I was fortunate to know all of my grandparents and three great-grandparents—and to see all of them battle significant and scary events in their last years. All of my older relatives were tough, independent people who lived on their own as long as they could. Here are their stories of retirement wreckage.

The Bear Market
My maternal grandfather was a chemist and was analytical by nature. He saved for retirement and left work early at age 62 in 1970. A wealthy executive friend turned him on to stocks. He never talked about any of it with me (I was just a young teen) but he couldn’t hide the fact that his account was slammed in the 1973-1974 market crash. Adding to his misery was the Arab oil embargo and gas rationing, which kept his new boat on the dock of their Florida home.

Fortunately, his house appreciated somewhat, and after my grandmother died, he sold their dream home and moved closer to family in North Carolina. Upon arrival, he was befriended by a very nice younger lady at church. Unfortunately, Mary was an opportunist who made herself at home, suggested gifts for herself and took money—actions that took some time for my mother and my aunt to figure out. He moved again to be closer to better supervision, this time to a nursing home in New Jersey near to where he and my grandmother used to live.

The Home Invasion

My paternal grandparents lived in a West Virginia town called Bethany, and my grandfather was president of Bethany College for nearly 20 years. Crime was the last thing they feared. It was a small town, and a safe one—or at least they thought so until the day someone kicked in their front door and made off with all of their silver and jewelry.

So they also headed south—to an independent living community on a golf course in North Carolina. My grandfather continued to speak and serve on boards until he passed away in 1994.

My grandmother was a great putter, ballroom dancer and concert pianist. She hosted a birthday party every year for herself and everyone in her North Carolina community who was over age 90. The local newspaper provided lavish coverage. She eventually became blind from glaucoma and moved to a nursing facility in Pennsylvania near her daughter and granddaughter. She lived to 101, and no one was more surprised than her.

Losing Your Mind (And Your Body)
My father-in-law was a big personality and a golfing fanatic, eyeing a retirement on the links in Hilton Head Island in South Carolina after unwinding his business. His melanoma diagnosis was a surprise, even though his twin had predeceased him.

He was a fighter, but when doctors told him more surgery would end his mobility, he gave in with his customary purposeful attitude. One of his final instructions to my wife was, “I’m worried about your mother. Something isn’t right.” He was only 75.

That something was Alzheimer’s disease, diagnosed a short time after my mother-in-law burned a pot cooking lemons on her stove. She was 74 at the time. My wife and her sisters shuttled back and forth, trying out home care aides and managing schedules around jobs and young kids. My wife visited so often we violated the limit of days we could be in New York state and paid a significant penalty in state taxes.

A fall broke her femur and set off a scramble to find assisted living. The costs were outrageous, but more alarming was the shortage of acceptable facilities and open beds. Only through tears of frustration did my wife secure a spot in a Westchester facility with a nursing pavilion—for $20,000 per month.

Unable to remember the names of any family, my mother-in-law lived in a shrinking world with heightened fear until she died. Everyone remembers her for her poise and pride and generous heart. Her final years cannot eclipse those memories.

People who talk about aging long before it’s happened often speculate about whether they would rather be of sound mind or sound body when they are old. In the end, it’s of little matter, because Mother Nature has a plan for you, and good luck talking her out of it.

The Hurricane
Sanibel Island and Captiva on the west coast of Florida have become popular destinations for those relocating from the Eastern Seaboard, especially after Hurricane Andrew leveled a lot of the Miami area in 1992.

I was surprised when my parents relocated to Sanibel in 2004, since they had never spent much time in Florida, where my maternal grandparents were residents for several years. My mother loved Florida, but my father hated it. After he relocated, he felt increasingly isolated. He was retired, and work had always been his identity. A well-known physician and academician, he led the Framingham Stroke Study and authored the federal standards for stroke rehabilitation. During his retirement, he penned a novel in hopes of growing a new passion, though it was rejected by a publisher (something I found out in 2016 after I cleaned out his office). I’m sure that was a blow.

In 2014 and 2015, my parents and I had a tough conversation about long-term-care costs and the possible need for continuous care. My mother declared she would never take up residence in a retirement facility. They owned retirement annuities from my dad’s employment, more than adequate to cover their modest living expenses. And they had paid off their home (their second in the area).

It was a battle with my mom, but we settled on buying a unit at a large continuous care facility just off the island in Fort Myers. Though my mother said she would never live there, the place turned out to be a godsend when my father received a pancreatic cancer diagnosis in the fall of 2015. He checked in to the nursing pavilion in October of that year and passed away the following February. He never went home.

My mother settled into her new life, motivated by close friends and her many responsibilities. She traveled some, taking trips to Scotland and Alaska with family in tow.

She had managed to get through years without weathering the blows of a strong hurricane. Hurricane Charley struck both islands in 2004, but my parents’ newly renovated house was OK. (My condo on Captiva was knocked flat, I should mention.)

Fast-forward to September 28, 2022, and Hurricane Ian, which buffeted Sanibel. My mother had to evacuate at the last minute amid an uncertain forecast and hunkered down with my sister on the mainland. When the terror ended, Sanibel had been overwhelmed by 150 mile per hour winds and a tidal surge as high as 18 feet against an island whose average height was 3.

With her friends, her annuities, her activities and the manageable pace of an island with a 30-mph speed limit, Mom had it all. Until she didn’t.

Just Plan That The Plan Will Fail
It’s impossible to predict what will actually happen, and the best financial advisors don’t do that. They help clients plan for the best, most reliable path. And then the really good advisors run that plan again with as many “what ifs” as they can think of. And none of these “what ifs” should be good surprises with positive outcomes. Nobody should expect a winning lottery ticket. Advisors should help clients plan for bad news or bad developments. Such planning helps protect clients and their families from those most feared situations. Because bad things happen to more people than you think—and very often to people you know.  

Steve Gresham is the managing partner of Next Chapter, a community of more than 60 financial service organizations dedicated to improving retirement outcomes for all.