THERE’S ONLY ONE THING I like more than writing about personal finance, and that’s drinking a salubrious cocktail. When I realized I could combine both, this article almost wrote itself.
Two decades ago, I read the best cocktail book ever written, The Essential Cocktail: The Art of Mixing Perfect Drinks by Dale DeGroff. He thought so highly of my bartending skills that he even inscribed my copy, though that’s a whole other article.

I OUTLINED 10 REASONS everybody should have an estate plan in a 2018 article—and what was true then remains true today, especially for those whose assets could be subject to estate taxes.
Under today’s rules, the federal estate tax applies to individuals with assets over $12.9 million. That might sound like a high number. But in 2026, the limit is set to be cut in half. In addition, many states impose their own estate tax,

MY PARENTS WERE products of the Great Depression. Dad was the frugal one. He was also a pack rat. He’d save pieces of wood for that shelf that he would build “someday.” For years, those pieces sat under the ping-pong table in the basement.
One night, Mom dragged the wood out to the street for the garbage collector to haul away. Later that night, Dad dragged the pieces back into the basement. Mom was the type to get rid of things that were no longer needed.

MY FATHER RAISED ME to think that, if I set my mind to it, I could do just about anything. He said that concentrated focus and drive would allow me to reach my dreams, and that there was rarely a time when I should settle for average.
Maybe it’s no great surprise, then, that I hate being average. I’m above average in smarts, the kind that gets you a side order of noogies as a second grader.

ONE OF THE CLEARER mandates for a Christian such as myself is to help the poor. Jesus said the poor “will always be with you.” It doesn’t take amazing powers of observation to see that he was correct. There are lots of ways to help the poor, with churches and thousands of worthy charitable institutions working to address the causes and effects of poverty.
Many years ago, I became acquainted with a large Christian organization called Compassion International.

I DON’T FIT THE USUAL profile of a HumbleDollar reader. I don’t have what I’d consider a high net worth, nor am I a college graduate. Still, I hope my story shows it’s possible to reinvent yourself.
Around 1920, my dad’s family moved—with few belongings but a willingness to work—from Tennessee to northwestern Ohio. My dad met my mom while working at Hostess Bakery, and he later worked at Willys-Overland, welding together Jeeps during World War II.

I’M 64 AND PREPARING to sign up for Medicare next year. I’ve done extensive research, including earning the Retirement Income Certified Professional designation. I’ve also written articles for HumbleDollar on Medicare coverage, Medicare premiums, Medigap and health savings accounts.
In addition, I’ve befriended Medigap salespeople, advised others on which plans to choose, and asked those on Medicare for advice on their experience with the program. I feel as if I’ve been preparing to take the Medicare filing “exam,” and I’m excited to sign up.

I GOT MARRIED IN 1980 at age 22. After 29 years of marriage, my wife and I went through a contentious divorce in 2009 and 2010. We’d grown apart and, during our last few years of marriage, discussed parting ways.
I moved out of our marital home of 16 years into an apartment. It was strange to be living by myself again. I was 51 at the time.
While adjusting to my new reality,

WHEN I WAS AGE SEVEN or eight, I had a glass piggybank where I saved all the small change that came my way. I loved the sight of all this money that I could save or spend as I pleased.  

One day, my mom needed to go to the grocery store for some bread and found she didn’t have enough cash. She asked to borrow from my almost-full bank. I gave the money to her,

MY FATHER WAS president of J.S. Collins and Son, a local hardware and lumber chain in southern New Jersey. Occasionally, he’d take me to the flagship location in Moorestown after hours. While he was back in his office doing important business, I wandered around the empty store and general office areas. At 10 years old, it was easy to get bored.
One day, I got the idea to pull out an empty drawer from one of the office desks.

BEFORE I RETIRED TWO years ago, my first thought—as a software engineer—was to come up with a detailed project plan. But that proved too difficult. Instead, I decided to settle on some tenets to guide my retirement.
To aid in my thinking, I listened to podcasts and bought books. The usual list of prerequisites for a successful retirement were clear: financial means, good health and a robust social network.
I worried most about the last item.

“YOUR CHECKING ACCOUNT balance is low.” It’s an alert none of us wants to receive, especially if we’ve just been paid. But that was the message that a friend—let’s call him Ron—got recently. A hacker had gained control of his account and started bleeding it dry.
Ron, it turns out, was lucky to have received that alert. Another friend—let’s call him Arthur—received no such alert when his account was also taken over by hackers this summer.

WE ALL LIKE TO THINK we’re consistent in our views. I certainly do. Yet, as I recall how I thought about the financial world two decades ago and how I think about it today, I’m amazed at how much my views have changed.
Here are five pieces of advice that I give now—but which I wouldn’t have given two decades ago:
1. Don’t waste time on investing. In the early 2000s, I thought endlessly about how to structure a portfolio,

MY WIFE KEEPS COMING up with ideas for where we should travel next. She says, “How about New Orleans, Savannah or Charleston?” My wife can’t get enough of traveling. I’d rather hang around the house for a while.
This year, we experienced long flight delays on our last two trips back from Europe, so right now I’m not anxious to get on another plane. The most recent headache was our flight home from Ireland.

OPPOSITES MAY ATTRACT—but that doesn’t always make for a happy financial relationship. For instance, tightwads and spendthrifts often marry, each hoping the other will change his or her ways or perhaps provide needed balance.
But that, of course, can lead to conflict—and couples may struggle to negotiate their differences. They wind up having the same argument over and over, and nothing’s accomplished until they listen to each other and try to find common ground.