Pass the Gravy, and Then Let's Talk About Estate Plans

Talking about finances with your family can be challenging. Questions such as, "When I die, will you be my executor?” or “My wishes after I pass are…” may not come up naturally when your home is filled with family members and the scents of the approaching feast. However, Thanksgiving is a time for families to gather and express gratitude, so the holiday can be the perfect opportunity to start a discussion about financial goals, values and securing your financial future together.

Below are some questions and topics to guide a conversation this Thanksgiving to help your family understand financial plans, set (or manage) expectations and overcome natural resistance. This list is by no means exclusive, and you shouldn’t feel like you have to wrap up all of these topics in one meal or meeting. Each family is navigating distinct circumstances — and these suggestions can encourage readers to consider what is most important for their family. The goal is not about resolving every issue. Rather, it is about beginning the conversation that sets your family up for success and opens the door to additional conversations in the future.

Set the table for a successful retirement

For those nearing this milestone, it’s important to share details with the people who matter most to you. For many, that includes grown children. Even if they still expect their parents to do their laundry when they come home, they are adults. It's essential to have open conversations to help them understand any upcoming shifts in lifestyle, how you have prepared financially for this next phase of life and to what extent you plan to use your resources.

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If part of your retirement plans includes downsizing and selling a family home, do your children know your plans and understand the reasoning behind them? Providing this clarity can foster a sense of shared responsibility and vision. This ensures a smoother transition into retirement and later-in-life financial discussions.

Pass the stuffing — and your will

Thanksgiving is a convenient time to locate your most important documents, in case something happens in the future. It’s not fun to think about, but this is relevant for everyone. From wills and life insurance to accounts and passwords, there is a lot of information that needs to be (quickly) accessible and to land in the right hands.

If your family, like many families, is spread out around the country, consider creating digital versions of the most important documents so they can be accessed remotely. If you’ve chosen an executor, does that person know about their role? Simply locating documents and knowing the answers to these basic questions is a win in itself.

Serve up some estate planning

For some families, it might be beneficial to discuss not only the location of estate planning documents but also what they contain. These topics are not easy to bring up. However, open conversations can help identify misaligned perspectives in the event that someone does pass away. For older generations, sharing what matters to you and why you’ve made certain decisions can reduce ambiguity and anxiety.

As an example, if you intend for some of your money to be given to a certain charity, do your children (or other beneficiaries, such as nieces and nephews) know that? Do they understand your reasoning? You might assume they do, but these kinds of assumptions often lead to conflict. A conversation can prevent such difficulty. Ultimately, it’s about giving peace of mind and making sure that — if something happens — everyone is on the same page.

Every family is unique, with everyone navigating different yet potentially delicate dynamics that can make broaching these topics seem difficult or even impossible. But having these conversations is crucial, and ultimately, speaking openly about financial topics can also bridge connection with your loved ones.

Diving into financial goals and providing clarity into what you value can help your family understand one another better. Often, starting the conversation is the most difficult step, and in the long run, your family will be grateful that you did.

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• Estate Planning Checklist: Five Tasks to Prioritize