How to Talk to Your Parents About Estate Planning Without Awkwardness
- Kris Tan
- Sep 22
- 4 min read
A guide on how to talk to your parents about estate planning before it’s too late.
Growing up in a Filipino Chinese household, there were rules, spoken and unspoken, about what you could say out loud and talk about. We talked about hard work, doing well in school, and saving money. But talking about death, regret, or legacy? Those were off-limits. Estate planning was not something we talked about.
My parents rarely spoke about their pasts, particularly about their immigration story from the Philippines to the United States. Not because they didn’t have stories, but because survival in a new country came first. Looking back, I realize just how much I don’t know. And how much I wish I’d asked sooner.
The truth is, my parents are still alive. And I’m grateful. Because that means I still have time.
But starting these conversations isn’t easy, especially in Asian cultures like mine where there’s cultural resistance to discussing death, grief, and end-of-life planning. In many Filipino families, silence around death is a kind of a love language (but let’s be real for Filipinos, making and eating food is their truest love language). Vulnerability can feel like a threat. And talking about death can feel like inviting it.
So here’s a guide on how to talk to your parents about estate planning and family legacy. Not a script, not a checklist, but a place to start.
It’s still difficult for me to have these conversations with my own parents. But you have to start somewhere. Because it’s never too early to talk about what matters. And eventually, it will be too late.
5 Approaches To Open the Conversation
Here are real ways I’ve learned to make space for the conversations that matter.
Begin with curiosity, not closure. Start with stories.
Don’t jump straight into “What do you want when you die?” Start with:
“What was your childhood like?”
“What did your parents teach you about family?”
“What was life like back in the Philippines?”
These open-ended questions gently invite aging parents to share their stories without pressure.
Use Storytelling tools to take the pressure off.
Not everyone likes direct conversations. One of the best things my brother and I did was use a digital storytelling service that sends weekly writing prompts. It gave our parents space to reflect, without needing to perform or “get it right.”
It made me realize how much we lose when we wait for the “right” time. Or when we assume the people we love will always be here to explain the photos, the recipes, the reasons behind the choices they made.
Other low-pressure approaches:
Record a voice memo during a walk or cooking session
Type notes into your phone after a meaningful conversation
These kinds of storytelling prompts support emotional legacy planning and help capture cultural identity.
Connect Estate planning with things they care about.
If your parent loves gardening, sports, or cooking, start there. My mom lights up when we cook together. As she walks me through ingredients, she naturally shares stories: who taught her, what it reminds her of, what she hopes I’ll remember.
These stories often reveal more than any checklist and end up as a door way into deeper conversations.
Normalize talking about legacy and end-of-life wishes.
You don’t have to start with legal documents. Start with a gentle angle:
“Have you thought about what kind of legacy you want to leave?”
“What do you want us to remember most?”
“Is there anything you’d want to write down or pass on?”
These questions support early-stage end-of-life planning without sounding clinical or intimidating.
When the time feels right, you can build on these conversations by asking if anything’s been documented, like a will or healthcare directive.
You might ask:
“Have you already written some of this down, or do you want help figuring it out?”
“Would you want to go over anything, just so we know what’s in place?”
Even if nothing is written yet, it opens the door. This overview of key estate planning documents outlines what’s typically involved and why it matters.
Accept that some doors stay closed.
Not every story gets told. That’s okay. Honor the silences too. Sometimes, just asking is enough.
What I Learned About Family, Culture, and Legacy
These conversations aren’t just about death; they’re about connection. They’re about understanding where we come from, so we can decide where we’re going. In Filipino Chinese families, where intergenerational silence is common, even asking can feel like crossing the line.
It still feels awkward sometimes. But each story we uncover feels like a small inheritance - not money, not property, but context, culture and meaning.
And part of honoring that inheritance beyond the stories is making sure its protected. Not just emotionally but practically. Understanding how your loved one’s finances and paperwork will be handled after death can ease future stress for everyone.
It Doesn't Have to be Perfect. Just Begin.
These conversations won’t always feel natural. They might be awkward. They might take time. And in families like mine, they might go against everything we were taught about what should or shouldn’t be said out loud.
But they’re worth it.
Every shared story, every memory preserved, is part of your family’s emotional legacy, one that might otherwise disappear. You don’t have to get it perfect. You just have to begin. Because asking isn’t just about gathering information. It’s about connection. It’s about love.
And one day, you’ll be so glad you asked.
End of an Era is built for these moments.
We’re not just a platform for paperwork; we’re a place to hold the things that matter. To capture stories, organize legacy, and guide your loved ones through what comes next. Because preserving someone’s voice matters just as much as settling their accounts.
Start now. Ask the questions. Save the stories.
Because one day, they’ll be all you have and everything you need.
