An interview with estate planner Sylvia Azoulay
“They don’t want to bring up the conversation because they’re not sure where it’s going to go,” says Sylvia Azoulay, LL.B., TEP, FEA, Vice President, Tax & Estate Planning at Richardson Wealth. “It’s not just the cottage they’re talking about — it’s the memories, the family dynamics, and sometimes mortality itself.”
Late August is when cottages across Ontario feel most timeless. Children etch their new heights into the porch post. Grandparents repeat familiar stories. The family packs up in the same ritual sequence as summers past. Beneath that comfort, though, expectations about the cottage’s future are anything but certain.
For some families the cottage is assumed to stay forever. For others it is more of a hope than a plan. And for many, no one really knows. That gap between expectations and silence is what makes the conversation so difficult. Most families want to talk about it, but they hesitate, unsure how to begin or what they might hear once they do.
Silence Isn’t Harmony
“The cottage has so much tied up in it — memories, emotions, identity,” Azoulay explains. “Parents worry: what if the conversation goes down the wrong path? What if it leads to conflict I can’t manage?”
For many, the difficulty runs deeper. “Some people won’t start the planning conversation at all — never mind the cottage,” she adds. “They’re not ready to face their own mortality, and for many in the older generation, money has always been a taboo subject.”
The cottage becomes the lightning rod, the one thing everyone can see, while unspoken questions sit just beneath. Can Mom and Dad keep looking after it? Are they planning to sell? Do they assume we want it, or that we don’t? Families care deeply about its future, yet many hold back, afraid of what those answers might bring.
When the Past Resurfaces
“Are people saying what they really think or want?” Azoulay asks. Often the answer is no. Families start politely, gauging the room, unsure how their words will land. Without trust or — “psychological safety” — it’s difficult to sort out the core issues and come to a resolution that will work.
What sits underneath is rarely about the property itself. It is whether siblings can get along, whether parents can still manage the upkeep, whether expectations are fair. Sometimes it runs deeper: rivalries and old resentments that reappear the moment everyone sits down together. “You pushed me off my bike when I was twelve, and I still don’t like you,” Azoulay jokes. The point is clear: old history has a way of showing up in the present.
“Productive disagreement is healthy,” she says. “But if people don’t feel safe saying what they really think, you end up with a plan that likely won’t work in the long run or conflict may ensue”
Opening the Door
Starting the conversation may not be easy — in fact, it rarely is — but it matters. It can be as straightforward as a parent saying they want to update their wills and need to know what’s realistic with the cottage. Or as gentle as the next generation asking, Have you done your wills, and how long ago?
Azoulay cautions that it still helps to read the room. “If there are signals the conversation could be contentious, it’s better to pause and think about the best approach,” she explains. “If a meeting goes sideways, it’s a lot harder to repair the trust.”
What matters is creating space for honesty without fear of negative repercussions. “If it feels “safe to talk” she notes, “you’ll often be surprised at how ready people are to express their thoughts. They’ve just been waiting for someone else to open the door.”
Assumptions Unravel
Another surprise comes when parents imagine their children will share ownership without difficulty. It often looks harmonious on paper, but in reality it requires structure. “Parents expect their children will get along smoothly,” Azoulay explains, “but when we talk through the details — costs, maintenance, holiday schedules, even who cleans up after a weekend — they see it’s more complex than they thought.”
That doesn’t mean it can’t work. In fact, siblings may benefit from thinking about co-ownership the way they would a joint business venture, where roles, responsibilities, and expectations are clearly defined. As I reflected to Sylvia, you’re not just sharing weekends at the lake — you’re entering into a partnership, only this one is charged with memory and emotion. With clarity, the cottage can remain a legacy. Without it, it risks becoming a burden.
Keeping the Family Intact
Families often try to manage these talks themselves, but history has a way of getting in the way. Old rivalries and uneven comfort with money mean the loudest voices are heard while others stay silent.
That’s when a neutral presence can help. “A facilitator’s role is to facilitate productive conversation, give everyone a voice, and keep the process on track,” Azoulay says. “Too much can go wrong when parents try to run the meeting themselves.”
Guidance also ensures the conversation becomes a plan: who owns what, how costs are shared, what happens if someone wants out. Those details may be uncomfortable, but without them the future of the cottage is left uncertain.
And for most parents, the goal isn’t just keeping the property. It’s keeping the family together. “They want to make sure that, above all, their children are still talking to each other after they’re gone,” Azoulay says.
By the time families sweep the last sand from the floor and load the car for the drive home, the rituals of summer feel certain. What isn’t certain is the future of the cottage itself.
Starting the conversation early gives families the best chance to protect both the place and the relationships around it.
This article was written by Matthew Williams, CFA, Senior Portfolio Manager and Investment Advisor at Richardson Wealth, based on an interview with Sylvia Azoulay, LL.B., TEP, FEA, Vice President, Tax & Estate Planning.
Sylvia Azoulay, LL.B., TEP, FEA, is Vice President, Tax & Estate Planning at Richardson Wealth. An estate planning lawyer with many years of experience, she advises high-net-worth families on wealth transfer, family dynamics, and succession. She is a member of the Society of Trust and Estate Practitioners and the Family Enterprise Exchange, and holds the Family Enterprise Advisor designation.