Every year, as Canadians make their way home for the holidays, we brace for the usual family dynamics the laughter, the chaos, the nostalgia. But there’s another tradition we tend to avoid: the uncomfortable but necessary conversation about money, wills, and inheritance.
We treat conversations about death and finances like they’re taboo, but ignoring them doesn’t make them less real. In fact, it often makes the aftermath far more painful.
A recent report from Fidelity Investments in the U.S. puts numbers behind the discomfort: 68% of parents haven’t told their kids what they’ll inherit or if they’ll inherit at all. More than a third simply don’t want their children to know. Another third say the conversation is uncomfortable. And honestly, who can blame them? Talking about mortality during a festive reunion isn’t exactly fun.
But with Canada in the middle of what experts are calling “the great wealth transfer” the staggering movement of $1 trillion from Baby Boomers to younger generations avoidance comes at a cost.
Financial planner Laura Whiteland says it plainly: “Ten out of 10 times, humans die.” Morbid? Maybe. True? Absolutely. And pretending otherwise doesn’t protect anyone.
The real trouble begins after someone passes when the grief is raw and adult children are left guessing what their parents owned, how to access it, or whether they even knew the whole picture. Shannon Terrell of NerdWallet Canada puts it bluntly: the worst thing is having a crucial question and realizing it’s too late to ask.
Anyone who has dealt with settling an estate knows the drill hunting through files, old bank envelopes, dusty insurance papers, and mystery accounts. Whiteland recounts how often people walked into the bank asking, “Did my parents have anything here?” That uncertainty can drag out the process for months, creating tension at a time when families should be supporting each other, not fracturing.
And the fractures can be surprisingly deep. Whiteland noted a case of four siblings falling apart not over millions, but just $18,000, simply because they didn’t trust each other. That’s the real danger of avoiding the conversation: money doesn’t have to be huge to create huge conflict.
So why bring this up during the holidays?
Because, as Bloom Finance CEO Ben McCabe points out, it’s one of the few times multiple generations are actually in the same room. A quiet moment not the moment before cutting the turkey can open the door to a gentle check-in.
Not a full interrogation. Not “What’s happening with the house?” or “Who gets the cottage?” Whiteland suggests starting with something small and meaningful: a set of grandma’s dinnerware, a family cookbook, the old cast-iron pan that has seen 40 Thanksgivings. These sentimental touchpoints are often the first step toward discussing bigger matters.
Ideally, though, parents should be leading this conversation.
If you are a parent, start with the basics: a will, power of attorney, beneficiary designations the simple but essential pillars of estate planning. And then, communicate it. Don’t leave your kids guessing.
One expert shared how her father called to ask if she’d serve as executor. She did her homework, understood the responsibility, and felt prepared a far better scenario than being blindsided during one of life’s hardest moments.
Talking openly also gives younger family members clarity. It turns inheritance from a mystery into something they can actually plan around whether that’s saving for a home, preparing for education costs, or making smarter borrowing decisions.
None of this is easy. It takes tact, grace, and sensitivity. As Whiteland reminds us, “You’re talking about someone’s mortality.” But by having these conversations now while everyone is healthy, gathered, and perhaps more sentimental than usual we can prevent confusion, conflict, and heartbreak later.
So this holiday season, amid the festive meals and family traditions, consider making room for one more tradition: an honest conversation about the future. It might just be the greatest gift you can give your loved ones.
