Let’s be real, estate planning isn’t at the top of your holiday dinner conversation list. In fact, it’s probably not even in your top 10... Or even 20. We don’t blame you! Conversations around death and wills can be extremely daunting and even awkward. 

But the truth of the matter is, it’s one of the most important conversations we should be having with our families. Yet, a recent Angus Reid study we commissioned showed that 2 in 3 (66%) Canadians have no clue about their spouse or parents' end-of-life wishes if they were to pass away. 

Don’t get us wrong, we’re not saying you should discuss where you’d like to be buried while at the family dinner table, but the extra time we spend with our families around the holidays provides a really great opportunity to have these difficult conversations. If 2020 has taught us anything, it’s that we should expect the unexpected. Having open discussions about your end-of-life wishes is a fantastic way to make sure everyone is on the same page because peace of mind comes from clarity and that’s an unforgettable gift you can give (and receive!) this holiday season.

What Makes Holidays A Good Time To Discuss Estate Planning?

For many of us, the holiday season is the one time of year we get to spend an extended period of time with our loved ones. Not only is a perfect time for us to enjoy each other’s company, but being with family allows us to reflect on the relationships that are most important to us. Being in a ‘family state of mind’ can bring some of the important considerations of estate planning to the top of our minds. 

While the holidays may look a bit different this year, it’s still one of the best times to start talking about your end-of-life plans. So here are our top 10 tips for having conversations around death and wills over the holidays.

1. Spark The Conversation By Sharing Your Own Wishes

Discussing your own death can be very difficult and emotional. As the person initiating the conversation, you may find it’s easier to break the ice by sharing your own wishes first! In addition, this can help your loved ones reflect on their own wishes.

2. Take Time To Listen And Show Respect

This one may feel pretty obvious, but hear us out. As the initiator, you may feel that the onus is on you to guide the conversation. You may need to be the first one to speak, but once you’ve opened the discussion, it’s really important to allow your loved ones time to express their own feelings and wishes. You may be surprised at the things they’d like to share with you! 

3. Share An Anecdote

Anecdotes are not only a great way to organically introduce estate planning into your conversation, but they can make the topic less scary and overwhelming. Some of our favourite anecdotes to start with include:

  • “Did you know that Prince passed away without a will? Even though it’s been several years, his estate is still moving through the court system.”
  • “I read that Aretha Franklin died without sharing her will and her family only found her holographic will almost a year after she passed away. They even found multiple versions that contradicted each other.”
  • “I was so surprised to hear Chadwick Boseman died without a will earlier this year.”
  • “My friend Sarah recently completed her will with Willful and she mentioned it was really easy and she feels really relieved now that she’s checked that off her to-do list.”

4. Prepare A List of Prompts & Questions

A conversation around death and end-of-life wishes isn’t cookie cutter. However, there are some key questions that can help ensure that you don’t miss the important details.

Download Our Prompts And Guide To End Of Life Discussions  →

5. Start With Lighter Topics

Especially around the holidays, starting with lighter topics can help make the conversation easier. It can be tempting to go right into the nitty gritty details, but for someone who is already apprehensive about the conversation, this can make the conversation overwhelming very quickly. Open ended questions like “What do you want your legacy to be?” or “What are some heirlooms that are important to you?” can help open the conversation on a lighter note.

6. Explain How Having The Conversation Can Help You

You’re probably thinking that this tip sounds a bit selfish, but for many of us, we’re more likely to discuss something we don’t want to, if we know that it affects someone else. A good tactic to encourage the discussion is helping your family understand that having plans in place means reduced time, energy, and costs at a time when you will already be grieving. By them sharing this info now, they’re doing you a favour long-term. For example, if you’re speaking to a parent, it may be helpful to highlight how knowing their wishes will help you wrap up their affairs as their executor.

7. Break Up The Conversation

The topic of death and estate planning can be very overwhelming, resulting in us feeling the need to wrap up the entire conversation as quickly as possible. But that can actually make an already difficult conversation more exhausting than it needs to be. As a result, you may find it more productive to break it up into bite-sized chunks so you aren’t biting off more than you can chew at once. This can be particularly important this year where many of us will be relying on virtual connections. Zoom fatigue is real, so we should be mindful of that!

8. Share The Consequences

Many Canadians probably haven’t thought about what happens if they die without a will. If you’re thinking of having this conversation with your loved ones, you likely already understand the importance of discussing end-of-life plans. However, they may not necessarily understand the consequences of not having a plan in place. While we don’t suggest scaring anyone into this important conversation, many individuals may benefit from understanding what happens if they pass away without an estate plan.

9. Create A Comfortable Environment

A “comfortable environment” can look different for every family and individual. Take the time to figure out where everyone who is participating in the discussion would be most comfortable. For some people, this is in the comfort of your own home with a beverage of choice, but for others a neutral environment may be more agreeable, such as taking a walk or hike. 

10. Be Patient

At the end of the day, thinking about your own death is scary. It’s natural for many of us to feel a need to avoid the conversation wherever possible, so it may take some time for your loved ones to understand the importance of sharing their end-of-life plans with you. The key to having a successful end-of-life conversation is for all parties to feel comfortable and not feel ambushed at a time that’s not right for them. The most important thing you can do is take the first step to indicate that you’d like to have this conversation. 

Helpful Tools:

Download our 10 Tips To Discussing End Of Life Wishes →

  • This guide is full of tips that can help you successfully have a discussion about end of life wishes and estate planning with your loved ones.

Download our Guide To Your End Of Life Wishes →

  • Navigate your end of life conversations with a list of questions and prompts, and a fill-in-the-blank form to record answers. Basically, it's the perfect document to store with your will!

Ask An Expert:

We sat down with various experts to chat about their take on how to have these difficult conversations around death and estate planning. Click below to see what they had to say: