🎃 The Scariest Things You Can Do To Your Executor

A few weeks ago, a woman called me in a panic.

She’d just received a letter from an attorney saying her uncle had named her in charge of everything — financial power of attorney, healthcare proxy, and trustee when he dies.

He’s still alive.

He’d hinted at this before, but every time she tried to ask questions, he dodged them. Now he’s in and out of the hospital, and she’s left wondering: What should I do?

I told her:
👉 Try—really try—to have the conversation now, before it’s too late.
👉 If he’s open to the conversation, ask a lot of questions to understand the role you’ll be taking on and what you’ll need in order to do your job. Remember, it’s not about being nosy. Its about being clear.
👉 And if he won’t talk, remember: you can always decline when the time comes.

In my opinion and as I outline in my book, Late To Your Own Funeral, there are Seven Deadly Sins of What Not to Do To Your Executor.

Her uncle had already committed two of them:
💀 Cloak and Dagger Wills: Keeping secrets from your executor.
💀 Failing to Map the Financial Terrain: Leaving no clue where your accounts or paperwork live.

And he’s dangerously close to a third:
💀 Guess Who?: Not telling your executor they’ve been drafted.

Here’s how not to scare your executor (or anyone else) half to death:
🎃 Tell them early. Don’t spring it on someone in a lawyer’s letter. Give them the courtesy—and the context—before they’re legally on the hook.

🎃 Make a cheat sheet. Write down your main accounts, property, and debts (or where to find them). No one should have to play “Where’s Waldo?” with your finances.

🎃 Talk about your wishes. Don’t assume people know what kind of care, funeral, or legacy you want. Have the conversation—awkward or not—so no one has to guess later.

🎃 Ask, don’t assign. Being executor or POA is a part-time job, not a favor. Make sure the person is in a position to assume the role.

🎃 Keep it simple—for real. If you say “my estate is simple,” check that it’s simple for them to navigate, not just simple in your head.

If you’ve already named an executor, take 15 minutes this week to send them a quick note:

“Hey, I just wanted to make sure you’re still okay with being my executor. Let’s set a time to talk about what that actually means.” It’s the most loving, least spooky thing you can do.

If you want to learn the rest of the Seven Deadly Sins (and how to avoid them), you’ll find them in my book Late To Your Own Funeral — but even if you never read a page, these few steps will make life so much easier for the people who love you.

Stay spooky (but organized)!