IF I’M HONEST WITH myself, I’ve been financially comfortable for so long that I’ve lost the ability to truly relate to those living paycheck to paycheck. But over a lifetime of working with people and their money, I’ve learned to be aware of signs that someone may be on the brink of breakdown—and could use some help.
I was only 22 years old when I had my first shocking experience with the power of money to cause a life to self-destruct.

I HAVE TO ADMIT IT, I’m one of those guys who likes to hide money. I have cash hidden in a couple of places in my house and even in the garage. And I’m not talking about a few dollars. I probably have more than $3,000 in denominations large and small tucked in envelopes. I also have a jar of coins.
You might ask, “Why in the world would someone have so much cash lying around the house?” I keep it on hand in case of an emergency.

A 156-YEAR-OLD newspaper company filed for reorganization in bankruptcy court last year. The company said it just couldn’t come up with the millions it owed to its pension plan. Some 24,000 current and future retirees were promised payments from that plan—and I’m one of them.
This is the story of what happened to our benefits after the pension plan failed.
For 10 years, I was lucky enough to cover Washington, DC, as a newspaper reporter.

MANY PEOPLE TELL ME they need, say, $1 million or $2 million to retire, effectively equating retirement with a dollar amount. But there’s more to retirement than just the financial side. It’s a major turning point that will alter virtually all of our priorities—how we spend our days, how we interact with loved ones, what we care about and what we hope to achieve.

Even if we focus only on the financial side, we can’t sum up retirement with a single number.

OVER A PRODUCTIVE 30-year career that ended in 1950, Willie Sutton robbed as many as 100 banks for gains worth $40 million today—without ever firing a shot. That sort of bank robbery is rare now and, when it happens, customers don’t lose a dime, thanks to FDIC insurance.
Today, Sutton—the Babe Ruth of robbers—wouldn’t waste time knocking over banks. Trillions of dollars held in millions of internet-accessible retirement and brokerage accounts are much softer and more lucrative targets.

A FEW MONTHS AGO, I decided to join a neighborhood golf club. Although I started playing when I was a teenager, I’ve never been that good. Since the group invited players of all handicaps, I thought it would be a fun way to get some exercise and meet new people.
I realized on the first day that I was probably the youngest player. Despite my rustiness, I was putting for birdies on both of the first two holes.

TODAY MARKS MY 200th article for HumbleDollar. Looking back, one recurring theme stands out: Managing our finances is, in a lot of ways, like managing our health.
Ask any doctor the recipe for good health and you’ll hear the same things: Exercise regularly, eat right, don’t smoke. It isn’t complicated—and yet it isn’t so simple. Environmental factors, genetics and bad luck conspire against us. Result: Even the most disciplined person isn’t guaranteed perfect health.

LEAVING BEHIND full-time work leaves a void. How will you fill it? In my semi-retirement, I’ve found four communities.
I grew up in Fort Worth, Texas, but moved throughout my career. Fifteen years ago, I returned to Texas and—as part of my relocation—”pioneered” working from home. I’ve spent the past few years reconnecting with classmates from elementary school through high school, meeting them individually for lunch and using Facebook to arrange annual mini-reunions. I’ve known some of these folks for more than 55 years.

THERE’S NO SINGLE, right way to legally crack the college admissions and financial aid systems. It’s up to teenagers and their parents to do the necessary work.

Still, it helps to have a tour guide—which is what you get with The Price You Pay for College, the new book from New York Times financial journalist Ron Lieber. Lieber’s book discusses why college costs so much, digs into the allure of elite schools,

WHEN I RETIRED, I WAS surprised by how many of my friends and former colleagues had a financial advisor. My thought: Why would folks pay someone else to manage their money when they could easily do it themselves?
But I found out early in retirement that hiring an advisor was a good idea. There’s a big difference between investing while drawing a paycheck and investing without one. When I retired, I realized that the money I was investing was all the money I’d ever have,

MY MOM AND DAD split up when I was seven years old. Money was an issue for the rest of my childhood. Mom was rarely able to work fulltime and, according to her, child support and alimony were never enough.

When I started working a newspaper stand at age 12, I was expected to give 25% of my daily take for rent. Mom also demanded that I save at least 10%. Depending on the headlines,

LONG-TERM-CARE insurance policies are, in my opinion, both a blessing and a curse. They’re a blessing because they can help cover critical and costly care when a family might have no other financial options.
But they can also feel like a curse. That’s because of what many owners of traditional long-term-care (LTC) insurance refer to as “the letter.” This is the renewal letter that policyholders receive each year. These letters provide a menu of renewal options,

EMERGENCY MONEY IS dead money—and it’s rarely looked more dead.
Just as we shouldn’t carry more insurance coverage than we really need, we shouldn’t hold more emergency cash than necessary. Why not? Excessive money spent on insurance and kept in our emergency reserve will likely come with a hefty opportunity cost. Indeed, thanks to the double whammy of inflation and taxes, our cash reserve will slowly depreciate, and that’s especially true given today’s rock-bottom interest rates.

YOU MIGHT RECALL Malcolm in the Middle, a turn-of-the-century TV sitcom in which the middle child often feels ignored. That’s kind of what goes on with midsized stocks.
Large-capitalization growth shares and small-cap value stocks seem to get all the attention these days. The former feature the FAAMG companies (Facebook, Apple, Amazon, Microsoft and Google) and other 2020 winners, while the latter are the darling of investors who embrace academic research showing strong long-term outperformance by small-cap value shares.

ALMOST 20 YEARS AGO, we renovated our entire Washington, DC, home. The memory is still quite fresh. If you’ve ever renovated a house, you’ll understand.
A home renovation has similarities to personal finance: You can do it yourself (DIY), you can pay someone to do it for you, or you can do something in between. This last approach has worked well for me—both with renovations and financial matters.
Our home consisted of a three-level townhouse.