Americans are undergoing what’s being deemed “The Great Wealth Transfer,” the largest intergenerational wealth transfer in history. Cerulli expects that wealth transferred “through 2048 will total $124 trillion,” with $105 trillion going to heirs, and $18 trillion to charity. While planning and being transition-ready can be time-consuming, they’re crucial to estate planning and building generational wealth. But new Fidelity Investments research found that this process isn’t just about preparing documents. Read: Here’s how to invest in the New York Knicks and other pro sports teams Fidelity’s 2026 Transition Ready Family findings challenge the common assumption that accumulating wealth and completing necessary forms alone is enough to prepare families for the future. In fact, the study found that while many senior Americans have taken planning measures, only 37% say “they have strong peace of mind about their future plans, and more than half of those who have completed plans still lack confidence.” There is a missing piece to lessen anxiety for this cohort of older Americans, which is often overlooked: having conversations and being honest and open with their family. Ryan Viktorin, vice president and financial consultant at Fidelity Investments, said the findings show that completing a plan and feeling prepared aren’t always the same thing. “Many people are doing the right planning activities, but our research suggests that confidence comes from making sure family members understand those plans and know what to do when the time comes,” Viktorin said. More than half of Americans who have completed planning activities still lack peace of mind The study found that a whopping 51% of seniors who took the necessary steps still feel anxious about their planning. And while parents who talk about their plans with their family are more than three times as likely to be highly confident in their planning, a third have never had these conversations with their adult children, according to the research. Viktorin said that many people approach planning as a series of tasks, such as creating an estate plan or updating beneficiaries. While those steps are important, she said, confidence often comes from knowing your family understands your wishes, knows where key information is located, and is prepared to act when necessary. On the other hand, families who combine planning with ongoing communication report significantly better outcomes. “Talking about a plan may be just as important as creating one. When parents share their plans with family members, they help ensure everyone understands important decisions and reduce the likelihood of confusion during a future transition,” she added. Necessary planning documents include, at a minimum, a last will and testament, Daniel Tirle, partner at CMLaw, said. For many, a revocable living trust can be a good option, he said, as it can make things much smoother after that person passes away, provided it is properly funded. “A few other very important documents are a durable financial power of attorney, an advance medical directive, and an appropriate HIPAA authorization. Beneficiary designations and asset ownership also must be reviewed,” he added. Why do families avoid these conversations? Conducting these conversations can feel overwhelming or uncomfortable, emotions underscored in an Empathy survey, which found that 57% of families share these feelings. Another culprit: damaged family dynamics “that prevent legacy conversations from happening or progressing.” In addition, the Empathy study found that 4 in 10 Americans cite uncertainty around family members’ roles and timing. CMLaw’s Tirle said that other reasons include parent and child who may each believe the other is “not ready,” due to fear of death, emotional discomfort, and cultural taboos. “This type of planning forces people to contemplate incapacity, death, dependence on family, and loss of control,” Tirle said. The issue is not primarily financial. It is psychological. In addition to these conversations combining three uncomfortable subjects, money, mortality, and family, some experts said there is also a deeper issue. “Estate planning forces us to define what we actually believe about money and legacy,” said Feroz Ansari, CFP, author of The Wisdom and Wealth Solution: Unlocking The Secrets Of Happiness, Purpose, And Financial Security, and adjunct professor at the University of California, Irvine. And some families may hesitate to seek professional help because the costs, including fees, paperwork, decisions, and awkward discussions, are immediate, while the benefits seem distant and uncertain. Fidelity’s Viktorin echoed the sentiment, noting that many parents don’t want to burden their children, while adult children sometimes worry they’re being intrusive. And the Fidelity study also found that some families think they’ve already talked enough, while others simply don’t know how to begin. “That’s why we often encourage families to start small. The goal isn’t to solve everything in one conversation, but to begin building a shared understanding over time,” she said. Pitfalls of not having these conversations, no matter how uncomfortable they may be, are numerous. For instance, they can lead to tension between family members, missed tax-saving opportunities, and prolonged litigation, Tirle said. “Some years ago, I worked on a case in which the father passed away without an estate plan, leaving 154 real estate properties and multiple children,” he said. “Each child hired lawyers, and they fought for close to five years over how to divide the estate. Other times, the surviving spouse or heirs have no idea where the assets are or how to manage them.” Another surprising finding in the Fidelity study is that even a major health event does not trigger such conversations. Ansari said that a health crisis may actually make communication harder because emotions are already elevated and stress levels are high. “Unknown choices confront families, which causes tension and makes the entire situation even more difficult. The worst time to have the first family planning conversation is during the crisis itself,” Ansari said. Beyond financial risks, the bigger drawback of not having these conversations may be emotional. When parents do not explain their intentions, children are left to interpret them, Ansari said. “Why did my sister receive more? Why was my brother chosen as trustee? Did Mom want the house sold? Why did Dad structure the trust this way? Unanswered questions can become resentment. Silence during life can become conflict after death,” he added. What should seniors talk about with their adult children? Viktorin said the goal is not necessarily to disclose every financial detail, but to ensure family members understand enough to carry out important plans when needed. Some useful topics include long-term financial goals and priorities, estate planning intentions, health care preferences, and future care wishes. In addition, she said, it’s crucial to discuss who would make decisions if assistance were needed, the roles and responsibilities family members may assume, where important documents are kept, expectations related to caregiving, finances, and wealth transfer, and desired outcomes during major life transitions. How can children help? Adult children can help by bringing up the subject gently and taking it one question at a time, Tirle said. “Asking, ‘If you ever needed help with your finances, whom should I call?’ can be a simple way to begin. As the conversation develops, they can ask whether the people named in the planning documents know about their roles and are willing to serve,” he added. He also recommended that children listen, give their parents time to think, and respect their decisions. In addition, practical help, such as organizing records or arranging a meeting with their parents’ tax or financial adviser, can also make the process feel more manageable. “If sibling relationships are strained, having an attorney or financial adviser guide the discussion can help keep everyone focused and prevent old disagreements from taking over,” he added. Finally, experts said that adult children don’t need to have all the answers. And as Viktorin noted, one of the most valuable things they can do is create space for open dialogue. In other words, ask questions, listen carefully, and help parents think through important decisions before a crisis occurs. “These conversations can help families move from assumptions to clarity, which is often where confidence and peace of mind come from,” she said. This story written for TheStreet by Nifty 50+
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