What I Didn’t Ask My Dad Before He Died: Because it’s Harder Once Your Person is Sick

I’m 40, which means I’ve somehow become the person people look to when things get hard… while I’m still looking for an adult for advice.

It’s called the sandwich generation: we’re building careers, some of us are raising kids, trying to keep our lives together, while watching our parents get older in noticeable ways.

And most of us are not talking about what that actually means.

I didn’t.

My dad died of lung cancer, but it wasn’t sudden. He was in the ICU for nearly two weeks, and those days were some of the most emotionally disorienting of my life. Machines, decisions, doctors asking questions we weren’t ready to answer.

Because we had never talked about it.

The truth is, I avoided those conversations. As a funeral director I was talking to strangers every day about their end-of-life wishes, but I never asked Dad.  Because once he was sick, it felt like giving up hope to ask about end-of-life care.

So I waited. And then time ran out.

A friend of mine went through something similar recently. Her dad was having heart issues, and in the middle of the stress, she called the 811 nurse line for guidance. One of the first questions they asked was simple: “What medications is he on?”

She didn’t know.

It caught her off guard. She’s close with her dad. They talk all the time. But not about that.

These aren’t dramatic, end-of-life-only conversations. They’re practical, everyday pieces of information that suddenly matter a lot when something the person can’t answer for themselves.

As millennials, we’re the ones booking the appointments, filling out the forms, managing the group chats, handling the bills, and keeping life running day to day. But when it comes to our parents, many of us are still operating like kids: assuming they’ll lead, assuming they’ll tell us what we need to know.

Most of them won’t.

They were raised in a time where you didn’t talk about death openly. You pushed through, you kept going, and you didn’t sit around discussing what happens when things fall apart.

So if these conversations are going to happen, it’s probably going to be because we start them.

It doesn’t have to be intense or perfectly planned. You can ease into it. Ask what medications they’re taking and where they are kept. Who their doctor is. Where they keep important paperwork. What matters to them if their health changes.

You can do that over coffee, on a walk, in the middle of a completely ordinary day.

What matters is that it happens before you’re sitting in a hospital room, trying to piece together answers under pressure.

I wish I had those conversations with my dad. 

There’s some peace that comes from knowing you’re carrying out someone’s wishes instead of trying to guess them, carrying the weight of “I hope this is what they would have wanted.”

We don’t get to control when death shows up. But we do have some say in how prepared we are when it does.

If you’re ready to start the conversation, I’d love to hear from you. Give me a call for ideas, support and The Empowered Estate planner.

You can also check out Christa Ovenell who offers Prep School: a guided course to approach end-of-life planning in a more holistic way. My mom and I did this together and Christa is a fantastic guide!

Connie Jorsvik of Patient Pathways offers support and guidance on navigating the healthcare system and practical support completing an Advance Directive.

I also host community conversations to broach this topic in a casual and thoughtful way. You can join find more information in my newsletter.