Dennis Friedman

WHEN MY DAD HAD cancer, we’d take walks through the neighborhood. One day, on our stroll, we met a neighbor, Ted. My dad introduced me. “This is my son, Denny, he’s taking care of me.”
Ted gave me a smile and said, “I hope my son will take care of me if I need help.”
Not long after that conversation, my dad was in hospice care. My mother and I were standing over his bed.

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 WIFE CALLS HER 99-year-old mother every morning. One morning, her mother asked, “Are you making big things happen?” After Rachel reminds her mother that she’s retired, her mother asked, “How do you make money?”
Although I chuckled when I heard the conversation, those two questions are probably on most folks’ minds as they prepare for retirement. First, how are they going to generate enough income to fund their retirement? Second, how are they going to stay busy doing meaningful activities?

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.

WE USUALLY HAVE Chinese food every Wednesday. It’s our weekly night out for dinner. While waiting outside our favorite restaurant for a table, I heard my wife call out, “Hey, Doe, our table is ready.” That’s what my wife calls me. It’s my new name. She used to call me Dodo. Now, she’s shortened it to Doe.
How did this nickname come about? One day, I called myself a dodo for a silly mistake I’d made.

MY WIFE AND I TOOK a two-week trip to Ireland. We flew to Dublin and stayed at the Hotel Riu Plaza. If you’re ever on the run and need a hiding place, just ask for a room on floor 2C. They’ll never find you because of the strange floor plan. All things considered, the Riu Plaza is a fine hotel at a reasonable price, with a good buffet breakfast to start your day.
After touring Dublin for four days,

WHEN I RETIRED, I thought about creating a website and writing about my retirement. I looked into what it would take to build a site and have someone edit my work. The more I thought about it, the more I realized the only ones who would probably visit my site would be my sister, brother-in-law and maybe a few curious friends. It wouldn’t be worth the time, effort and money—especially when HumbleDollar offers all the benefits an unknown and inexperienced writer needs.

AS I MENTIONED IN an earlier article, I’ve been writing for HumbleDollar since 2017. Along the way, I set a personal goal of writing 100 articles, not counting the 36 shorter blog posts I’ve penned. This is my 99th article. I’m almost there.
It may not seem like a lofty goal to many people, but to me it’s been a challenge. After I wrote my first article, it took me a year to write another one.

MY WIFE IS OUT OF town for a while, so I have a lot of free time on my hands. I asked Carl, an old schoolmate, if he’d like to have lunch. I thought it would be a chance to give Carl a couple of copies of the HumbleDollar book, My Money Journey.
I didn’t think Carl would actually read the essay I wrote, let alone the whole book.

WHAT’S THE BEST DAY of the year to retire? Many people think it’s Dec. 31. But I used to think my ideal retirement date would be the day in February when the Cleveland Guardians played their first spring training baseball game. What better way to start my retirement than seeing my childhood baseball team in Arizona get ready for the upcoming season? When I wasn’t watching baseball, I could visit the Grand Canyon and Sedona.

I’M ONE OF THE 30 writers who contributed an essay to My Money Journey. As the book’s publication drew closer, I found myself worrying about how readers would react to my story.
Will they see me as someone who saved a lot of money because I was thrifty—or because I was cheap? As I mention in the book, I was embarrassed about my spartan lifestyle, including the crummy apartments I lived in and the cars I drove.

MY WIFE AND I VISITED Italy this year. We flew to Venice, where we stayed three days, and then hopped a train to Florence, where we spent the next five days. After that, we rented a car for three days and toured the Tuscany countryside, before catching a train to Rome for our final six days.
I learned a lot about Italy, but I also learned some things about myself. Here are 11 takeaways from our trip:
1.

I WROTE MY FIRST article for HumbleDollar in 2017. I’d been retired for nine years and I had plenty of material. I’d made a lot of mistakes with my money over the years.
I was truly a humble writer then, and I still am. My early articles weren’t my best. It was a learning experience. I wrote them using the notes app on my old iPhone 5—an app that was designed for jotting down quick thoughts,

WHEN I TOLD MY employer I was retiring, I received phone calls from coworkers I hadn’t heard from in years. One of them was Peter. We were hired about the same time.
Peter congratulated me, and said he’d be retiring too—if he’d joined the company’s pension plan. For some reason, like a few of my other coworkers, he never took advantage of the benefit, which required employees to make regular payroll contributions.
Peter did retire about five years later.

WHEN I RETIRED, I thought a successful retirement was primarily about money—about making sure I had enough income to fund daily expenses for 30 or more years. But now that I’m in my 70s, my investments don’t seem quite so important to me.
Indeed, other things in my life strike me as just as crucial as my investment portfolio’s size. Some say retirement is like a three-legged stool. No, not the traditional three-legged stool of personal savings,