There’s never a good time for your mom to break her foot. Same goes for your dad. But that’s what happened in the Robison family, with two young girls at home and two parents in casts. 

Talking about dying isn’t too different. There’s never a great time for the convo, but unlike both parents breaking a bone at the same time, it’s almost guaranteed to happen.

To give you a crutch before the crisis, we went straight to someone who’s lived through both. We spoke with founder, podcast host, and author Becky Robison for the questions to ask before it’s too late.

🧑‍✈️ Captain “Sully” Sullenberger, the pilot who safely landed 155 people on the Hudson River, shared that he has early-stage Alzheimer’s and hopes speaking publicly helps other families feel less alone.

💔 Kris Jenner shared that her mother, Mary Jo “MJ” Shannon, a familiar face on the family’s TV show, died at 91.

🧠 The AP reports that a blood test may help identify healthy older adults at higher risk for Alzheimer’s years before symptoms appear.

😬 Georgetown University researchers found a supervised THC/CBD treatment reduced agitation in people with late-stage dementia, with one big caveat: grabbing it from a dispensary is not the same thing.

🕊️ Oscar winner Brenda Fricker, beloved as the Pigeon Lady in Home Alone 2, died at 81.

Here's the thing about your dad: he knows a lot of stuff and some of it you're going to need. It’s sad stuff that feels better to punt because there’s always next time. Until there isn’t a next time. At 35 years young, Becky Robison learned the hard way, and then she did something about it. She wrote down the questions you should ask before what can be the worst possible moment of your life.

Becky Robison lost her mom in 2020 after a long fight with liver disease. Three years later, she lost her dad to pancreatic cancer, a battle that was tragically brief. She was 35 years old, newly named executor of his estate and successor trustee of his living trust, and she had absolutely no idea what any of that meant in practice.

She phoned a few friends and asked her aunts and uncles. They couldn't remember what they'd done for their own parents, or all they could recall was the grief. She asked family friends. Helpful, but piecemeal. She asked the internet. The internet, famously full of everything, did not have all the info in one place.

So Becky, an eldest daughter with a fix-it-myself problem and a dark sense of humor built the resource she needed: deadparentswhatnow.com. She created a living document she updated in real time as she navigated funeral homes, probate court, surprise assets (more on that in a minute), and selling a home. Readers started writing in with situations she hadn't covered: autopsies, timeshares, you name it. The site grew and editors took note. 

The result is her book, My Parents Are Dead. What Now? A Panic-Free Guide to the Practicalities of Death, plus a podcast, Bitching & Mourning, co-hosted with Emmy-nominated comedy writer Alison Zeidman. Grief and humor make a surprisingly attractive couple. 

Becky's book includes 17 questions to ask your dad while he’s still here to answer. Gray Monster readers already know the greatest hits, including advance healthcare directives, living wills, and powers of attorney so we asked Becky for the less commonly asked q’s. Here’s what she shared:

1. Who's the executor or successor trustee? If it's you, ask to read the paperwork now. Knowing what you're up against before you're up against it is helpful intel. 

2. Do you have a list of your assets and what they're worth? The executor is legally required to account for everything. Becky learned mid-grief that her parents owned an entire commercial building she didn't know about. House rule: no surprise assets. Write it all down.

3. What about your digital assets? Passwords are an absolute yes. But passwords to what? Cryptocurrency? Dad's unpublished sci-fi novel living in a Google Doc? A password manager with login deets beats a notebook with combos of the family pet name and your birthday. 

4. What do you want to happen to your body? Burial, cremation, aquamation (water cremation), human composting are all options worth discussing. And the follow-up question: where's the money for it coming from? 

5. Do you want a funeral or a memorial service? What should it look like? Location, religious or cultural customs, songs, reading - if Dad wants it to happen, it’s good to get the pre-death download. Becky held her mom's service at the family's favorite pizza joint. Her dad, an architect who loved golf, got his at a golf clubhouse he designed, with his golf caps handed out as party favors. Make getting the specifics par for the course (sorry, we had to). 

6. Are you an organ donor? Becky's family was asked about donating her dad's corneas within hours of his death and had to scramble to check his driver's license. It’s good to know what’s good to go to someone else.

7. Who should I notify when you die? Get the list of names and contact info while you still can. Digging through Dad’s phone contacts is confusing, emotional, and you may dial up a cousin he secretly couldn’t stand.

8. What do you want in your obituary? Any life stories that can't be missed? Can you write it together? Becky advises turning it into a conversation. 

9. What should I do with your beloved Fido? Legally, pets are property, and Dad’s will should account for them. "My daughter will take the dog" is an assumption. Can she? Does she want to? Does her building allow it? Ask Dad to name a person, confirm they're in, or set up a pet trust.

10. Will you add me as a legacy contact on your social media? This is so accounts can be accessed and closed, especially ones with a credit card attached and the ignorant HBD posts don’t hit your feed. 

Becky acknowledged there's never a perfect moment for the uncomfortable convo, but advised looking for unconventional openings. A celebrity your dad loved passes away? Give it a go. "I wonder how their family handled everything. What would we do?"

If that fails, and it might, Becky offered the single best framing we've heard: ask Dad to do it as an act of parenting. He’s still your dad and you still need him. Shoot him straight she says, "You won't be here when it happens. I need your help now."

You can’t fail this one. Answers and another quiz drop next week.

You said it. This week’s submissions.

"My dad is home from the hospital and now I'm taking care of him. It's overwhelming."

"Pool days with my mom are helping us both. The smoke in the air is impacting our sanity."

"I survived Eldercare Summer: Surgical Edition."

"Mom hates assisted living and wants to move in with me... but only if I build her an in-law apt."

"Mom's long time friend Susan has turned into an ally of mine."