Holiday Season: Embracing Awkward Conversations about Estate Planning

December 20, 2023

The holiday season is upon us, bringing joy, warmth, and the inevitable awkward family conversations. As you gather with loved ones, surrounded by the glow of twinkling lights and the aroma of festive meals, consider taking advantage of this precious time to discuss a topic that often remains in the shadows—estate planning.

Picture this: the family is gathered around the dinner table, and someone bravely steers the conversation toward the future, saying, “I have my estate plan taken care of already.” It might sound like an unconventional holiday discussion, but it could be one of the most thoughtful and caring gifts you give to your family.

Many individuals spend the holidays with adult children and grandchildren, making it an opportune time to address important matters such as medical decisions, financial choices, and other aspects of estate planning. Here’s why you should embrace these potentially awkward conversations and how to navigate them gracefully.

Fostering Open Communication

The holidays provide a unique environment that encourages open and honest communication. Surrounded by the warmth of family ties, these moments can serve as a catalyst for addressing topics that might otherwise be difficult to broach. By initiating discussions about estate planning, you create an atmosphere of transparency and trust within your family.

Planning for the Unexpected

Life is unpredictable, and having an estate plan in place ensures that your wishes are known and respected in the event of unforeseen circumstances. Conversations about who you want to make medical decisions for you and how those choices should be made are crucial aspects of estate planning that can provide peace of mind for both you and your loved ones.

Designating Financial Decision-Makers

Discussing who you want to make financial decisions on your behalf is another vital component of estate planning. This includes considerations such as managing your assets, investments, and other financial matters. By openly sharing your preferences during the holidays, you empower your family to act in your best interests should the need arise.

Legacy and Family Values

Estate planning is not just about distributing assets; it’s an opportunity to pass on your values, traditions, and life lessons to the next generations. Use the holiday season as a backdrop to express the importance of family unity, responsibility, and the significance of planning for the future.

How to Approach the Conversation

Bringing up the topic of estate planning may feel daunting, but with a thoughtful approach, it can become a meaningful and even uplifting conversation. Start by expressing your love and concern for your family’s well-being. You can say something like, “I’ve been thinking about the future, and I want to ensure that our family is prepared for anything that comes our way.”

Encourage open dialogue by asking for input and opinions. Share your own thoughts and decisions regarding your estate plan, emphasizing that this is an ongoing process that may evolve over time. Consider involving a professional estate planning attorney to facilitate the conversation and provide expert guidance.


This holiday season, consider giving the gift of peace of mind to your family by engaging in those potentially awkward but crucial conversations about estate planning. Embrace the warmth of the holiday atmosphere to foster open communication, plan for the unexpected, and share your values and legacy with those you hold dear. In doing so, you not only provide a sense of security for your family but also pave the way for a more united and prepared future.