A birthday can be the moment it hits you. For one couple I wrote about in Wealth Your Way, it was planning a mother’s 70th when they realized they had no real idea what her parents’ financial or care situation looked like, and weren’t sure they’d have any legal standing to help if something went wrong. That kind of realization rarely arrives on schedule. It can show up while checking a calendar, driving home from a visit, or noticing a parent seems a little more tired than usual lately.
I hear some version of that story more often than you’d think. Not because families don’t care about each other. But because the conversation feels heavy, and it’s easier to assume there’s more time to have it later.
Why We Put It Off
In my experience, families put off these conversations for a few consistent reasons. Today’s schedule feels more real than something that might happen years from now. A parent getting older — or the discomfort of needing care after a lifetime of caring for others — is hard to sit with. And plenty of people assume the topic will be expensive or complicated before they’ve even brought it up.
None of that makes a family careless. It makes them human.
As I mentioned in my conversation with Cole Craven from MOVE Health, I think of a client who called me at the end of last year following an unexpected layoff from an employer he’d worked with for decades. We’d talked about his finances plenty of times over the years. We’d never once talked about what would happen to his health coverage if that job ever went away. It wasn’t something we purposely set aside. The subject simply hadn’t come up, until it was the only one that mattered.
This wasn’t always front of mind for me in financial planning either. For years, I was comfortable referring healthcare conversations to a local resource or two. However, as my business expanded beyond my home state, I realized I needed to work closely with a healthcare planning team with a broader reach.
I’ve noticed that most adult children don’t know where their parents keep the important paperwork. Nobody’s hiding anything, but nobody is asking either. Asking feels like admitting something neither person is ready to admit yet. Families get further with a single honest question than they do with an entire binder of documents.
What It Feels Like From the Other Side
Parents feel this differently. For a lot of them, the fear isn’t the conversation itself. It’s what it might set into motion: losing the house, losing the car keys, losing the sense that they’re still the one making decisions.
“I don’t want to be a burden to my kids” shows up in nearly every version of this. It’s real humility, and it often sits alongside something harder to admit: the discomfort of becoming the one who needs care, after a lifetime of being the one who gave it.
Epictetus separated what’s in our control from what isn’t. Whether a parent eventually needs more help than they do today isn’t something anyone gets to decide. How a family prepares for that, together instead of separately, is. Parents who invite their kids into the conversation early tend to hold onto their independence longer, not shorter. Clarity isn’t the thing that takes control away. Silence is. The hesitance itself is usually bigger than the reality once a family actually starts talking.
Healthcare Is Part of This Conversation Too
Financial planning conversations tend to stop at accounts and investments. For families navigating aging parents, healthcare decisions carry just as much weight, and they get put off for the same reasons.
A recent industry survey found that 65% of clients want their financial advisor to talk with them about health insurance or Medicare. Only about 4% of advisors are actually doing it. That gap is a big part of why I’ve engaged with MOVE Health, a firm that focuses specifically on healthcare planning, so this piece of the picture doesn’t get left out.
Cole Craven, who leads MOVE Health, has told me that the healthcare question is often the one that stops people in their tracks, even when everything else about retirement is ready to go. He’s shared that watching his own in-laws hit that exact moment — financially ready to retire, kids through college, house paid off, but suddenly unsure about coverage — is part of what led him to build a firm around it. Roughly 40 million Americans fall into the window between an early retirement and Medicare eligibility at 65, and that coverage gap is easy to underestimate until it’s sitting in front of you.
One thing Cole has told me that’s stuck with me: most of the urgent-sounding mail and phone calls people get around age 65 aren’t about real Medicare changes. They’re marketing. Medicare has been around since the 1960s, and if something were genuinely changing at that scale, it wouldn’t show up as a robocall. His team typically starts that conversation four to six months before someone turns 65. That’s enough time to actually understand the options instead of reacting to whatever lands in the mailbox that week.
Watch my full interview with Cole here.
What Clarity Actually Looks Like
Clarity doesn’t mean having every answer today. It means knowing where to look when you need one.
In Wealth Your Way, I break down the handful of documents that tend to matter most: a healthcare power of attorney, a financial power of attorney, a living will, a last will and testament, and in some cases a trust. None of these are exotic. They’re the practical version of a family already knowing what a parent wants, and who’s authorized to act on it.
But clarity isn’t only paperwork. It’s also the smaller conversations that tend to get skipped: whether a parent actually wants to stay in their home as they age, and what that home might realistically need to make that possible. Who they’d actually want making medical decisions, not just who’s listed on a form. Whether independence matters more to them than being close to family, or the other way around. Questions like these live outside any legal document, and they’re often the ones that matter most when a decision has to be made.
This doesn’t require solving everything in one sitting. It just requires a starting point.
A Conversation in Practice
That starting point doesn’t have to be complicated. A while back, I sat down with Kimberly Akers and her mother, Karen, for an episode of the Walks With Mom podcast. What struck me wasn’t anything either of them said about finances specifically. It was how naturally they moved between topics: joking one minute, direct the next, neither one treating the conversation as fragile.
This isn’t just a podcast topic for Kim. It’s her career. She co-owns Amada Senior Care in Phoenix, where her team helps families navigate in-home care and long-term care insurance claims. That’s the same kind of coverage that made the difference for a client I wrote about in Wealth Your Way, whose policy covered the bulk of her care after an unexpected stroke.
That’s closer to what this actually looks like in practice than any checklist I could hand someone. Families who’ve had one honest conversation tend to find the next one easier.
Starting Before It Becomes Urgent
I think about Christopher and Laura sometimes, the couple whose story opens this piece. Their first conversation with her parents didn’t resolve everything. But afterward, Laura told me, “We feel so much better. There’s still a lot to figure out, but at least now we’re all on the same page.” That’s usually the win: not certainty, but the start of it.
The goal was never to have every answer at once. It’s to ask one question, or finally answer one you’ve been avoiding.
If you’re not sure where to start, Wealth Your Way is a good place to look, especially the estate planning chapter. If healthcare is the piece that feels most uncertain, that’s exactly what MOVE Health is there for. And if you’d rather just talk it through, that’s what I’m here for.
Walks With Mom is an independent, third-party podcast. Resilient Wealth is not affiliated with and does not control its content. The views expressed are those of the participants and do not necessarily reflect the views of Resilient Wealth.
