I RECENTLY HAD THREE retired men visit my psychology practice, each grappling with depression. Just as women face special challenges during their senior years, so too do their husbands, fathers and male friends.
Who hasn’t been seduced by those syrupy commercials where an elderly couple hold hands while walking a sun-kissed beach? Retirement is advertised as a magic carpet transporting us to a well-earned destination of meaning and frolic. But the reality is more complicated.

HEALTH SAVINGS accounts (HSAs) were introduced in 2003, and have since become commonplace in employee benefit plans. My experience with HSAs dates to 2004, when my employer offered $400 in one-time seed money as an incentive to sign up.
HSAs differed from existing health-care flexible spending accounts, and offered some features I preferred. To me, the HSA’s most appealing feature was that I controlled the money. There’s no “use it or lose it” rule,

LAST MONTH MARKED two years since I leapt into the unknown and left the security of the corporate world to begin a second act as an independent writer. How’s it gone? Have things panned out as I hoped, financially and otherwise? 
Let’s be clear upfront that this move was never about making money. It was about taking a shot at my long-held dream of being an author. I’d put that dream on the back burner for three decades as I did what was necessary to support my family.

I FIGURED IT MUST have been the spaghetti from dinner at the dining hall. What else could have given me such sharp abdominal pains? Perhaps I had food poisoning that would eventually pass. That night back in the apartment, I couldn’t sleep due to the pain. I got up every half hour or so and headed to the bathroom. Strangely, I was unable to relieve myself. In addition to severe pain, I felt constipated.

WHAT’S THE FIRST RULE of personal finance? To answer this question, let’s look at the financial lives of two notable individuals, starting with musician MC Hammer.
When Hammer gained fame in the 1980s, he made millions. But unfortunately, his spending quickly outpaced his income. Hammer bought 19 racehorses, employed a personal staff of 200 and built a $30 million house with a 17-car garage. The result, sadly, was bankruptcy.
If MC Hammer represents one extreme of financial management,

I’VE KNOWN AT LEAST half-a-dozen folks who regularly carried five-figure credit card balances. In fact, I was once friends with a woman who had $100,000 in card debt—not just a staggering sum, but also a warning sign about her spending habits that I should have heeded far earlier than I did.
Folks who flock to HumbleDollar tend to be financially disciplined, so this sort of behavior will no doubt spark tut-tutting among some readers.

FOR MUCH OF MY ADULT life, I’ve read about marriages in turmoil because the wife earns more than her husband. That’s always bewildered me, because I spent most of my career being a very happy trailing spouse.
My wife and I met in our early 30s while trying to rescue a three-year-old stuck on an elevator. This was more than three decades ago. I was divorced and working as a journalist, and had taken my son with me when I needed to drop by the newsroom early one weekday evening.

I GRADUATED FROM the University of Central Florida in 2001 with a degree in information management systems. Thanks to academic scholarships, working part-time and family support, I graduated debt-free and, indeed, had some $15,000 in savings. Amid the economic turmoil of the dot-com bust and subsequent recession, I was fortunate to land a fulltime job at Fiserv, a banking software company.
That’s where I met my wife. We were engaged six months later and married in 2002.

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.

I’D JUST ARRIVED IN the charming, car-free village of Murren in the Swiss Alps, and was trying to find my B&B on the helpful signpost near the station. Stepping back for a better view, I tripped over the curb, with my backpack pulling me further off-balance. I went down with my left wrist under my hip.

Two wonderful British couples rushed to my assistance. One pair took my backpack to my B&B and the other escorted me back down the mountain to a doctor’s office.

SEVERAL MONTHS AGO, I received a phone call that left me shaken and bewildered. The voice on the other end claimed to be from the Social Security Administration. The caller informed me that my Social Security number had been compromised in a significant security breach. My heart raced as I contemplated the potential consequences, even as the urgency in the caller’s voice gave me little time to think.
The caller asked for my personal information,

MY MOTHER WAS AN elementary school teacher, with a large break in her work history to raise three daughters. My father spent three years in the Navy before enjoying a successful career as a business executive in sales. Because of my father’s job, we moved a lot when I was growing up. My parents bought and sold eight homes during their working years.
They eventually settled in Connecticut and retired in their early 60s.

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?

DON’T LOOK NOW, but value is beating growth—just not here in the U.S.

From May 31 through Sept. 29, iShares MSCI EAFE Value ETF (symbol: EFV), which invests in developed foreign markets, is up 5.6%, while iShares MSCI EAFE Growth ETF (EFG) is down 6.5%. That brings the year-to-date performance of the two funds to 9.6% for the iShares value fund and 4% for the iShares growth fund. Meanwhile, the style-neutral iShares MSCI EAFE ETF (EFA) is up 6.9% in 2023.

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.