How to Talk About Estate Planning at the Holiday Table
Holiday tables are just big, chaotic family meetings with better snacks. Between catching up on jobs, grandkids, and who brought the good pie, there’s usually a moment when the room softens and the conversation gets a little deeper. That little window is gold. It’s a chance to talk about something that doesn’t fit easily into everyday life: “What happens if something happens to me?” Between talk about travel, new babies, or even recent Social Security changes for 2025, there’s room for one more conversation that really matters.
This isn’t about being morbid. It’s about love, clarity, and reducing chaos for the people you care about most. Whether you’re talking to your aging parents about their estate plan, or to your adult children about how you’d want to be cared for if you were incapacitated, these conversations are a gift. They answer questions like: If I couldn’t make decisions, who is legally allowed to talk to doctors for me? Who can pay my mortgage or access my accounts? If I died, is there a will that reflects what I actually want? Or does the state get to decide what happens because nothing’s been put into writing?
When there isn’t a plan, families are suddenly thrown into the deep end. Besides grieving, there is also guessing, and often arguing, about dealing with hospitals, bills, and courts. When there is a plan, your loved ones have a map. A healthcare proxy or medical power of attorney can speak with doctors. The financial power of attorney can pay the mortgage and keep the lights on. A will or trust can guide where your assets go and who is in charge. The hard part isn’t usually signing the documents; it’s starting the conversation. So here are three gentle, practical ways to open that door during the holidays.
Conversation Starter #1: “If something had happened to you last week…”
This one is direct, but powerful:
“If something had happened to you last week and you are either gone or unable to make decisions, how would you want your health and your money to be handled? Is there a plan for that?”
You can tailor it depending on who you’re talking to:
With parents:
“Dad, if something happened and you couldn’t speak for yourself, who would you want to speak to the doctors? Do they know that? Is anything set up legally so they can?”With your spouse or partner:
“If one of us got in an accident and couldn’t manage things, does the other one have everything they’d need? Access to accounts? Clear instructions? Or are we making future-us figure it out?”With your adult kids:
“If something happened to me, I don’t want you scrambling. I want you focused on being together, not hunting for passwords. Let’s talk about what exists now and what still needs to be done.”
This question brings the abstract “someday” into the very recent past, “last week.” It makes the stakes real, without being dramatic. It invites a practical, caring conversation: Do we have a will? Do we have healthcare and financial decision-makers named? Does anyone know where those documents are?
Conversation Starter #2: “I don’t want to leave you guessing.”
This works beautifully when you’re talking to your kids or grandkids:
“I’ve been thinking about the future, and I don’t want to leave you guessing about what I’d want if I were ever incapacitated or gone. Can we talk about that for a few minutes while we’re all together?”
From there, you might share:
Who you’d want to make medical decisions if you couldn’t speak for yourself.
What “quality of life” means to you in serious health situations.
Who you’d want to handle practical things like paying bills or managing your home.
Whether you already have documents, like a will, trust, power of attorney, or healthcare directive, or you need to put those in place.
This isn’t about listing every account balance at the dinner table. It’s about values and roles: who you trust to do what and how you want them to think about those decisions. You can always follow up one-on-one later with details, documents, and a professional.
Conversation Starter #3: “Does the state have the plan, or do you?”
This one is especially useful with parents or siblings:
“Right now, if something happened to any of us and there wasn’t a will or estate plan, the state would decide who gets what and who’s in charge. Is that actually the plan we want—or do we want to be the ones deciding?”
You’re not accusing; you’re inviting everyone to step into adulthood together.
From there, you can gently unpack:
If there’s no will:
The state has a default formula for who inherits and who has authority. That might not match your family’s reality, especially with second marriages, children, estranged relatives, or special needs.If there is a plan, but no one knows it:
“Has anyone besides you seen the documents? Do we know who your attorney is? Where are the originals kept?” A secret plan is almost as stressful as no plan.If roles aren’t clear:
“If you were in the hospital, who would the doctors talk to first? Who would pay the mortgage or rent while you’re recovering? Do they know they’re in that role?”
This question shifts the tone from “estate planning is about death and money” to “estate planning is about control, clarity, and kindness.”
One Conversation, Many Blessings
Holiday gatherings are already about tradition, legacy, and the people we love most. Folding in a conversation about future wishes is completely aligned with that. You’re not “ruining the mood”; you’re protecting and preparing your loved ones for an inevitable future.
You don’t have to solve everything over one pumpkin pie, one candle-lighting, or one flight home. Your job is to open the door:
Ask one thoughtful question.
Listen more than you talk.
Offer to help find a an estate planning attorney, certified financial planner, or bothto turn intentions into a real plan.
At the end of the day, documents like wills, powers of attorney, and healthcare directives are just paperwork. The real heart of this is simple: The people you love deserve clarity, not chaos.
Use this holiday season to give them that gift—one honest, loving conversation at a time.