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By Peter Miles
President
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The Great Wealth Transfer could leave families richer on paper and poorer in every way that matters.
Without honest conversations before inheritance changes hands, siblings can become adversaries, family businesses can collapse, and communities can lose employers.
We must stop treating inheritance as a private financial transaction. It is a family responsibility.
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An estimated $124 trillion is expected to move between generations in the United States over the coming decades, with annual transfers from Baby Boomers projected to approach $5 trillion by 2048, according to Bank of America Private Bank’s 2026 Study of Wealthy Americans.
The question is whether families are prepared to receive it together.
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The warning signs are already here. In its 2026 Wealth Transfer Study of affluent families, Wells Fargo found that 61 percent of surveyed adult children reported negative family experiences tied to inherited wealth, including hurt feelings, disputes over fairness, estrangement, and legal battles.
Yet only 21 percent of parents said they had held detailed conversations with their children about their estate plans. The gap between what parents believe they have prepared and what their children understand is a recipe for conflict.
I have seen how grief and money can turn a painful moment into a family crisis. People grieve differently. One person may need time to mourn; another may throw themselves into paperwork and practical decisions.
That urgency can be mistaken for greed. Without context, even well-intentioned actions can look like betrayal.
A will or trust matters. These documents carry legal force and can protect a family’s intentions. But they cannot explain why one child is taking over a business while another receives different assets, or repair a relationship after resentment has hardened.
A plan nobody understands is only paper waiting to become evidence in a dispute.
Uncomfortable Conversations
Parents should explain their intentions while they can. Children should ask questions respectfully, rather than wait for a crisis.
Trustees and executors must understand their legal duties and communicate clearly. If a family business is involved, future leaders need to know their responsibilities before a funeral, not after one.
The setting matters. Announcing a final decision over Thanksgiving dinner is not the same as arranging a calm conversation with a trusted professional.
Holidays are rarely the right place to unveil an inheritance plan or settle old grievances. A neutral adviser can explain the reasoning, clarify roles, and give everyone room to ask questions without turning the discussion into a contest.
These conversations are uncomfortable. Death is uncomfortable. Money is uncomfortable. Together, they can feel impossible to discuss.
But silence does not protect a family. It leaves people to fill the gaps with assumptions, and assumptions become accusations when grief is raw.
An Inheritance of Bitterness
The consequences reach beyond the family. A business fractured by an inheritance fight may close, taking jobs and local investment with it.
Wealth that could have funded new ventures or helped the next generation build stable lives can instead be consumed by legal fees and years of division. The transfer becomes an inheritance of bitterness, not a launchpad for opportunity.
There is another outcome within reach. Families that talk early can preserve relationships, pass on values as well as assets, and give heirs a shared understanding of what the wealth is meant to do.
A business can continue under prepared leadership. Heirs can invest, create jobs, and support local institutions. That is how wealth becomes a legacy rather than a source of damage.
Do not wait for a diagnosis, a death, or a family gathering to force the issue. Schedule a dedicated meeting. Bring the will, trust, business succession documents, and the people who will carry out the plan.
Ask what each person understands, explain difficult decisions, and agree on responsibilities. Review the plan as circumstances change.
As I learned in aviation, preparation does not guarantee clear skies. It gives people a way to respond when conditions change. Families need the same discipline.
The Great Wealth Transfer is already underway. We can let it test our relationships after it is too late, or start the conversations now and make sure what we pass down is worth more than money.
Peter Miles is president of St. Croix Wealth Management, which he founded in 2017 after a career in aviation and banking. All views are his own.
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