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.

I’D PLANNED CAREFULLY. All I needed was to get from the Oslo airport to an Airbnb about eight miles away. It was 12 minutes by bus, the host firmly proclaimed.
I’d disembarked from a ship early that morning in Kirkenes, near the Russian border. I’d paid about $20 for a bus ride to the nearest airport, and then flown 850 miles to Oslo. Now, I was ready for the local bus and that 12-minute ride to the Airbnb.

MANY RETIREES ARE looking for ways to supplement their income. Others would like something interesting to occupy their time and allow them to stay productive and engaged—and, if it brings in a few dollars, all the better.
We’re fortunate to live in the internet age, with the opportunities that it offers. Previously, retirement-income sources consisted mainly of pensions, stocks, bonds, rental real estate and part-time work. Today, there are many other choices, including a few you may not have heard about.

A LOT HAS BEEN written, here at HumbleDollar and elsewhere, about the “when” of retirement. Not surprisingly, there are strong opinions.
For example, I’m a member of a Facebook group where the overwhelming consensus is, “Don’t work one single day longer than you absolutely have to.” Of course, many people don’t have the luxury of choosing their ideal retirement date because life intervenes: They get let go from their job or experience health issues that dictate the answer to the “when” question.

MY FATHER HAD FOUR brothers: Bob, Jack, Don and Dick. Born in 1918, Dad was the oldest. Bob was next, born the following year. Jack came along in 1922 and Don in 1926. Dick, born in 1931, brought up the rear.
I never met my Uncle Bob. By the time I was born, he and his wife lived more than 1,000 miles away, and my parents were never close to them. Uncle Don was my favorite.

I WAS HAVING DINNER in Santa Fe, New Mexico, with a new friend, Joseph. He told me of his frustration with his financial advisor. The two might meet for an hour, but afterward Joseph still didn’t know what to do.
“Explain it to me like I’m five,” he said to me. So I did.
Joseph has a PhD from an Ivy League university, so he doesn’t need a kindergarten story. Yet I understand his frustration.

FELLOW HUMBLEDOLLAR contributor Marjorie Kondrack concluded a recent article by saying she’d “never been to Paris or Prague, Timbuktu or Tokyo.” I had always thought of Timbuktu as an imaginary, faraway place. Only recently did I discover that it actually exists.
Timbuktu is a town in Mali with a population just north of 50,000 people. But according to Wikipedia, thanks to gold and salt that could be found in the area, it was once a “world-renowned trading powerhouse” with a population of 250,000.