumer Finances, which is based on in-depth interviews with some 4,600 families.
You can read the Fed’s analysis here. Below are some key insights from the latest survey:
Net worth. The typical (or “median”) net worth—meaning the value of all assets minus all debt for those American families halfway down the wealth spectrum—was $192,700 in 2022. 

LIKE MANY OF MY generation, I grew up in a family that never talked about money. I had some sense that I should save, but no sense of where to save. This made me susceptible to a lot of advice—both good and bad—that shaped my financial journey.
I married a teacher and I became a school-based speech pathologist. I knew we’d never be rich, but we would have a comfortable life. In those early days,