The holidays tend to bring us all together in the best kind of way. We eat too much, we quote Christmas Vacation to each other for the 98th time, and if we’re lucky, nobody brings up politics.
But this year, maybe there’s another topic you might want to bring up with the fam that might make them more uncomfortable than even politics: estate planning.
Talking with the kids about what happens after we’ve kicked the bucket isn’t exactly going to fill everyone with holiday cheer. But the truth is letting your loved ones know that you have an estate plan may be one of the kindest gifts you can give them.
While you don’t have to do it at the table when you’re passing the gravy boat, you may want to look into doing this before grandma’s polished off the bellinis.
And if this is your first time broaching this subject, there’s no need to get crazy. Just have a Level 1 conversation.
Level 1: Letting Them Know a Plan Exists
If you want to broach the subject, maybe just start this way: Tell the person who would be first in line to help settle your affairs:
- Where the documents are and
- Who they should call.
That’s it. You can stop there.
No need to make everybody uncomfortable. You’re simply making sure that the person who one day might be in charge of your estate doesn’t have to look through old shoeboxes to find your will.
Your kids will thank you.
Someday.
But if you think they can handle it, maybe you move on to Level 2.
Level 2: Letting Them Know the Plan
If you think they’re good with it (or if your family is somewhat well adjusted) you can talk in a little more detail.
Now, this doesn’t mean you need to deliver a speech before dessert. Instead, it can be a short, honest conversation off to the side:
- “Here’s what I’ve planned.”
- “Here’s why I chose the people I chose.”
- “And here’s what will matter most to me when the time comes.”
It’s easy to avoid these discussions because we assume they’ll be emotional or uncomfortable. But in my experience, the opposite usually happens.
They tend to bring families closer together.
Unless you cut one of them out of your will. That one typically doesn’t go over well.
And, finally, if you really want to go for it, you can move on to the Level 3 conversation.
Level 3: Telling Them Your Wishes
Almost everyone believes their kids (or loved ones) would “do the right thing” in a medical emergency.
But here’s the problem: what if you haven’t told them exactly what “the right thing” is? Chances are, they’ll do everything possible to keep you alive… even if that’s not what you would want.
And of course, it’s not because they wouldn’t respect your wishes. It’s because they won’t know what they are. They love you. And it’s hard to think clearly with charged emotions.
Having this conversation does two things:
- It gives your family clarity so they can carry out your wishes, and
- It gives you peace of mind to know that your wishes will be met.
It’s maybe not an easy conversation, but it’s one that ends up being a gift to your loved ones at a time when they’ll need it the most.
Uncomfortable Now, Grateful Later
Look, you don’t need to hash out your entire estate plan over the holidays. You don’t even need to buy matching Coors Light Holiday Chill fleece sweatshirts available for $16.98 at Sam’s Club, but maybe you should look into those.
At the very least, letting your loved ones know that you have an estate plan might be the holiday gift that nobody wants, but everybody is better off getting.
Now go and talk to your family about your own mortality!
Happy holidays!
And if you are worried that the conversation might kill the holiday mood, don’t be. Worst-case scenario, your family changes the subject to something more cheerful… like politics.
That’s all for this month. See you in the new year.









