Most families don't plan for caregiving — they stumble into it.
In my family, the stumble was my parents' head-on car collision on their way home from church. It could be a fall at home. Or a hospitalization while traveling. Or a diagnosis that turns "someday" into "now."
For families with substantial assets, caregiving challenges don't disappear. They compound.
Financial advisors are trained to help clients prepare for uncertainty. Yet even among highly sophisticated families, aging parents and caregiving are often addressed reactively — after a crisis forces decisions under pressure.
That's a missed opportunity.
Caregiving is no longer a niche issue. Nearly one-third of caregivers are part of the sandwich generation, supporting both children and aging parents.
This dynamic is especially complex in high-net-worth families, where decisions involve not just money but privacy, control, family dynamics and legacy. This is precisely where trusted advisors add the most value.
Clients don't expect advisors to have all the answers. They do expect leadership, perspective and the ability to guide conversations others avoid.
Here are six understandings that advisors need to internalize.
1. Wealth just changes the shape of the problem.
Money can buy exceptional support. It cannot buy clarity, alignment or emotional readiness.
In one client's case, her three adult children fought over the timing and process of selling the family home after she moved into a continuing care retirement community. It exponentially increased the client's stress during an already difficult transition, as well as the time and expense required to prepare, list and sell the home.
2. Advisors must lead the conversation.
Advisors sometimes assume that affluent families are "covered" with their financial resources and a team of professional advisors who will figure it out when the time comes. In practice, wealth typically compounds the complexity.
◆ Multiple homes across states or countries
◆ Sophisticated trust and entity structures
◆ Adult children living far apart
◆ Long-standing family roles and power dynamics
◆ Parents who are deeply independent and accustomed to control
I regularly encounter families who have ample financial resources but struggle to address these issues because no one wants to be the first to raise sensitive topics.
Clients are often relieved when their advisor leads. They're thinking about these issues — they just don't know how to open the discussion. When I recently recommended that a client update their estate plan to reflect one spouse's declining capacity and to name their adult daughter as an agent and co-trustee, relief flooded the caregiving spouse's face. I saw the same relief when the adult daughter joined our conversations and participated in the update.
3. Caregiving is a living, evolving experience.
The advisor's role isn't to engineer a perfect solution up front. It's to help families prepare, test assumptions and adapt as circumstances change.
Well before my parents' accident, my sister and I set up a shared password manager for their online accounts, had access to their health care portals, had joined meetings with the estate attorney and were agents for health care as well as legal and financial decisions. When the hospital chaplain called to report that our mom was in emergency surgery and our dad was also hospitalized, we were in a position to step in to support on all fronts. After they returned to their home, we reassessed the situation and took additional steps on medical, legal and financial fronts.
We built our support and communication systems over time, at a pace our parents were comfortable with.
4. Start early — before complexity becomes a constraint.
With high-net-worth families, waiting often narrows options. The most effective caregiving planning starts early and unfolds gradually.
Three entry points integrate naturally into existing advisory relationships:
◆ Financial modeling and liquidity planning.
When reviewing projections, frame care as a scenario, not a prediction.
You might say: "Part of comprehensive planning is anticipating possibilities and assessing the flexibility of your resources if health or care needs change — for you or for your parents."
This opens the door without triggering defensiveness.
◆ Estate plan stress-testing.
Sophisticated estate plans can fail in moments of urgency.
Is the named trustee or agent realistically able to serve if health declines?
Are decision-makers accessible across jurisdictions?
Who is in a position to act quickly if something happens while traveling or living in another home? Does that person have everything necessary at their fingertips?
At this level of wealth, the issue isn't documentation — it's execution.
◆ Multigenerational engagement.
Proactively build relationships with adult children before they're suddenly in charge.
This doesn't require a formal family council. It can begin with a simple question: "If something happened, who would you want involved — and how would decisions flow?"
Clarity now prevents confusion later.
5. Money isn't the hard part.
In working with families, one truth comes up repeatedly:
The hardest part of caregiving isn't the money. It's navigating family relationships and conversations. In my experience and observations with clients, parent-child and sibling dynamics often emerge in forceful, challenging ways.
Parents fear loss of autonomy. Adult children fear overstepping — or being blamed. And siblings revert to entrenched roles that may predate wealth itself.
In wealthy families, decisions are further complicated by:
◆ Privacy concerns
◆ Existing staff or advisors with unclear authority
◆ Differing philosophies among children
◆ Parents who equate help with loss of independence
Money can fund world-class care. It can't force agreement.
Or, as I often tell clients: "Money can buy help, but it can't buy alignment."
6. Clients respond to structure.
High-net-worth families don't need vague reassurance. They need structure.
Here's a practical, repeatable framework that advisors can use.
◆ Map people and authority.
Caregiving is a team sport, and most families don't know the positions.
Who has legal and financial authority? Who handles health care decisions? Who communicates with staff and advisors? Who steps in if a primary decision-maker can't serve?
This reduces friction before emotions escalate.
◆ Build an access and coordination plan.
In a crisis, speed and coordination matter.
Help families organize centralized account and entity summaries, where estate documents and directives live, medical information and portals, and key contacts across advisors and staff.
The objective is continuity, not perfection.
◆ Address housing and transportation proactively.
Moves and driving decisions rarely happen on a clean timeline.
Encourage families to explore options early. Retirement communities and concierge care often have long lead times. Trial periods preserve choice and dignity, and decisions are easier before safety becomes urgent.
A phrase that resonates with clients: "We're not taking options away — we're protecting them."
◆ Anchor decisions to values, not logistics.
Drawing on Atul Gawande's "Being Mortal," shift the focus from mechanics to meaning.
What defines a good day? Which tradeoffs are acceptable? Which are not? What matters most: independence, comfort, proximity to family?
These conversations guide better decisions when tradeoffs become unavoidable.
◆ Establish a cadence for family communication.
Care plans aren't static.
Recommend an annual or semi-annual family check-in to refresh roles and responsibilities, revisit preferences and adjust as health or circumstances evolve.
Regular conversations prevent reactive decisions.
Sarah Wotherspoon is a managing director and advisor at Wealthspire, an independent wealth management, retirement advisory, and business management firm.
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