IN 1980, MY FIRST WIFE and I spent the Labor Day weekend with friends on Cape Cod, Massachusetts. We went out for breakfast and I drank a lot of coffee. Our friends were planning a day at the beach. This is not a good idea for me because—being of Irish descent—I come in two colors, red and white. Either I look pale and sickly or I’m red as a beet. To avoid this latter state,

I WAS BORN ON THIS day in 1943. Today, I must acknowledge being old. I remember, years ago, scanning the obituaries and checking the age at death. Seventy-five seemed like a good run. Not anymore it doesn’t.

At age 40, I gave up the occasional pipe and vowed, if I made it to 80, I’d take it up again. That’s not going to happen. Not smoking may be a factor in getting this far.

WHEN I WAS GROWING up, my father would drag me to his office in lower Manhattan a couple of Saturdays each month. He always claimed it was to teach me “the value of a dollar.”
He was raised below the poverty line, and felt my mother spoiled me and that I needed to learn what it meant to work. I now realize he was right, but back then I thought he just wanted an audience who he could then impress with his business exploits.

AS WE GET OLDER, the financial hits often grow far larger, for two reasons. First, we’re typically wealthier, which means the potential dollar losses are bigger. Second, as we age, there’s greater risk of hefty health-care costs, notably long-term-care expenses.
Almost everybody endures at least a few big financial hits during their lifetime. Perhaps you lose your job, and it then takes many months to find work. Maybe your parents need nursing-home care and you end up footing part of the tab.

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,

MY WIFE AND I PLANNED our retirement using several standard assumptions, including how long we might live. Dorothy was healthier than me, so we assumed I’d be the first to go. But on June 30, she died suddenly, and I was the one left to deal with the fallout—including the many pesky, practical details.
Those details were bureaucratic and technical, and it didn’t take long to complete them. Dealing with the funeral home, Social Security and various financial institutions was straightforward.

MANY OF US SAY THAT, if we have to die, we’d like to die comfortably in our home. Luckily, hospice—a Medicare-covered model of gentle, holistic end-of-life care—is ready to help with that goal.
Maybe.
At age 78, my divorced father was diagnosed with Stage 4 colon cancer. He later admitted that he’d skipped getting any colonoscopies. He was a savvy health-care researcher and, via drug trials, controlled the spread of his cancer for four long years.

SELLING A HOUSE should be easy. Hire a realtor, find a buyer, the realtor takes a percentage and it’s a done deal. If only.

Try this version instead. Before we could sell our house in 2020, we had to fix a list of defects, including power washing the roof, having a dead tree removed, digging up an already drained oil tank and tearing up the pavers in the driveway to get at the tank.

I RETIRED ON MAY 27, 2022, which was my 55th birthday. I chose my birthday because it was the earliest date I could leave my job and still be eligible to receive the early retiree health-care benefit offered by my employer.
Mentally, I was ready to go. I’d been employed at a small liberal arts college for 24 years. I’d been there long enough to see an almost complete turnover of the faculty and staff in my department.

RETIREMENT IS SAID to be a time for reviewing and reminiscing. We try to understand who we were and how we came to be who we are. But the health trials of the retirement years can also project us into the future. When couples enter their twilight years, they begin to contemplate how they’d cope if the other died first. I believe “survivor rehearsal” is one way our biology helps us to contain the fear of having to cope on our own.

I’M IN EXCELLENT health. I avoid overindulging on sugar and carbohydrates. I exercise every day. I hope to live well into my 90s, if not longer.
What if I don’t live nearly that long? From a financial perspective, it makes little difference if I pass away before I tap my retirement funds. The value of most of my accounts wouldn’t be affected by my premature demise. My husband would simply inherit my 403(b) and Roth IRA accounts.

EARLIER THIS YEAR, HumbleDollar unveiled its Two-Minute Checkup. All you need to do is input up to nine pieces of information and it spits out advice covering 10 areas of your financial life. When I tried it, I thought it was great—except for one thing. The amount it suggested my wife and I have in emergency cash was $13,000 higher than what we currently had.
I felt comfortable with the amount of cash we were holding,

SARAH AND I GOT married earlier this summer. We’ve always been on similar pages when it comes to money. We both track our finances with gusto. She’s one of the few people I know whose budgeting spreadsheets are more intricate than mine.
We both try to spend reasonably and save consistently. We’d rather devote money to a vacation or an occasional late-night pizza than to fancy things or swanky surroundings. One indication: During the pandemic’s initial lockdown,

MANY YEARS AGO, I read an article that posited that U.S. income inequality is due, in part, to the unwillingness of unemployed and underemployed Americans to move to a new state or city to take a better job.
It mentioned three reasons for this reluctance. First, folks didn’t want to sell their home, which may have decreased in value due to the recession that caused the bad job market in the first place. Second,

I RECENTLY LEFT MY job without having another lined up. Upon quitting, I noticed an immediate mindset shift: I went from thinking about how to grow my money to, instead, thinking about how to preserve it.
As a trained financial planner, I know that many workers will face a similar mental transition as they begin to wind down their careers. But I was surprised at how quickly it happened to me. After all, I’m only age 39,