10 questions to ask your parents (while it’s not too late)

From the practical to the sentimental, here's a starter list to head off turmoil and regret.

Warmup

We’d just finished Wordle and The Mini crossword, when I suggested a different pastime.

Let’s call it: What’s Your Password?

This was two weeks ago. My folks and I were up early, watching the river and drinking coffee.

During my two-week visit, I’d procrastinated doing this thing I didn’t want to do (and they really didn’t want to do).

Which was to have the-conversation-nobody-wants-to-have about what I need and want to know in case one of them (now in their early 80s) gets really sick, hurt, incapacitated or dies.

Practical things.

Sentimental things.

My mom got another cup of coffee. My Dad let Jack, their massive Goldendoodle, sit with us on the couch to add some levity. (You can read their advice for making this process go better in “The Parental POV” section below.)

And then we just got it done.

Post

To be sure, my parents have done well preparing me for worst case scenarios.

I already possessed copies of their will and medical directives, knew their lockbox code and general wishes for how and where they’d like to spend their final years.

And they are both back in the gym, working with a trainer and tackling personalized workouts I create for them. You should see my mom whip the TRX battle ropes.

But there still were a lot of unknowns. Their estate attorney’s name. Which bank branch housed their lockbox. What were the email addresses and passwords associated with key accounts? What exactly was the heart health history on my father’s side so I can be monitored?

As a country, we’ve historically not been very good at these kinds of conversations — particularly financial ones — often waiting until a crisis hits, which adds strain to an already awful situation.

As an only child, I feel a sense of urgency to go through this process now with my parents.

But these questions can be a roadmap for conversations with anyone in our families, or even friends we’re close to and might want to support in difficult times.

You’ll likely have more important things to add to the list below. And I’d really like to hear them.

The Practical

1. What is a list of the critical bills you pay every month?

2. Where are your passwords kept for your most important financial and home accounts?

3. Where are your critical documents stored? (Is there a key or a code?)

4. What are the most important aspects of your medical history — and your parents’ medical history that I should know for my own health? (How did my grandparents’ die?) More questions here.

5. What are your medical directives? (Please make me copies.)

6. What childhood vaccines did I receive?

The Sentimental

1. What are your favorite pictures of us as a family? (And where are they?)

2. What is your favorite food dish so I can learn to make it?

3. Can you share with me the history of any important family artifacts?

4. What is the story of the day I was born?

I’m still working on some of these sentimental ones ^^ — and learned a lot from this Reddit thread. My mom also is rolling her eyes about the food dish question because she knows how much I hate to cook and doesn’t believe this will ever happen.

However, I DO intimately know the story of the day I was born.

It involves a fishing boat, a small seaside motel, and Shoney’s restaurant.

We’ll save that tale for another time. :)

The Parental POV

I shared this post in advance with my parents. They made some important points:

Point 1: My mom suggested that she and my father also possess a copy of MY important documents, attorney contact info and health directives.

“You’re on a plane a lot more than we are,” she noted. “Plus you like to scale slippery walls, climb ropes and plunge down rocky mountains in your free time.”

Fair. I’ve added to my to-do list.

Point 2: How granular you get with sensitive topics such as finances depends in large part on the trust established between parents and children.

“Sibling rivalry can make things more difficult, and some parents are going to feel threatened (for lack of a better word) by having their very personal information shared, even with a child or children,” my mom says.

A middle ground can be letting children know where passwords or financial information can be found in case of an emergency — and keeping an up-to-date, legible list — but not necessarily handing over the data in the short-term. Parents have a right to their privacy too.

Point 3: Don’t make every visit home a session in end-of-life planning.

What is “overwhelmingly true at our age is the sense that your journey through life is ending so soon,” my mom says. “Instead, we want to just enjoy and have more fun and be with the people we like and love and live as fully and happily as possible.”

In our family, that includes bonding with battle ropes and kettlebells . :)

Cooldown

Again, I’d love to hear your suggestions in the comments below or through email. If enough come in, I’ll write a follow up post.

Speaking of suggestions, for the next N2L newsletter I’ll be reaching out to some of you directly for some contributions. I think it’ll be a fun one. Stay tuned … (literally and metaphorically — you’ll understand what I mean soon!)

Thanks for reading N2Lers. As always, find something you love. Dig in. Stick with it when things get hard.

Wendy

Sources:

1. Fidelity Investments Research: Americans Ready to Break the Cycle of Avoiding Family Discussions on Once Taboo Financial Topics. November 19, 2024. Link.

2. 5 Questions You Should Ask Your Parents (for the Sake of Your Health). Healthline. Link.

3. What questions should one ask their parents while they still have the chance?. Reddit. Link.