For many advisors working with Gen X and older millennial clients, portfolio construction and retirement income are only part of the job. As they build deeper relationships with households in their peak earning years, they run into the harder work is around aging parents, shifting family roles, and what happens when health or cognitive ability starts to decline.
Those are not just edge cases, said Sarah Wotherspoon, managing director and advisor at Wealthspire, who has a focus on midcareer professionals in the “sandwich generation.” Based on two decades of experience on the job – as well as challenges she and her sister faced in caring for two ailing parents – she knows that emotional and practical barriers that can stall planning even for clients with substantial assets.
"About 29% of caregivers are sandwich generation folks. I have so many friends and clients who are in the same situation that I am," she said in an interview with InvestmentNews. "This isn't really a theoretical issue for me."
One common theme that complicates conversations about aging parents, Wotherspoon said, is the deep-seated attachment many parents have to their independence.
“When adult children start getting involved, parents can often hear that as the kids trying to take over,” she said. That perception can turn seemingly simple decisions – who is driving, who pays the bills, who talks to doctors – into high‑stakes arguments.
Privacy also matters. After decades of handling money, legal affairs, and health care, and some parents may not be comfortable discussing those details with their adult children, who in turn may feel uneasy prying into issues that are “none of the kids’ business.” That leaves advisors walking a fine line between respecting confidentiality and gathering enough information to build a realistic plan.
Wotherspoon also sees challenges from unresolved history among siblings and between parents and children, which tend to resurface just when clarity is most needed. Family feuds, perceived favoritism, and past grievances can quickly derail meetings that are supposed to be about powers of attorney or care options.
“It can seem ridiculous to bring this up, particularly for adults, but it is real,” Wotherspoon said. “It completely affects these conversations and the relationship.”
Layered over all of that is a broader reluctance to confront aging and mortality. While families may agree that planning is important, getting to the hows, whos, and whens of planning can be tough, especially for clients who are afraid it'll just hasten the inevitable.
Because clients rarely arrive asking to talk about their parents’ decline, Wotherspoon encourages advisors to use familiar planning tools as easy on‑ramps. For example, when modelling retirement cash flows for a couple, she recommends adding a few targeted questions about their parents: Where are they living now? How might that change over the next two to ten years? Is it realistic that the clients might provide financial support or need to live closer at some point?
Estate planning reviews are another natural entry point. When updating wills, trusts, and powers of attorney with a client’s attorney, advisors can ask whether the named decision makers still make sense given their current health and residence. A spouse who is starting to decline cognitively but still listed as co‑trustee, for example, may prompt a conversation about adding or elevating another trusted person.
For sandwich‑generation clients, Wotherspoon also asks whether their parents have estate plans and current health and financial directives – not to dig into expected inheritances, but to establish whether any structure exists. For parents who are intensely private, it's worth considering a low‑pressure introduction first, such as lunch with the advisor and adult children, so that everyone knows who to contact in an emergency even if numbers are not shared.
But whatever they do, she says advisors should not expect a single breakthrough moment. “These are not things you solve with one conversation or one meeting,” Wotherspoon said, stressing that aging‑parent planning is a recurring thread that is revisited and expanded over time.
Once the topic is on the table, Wotherspoon said advisors can bring order to a stressful subject by using a simple but repeatable framework. Among other items, she said it's crucial to clarify roles and responsibilities.
Advisors can help families distinguish between who is formally named in documents and who will actually handle specific tasks. One person might be better suited for managing finances and working with advisors, while it might make sense for someone who lives nearby to oversee medical appointments and daily check‑ins. Getting that division of labor into the open reduces confusion and resentment later.
Wotherspoon also encourages clients to make sure signed, up‑to‑date legal documents are stored somewhere the right people can reach them quickly, ideally through secure digital storage; the same goes for core financial accounts and online medical portals. Having the ability to pull up accurate information on a phone can pay dividends, she said, as it would minimize mistakes during a hospital call or care meeting.
There's also planning for housing, transportation, and care preferences over time. While advisors don't need to push parents into immediate changes, they can walk families through likely “next steps” if driving becomes unsafe or living alone is no longer practical. That might mean mapping out in‑home support, nearby independent‑living or assisted‑living options, and how each scenario affects cash flow.
Finally, Wotherspoon says adult children and parents often don't see eye to eye on care preferences. To help clients find a healthy middle ground between safety and independence, she takes inspiration from Atul Gawande’s “Being Mortal,” which addresses how to have caring conversations with aging people as they approach the end of their life.
“What the adult child thinks a good day is, is not what the parent thinks it is,” she said.
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