How to Talk to Your Parents About Their Will —Even If They Don’t Want To

Every May, my sister, my dad, and I would buy a handful of balloons, usually blue, sometimes red, and take them out to an open field. We’d write short notes on little pieces of paper, tape them to the strings, and then let them go, sending them into the sky for our grandfather (Mel, the man I was named after.) It was our quiet tradition. I knew my grandfather died young. I knew how much he mattered to my dad.

What I didn’t understand until recently, when I finally pieced it together, was how much his death at 32 shaped my dad’s entire relationship with mortality. And how that silence, that avoidance, now leaves the rest of us unprepared.

34% of millennials don’t know if their parents have an estate plan. I’m one of them. Not because I haven’t asked, but because my dad won’t answer. For him, planning for death feels too close to reliving it.

That kind of silence, shaped by grief and trauma, is more common than we think. And it’s one of the biggest reasons these conversations are so hard to have in the first place. But avoiding them doesn’t protect us, it leaves us vulnerable.

How Trauma Shapes Our Avoidance of Death — and Planning

For some people, talking about death feels like reopening a wound. Losing someone suddenly or early in life, especially under painful circumstances, can change your relationship with mortality in ways that are hard to explain.

That was true for my dad. Losing his father to a heart attack at 10 left an unspoken scar on his heart. Psychologists call this experiential avoidance: when people instinctively steer away from thoughts, feelings, or conversations that trigger distress.

Death can remind us of unresolved grief. It can shake our belief that life is predictable or safe. And when that happens, even thinking about things like wills or estate plans can feel overwhelming — like you’re inviting more loss.

In that space, silence becomes a form of protection. But while avoidance may shield us from short-term pain, it often leaves the people we love without guidance, clarity, or peace when the inevitable finally happens.

Why Some People Are Comfortable Talking About Death

A Different Relationship with Mortality

Not everyone avoids the topic. My grandma doesn’t shy away from it. She talks about it openly sometimes even with humor.

“Throw a party when I go,” she’ll say with a smile.

Losing her husband wasn’t something she chose, but it shaped her. Instead of letting that pain close her off, she allowed it to open her to conversations, to preparation, and to a more peaceful relationship with mortality.

For her, death isn’t something to fear or ignore, it’s a part of life. And preparing for it is one of the ways she shows love for the people she’ll one day leave behind.

Resilience Through Experience

Her comfort likely comes from a kind of emotional resilience she developed that was shaped by time, perspective, and experience.

Where trauma can create silence, resilience can create clarity.

Psychologists define resilience as the ability to adapt well in the face of adversity, grief, or stress. But it’s not about forgetting those hardships, it’s about integrating them into how you live, how you relate to others, and how you prepare for the future.

When my grandma lost her husband, she didn’t deny the grief, she carried it. But she carried it in a way that allowed her to keep living. And that makes space for the hard conversations — like how she wants her legacy handled when the time comes.

How to Talk to Someone Who’s Experienced Trauma Around Death

Bringing up estate planning can feel impossible, especially with someone who’s lived through sudden loss or grief. But that doesn’t mean you shouldn’t have the conversation. It just means it requires empathy, not urgency.

Lead with Emotion, Not Logistics

The goal isn’t to check boxes or dive straight into legal documents. It’s to show care.

Instead of launching in with “Do you have a Will?”, start with the why.

Try:

“I’ve been thinking a lot about how much you mean to me. I just want to make sure we’re prepared for anything so we can honor your wishes.”

This shifts the focus from scary paperwork to what really matters: love, care, and peace of mind.

Normalize the Discomfort

Acknowledge that this might feel awkward or hard for both of you. That simple honesty can help lower defensiveness.

You could say:

“I know this isn’t easy to talk about. And I don’t expect us to have it all figured out today. But I’d love for us to start the conversation.”

Don’t Push for a Full Download

For people with trauma, emotional safety is everything. If they seem overwhelmed, shut down, or change the subject, that’s okay. Respect it. Therefore the door stays open.

Sometimes, one honest moment now leads to a deeper conversation later.

Silence Doesn’t Protect Us, Planning Does

For many families, talking about wills, trusts, and estate plans feels uncomfortable. But avoiding the conversation doesn’t prevent loss, it only leaves us unprepared when it happens.

Having these conversations, even when they’re hard, is one of the greatest gifts we can give the people we love.

Whenever you or your family are ready, Trust & Will is here to make those next steps simple, approachable, and full of care.

Trust & Will makes estate planning simple so you can create a customized, state-specific plan from the comfort of your own home. Take our free quiz to discover which estate plan best fits your needs today, to secure your family’s future.

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