The Holiday Season: The Perfect Time for Joy, Laughter, and Estate Planning

For many families, the holidays are a time to avoid sensitive subjects. Siblings steer clear of old arguments, parents in troubled marriages get along for the sake of their kids, and politics stay safely within the realm of Facebook.

But the holiday season is a time when many of us see and speak with our family members for the first time all year. These cherished moments serve as a golden opportunity for difficult conversations that can’t be discussed over texts or emails. Estate planning is one of those conversations.

Estate planning is an all-encompassing term for high-stakes topics. When we discuss our estate plans, we often ask the following questions:

  • Who will my beneficiaries be?
  • What will my beneficiaries receive?
  • Who will be the executor of my will?
  • How will the government distribute my estate?
  • Who will care for my dependents when I am no longer around?
  • Are my children ready to manage my business?
  • Is it time to find a nursing home or assisted living facility for my aging parents?

Finding (and agreeing upon) answers to these questions is a serious undertaking. Why would we choose to talk about wills, guardianships, or long-term care for aging loved ones at a time when we would rather reminisce over fond memories or enjoy the moment? With thorough planning and tactful conversation techniques, however, looking ahead will not tarnish the joys of the holiday season.

5 Tips for Estate Planning Conversations over the Holidays

With the proper care, estate planning while everyone is gathered together can provide an opportunity for us to express gratitude, strengthen relationships, and build the foundations for our loved ones’ successful futures. Here are 5 key tips to encourage a productive and respectful estate planning session this holiday season.

  1. Create a priority list. What discussion points are absolutely essential? Finding a nursing home for a parent with rapidly declining health, for example, may be an urgent matter. On the other hand, some issues can reasonably wait for a later time. If you want to pass on your business to your children, but you have a spouse who can manage it until they get older, this discussion may not need to happen immediately. Having a priority list will help you ensure your family discusses the most pressing issues before the flights back home.
  2. Consider enlisting someone’s support ahead of time. If you know this conversation will be difficult, having an ally (e.g. a close sibling) who is equally prepared for the discussion could help you get your points across. Bringing up sensitive topics or dilemmas is always easier when you are not alone.
  3. Don’t underestimate the power of preparation. Even if you know exactly what you want to discuss, or what you want to get out of the conversation, practicing will never hurt. Coming up with tactful wording may be a challenge, especially if people get emotional or reactive in the heat of the moment. Some may even choose to write out their thoughts in a letter and send it ahead of time or read it aloud to the whole family.
  4. There’s no such thing as perfect timing—but aim for it anyway. It always feels like the wrong time to bring up difficult subjects, but some moments are more appropriate than others. Are young children in the mix? Consider waiting until they have gone to bed, so you know you won’t be interrupted. Alternatively, discussing complex financial issues may be easier earlier in the day, before your family has begun any heavy drinking.
  5. Set boundaries. Not all families get along, and estate planning may worsen preexisting tension. Before you begin the discussion, consider setting ground rules, such as one person speaking at a time, or everyone writing down their thoughts and concerns before sharing them. You may want to establish certain off-limits topics that aren’t relevant to your discussion goals.

Estate planning involves choosing certain family members over others, assessing the responsibility and dependability of your siblings or children, and making difficult decisions that some would rather avoid indefinitely. But when you use these 5 techniques, you invest crucial time into both your estate and your loved ones.

Do You Need Skilled Legal Support for Your Estate Planning Needs?

At the Law Office of Robert J. Maher, PC, our attorney has over a decade of experience helping our clients accomplish their estate planning goals. Our team will help you navigate the complexities of New York law, organize your assets in a way that protects your family’s financial future, and convey your final wishes in a comprehensive set of airtight documents.

Schedule your initial consultation with Attorney Maher by calling (646) 681-1977 today.
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