Dennis Friedman

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,

I’LL TURN AGE 72 this year. Since I’ve retired, my wife and I have had some wonderful experiences. Our travel adventures are full of great memories that I’ll cherish for the rest of my life.
Still, as great as those adventures have been, they aren’t nearly as important to our happiness as living a healthy, pain-free life without physical or mental limitations. That’s something that’s hard to beat. It gives you a different outlook.

I GOT AN EMAIL last month that also went to half-a-dozen other HumbleDollar writers—those of us who have been the site’s most prolific contributors. It came from HumbleDollar’s editor. His request: Please come up with a list of your 10 favorite articles that you’ve written for the site.
I immediately knew what type of article I’d select—ones that weren’t just about personal finance, but rather were about more than money.

WHEN I LOOK BACK at 2022, my wife and I had a good year. We avoided COVID-19 even as we did things we’d been yearning to do for a long time. We enjoyed our time traveling, and visiting family and friends. Even doing the little things that we take for granted was a pleasure. Indeed, this year felt like a return to normal.
Of course, everything hasn’t come up roses. Our investment portfolio is down 12.6% as I write this article.

WHEN I WAS IN MY 20s, I was lucky to work for a company that offered a pension plan—and that put me on the road to retirement. Today, unfortunately, company pensions are rare. How can you ensure a comfortable retirement? Try shooting for these age-related milestones:
Age 25. Start saving at least 15% of your gross income. As I mentioned in an earlier article, a Fidelity Investments study found that if you save 15% of your gross income every year from age 25 through 67,

WHEN I WAS AGE 10, we moved from Ohio to California. My father got a job by answering a help wanted ad in a local newspaper. When we first arrived in 1961, we lived in a 36-unit apartment building in Inglewood. It’s located about two miles from the Forum, where the Los Angeles Lakers and Kings sports teams used to play their home games.
One of our neighbors in the building was an older gentleman called Jack Tarentino.

I DECIDED TO TAKE a peek at our investment portfolio. I try not to look too often. But I was curious to see how our assets were holding up in this bear market.
What did I learn? Our retirement savings were down more than $500,000 this year, thanks to a combination of investment losses and our spending. Most of our shrinking balance is the result of falling stock and bond prices.
Still, our spending this year on travel has increased sharply.

I WISHED I HAD MY friend Chuck’s memory. He can remember things from our college days as if they happened yesterday. My memory isn’t nearly as good. There are, however, a few moments I’ll never forget.
I remember in high school when a classmate asked a girl, who was also in our class, if he could have her leftover orange peels. I knew Floyd well enough to know he went to school hungry some days.

WHEN I TURNED AGE 24, a friend and I took a road trip from San Francisco to Vancouver. It was 1975. I was excited—it would be my first visit to Canada.
I didn’t know what to expect when we got to the Canadian border. All I knew was we didn’t need passports. The border officer gave us a suspicious look. After being on the road for a spell, we didn’t look our best. I was unshaven and wearing my usual T-shirt and jeans.

MY WIFE AND I GET together occasionally with our neighbors for a glass of wine. We became good friends with Larry and Kathryn since they moved into our neighborhood. They‘re retirees, just like us.
When visiting them, they often serve cheese and crackers. One day, Larry said to me, “Try one of these whole wheat crackers. They won’t hurt you. I can’t say the same thing about the cheese, though.” He knows I try to eat healthily.