Memorial Day has a way of cutting through the noise. For one weekend, people slow down, gather with family, and think about what actually matters. For those of us who have spent decades building something, that reflection can turn toward a question worth sitting with: when you are gone, what will you actually leave behind?
However, as you reflect, it’s important to look beyond just assets. The families who navigate wealth transfer best realize that the values behind the wealth matter as much as the dollars.
Most Families Are Less Prepared Than They Think
According to Caring.com’s 2024 Wills and Estate Planning Study, only 32% of Americans have a will, the lowest rate since 2020. Among those without one, 43% cite procrastination as the main reason.
That pattern holds even for people with significant assets. According to research compiled by Vanilla, over a third of American adults say they or someone they know experienced family conflict directly because an estate plan was not in place. That is a preventable outcome, and it happens far more often than it should.
The families I have worked with for decades are not immune to this. Good intentions do not, on their own, translate into a good plan. At some point, the conversation has to happen, and the documents have to be done.
A Legacy Plan and an Estate Plan Are Related, but They Are Not the Same Thing
An estate plan handles the legal and financial mechanics of transferring your assets. It is essential. A legacy plan goes further and addresses the values, purpose, and meaning behind what you are leaving.
Think about it this way. You can have a technically perfect estate plan, with updated beneficiaries, a funded trust, and proper titling on every account, and still leave your family without the clarity they need. What did you want the money to do? What values were you trying to extend? What did you hope they would understand about how you built it?
Those questions do not live in a legal document. They live in conversations, in letters, in family meetings, and in the relationships you build while you are still around to build them. The legal structures carry the assets. The values carry the meaning.
What a Values-Based Legacy Plan Actually Looks Like
Families who approach legacy planning intentionally tend to address a few areas that are often skipped in standard estate-planning conversations.
The first is a clear articulation of what wealth is for. A family that has built a successful business over 30 years has very different values around money than a family that inherited its wealth. Getting those values stated explicitly, in whatever form works for your family, can help the next generation make decisions in the spirit of what you intended rather than guessing.
The second is their preparation. Having the right legal documents in place matters far less if the people receiving the assets have no framework for managing them. This is one area where including the next generation in planning conversations early can create a meaningful difference over time.
The third is keeping the plan current. Beneficiary designations, trust structures, and estate documents need to be reviewed regularly as your life and the law change. A plan built ten years ago around a business you no longer own, or that still names an ex-spouse, can create significant problems. Reviewing it on a schedule rather than waiting for a crisis is how good intentions actually become a good outcome.
The Conversation Most People Keep Postponing
Memorial Day is a useful signal that we do not get unlimited time to have the conversations that matter. The families I have seen navigate wealth transfer most successfully are not the ones with the most sophisticated legal structures. They are the ones who talked openly about money, values, and expectations while everyone was still at the table.
According to research from Vanilla, 83% of investors are concerned that the current wealth transfer will not go smoothly. That concern is warranted. However, it is also addressable. The solution tends to start with a conversation rather than a document, and the earlier those conversations begin, the more prepared everyone tends to be.
If your legacy plan has been sitting on the to-do list, use this weekend to move it forward. Take the next step: contact me today to discuss what that process could look like for your family.
TL;DR: Family legacy planning addresses both the legal transfer of assets and the values you want to pass on. Research shows that most Americans, even those with significant wealth, are less prepared than they realize, which often affects their families. Establishing the right structures and having honest conversations with those who will inherit your wealth are best done well before they become urgent.
