My Family Made Me Do It

This week’s blog comes from Steve Gresham, Managing Principal of NextChapter, a leadership community dedicated to improving retirement outcomes for everyone. Steve is also Senior Education Advisor to the Alliance for Life-time Income. Prior to founding NextChapter, Steve held several senior leadership positions in investment and wealth management. As the Executive Vice President and head of the Private Client Group at Fidelity Investments, he led Strategy for the Retail Division from 2009-2017, when it grew from $700 billion to more than $3 trillion AUA.

Steve also served eight years on the faculty of Brown University’s Taubman School of Public Policy, and is the author of five books about wealth management, Including “The New Advisor for Life” (John Wiley & Sons, 2011). He is a graduate of Brown University.

Steve’s story highlights the challenges families face while navigating care late in life; as well as the need for planning and support services across the extended care market. HCG Secure and NextChapter are aligned in our missions to offer greater support, resources, and solutions toenable individuals to age with confidence.

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 later 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 

One of my grandfathers was a chemist – analytical by nature. He saved for retirement and left early at 62 in 1970. A wealthy executive friend turned him on to stocks. He never talked about any of it with me – just a young teen – but he couldn’t hide when the 1973-74 market crash slammed his account. Adding to his misery was the Arab oil embargo and gas rationing, keeping his new boat on the dock.

Fortunately, the house appreciated somewhat and after my grandmother died, my grandfather 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. It took some time for my mother and my aunt to wise up to Mary’s con game and my grandfather moved again to a nursing home in New Jersey.


The Home Invasion

My other grandparents lived in the small West Virginia college town where my grandfather had been president for nearly 20 years. Small and safe, they thought, until the day someone kicked in their front door and made off with all of their silver and jewelry.

Crime was the last thing they feared in Bethany, WV, 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 the community aged 90+. The local newspaper provided lavish coverage. She eventually became blind from glaucoma and moved to a nursing facility in Pennsylvania nearby her daughter and granddaughter. She lived to 101 – no one 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 after unwinding his business. The melanoma diagnosis was a surprise, though his twin had pre-deceased 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 – at age 74. 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 a facility. 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 (NY) assisted living and nursing pavilion – for $20k/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 that view.

People talking about aging long before it’s real, often speculate about whether they want to be of sound mind or body when they are old. Neither path offers a good ride – and good luck talking Mother Nature out of her plan for you.


The Hurricane

My Florida grandparents lived on Sanibel Island for 18 years without a single hurricane. When Andrew crushed the Miami area, more refugees headed West – to the Gulf Coast.

My parents never spent much time in Florida, and I was surprised when they decided to relocate to Sanibel in 2004. They had a small house up North but ultimately found one place simpler and easier. The week after they finished renovations, the first hurricane in a long time, Charley, struck Sanibel and Captiva. Their house was ok, my condo at South Seas was knocked flat.

My father hated Florida. My mother loved it and was soon involved in everything. My father was increasingly isolated – his work had been his identity. Always a great author and editor of medical texts, he penned a novel in hopes of growing a new passion. It was rejected by a publisher – a fact I learned only when I cleaned out his office after he died in 2016. I always wondered why he stopped writing.

Around 2014-15, my parents and I had a tough conversation about long term care costs. They owned retirement annuities from my dad’s employment, more than adequate to cover their modest living expenses. They paid off their home.

It was a battle with my mom, but we settled on buying a unit at a large continuous care retirement facility just off the island in Fort Myers. Mom declared she would never take residence, but the decision proved a godsend when my father was diagnosed with pancreatic cancer in the fall of 2015. He checked in to the nursing pavilion in October and passed away in February. He never went home.

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

Fast forward to September 28, 2022, and the assault of Hurricane Ian. Evacuating at the last minute amid an uncertain forecast, Mom hunkered down with my sister on the mainland.

When the terror ended, Sanibel had been destroyed by 150 mph winds and a tidal surge as high as 18 feet. With an average height of just three feet, Sanibel was overwhelmed.

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” are good surprises with positive outcomes. They don’t expect a winning lottery ticket. They plan for bad news or bad developments so they can help protect clients and their families from those most feared situations. Because they happen to more people than you think – and very often to people you know.


You can check out more of Steve’s advice and experiences on the Insights page at

As an HCG Secure policyholder, take advantage of your available non-insurance benefits ahead of your time of need, so you have increased peace of mind, and you’re ready for all life’s “what ifs.”