How to Talk to Your Parents About End-of-Life Wishes Before the Holidays

The equinox has passed. The light and the dark came out even. And then the year tipped.

For one day, we experienced balance. Day and night were as close to even as they come. Then Wednesday arrived, and the dark started winning by a few minutes each day, just as it does every year, without asking.

Florida doesn't announce it the same way other places do. There are no colors turning, no sweater weather—at least not yet. But the light is coming in at a different angle now. The afternoons end sooner than they did in August. Something has shifted, even if the temperature hasn’t gotten the message.

The Holidays Are Approaching

Here’s what else has changed: the holidays are on the calendar now. They’re not just around the corner—they're visible. Flights get booked this month. Someone starts a group text about Thanksgiving. The year that felt wide open in June now has a shape again, and that shape includes everyone in the same room.

This makes it the right month to think about a conversation you’ve probably been putting off.

In my work as an end-of-life doula, families often tell me they’re waiting for the right time to talk with their parents about what they would want. They wait for a quiet moment. They wait until everyone’s together. They wait for it to come up naturally.

So it waits until the holidays. And the holidays are the worst possible time to have it.

Not because the topic is too heavy for a celebration. But because the conditions are wrong. There are too many people in the room, most of them with opinions. There’s a sibling who flew in and has to fly out. There’s wine. There’s a schedule. There’s a version of your dad who is performing being fine because that’s what he does when the whole family is watching. Nobody has the time or the privacy to say something true, and everyone knows that whatever gets said will be discussed in the car afterward.

The holidays are not a planning meeting. They’re a performance with a meal in the middle.

A Better Time to Talk

But the weeks before them are different. Right now, your mom is alone in her kitchen on a Tuesday. Your dad is in the car with you on the way back from an appointment. There’s no audience, no clock, and no one waiting for their turn to talk.

So here’s the small thing I’d offer for the turning of the season: have the conversation before the gathering, not during it.

It doesn’t have to be the whole thing. One question is a beginning.

If you got really sick, who would you want making decisions for you?

Or: Is there anything you’d want me to know that we’ve never talked about?

Or the easiest one, the one that works because it makes you the subject instead of them: I’m getting my own paperwork in order. Have you ever done yours?

You’re not asking them to plan their death. You’re asking them to share something, so you’re not guessing later.

And if it goes badly—if they change the subject, or say “let’s not do this right now,” or tell you they’ve already handled it in a way that suggests they haven’t—that’s not a failure. That’s information. You can come back to it in two weeks. The whole thing does not depend on a single conversation going well.

Avoidance is not an advance directive.

Practical Considerations

A few practical notes, because the season is short: in Florida, a healthcare surrogate designation and a living will are the two documents that do the most work, and neither one requires a lawyer. If the person you’d name lives out of state, name them anyway—proximity isn’t the requirement, willingness is. And if you find yourself putting your own paperwork off, you’re not alone in that. Most of the people who do this work with me start by admitting they haven’t done their own.

This is work I do with families, either for their own planning or as a third person in the room when the conversation needs one.

Finding Support

If any of this brings up something that’s harder to carry alone, you’re welcome at Grief Circle, held monthly on Zoom. It’s free. There’s no script and no requirement to share. Come for someone you lost last week, or someone you lost twenty years ago. All of it belongs.

Embracing the Change

The light will keep tilting. By the time the table is set and everyone is in the same room, the afternoons will be short, and the year will be almost spent. You can’t hold the balance—it was only ever one day. But you can use these weeks before to ask one question, on an ordinary Tuesday, with no audience and nothing riding on it.

That’s not a hard conversation. That’s just a Tuesday.