Fifteen years ago, when the subject of long-term care came up in a client meeting, the common response was somewhere between easy dismissal and dark humor. People didn’t want to think about that reality. It felt distant, abstract, and more than a little uncomfortable.
That’s changed.
The same baby boomers who waved off the conversation in their early fifties are now in their late sixties and seventies. They’ve watched parents navigate assisted living. They’ve seen siblings and friends face health crises that came sooner than expected. What was abstract and easy to dismiss has become concrete, and the question has shifted from “do I need to think about this?” to “what do I actually do?”
What Long-Term Care Actually Looks Like
Here’s a scenario that plays out more often than many people expect.
A couple, both healthy and active in their mid-sixties, doesn’t give long-term care much serious thought. A decade later, the husband develops a health condition. His wife becomes his primary caregiver - first at home, then with increasing outside help. He eventually passes, and she lives independently for several more years. Then her own health needs begin. Her kids are in different cities. In-home care becomes necessary, then an assisted living facility, then skilled nursing.
The costs at that stage - which can be north of $100,000 per year for skilled nursing in a lot of markets - land on whatever assets remain. Social Security helps. The portfolio helps. If the house is sold, that can help too. But the math can get tight quickly, especially if both spouses require care simultaneously or if cognitive decline extends the timeline of needed support.
None of this is meant to be frightening. It’s meant to be useful. Because many of these scenarios can be planned for, at least partially, if the conversation happens early enough.
Some clients have the assets to self-insure - meaning their portfolio is large enough to absorb long-term care costs without threatening their financial security. For them, a long-term care insurance policy may not be the right tool. For others, especially those whose assets sit in a middle range where a prolonged care event could genuinely deplete savings, the calculus is different. There are also planning strategies - including certain trust structures designed to preserve assets while maintaining eligibility for Medicaid if that becomes relevant - that are worth knowing exist.
The Conversation That Shouldn’t Wait
The families who handle these transitions well are the ones who started talking early.
Not just about finances - though the financial piece matters enormously - but about preferences, expectations, and wishes. Where does someone want to live as their needs increase? How do they feel about in-home care versus a facility? Who in the family is positioned to be the point person? What does the person themselves actually want, while they’re still in a position to say?
These conversations are uncomfortable. Many families put them off. And then a health event forces the issue under pressure, in the middle of grief or crisis, when everyone may not be equipped to think clearly.
The financial planning piece is actually the easier part. Accounts can be restructured, strategies can be implemented, documents can be updated. What can’t be recovered after the fact is the conversation that didn’t happen.
What People Actually Want to Leave Behind
When clients in their sixties think about legacy, many of them aren’t focused on it yet. They’re thinking about living well for the next twenty or thirty years, managing healthcare costs, and not being a burden on the people they love. The legacy conversation, in the sense of what gets left behind financially, tends to become more pressing when we move into our eighties or when the happy event of grandchildren enter the picture.
Grandchildren have a way of changing the conversation entirely. The client who said for years that he didn’t care much about leaving money to his kids will turn around and ask very seriously about 529 accounts, gifting strategies, and Roth conversions for a grandchild as they get older. The motivation isn’t abstract wealth transfer - it’s wanting to see it, to participate in it, to know that a small head start done soon can make a real difference in someone’s life.
That is worth planning around. Annual gifting, educational savings, and strategies like the 529-to-Roth conversion can all be structured intentionally rather than left to chance.
What Aging Gracefully and Confidently Actually Looks Like
After watching many people move through this stage of life - the ones who do it well and the ones who struggle - a few things stand out.
The people who age more gracefully have settled the financial anxiety. Not eliminated all uncertainty; that’s not possible. But settled it enough that money isn’t the thing keeping them up at night. There’s a plan. There are people involved whom they rely on. The financial piece is handled.
That foundation creates room for everything else: the relationships, the purpose, the freedom to own their time. Financial anxiety has a way of crowding out everything else, and its absence creates space that gets filled with better things.
The people who struggle more, in contrast, often waited too long to address the financial piece - and found themselves making decisions reactively rather than intentionally. Not because they weren’t capable of planning. Because the conversation got postponed, year after year, until circumstances forced a decision to be made, usually with far fewer options.
One of the more valuable things someone in their late fifties or early sixties can do for their future self is to have those conversations now, while options are still open and time is still on their side.
It doesn’t have to be complicated. It just has to happen.
Rawe Financial is a family-owned financial services practice in Northern Kentucky, helping individuals and families navigate retirement. If you are thinking about what your future may hold, let’s have a conversation.