With some major US holidays approaching, a new report suggests family gatherings will not spark conversations about family finances, specifically estate planning.
That is the central finding of Trust & Will's 2026 Death and Inheritance Report, released October 2, 2026, which surveyed 5,000 U.S. adults on when, how, and whether families discuss inheritance and what consistently gets in the way.
One in four Americans has never had a family discussion about estate planning, inheritance, or end-of-life wishes, according to the San Diego-based digital estate planning platform. An additional 8 percent cannot remember ever doing so. The findings extend Trust & Will's earlier 2026 Estate Planning Report, which found that 56 percent of U.S. adults have no estate planning documents at all.
Thanksgiving is the eighth most common occasion prompting family conversations about inheritance, named by just 6 percent of Americans, and only 5 percent say their most recent conversation actually happened there.
The most common answer is that no occasion prompts it at all; 22 percent of Americans say the subject simply comes up with nothing attached, and 38 percent of the most recent family conversations about inheritance took place during an ordinary visit or phone call.
Christmas presents the sharpest contradiction in the study. It is simultaneously the most common holiday trigger for these conversations (named by 16 percent of respondents) and the occasion Americans would most actively avoid for the same purpose, named by 37 percent. That is more than double any other occasion. Christmas ranks first for avoidance in all 50 states.
"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."
Trust & Will asked respondents to rate the awkwardness of raising estate planning at five specific settings.
The results invert most expectations. A family member's birthday is rated as awkward by 63 percent of Americans, the most uncomfortable setting in the survey. Thanksgiving dinner follows at 62 percent, and a major sporting event at 59 percent. A funeral or wake, by contrast, is rated as awkward by just 41 percent. An ordinary phone call is the easiest setting of all, at 32 percent.
The 18-point gap between a birthday and a phone call tells advisors something actionable: the obstacle is not the subject. It is the fear of ruining the occasion. Clients who are already 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 easiest on-ramp.
For advisors who follow InvestmentNews coverage of estate planning and the great wealth transfer, these findings underline a recurring theme that families are not avoiding the paperwork because they do not value it, but they are avoiding the conversation that has to come first.
Forty-six percent of Americans expect to receive an inheritance from a family member. Of that group, half have never formally discussed it with the person leaving it. Twelve percent of those expecting an inheritance expect to inherit debts or liabilities.
The gap between expectation and reality is even more pronounced among those with direct experience. Among the 4,304 respondents who lost a close family member in the past five years, 40 percent say that person died without a complete estate plan: 28 percent with no plan at all, and 12 percent with one that was incomplete or out of date.
Set those two findings side by side and the advisory opportunity is clear. Nearly half of American adults are counting on an inheritance, while roughly four in 10 who have already experienced a family death found no workable plan waiting.
InvestmentNews has previously reported on how estate planning has become a client retention issue with 68 percent of advised clients saying they would consider switching advisors to gain access to estate planning services.
Women are more likely than men to initiate these conversations (42 percent compared with 38 percent) and their discussions cover more ground.
However, 56 percent of men know where their older relatives keep estate documents, compared with 44 percent of women. Men are also more likely to expect an inheritance at 55 percent, against 40 percent of women.
The pattern holds a practice implication. The person doing the work of opening the conversation is not reliably the person who ends up with the information.
The generational breakdown also deserves attention for advisors building next-generation strategies. Trust & Will identified Gen X (typically 45 to 60 years old) as the least prepared cohort for the second consecutive year. In the 2026 Estate Planning Report, 62 percent of Gen X were found to have no estate planning documents at all. In this study, 28 percent of Gen X respondents have never had a family conversation about inheritance, the highest rate of any generation.
Americans who lost a close family member in the past year are more than twice as likely to have discussed inheritance recently. Sixty-five percent of that group had the conversation within the past 12 months, versus 31 percent of those without a recent loss.
Having an estate plan of one's own also appears to be intergenerational. Americans with a completed will or trust are more than three times as likely to say the relative they lost also had one - 63 percent versus 18 percent of Americans who do not intend to create a plan.
For advisors, the study also surfaces a notable data point about professional engagement: only 8 percent of American families say a financial advisor, attorney, or another professional was the one who started their conversation about inheritance.
Advisors who make estate planning a standard agenda item — rather than waiting for clients to raise it, can close that gap. As InvestmentNews has reported on the dynamics of the Great Wealth Transfer, early and proactive conversations are increasingly what separates advisors who retain assets through generational transitions from those who lose them.
The survey was conducted by market research company Talker Research between August 19 and September 2, 2026, using a random double-opt-in online methodology. The margin of error for the full sample is plus or minus 1.4 percentage points at the 95 percent confidence level.
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