How to Use the Holidays to Start Conversations About Caregiving
The holidays are one of the few times of year when many families actually slow down and gather under one roof. And nowadays, it can be rare to have everyone in one place: parents, siblings, adult children, maybe even grandkids.
That’s why I often tell clients—especially women in their 40s, 50s, and 60s—to think of this season as more than just celebration time. It’s also a natural opportunity to start, or gently revisit, some of the important family conversations that tend to get delayed—until life forces them.
I don’t mean diving into legal documents or spreadsheets between dinner courses. I mean planting seeds, asking questions, and starting casual conversations that can make future decisions clearer and less stressful for everyone, particularly when it comes to aging and caregiving amongst your family.
If You Have Aging Parents
If you have aging parents, you and your siblings might already be handling more than you realize. Perhaps you’re helping to manage doctor appointments, errands, bills, and little favors that have slowly become routine. The holidays are a good time to raise this kind of topic gently while everyone’s together. Try saying things like:
“Mom, Dad, my financial advisor encouraged me to ask a few questions about your plans—not to pry, but just so I know how to help if you ever need it.”
“Would it help if one of us started keeping track of medical contacts or accounts, just so nothing falls through the cracks?”
“I know you’re still independent, but I just want to make sure we’d all know what to do if something unexpected ever happened.”
“Mom, Dad—have you updated your will or powers of attorney recently? If not, maybe we can help you get that done in the new year.”
These questions aren’t confrontational; they’re caring. They open the door to future planning, while showing respect for your parents’ independence.
If You’re The (Aging) Parent
For many people, the holidays are the one time adult kids are all in one place and relaxed enough to talk. You don’t have to walk them through your full financial plan, but it could be a good opportunity to give your children a sense of direction that may help give them clarity they didn’t know they needed.
You might say:
“My advisor suggested I loop you in on a few things next year—would you be open to sitting down with us sometime?”
“I’ve started organizing all our important documents so you’ll know where everything is someday. It’s not urgent, just helpful to have in place.”
“I want you to know what my wishes are, so if you ever have to make decisions for me, you’ll feel confident doing it.”
“We’ve talked about helping with college for the grandkids. Can we schedule some time to put some structure around that in the new year.”
These comments signal transparency and confidence, and they model responsible planning for the next generation.
If You’re In The Middle
Many women find themselves sandwiched between caring for parents and helping their own kids or grandkids. That’s a lot of responsibility, both emotionally and financially. The holidays can be a good time to talk openly about what’s realistic and how to share the load.
Here’s how those conversations might sound:
“It might help if we all talked together in January about how to share the caregiving load. My advisor could even help us map out a budget or plan for it.”
“I love being able to help Mom, but I think we need a plan so it doesn’t all fall on one person.”
“Would everyone be okay splitting certain expenses or tasks? I can handle appointments if someone else can take on the paperwork.”
“Let’s talk about what happens if Mom needs more help next year—do we all agree she’d prefer to stay home rather than move?”
These aren’t easy discussions, but they’re far easier to have before there’s an emergency.
Why These Conversations Matter
These conversations aren’t really about money. They’re about care, values, and feeling more confident in what comes next.
And the goal isn’t to solve everything in one night. It’s simply to start talking. Because when families communicate early and often, everyone’s better equipped to make thoughtful choices later.
So as you gather this holiday season, in between the gifts and the laughter, consider taking a quiet moment to plant a few seeds for the future. A simple conversation today could save your family heartache, confusion, and stress down the road.
And that, to me, is one of the most meaningful gifts you can give.
If you’re navigating decisions about aging parents or caregiving responsibilities, you don’t have to do it alone. We help families build clear plans for care, communication, and financial confidence. Schedule some time to talk to me: https://calendly.com/winstone-wealth-partners/financial-consultation-with-lauren-smith
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The foregoing information has been obtained from sources considered to be reliable, but we do not guarantee that it is accurate or complete, it is not a statement of all available data necessary for making an investment decision, and it does not constitute a recommendation. Any opinions are those of Lauren Smith and not necessarily those of Raymond James.