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Navigating Estate Planning During the Holidays

  • Writer: Plan Wise Legal
    Plan Wise Legal
  • Oct 21, 2025
  • 5 min read

Updated: Jan 5

Understanding the Importance of Estate Planning


Estate planning goes beyond just distributing assets at our death; it involves critical decisions for us during our lives in addition to those decisions that shape our family's future. Common steps include creating a will, setting up trusts, assigning powers of attorney (POA), and discussing healthcare directives. An interesting statistic shows that about 60% of Americans do not have a will, which can lead to confusion and disputes later. When parents openly communicate their estate plans to their adult children, it minimizes misunderstandings, gives time to address potential conflicts, and allows the parents to communicate their reasoning.


Meanwhile, adult children should pay attention to changes in their parents’ health, as health concerns can lead to adjustments in their estate planning needs. For example, if there was a recent health scare or if our parents are having a harder time getting around, discussing who will act as POA can help clarify responsibilities and reduce stress during critical moments.


Timing is Everything - Let's Discuss Estate Planning


The holiday season provides a unique opportunity for these discussions. Family members generally feel more reflective, relaxed, and open during gatherings, making it easier to tackle sensitive topics. However, we must approach the subject thoughtfully.


What is the best way to discuss estate planning during the holidays? Some initiations may feel organic and occur naturally. For instance, bringing up a cherished family recipe may lead naturally to the topic of who will inherit cherished family heirlooms. Another initiator may be sharing what our in-laws or family friends are going through or how they have handled their planning. If a family member passed away in the last year, we can ask how their kids and everyone are doing. These discussions are common and often happen regardless but can be a good opportunity to reflect on planning.


How to Approach the Topic


When approaching estate planning, sensitivity to our parents' feelings is crucial. Many parents don't want to be a burden to their children, are uncomfortable with the change in family dynamics that relying on their children may create, and many are afraid that admitting their struggles may lead to an overreaction that costs them their independence. It can be helpful to remind them that their delay is more likely to push the tough decisions onto the children who will be going through a stressful situation and who will be nervous they "do the wrong thing." Also, in larger families, we can have too many cooks in the kitchen, and an effective plan often creates an order of responsibilities.


As the child, it is essential to frame the conversation around care and concern. For example, we might say something like, “I want to ensure you have everything in place so that you can continue living comfortably.” This approach emphasizes our desire to support their well-being rather than focusing on inheritances. Also, everyone should understand it is what the parents want to do, not what the children want to do. Nobody should be bound by any plan that was discussed; these things change over time, and what makes sense today may not make sense tomorrow.


The Definition of Fairness


Discussions about what is fair regarding estate planning can become complex. Each family member may perceive fairness differently, and it's important to acknowledge that it doesn't always mean equal distribution.


For instance, a parent might decide to leave the family home to one child who has taken on a larger caretaking role while providing financial support to others. It's vital to respect their decisions, even if they do not align with personal views. Open discussions can help clarify intentions and alleviate feelings of resentment. Additionally, the children need to be prepared to remind their own spouses that fair will be determined by the parents alone.


Respecting Independence


Many parents value their independence and may feel uneasy discussing estate planning. It’s essential to let them lead the conversation about their goals and preferences. Instead of pushing for specific outcomes, we should work to understand their visions for the future.


Encourage our parents to share their thoughts and feelings about their plans. This not only shows respect for their autonomy but also opens the door for a more candid dialogue about their needs and desires. We are there to listen and give feedback as it is requested. Often, they will ask for our opinion, but we must understand they may not heed our advice.


Planning Ahead


While the holidays can be a great time to start discussions about estate planning, creating and executing a plan requires more focused attention. Before family gatherings, adult children should reflect on their own needs. If we have done our own planning, it can be a great discussion opener to share our experience or get our parents' thoughts on our situation.


Additionally, if there are multiple siblings, it might be a good idea to have a quick discussion ahead of time to share any concerns. This way, everyone can share their thoughts without hurting their parents' feelings and share the tasks that each person currently does for their parents to get an idea of how much help our parents are receiving.


This preparation allows us to present a thoughtful plan that addresses our parents’ needs while factoring in family dynamics. It can also help minimize conflicts and ensure everyone feels acknowledged during discussions.


Navigating Uncomfortable Conversations


Discussions about estate planning can be challenging. Different feelings and opinions surface, so it’s crucial to approach these conversations with an open mind. Encourage everyone to express their thoughts honestly, which can be difficult but essential for understanding one another's wishes.


Studies show that families who engage in open discussions about estate planning are less likely to experience conflicts later on. A little discomfort during these conversations can lead to deeper family bonds and clarity in understanding shared goals.


The Role of In-Laws


When discussing estate planning, it's generally best to keep in-laws out of the conversation unless they have direct involvement in the family plan. This helps prevent too many voices in the room and allows the immediate family to remain the focus.


Keeping the discussion to the core family unit fosters a more open environment, encouraging honest exchanges without the added pressure of in-law dynamics complicating the situation.


Final Thoughts on Family Discussions


Navigating family discussions about estate planning during the holidays might seem daunting, but it can also be a chance for growth and understanding. By approaching this topic with sensitivity and respect, families can strengthen communication and ensure that everyone’s needs are considered.


Remember, the goal is not to establish a finalized plan right away but to share thoughts and feelings about the future. With careful preparation and a willingness to listen, families can turn potentially uncomfortable discussions into meaningful conversations that enhance their relationships. Often, these discussions encourage our parents to take the initiative to meet with an attorney to get their estate plan completed. First, because they have momentum and understand how it can help everyone, and second, it avoids having to have the talk again next year.


As we gather with loved ones this holiday season, consider taking a moment to discuss estate planning. Although it may not be a festive topic, it can pave the way for peace of mind for everyone involved.


Embracing the Future Together


In conclusion, estate planning is a vital part of our lives that deserves attention. By opening the door to these conversations, we are not only securing our future but also fostering a deeper connection with our loved ones. Let’s embrace this opportunity together, ensuring that our families are prepared for whatever lies ahead.


---wix---

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