LIKE MANY OF MY generation, I grew up in a family that never talked about money. I had some sense that I should save, but no sense of where to save. This made me susceptible to a lot of advice—both good and bad—that shaped my financial journey.
I married a teacher and I became a school-based speech pathologist. I knew we’d never be rich, but we would have a comfortable life. In those early days,

I READ QUITE OFTEN on HumbleDollar about the trials and tribulations of those planning for retirement—questions like when to retire, where to retire, what will my expenses be, when to take Social Security, how to minimize taxes, how much money to save, how much to spend.

I approached retirement quite differently. Even I’ll admit I’m not typical, and perhaps only questionably normal. I tend to set major long-term goals with modest attention to details.

WHEN MOST PEOPLE retire, they have a good idea where they’ll live. It might be where they currently reside, or where they vacation, or a place near their children or grandchildren. Whatever the case, there’s usually a limited number of possibilities.
But what if you move to a new city for the last two years of your working life, never vacation in the same place twice, don’t own a vacation home, are childless and—upon retirement—sell your home,

MY HUSBAND WAS STILL working at age 65 when he went into heart failure. After heart surgery, he wanted to return to his job as the warranty administrator at a large New Jersey auto dealership. But we worried that the commute would be too taxing. He traveled 55 miles each way to and from his job, and it could take hours and be treacherous when the weather was bad. When additional complications ensued from the surgery,

HERE’S ONE OF THE most important lessons I’ve learned in retirement: Bad health will limit what you can do—or feel like doing—no matter how much money you have. Good health is the biggest determinant of how rich and fulfilling your retirement years will be.
You and you alone are responsible for your health care. It’s not your spouse, your children, your friends or your doctors. It’s you. Nobody should have to beg you to see a doctor.

HOW MUCH OF YOUR retirement planning revolves around your kids and grandkids? Your estate planning goals probably include bequeathing a meaningful sum. Perhaps moving closer to your kids and grandkids is part of your plan. Whether you consciously think about it or not, you may be counting on your children to help out if needed during your final years. That seemed to be my father’s plan.
But what if you don’t have kids? How different would your retirement plan look?

IT’S TIME TO THROW out our broken retirement system and start over. My first article for HumbleDollar, published more than five years ago, was titled Choosing Badly. It was about the inability of most employees to make good use of their 401(k) plan.

Guess what? Nothing’s changed.

Today, some 401(k) plans still have too few investment choices, while others have too many. There are multiple options that people don’t understand, such as target-date funds compared with index funds,

AFTER MY FIRST TWO years of studying electrical engineering at Virginia Tech, I got an internship at Frito-Lay working at its research headquarters in Irving, Texas, far from my New Jersey home. I was paid handsomely, treated well, had access to state-of-the-art computer equipment—and was miserable.
Some of that stemmed from spending the summer away from friends and family. But I was also having a career crisis even before my career began.
I wasn’t sure I wanted to work as an engineer for the next 40 years.

LIKE MANY WHO THINK about where they’d like to retire, we’ve always had a vague list of wants: comfortable climate, walkability, good health care, access to cultural events and outdoor activities, friendly tax regime, reasonable cost of living, that sort of thing.
I wrote previously about feeling stuck for many years in a place where we didn’t want to stay, but also not really having one place where we felt drawn to settle, whether for a few years or permanently.

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?

IT WAS JULY 2003. My wife and I were in our early 50s. We had jobs we liked and we lived comfortably. Our two children were about to go to college, and we had a plan for covering the cost. We had renewed our marriage vows on our 25th anniversary. We had no debt.
But I began thinking.
What would our financial situation be if we retired and our only income was Social Security? That was entirely possible.

MY WIFE AND I ARE super-savers. For us, that means we save as much as permitted each year in the retirement plans available to us. Once we’ve done that, we invest in our regular taxable accounts, where there’s no limit on the amount we can contribute.
We’re under age 50. That meant that, in 2022, the maximum contribution was $6,000 each to our IRAs and $20,500 each to our 401(k)s. Because the contribution limits increase with inflation,

FULL OF PROMISES AND plans, we start retirement in our 60s. It surprises me when people reach age 65 and say, “I don’t feel old.” That’s because, at 65, we aren’t.
We’re still in our go-go years. We still have the time and energy to conquer the world, visit new places, experience new adventures. The 70s, by contrast, are the slow-go years. Maybe we need replacement parts, to slather on Bengay, to load up on Advil.

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.

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.