Key Takeaways
- Talking about money or inheritance may feel uncomfortable—but open, honest conversations about your estate plan are one of the most caring gifts you can give your family.
- The holidays can be a natural time to begin these discussions while everyone is together and able to plan thoughtfully.
- Learn what to include in your estate plan, when to start the conversation, and how to approach it with empathy and confidence.
The holidays are a time for connection, reflection, and gratitude. But amid the celebrations, they also offer something more meaningful—a chance to talk about what truly matters most. For many families, that includes how to protect, preserve, and pass on what they’ve built.
Talking about money or inheritance may feel uncomfortable–and you’re not alone if you’ve avoided these conversations in the past. According to Caring’s Will Survey, just 25% of the U.S. adults surveyed have a will at all. Death and estate planning are considered the most difficult topics to talk about, according to a survey by Trust & Will.
These are personal, emotional topics, but having open, thoughtful conversations about your estate plan is one of the most important things you can do for the people you love. As families gather this season, it’s a time to share not just gifts—but also plans that bring lasting peace of mind.
Here’s what your estate plan should include and how to approach these challenging conversations with empathy and confidence.
What is included in an estate plan?
An estate plan is more than a set of legal documents—it’s a roadmap for your family’s future. It outlines how your assets, home, and personal wishes will be handled when you’re no longer able to make those decisions yourself.
An estate plan typically covers:
- A will or trust outlining how your assets will be managed
- Beneficiary designations for retirement accounts or insurance policies
- Healthcare directives, including a living will
- Powers of attorney for financial and healthcare decisions
Why estate planning conversations are important
Having an estate plan—and talking about it openly—may ease some of life’s hardest moments. Without clear instructions, loved ones are often left to make difficult decisions under pressure or during grief. A well-communicated plan eliminates uncertainty, reduces the risk of family conflict, and ensures that your wishes are followed exactly as intended.
It could also help protect your family’s financial well-being. From avoiding costly probate delays to managing taxes efficiently, estate planning may preserve more of what you’ve built for the people and causes you care about.
Still, it’s natural to hesitate. Talking about money, aging, or the future may feel uncomfortable—and for some, even a little ominous.
“It’s almost like a superstition that people have that if they start talking about their estate planning documents, they’re going to get that terminal illness, because they’ve spoken it into existence,” Michael Zahrt, a business and estate planning attorney in Grand Rapids, Michigan, told financial publication Quartz.
But starting the conversation early is one of the most thoughtful things you can do. It’s not about inviting bad luck—it’s about creating peace of mind. An open dialogue now prevents confusion later and gives your loved ones the confidence to carry out your wishes.
As families gather this season, it’s a chance to share not just gifts, but plans that bring comfort and clarity for the years ahead.
When to start the estate planning conversation
The best time to start an estate planning conversation is before it’s needed. These discussions are most productive when everyone approaches them thoughtfully. Rather than waiting for a major life or medical event, look for natural opportunities throughout the year to begin the dialogue. For example:
- Retirement milestones: When someone retires or begins drawing Social Security, it’s an ideal time to review financial goals and long-term plans.
- Health check-ins: After an annual physical or as parents or grandparents age, it’s helpful to ensure everyone understands healthcare wishes and responsibilities.
- Year-end financial reviews: When families are reviewing investments, taxes, or charitable giving, it’s a natural time to bring estate planning into the conversation.
And of course, the holiday season may be a meaningful time to start these conversations. It’s often one of the few times a year when extended families gather in person—making it easier to talk openly and ensure everyone is part of the discussion.
What topics should you cover in an estate planning conversation?
An estate plan is deeply personal, so every family’s discussion will look a little different—but covering a few key topics can help ensure your plan is both comprehensive and meaningful.
Start with these essentials:
- Wills and trusts: Clarify how your assets will be distributed and who will be responsible for managing them. A will outlines your wishes, while a trust could help streamline the process and potentially reduce delays or costs.
- Beneficiaries: Review who’s listed on retirement accounts, insurance policies, and investment plans to ensure everything aligns with your current intentions.
- Home equity and property planning: Discuss how your home or other real estate fits into your plan. For some, that may include options like a reverse mortgage – such as a HECM or proprietary reverse mortgages, or home equity line of credit (HELOC) to support financial needs later in life.
- Healthcare wishes: Outline medical preferences and appoint someone you trust to make healthcare decisions if you’re unable to. This may include a living will or healthcare power of attorney.
- Document storage and access: Make sure your loved ones know where to find key documents—wills, deeds, insurance policies, and account information—and how to access them when needed.
- Sentimental items: Don’t overlook the emotional side of your legacy. Personal belongings, family heirlooms, and keepsakes often hold more meaning than financial assets.
- Legacy and charitable giving: If you plan to support causes or create a charitable fund, discuss those intentions to ensure your loved ones understand and will follow your wishes.
You don’t have to cover every detail at once. The goal is to build understanding, reduce uncertainty, and give your family the confidence to carry out your wishes with clarity and care.
How to approach estate conversations with care
Starting an estate planning conversation might feel uncomfortable, but it doesn’t have to be. The goal isn’t to finalize every detail—it’s to open a dialogue that brings comfort and clarity to everyone involved.
Here are a few ways to make the conversation more natural and productive:
- Start conversations early: Don’t wait for a crisis or major life change. Bringing up estate planning while everyone is healthy and calm allows for thoughtful, inclusive decision-making.
- Use gentle openers: Try phrases like: “We’ve been thinking about how to make things easier for everyone in the future.” or “We want to make sure our plans reflect what matters most to the family.”
- Choose a comfortable, low-stress setting: Pick a relaxed environment—maybe a quiet morning over coffee or an afternoon walk—where everyone feels safe to talk.
- Ask questions: Rather than leading with instructions or numbers, invite perspectives: “What matters most to you about how we handle the house?” or “How can we make sure everyone feels included?” Questions create connection and understanding.
- Encourage ongoing dialogue: Estate planning isn’t a one-time discussion—it’s a series of conversations that evolve as your family and finances change.
When approached with empathy and openness, these discussions may help you strengthen relationships and give everyone peace of mind for the future.
Bringing financial clarity to the holiday season
Estate planning isn’t just about documents and decisions—it’s about peace of mind. Having these conversations now helps ensure your family understands your wishes and may make navigating a difficult time easier.
The holidays are a time to celebrate what we’ve built and who we share it with. As you gather this season, consider giving your loved ones the gift of clarity and comfort—a plan that reflects your values, protects your legacy, and provides guidance for the years ahead.
Starting the conversation may feel difficult, but it’s one of the most meaningful acts of love you can offer your family.
A reverse mortgage may be an important financial tool for later in life. To find out if it is a good fit for your situation, call the Finance of America team at (800) 841-3723.
Disclosures: These materials were not provided by HUD or FHA and were not approved by FHA or any government agency. A reverse mortgage is a loan that must be repaid. When the loan is due and payable, some or all of the equity in the property no longer belongs to the borrowers, who may need to sell the home or repay the loan with interest. The borrower must meet all loan obligations, including living in the property as their principal residence, and paying property charges such as taxes, fees, hazard insurance, and ongoing home maintenance. Failure to meet these obligations may result in default and foreclosure. Not tax advice. Consult a tax professional. For licensing information, visit www.nmlsconsumeraccess.org.
Danielle Antosz is the web content manager at reverse mortgage lender Finance of America Reverse LLC. The views expressed in this article are those of the author alone and do not necessarily reflect the views and opinions of their employer. This article is not intended to provide financial planning, wealth management, legal, or tax advice. For tax advice, please consult a tax professional.
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