Holidays are, for many families, a gathering of multiple generations and if entered into properly, could be an uplifting opportunity to discuss both past living and future planning. A start could be a video or just the opportunity for the elders to talk of their lives including successes and mistakes.
This would almost always often encompass the financial aspect. Expressed wishes and hopes can lead them to talk of where things are at and what things are needed.
And, at the least, a future time for greater discussion or follow up can be agreed upon. Children, both adult and younger should be included so that values and examples of good valued action can be passed along. Getting the family together represents a significant opportunity for engaging in estate planning over the holidays.