Thanksgiving has a way of putting three generations of a family in the same room at the same time, something that does not happen often outside the holidays. It is also, whether anyone plans it or not, one of the more natural moments to talk about money, legacy, and what happens down the road. Most families avoid the topic entirely, or they wait until it is forced by a health scare or a death. Neither approach tends to go well.
Why this conversation gets avoided
Money and inheritance carry a lot of emotional weight, and there is a real fear that bringing it up will sound like it is about who gets what. Parents worry about seeming like they are keeping score, or that talking about their estate plan will make their kids anxious about their health. Adult children worry that asking questions will look like they are waiting for something. The result is that families with substantial, carefully built plans often have not actually talked about them, and the first real conversation happens after it is too late to ask questions.
What actually helps
The goal of a holiday conversation is not to review account balances or walk through a trust document at the dinner table. It is to open the door. A parent might simply share that an estate plan exists, that it has been reviewed recently, and that there will be a time to sit down together, with advisors involved, to talk through the details. That is often enough to relieve a lot of unspoken anxiety on both sides. For families further along, it might mean introducing adult children to the advisors, attorneys, or trustees who will eventually be part of their financial life, so those relationships are not starting cold at a difficult moment.
A few starting points, not a script
There is no single right way to open this conversation, and trying to force a structured discussion at the table often backfires. What tends to work better is low-key and ongoing: mentioning that a plan is in place, asking adult children what questions they have without expecting a full conversation on the spot, or simply naming that this is something the family will revisit together in the new year. The point is not to resolve everything over pie. It is to make the topic normal enough that the next conversation is easier than this one.
Where to go from here
If your family has not had this conversation yet, the holidays are as good a starting point as any, not because you need to cover everything at once, but because the opportunity to have everyone together does not come along often. When you are ready to go further, whether that is a formal family meeting, introducing the next generation to your advisory team, or revisiting how your plan reflects your family’s current reality, that is a conversation we are glad to help facilitate.
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