How To Have Important Virtual Conversations With Family This Holiday Season

December 18, 2020

Needless to say, this year has been filled with new challenges and firsts—many of which have been done virtually and away from friends and family. And now, with the holiday season quickly approaching, we’re continuing to get creative, figuring out ways to remain connected, and have some serious and important conversations, with the people we love most. We tapped tech expert, entrepreneur and influencer Erin Bury to get her top tips for having meaningful and timely discussions around money, estate planning and other bold topics, virtually, this holiday season. —Vita Daily

Hi Erin! Please tell us a bit about yourself to start.

I’m the co-founder and CEO at Willful, an online will platform started by my husband, Kevin Oulds. My background is in technology and marketing, so estate planning wasn’t something that was on my radar, but after Kevin’s uncle passed away unexpectedly a few years ago and his family was left scrambling to figure out his wishes for key end-of-life decisions, we thought there had to be a better way to put these plans in place. Estate planning has been done the same way for decades—making appointments, visiting lawyer’s offices, filling out paperwork—and as consumers we wanted to build a tool that would make it more affordable, convenient and easy to create a will. After spending years immersed in this space, I’ve become extremely passionate about empowering Canadians to have the conversations around end-of-life—it’s an inevitability for all of us, yet it’s something we avoid at all costs.

Most people try and keep the holidays light and loving, but why would you argue it’s the perfect time (and, really, the perfect year) to have serious and important conversations, in a meaningful way?

I think there’s a perception that conversations about death can’t be light and loving. But actually, I think the most loving thing you can do is ask your family about how you can honour their legacy when they’re gone, and to empower yourself with their choices and wishes so you can feel good about them after they’re gone. If 2020 has taught us anything, it’s that the unexpected can happen at any time, and that we should be prepared in advance for the things that might happen tomorrow. Of course none of us plan to pass away until we’re old and grey, but putting a plan in place in advance ensures that you’re reducing the burden on your loved ones when that happens. I recently had a conversation with my mom about her funeral and burial wishes (over wine of course!), and while it might seem like a heavy conversation, it actually did feel very light and loving, and it absolutely made me feel like a weight was lifted off my shoulders—now I know I’ll make decisions that came directly from her, instead of having to guess at what she would have wanted. The holidays are typically a time where families get together (either in person or virtually this year), and that means they’re the perfect time to chat about legacy between Netflix binges.

Pretty much all Canadians are having to do the holidays with loved ones virtually this year; what are your top tips for connecting meaningfully about things like estate planning and end of life wishes, when we can’t be physically together?

The holidays look very different this year, but I know that even if I can’t be physically present with family as I usually would, I’ll be connecting virtually with my close and extended families. In fact this year more than ever, it’s become normalized to get together with extended family—so it makes it the perfect opportunity to spearhead a conversation about legacy. No one wants to be the buzzkill on the Zoom call, so I recommend starting with why it’s important: our research shows that almost half of Canadians have witnessed a disagreement or argument after a loved one passed away, so you can start with a personal story about how lack of planning caused an issue (or share a story about a friend if you haven’t personally experienced this). It’s also important to highlight why you’re asking—it’s not become you’re waiting to get your hands on an inheritance; rather it’s because you’ll be in charge of making key decisions and wrapping up loved ones’ lives when they pass; so you want to ensure you’re equipped to do that. Finally, it’s important to consider the language you use. Instead of diving in with “What do you want to happen when you die?” consider using language that’s more approachable—for example “What do you want your legacy to be?” and “What type of celebration of life would you want?” And of course: record these wishes! Either record the conversation, or take notes, so you can find them when needed.

In a slightly different vein, how are women redefining the death landscape here in Canada and creating a more modern death industry, and how does this relate to our connecting with loved ones this holiday season?

I’ve worked in Toronto’s startup and technology space since 2008, and “death tech” was not a thing until very recently. I’ve since met so many women who are redefining how we talk about, plan for, and deal with death in a digital age, and who are modernizing an industry that’s desperately in need of it. Mallory Greene from Eirene, a direct-to-consumer cremation company, is one great example—she used to work at Wealthsimple, and has brought the same approach to design and simplicity to her platform. Effie Anolik founded Afterword, which helps with virtual celebrations of life, after her own experience with losing her father. I think we’re all bringing empathy, modern thinking, and a desire to help Canadians to a very outdated space, and I think we are hopefully helping to spark conversations that otherwise wouldn’t be happening.

What topics will you be bringing up with your family, virtually, this holiday season?

As the CEO of an estate planning company, I’ve become the go-to in my friends and family network for all things end-of-life—so at this point, they expect me to bring it up! I see this as a good thing – it’s brought death out of the shadows and into our normal conversations, which means that we chat often about our wishes and our legacy, and about where to find key documents. I have divorced parents who are both remarried, so I know I’m going to be an executor several times—and it’s a big job. For anyone reading this, I urge you to have these conversations not only so you can share your own wishes; but because you will at some point be responsible for wrapping up a loved one’s life. The more info you have, the less you will have to search and struggle with those decisions at a time when you should be grieving. This holiday, I’ll be reviewing the questions in Willful’s guide to discussing estate planning with family—it outlines 27 questions that can spark conversations.


  1. Olivia Margaret Clow

    January 3rd, 2021 at 1:19 pm

    I can’t find the one for self care contest. But it would be wonderful to win the self care package entered on Facebook and IG . It’s been a very hard year on my health . And I need to take better care for me.

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