My work with consumers, clients and advisors over many years has revealed to me three groups of retirees. The first are those who are “all set.” The second are those who are screwed. The third are those who are screwed but don’t know they are screwed.

Consider the both remarkable and unremarkable story of Amy Goyer, told recently in The Wall Street Journal. A longtime executive leader with AARP, she is an expert at understanding longevity and planning. She knows the pitfalls that too often claim hopeful retirees and trash their plans. And yet she too succumbed to myriad unexpected demands caring for her aging parents. Those demands led to her personal bankruptcy.

Her story is remarkable because of her selfless candor and willingness to share her experience. And it is unremarkable because it is so common.

The human brain is not naturally wired to long-term planning. That’s scientific fact. Most people suffer from what Nobel laureate Daniel Kahneman calls “narrow framing,” which is the tendency to minimize the size and scope of situations and therefore fail to see their full implications. We see the tree. We miss the forest.

But even when we plan, retirement planning relies on predictions, many of which are spitball guesses for most people. Have enough money for retirement? How do you know unless you either have a fortune (most people don’t) or you have an accurate read on your full assets and benefits (after taxes, please), the future prices of those assets, the rate of inflation, your health in retirement—and the expected date of your death. Wait, we also need to know if you will be responsible for anyone else in that retirement. And for how long. And how much it will cost.

Because most people won’t guess accurately when answering these questions, we need to adjust the view of our roles and consider ourselves “retirement recovery specialists.” I don’t think this name is a marketing coup, and it will be improved by more creative folks than me. The key thing is that we must end the stigma against those who are unprepared and just assume that everyone is. Even the multi-millionaires may get trapped in a lifestyle they can’t afford or face life-changing healthcare crises. Just as likely for the wealthy is the need to find meaning, a new chapter, or risk boredom and loneliness. Retirement is not just financial, it is emotional.

If we are going to be good at this retirement recovery role, we need to be prepared like ninjas for the common planning challenges.

Advisors very often are confronted with “moments that matter.” By these, I mean critical situations clients or their families are in when they need critical help. Very often the advisors are only getting involved and trying to catch up when the train is already leaving the station.

I have talked with other advisors and we’ve discussed what these moments are. The following stories emerged from that research.

An Unexpected Health Event
I remember vividly a client of my firm named Sue, whose husband missed only one day in 33 years at John Deere. He collapsed at a pro-am golf tournament and was told he had a brain tumor. He had never worked closely with a financial advisor and now Sue needed help. Their advisor, my colleague Alicia, met with Sue and five of her friends, who all had similar situations. Alicia acquired them all as clients. But the starting point was the establishment of trusted contact information, powers of attorney and medical proxies. None of the five families had those basic documents in place.

Trouble Making Financial Decisions
Another colleague of mine, an advisor named Christian, had a longtime client who always drove herself to his office. But one day she admitted to him she could not remember where she had parked. And it was not the first time. Christian assured her she was safe, and he contacted her son who lived nearby. Additional measures Christian recommended included a fraud monitoring service; an updated power of attorney; and the update of other documents, including the living will. Christian now works closely with both sons.

A Recently Widowed Client With Adult Children
Another client of my old firm, let’s call him Bill, was an engineer and also a very confident investor. He built computers and did the taxes. He brushed off his financial advisor’s suggestions about managed accounts and income products with the firm. The advisor assigned to him wrote him off as a poor prospect for planning. But after he died, his wife, we’ll call her Jackie, engaged fully with the advisor at the suggestion of her oldest daughter. Seeking to save her children the stress of watching over her finances, Jackie opted for both a professionally managed account and protected income solutions, a complete turnabout from Bill’s approach.

'Gray' Divorce Creating Financial Insecurity
Divorce rates are rising again across the board (thank you, Covid-19) but older people are divorcing at higher rates. Whether it’s gray divorce or splits among younger people, it can put a severe strain on anybody’s retirement savings, and when you or your team members are asked to help in these situations, you must be ready to demonstrate empathy and perform solid analysis. It doesn’t matter how wealthy the families are. Divorce at any level of wealth invokes intense emotions and intergenerational conflicts.

Retirees Worried About Healthcare Costs
Health is the No. 1 priority of clients across all adult age groups—health, wellness and the financing of healthcare. They have to ask themselves if their documents are in order and who will be the medical proxies making their decisions. How will they arrange financing for their health—with Medicare or long-term care? How will they be able to customize cost estimates using local rates of healthcare costs, their family health history and longevity projections? I work with Whealthcareplan.com to confirm significant differences by county, which is important, especially if clients are considering different locations for “retirement.” Advisors often turn to national surveys to answer those questions, even though these things often require local answers. We can do better.

Older Adults Want To Age In Place
My mother is an 87-year-old widow with limited mobility but a sharp brain. She resists assisted living because she believes she’ll lose independence. Losing her home also means giving up her car. But her safety, and that of other people, is more important. And it’s likely that her expectations are going to be more ingrained as she ages.

Situations like this require retirement advisors to have proactive discussions, early on, with seniors about their living transitions. The talks should come well in advance of the proximate need. There is a widely held belief that people can age in place if they get in-home care. But as the pandemic showed, we can’t assume that caregivers will always be available. In fact, qualified, reliable and trustworthy caregivers will likely be scarcer than top financial advisors.

“These life moments are like dominoes. If one falls, the others tend to follow,” says Tom West, an advisor and council member of Next Chapter, our retirement think tank. Of course, this work is no game, and there may be no more valuable “moments” for financial advisors to prove their value.

As a start, you can tell clients these stories and query each of them on what their preferences and game plan will be. Let the games begin.   

Steve Gresham is CEO and founder of the Execution Project LLC and managing partner of Next Chapter. He was formerly head of the Private Client Group at Fidelity Investments. He also serves as senior educational advisor to the Alliance for Lifetime Income and is the author of The New Advisor for Life.