Talking About Your Estate: Why Having These Conversations Matters Most

I was outside watering my garden when I saw Sandra come by. She’s my neighbour—friendly, always ready to lend a hand, and someone I enjoy talking with.

We smiled and started chatting, just like usual.

Knowing that I talk to families about estate and legacy planning, it made it comfortable for her to start talking about her family.

Sandra told me she’s been thinking a lot about her family lately. She worries about what might happen if she gets sick or can’t make decisions anymore.

She said: “I know I need to do something about it, but I don’t know where to start. It feels so hard to even bring up estate planning.”

That’s when I realized—Sandra isn’t alone. Many people feel the same way. Talking about the end of your life or what happens after you’re gone can be uncomfortable. But it’s very important. It’s about caring for your loved ones and making sure your wishes are known.

So, I want to share with you why estate planning conversations are so important and how you can start them—just like I talked with Sandra.

Sandra's story is not unique. Death is a subject no one wants to talk about because we are afraid that talking about the loss will become a reality.

Everyone has a story of their own or knows somebody where there was a damaging family fight born out of the silence of ignoring future loss.

We can break the cycle of silence. We can transform the way we think about, talk about and prepare for death.

Why are these conversations so important? Many postpone it.  They think, "I’ll deal with it later", or say, "It doesn’t matter when I’m gone."

But imagine being in the hospital, stuck on a ventilator, and your loved ones don’t know what you want. Intensive care is no place to find out that there is no Will.

When you talk about your estate—which means your money, house, and things you own—it helps to avoid confusion and arguments. It lets your family know what’s important to you.

This is called estate planning.

Having these talks also makes it easier for your loved ones. When they know your wishes, they won’t worry or feel guilty. Instead, they can focus on taking care of you, and each other.

What kind of family do you want to have? Do you want one that avoids talking, keeps secrets, and hopes everything will be fine, or one that is open, prepared, and loves enough to plan?

How Do You Start This Conversation?

It might sound scary to bring up the topic, but it doesn’t have to be. Here are some simple ways:

• Pick a good time: Find a quiet moment when everyone is relaxed and not in a rush, such as a day after a holiday get-together. I don't recommend doing this at the dinner table.
• Be honest: Say something like, “I’ve been thinking about what I want for the future, and I’d like to talk about it.”
• Share your feelings: It’s okay to say you find it uncomfortable. Many people do.
• Start small: Talk about one thing at a time—like your wishes for health care or who should take care of your pets.
• Ask questions: Find out what they think, too. It’s a chat, not a test.

Sandra told me she decided to talk with her daughter about her Will and what she’d want if she weren’t able to make decisions anymore.

She said, “I was nervous at first, but my daughter was happy I shared my thoughts. Now, I feel lighter knowing she understands what I want.”

Common Fears About These Talks

Many people worry that talking about death or the future is too sad or uncomfortable. Some think it will upset family members, or they don’t want to think about bad things happening.

But here’s the truth: These talks are about love and caring. They help everyone feel more secure and prepared. It’s better to have these conversations early, so your family isn’t left guessing or fighting later.

Another fear is that it’s complicated or expensive to get things set up. The good news is, you don’t need to do everything all at once or spend a lot of money. You can start by making a simple plan with help from a lawyer or using online tools to write a Will.

Why Putting It Off Can Be a Problem

I asked Sandra what made her finally decide to start talking about her estate. She said, “I realized I was waiting for the perfect moment, but I kept putting it off. Then I thought, what if something happens suddenly? I don’t want my family to be confused or stressed because I didn’t make my wishes clear.”

That’s a good point. Life can change quickly, and waiting too long can make things harder. If something happens unexpectedly, your family may not know what you want. They might fight or make decisions you wouldn’t have agreed with.

Even if it feels difficult, it’s a gift you give to your loved ones; peace of mind knowing they will do what you want.

The First Step Is Easy

You don’t have to do everything at once. Start small. Maybe talk with your spouse or a close family member. Ask them what they think if you’re unsure.

Through these conversations and actions, we can spare our loved ones the pain of being lost, along with the grief when we are gone.

The legacy we leave is not going to be measured in money or possessions. But rather in the peace which we can leave behind for those we love by having the conversations we dread.

But we need to have those conversations now.

David E. Edey, CEA, is the author of Executor Help – How to Settle an Estate, Pick an Executor and Avoid Family Fights and host of the Executor Help Podcast. Stories of Life, Death and Legacies. www.davidedey.com