I’VE TALKED IN EARLIER articles about asset-liability matching. It’s ​a concept popular with insurance companies to manage investment risk. It’s a very formal approach and not one I would expect an individual investor to follow too literally. But it’s a notion that, in general, can help individuals make asset allocation decisions.
In his book, The Outsiders, William Thorndike highlights another well-known principle in corporate finance that can also be applied to personal finance: It’s called capital allocation.

EARLIER THIS YEAR, HumbleDollar unveiled its Two-Minute Checkup. All you need to do is input up to nine pieces of information and it spits out advice covering 10 areas of your financial life. When I tried it, I thought it was great—except for one thing. The amount it suggested my wife and I have in emergency cash was $13,000 higher than what we currently had.
I felt comfortable with the amount of cash we were holding,

I’M TOO EMBARRASSED to reveal how long it took my wife and me to prepare our wills. We knew this important task was near the top of almost every financial “to do” list—a list that, it seems, we’ve spent our adult lives slowly working our way through.
We’d discussed the details of our wills, including the crucial decision of who would care for our minor child in the event both of us died. Despite this,

SIX YEARS AGO, I made one of the worst investments of my life.
I got a dog.
Ignoring the age-old advice to never invest in anything that eats, I signed up for a purebred German shorthair pointer puppy. I thereby locked myself into an indefinite stream of future cash outflows in the form of dog food, treats, supplies, annual checkups, vaccinations, flea and tick treatments, heartworm pills, procedures and other expenses required for keeping man’s best friend healthy and happy.

STEVE MARTIN HAD a joke on “how to become a millionaire” during his 1970s stand-up routine. “First,” he would say with a mock-serious glare at the audience, “get a million dollars.”
There are piles of books written about how to invest your money. Far fewer explain how to make money in the first place. To balance the scales, I’ll offer this suggestion: If you’re still working, this would be a great time to interview for a new job.

WHEN I BEGAN MY journey to becoming a professional wrestler in 1994, I didn’t give much thought to the money aspect of the business. Wrestling was a secret organization similar to magicians or, frankly, the Mafia. Information wasn’t readily available on the industry’s economics. I simply had a burning desire to be a part of this crazy circus that I’d always loved as a fan.
As I began training to be a wrestler under Skandor Akbar in Dallas,

I RETIRED TWO YEARS ago this week. I’d been in a job that was a bad fit for my skills, experience and university degrees. The pay was paltry, but it was the only job I could find four years earlier.
I calculated that my Social Security and state pension would match my take-home pay because they were based on my highest earnings, which were many years earlier. COVID-19 was a threat to old guys like me and my employer was offering a modest retirement incentive,

I’VE NEVER BUDGETED, meaning I’ve never planned every expense in detail. But I know many people do, especially as they look ahead to retirement.

This doesn’t mean I don’t know what I spend. My utility bill is $127 a month, my homeowners’ association fee is $870, my property taxes are $3,117 a quarter and my BritBox subscription is $5.99 a month. Or is it $6.99?

By the end of each month, our two credit cards are paid in full.

I AM NOW AGE 78—the same age at which my father died 34 years ago. I’m starting to think about dying, though I have no immediate plans to do so.

Of course, my father effectively smoked himself to death, unleashing a combination of heart disease and emphysema. I’ve been a no-smoking zone my entire life. No, I’m not depressed and I’m not being maudlin. But if Queen Elizabeth can’t go on forever, what hope is there for us commoners?

MY INVESTING BEGAN in the mid-1980s with savings bonds. Initially, it was a way to set aside some emergency money. I would automatically buy EE bonds through payroll deduction and have the bonds sent to my home. This gave me a sense of accomplishing something for the future. It also showed me that you won’t miss something—money, in this case—if it never makes it into your hands.
Some argue there are better saving and investment strategies.

A FAVORITE QUOTE in the world of personal finance comes from Ernest Hemingway’s 1926 novel The Sun Also Rises.
“How did you go bankrupt?” Bill asked.
“Two ways,” Mike said. “Gradually, then suddenly.”
Money troubles are a common theme throughout literature. Charles Dickens probably summed it up best. In David Copperfield, a fellow named Micawber laments: “Annual income twenty pounds, annual expenditure nineteen six, result happiness. Annual income twenty pounds,

IN THE NAVY, THEY USED to say, “You don’t get what you expect, you get what you inspect.” Inspections played a major role in how the Navy determined the competency and capability of a warship. For nuclear-powered submarines, the most important inspection was the Operational Reactor Safeguard Exam, or ORSE, which rhymes with horse.
A team of experts thoroughly inspected all aspects of a submarine’s nuclear power plant. This covered everything from material readiness (“verdigris on valve stem”),

MY WIFE AND I JUST returned from the first extended road trip of our retirement. We were away two weeks, drove 2,800 miles and visited 10 states. The primary reason for the trip was to stay five days on a houseboat on Beaver Lake, Arkansas, with seven friends.
We broke the trip into three phases. The first part took us from New Jersey to northwest Arkansas in two-and-a-half days. Along the way, we stopped in St.

WHEN OUR KIDS applied to colleges, the smallest detail of each campus visit mattered a lot. If our daughter admired the student leading our tour, the school skyrocketed in her estimation. If the class our son attended to “get a feel for the place” turned out to be a test period, Grandpa’s alma mater was forever struck from consideration.
In economic terms, the college decision features asymmetric information. Colleges know a lot about us from our detailed personal and financial applications.

MY WIFE SARAH AND I recently dusted off our old Scrabble board. We reviewed the rules and were reminded of the Scrabble Bingo—the 50-point bonus awarded to a player who figures out how to play every letter tile from the tray on a single turn.
Neither of us could remember ever achieving the Scrabble Bingo. That wasn’t surprising, we reasoned, because it’s rare for all the stars to align. You’d need the right combination of seven letters,