The Conversation We Can’t Afford to Put Off

By: Mike Schmitt, Rubra Group

There’s a moment in many families when the room goes quiet. Someone brings up “what happens when…” and eyes drop to the floor. We change the subject. We tell ourselves, “We’ll talk about it later.” But later often comes in the middle of a crisis, when stress is high and clarity is low.

The truth is, conversations about aging, end-of-life wishes, and legacy are some of the most important talks we’ll ever have as families. Done well, they protect dignity, prevent confusion, and—believe it or not—can even strengthen relationships.

Why This Matters Now If you’re reading this, there’s a good chance you’re already thinking about how to navigate these waters with your parents, a spouse, or another loved one. You’re not alone.

Over the next 20 years, trillions of dollars will pass from one generation to the next in the United States. But alongside the transfer of assets is something even more important—the transfer of values, stories, and wishes. When these aren’t shared, families are left guessing.

Here’s the surprising part: these talks aren’t just about “the end.” They’re about making the most of the time we do have and ensuring that a loved one’s voice continues to guide decisions even if they can’t speak for themselves.

The Barriers We All Feel Why do so many of us delay these conversations?

• Fear of causing discomfort – We don’t want to upset a parent or seem like we’re rushing them.

• Not knowing what to say – It feels awkward without a roadmap.

• Family dynamics – Old patterns or unspoken tensions can make deep talks tricky.

Here’s the good news: these challenges can be overcome, and often the anticipation is worse than the reality. The trick is to approach the topic in a way that feels natural, respectful, and centered on care—not as a formal interview or checklist. The goal is to create a safe space where your loved one feels heard, valued, and in control of their own story.

How to Begin (Without It Feeling Like an Interrogation)

1.     Lead with love, not logistics. “Mom/Dad, you’ve always taken care of us. I want to make sure we can take care of you in the way you’d want.”

2.     Make it about them, not about the paperwork. This is their story, their wishes, their legacy.

3.     Start small. One topic at a time—health care wishes today, finances another day.

4.     Use life as a natural bridge. A news article, a friend’s story, or even a TV show can open the door: “That made me think… have you thought about how you’d want things handled?”

5.     Listen first. Your role is to understand before you organize.

Taking these steps won’t just help you gather information—it can strengthen your connection. Each conversation builds trust and shows your loved one that their voice matters. Over time, these talks become less about “end of life” and more about honoring a life well lived.

A Surprising Benefit Families who have these talks early often say it brought them closer. Parents feel relief knowing they’ve expressed their wishes. Adult children feel honored to be trusted with them. And when the time comes to make decisions, there’s confidence instead of conflict.

Next Steps You Can Take This Week

• Choose one conversation starter from the list above and use it with a loved one.

• Write down what you hear. You don’t have to organize it all yet — just capture their words.

• Schedule a follow-up to cover another area.

• Share your own wishes. These talks work both ways.

Because here’s the thing—these conversations aren’t about endings. They’re about ensuring the people we love most are honored in the way they deserve.

Continue the journey

Read more in our book “Family Fortune”. Order the full edition here: https://a.co/d/85wRoB2

Schedule a complimentary thirty-minute strategy call to map your own documentation plan: Meet with Mike Schmitt

These really are conversations of love, compassion, and listening and they are important.