The holidays bring families together for food, traditions, and catching up. They can also offer something that’s harder to find during the rest of the year: a chance to talk in person.
And while wills, trusts, and healthcare decisions probably aren’t on anyone’s list of favorite dinner topics, they deserve a little time between “When are you getting here?” and “Who’s bringing the stuffing?”
Whether you’re raising young children, enjoying an empty nest, or helping your own parents plan ahead, a thoughtful conversation now can give everyone more clarity.
You don’t have to solve everything in one sitting. Start the conversation, agree on a next step, and get back to the turkey.
1. Give Everyone a Little Heads-Up
Most people don’t love being surprised with, “So, have you updated your will?” while passing the gravy.
Instead, suggest a quiet time during the visit. A walk, morning coffee, or a few minutes before the holiday festivities can feel more comfortable than a conversation in front of the whole table.
Try:
“While we’re together, could we set aside a little time to talk about our family’s plans? Nothing urgent. I’d just like us to know what’s in place and what still needs attention.”
The goal is to open a door, not schedule a family interrogation.
2. Lead With Why You Care
Talking about estate planning can feel awkward when someone worries you’re asking about an inheritance or questioning their decisions.
Keep the focus on supporting them and understanding their wishes.
“I want to make sure we could help you the way you’d want if you ever needed us.”
Or:
“We’ve been thinking about our own planning, and it made us realize we haven’t talked about what you would want.”
You don’t need account balances or a preview of who gets what. Start with whether a plan exists, who has been chosen to help, and where important documents can be found.
3. Young Parents: Talk About the People Who Would Step In
When you have young children, estate planning conversations often begin with a very personal question: Who would care for them if you couldn’t?
Before naming a guardian, talk with the person you’re considering. Explain what matters to you, ask whether they would be willing, and give them room to think.
You might say:
“We’re working on a plan for the kids, and we’d like to talk with you about being their guardian. We don’t expect an answer today, but we’d love to share what we’re thinking and hear your thoughts.”
It’s also helpful to discuss who could care for your children in an immediate emergency, especially if your intended long-term guardians live far away.
These conversations can include the everyday things that make your family yours: routines, relationships, traditions, and the values you hope your children grow up with.
4. Empty Nesters: Let Your Adult Children In on the Plan
Your children may be grown, but they still need guidance about what you would want and whom you’ve chosen to help.
You don’t have to share every financial detail. Give them a practical overview:
Where your estate planning documents are stored and how to access them.
Who you’ve named to handle financial, healthcare, and estate responsibilities.
How to contact your estate planning attorney.
Any wishes or instructions you want them to understand.
A simple opening could be:
“We’ve put some plans in place, and we want you to know where things are and who to call. You don’t need to remember everything. That’s why we’ve written it down.”
If your documents were created when your children still needed babysitters, it may also be time for a review.
5. Ask Your Parents About More Than a Will
“We have a will” is a helpful starting point, but it doesn’t answer every question.
A will alone does not avoid probate. Whether assets need to go through probate depends on how they’re owned and whether arrangements such as trusts or beneficiary designations are in place.
Instead of trying to evaluate your parents’ documents yourself, ask:
“Have you talked with your attorney about what would happen with the house and accounts after you’re gone?”
Or:
“Has someone reviewed your plan recently to make sure everything still works together?”
The purpose is to help your parents put their wishes into action and reduce the paperwork, uncertainty, and avoidable complications their family might otherwise face.
For more ways to approach this discussion, read our post, How to Talk with Your Aging Parents About Estate Planning.
6. Make Room for Healthcare Wishes
Estate planning also includes decisions that may need to be made during your lifetime.
In Massachusetts, a Health Care Proxy allows you to name someone to make healthcare decisions if you become unable to make or communicate them yourself. Talking with that person about your wishes helps them understand the responsibility.
Start with questions like:
“If you couldn’t speak for yourself, who would you want talking with your doctors?”
“What would you want that person to know about your wishes and what matters most to you?”
You don’t need to work through every possible medical situation over a holiday weekend. Knowing whom you trust and beginning to explain your preferences is a meaningful first step.
7. Consider a Gift That Won’t Need Batteries
If your family typically gives larger gifts or financial contributions, help with estate planning could be a thoughtful alternative this year.
For young parents, it can be a comfortable way to bring up something they’ve wanted to do but haven’t yet prioritized.
Try:
“If you’re looking for a gift idea for us this year, we’d really appreciate a contribution toward our estate plan. Getting guardians and the right protections in place for the kids would mean a lot.”
Grandparents can offer, too:
“Would you be interested in us helping with an estate plan as your family’s gift this year?”
Keep it optional and free of strings. The people creating the plan should choose their attorney and make their own decisions.
It may not fit under the tree, but neither does peace of mind.
One Conversation, One Next Step
You don’t need a finished estate plan by dessert.
Maybe the next step is finding existing documents, talking with a potential guardian, or booking a call with an estate planning attorney. Choose something manageable and decide when you’ll follow through.
At The Parents Estate Planning Law Firm, we help young families and empty nesters understand their options and create plans that reflect the people and priorities that matter most.
Schedule a free 15-minute call with our Client Services Coordinator, or call 978-263-6900. We’ll help you figure out where to start.
Then you can get back to the turkey and stuffing. And the annual debate about whether there’s such a thing as too much pie
