As the holiday season approaches, a new report from Trust & Will suggests that family gatherings will not be the catalyst for estate planning conversations. The San Diego-based digital estate planning platform released its 2026 Death and Inheritance Report on October 2, 2026, based on a survey of 5,000 U.S. adults. The findings reveal that one in four Americans has never had a family discussion about estate planning, inheritance, or end-of-life wishes, with an additional 8% unable to recall such a conversation.
The report builds on Trust & Will's earlier 2026 Estate Planning Report, which found that 56% of U.S. adults lack any estate planning documents. This new data underscores a persistent gap between the importance families place on inheritance and their willingness to address it openly.
Holidays are not the catalyst
Thanksgiving ranks as the eighth most common occasion for inheritance discussions, cited by just 6% of respondents, and only 5% say their most recent conversation occurred there. Instead, 22% of Americans say the topic arises with no specific occasion, and 38% of recent conversations took place during an ordinary visit or phone call.
Christmas presents a striking contradiction: it is both the most common holiday trigger for these discussions (16%) and the most avoided occasion, with 37% of respondents naming it as the setting they would least prefer. This avoidance is consistent across all 50 states, making Christmas the top choice for avoidance nationwide.
“We expected families to put this off because it's about death. What the data actually shows is that they put it off because it's about joy, and nobody wants to be the one who brings estate planning to a birthday party,” said Cody Barbo, Co-Founder and CEO of Trust & Will. “Once you see it that way, the fix is obvious. You don't need a special occasion. You need an ordinary Tuesday.”
Celebrations are more awkward than funerals
The survey asked respondents to rate the awkwardness of raising estate planning in five settings. A family member's birthday tops the list at 63%, followed by Thanksgiving dinner at 62% and a major sporting event at 59%. In contrast, a funeral or wake is rated as awkward by only 41%, and an ordinary phone call is the easiest setting at 32%.
This 18-point gap between a birthday and a phone call offers a clear takeaway for advisors: the obstacle is not the subject matter but the fear of ruining a celebratory moment. Clients who are comfortable discussing difficult topics with their advisor may need help understanding that the same logic applies at home—a quiet weekday call is often the most effective on-ramp.
Expectations vs. reality
Nearly half of Americans (46%) expect to receive an inheritance, yet half of that group have never formally discussed it with the person leaving the inheritance. Additionally, 12% of those expecting an inheritance anticipate inheriting debts or liabilities.
Among the 4,304 respondents who lost a close family member in the past five years, 40% say that person died without a complete estate plan—28% had no plan at all, and 12% had one that was incomplete or outdated. This gap between expectation and reality highlights a significant advisory opportunity, especially as fear of outliving savings remains a top concern for older Americans.
Gender and generational gaps
Women are more likely than men to initiate these conversations (42% vs. 38%), but men are more likely to know where estate documents are kept (56% vs. 44%) and to expect an inheritance (55% vs. 40%). This disconnect suggests that the person opening the conversation is not always the one who ends up with the information.
Generation X (ages 45-60) stands out as the least prepared cohort for the second consecutive year. In the 2026 Estate Planning Report, 62% of Gen X had no estate planning documents, and in this study, 28% of Gen X respondents have never had a family conversation about inheritance—the highest rate of any generation.
What moves the needle
Recent loss is a powerful motivator: Americans who lost a close family member in the past year are more than twice as likely to have discussed inheritance recently (65% vs. 31%). Additionally, having an estate plan of one's own appears to be intergenerational—those with a completed will or trust are more than three times as likely to say the relative they lost also had one (63% vs. 18%).
For advisors, these findings reinforce the importance of proactive client conversations. As AI use boosts investor trust in human advisors, the human touch remains critical in guiding families through these sensitive discussions. The data suggests that the best time to talk is not a holiday, but an ordinary day—and advisors can play a key role in facilitating that dialogue.
