Talking About Estate Planning During Thanksgiving: A Guide for Families

As families gather around the Thanksgiving table, it presents a unique opportunity to engage in meaningful conversations that extend beyond the traditional holiday topics. One such important discussion is estate planning. While it may seem uncomfortable or even taboo, openly discussing estate planning can provide clarity, avoid future conflicts, and ensure the smooth transfer of wealth from one generation to the next. In this comprehensive guide from Gentreo,, we will delve into the importance of talking about estate planning during Thanksgiving, provide strategies for initiating the conversation, highlight key topics to discuss, and offer guidance on how to navigate this sensitive subject with your loved ones.

The Significance of Estate Planning Discussions

Estate planning is an essential aspect of financial planning that involves making decisions for when you are alive and for after you pass away. It’s about making arrangements for the distribution of assets, healthcare decisions, and the protection of one’s legacy. Unfortunately, the lack of communication and proactive planning in families often leads to significant financial repercussions. According to a study published by NASDAQ, an estimated 70% of wealthy families will lose their wealth by the second generation, and 90% will lose it by the third1. This statistic emphasizes the importance of open dialogue about estate planning to preserve and protect generational wealth.

Initiating the Conversation

Broaching the topic of estate planning during Thanksgiving requires sensitivity, tact, and respect for privacy. It is crucial to create a comfortable and non-threatening environment for the discussion. Here are some strategies for initiating the conversation:

  1. Share Your Personal Experience

One effective way to start the conversation is by sharing your own experience with estate planning. By discussing your own preparations and research, you can establish credibility and demonstrate the importance of proactive planning.

  1. Utilize Third-Party Resources

Sharing this guide from Gentreo is also a great start so everyone can start form the same place as this can help alleviate any discomfort. You can also share other Gentreo articles that are relevant to your family’s person situations that might highlight the benefits of estate planning. These resources can serve as conversation starters and provide valuable insights from experts in the field.

  1. Highlight the Consequences of Inaction

Sometimes, individuals may be hesitant to discuss estate planning due to a fear of confronting their own mortality or concerns about family dynamics. In such cases, sharing stories of families who have faced challenges or disputes after the passing of a loved one can help emphasize the importance of proactive planning. By highlighting the potential consequences of inaction, such as family conflicts and legal complications, you can encourage your family members to consider the benefits of estate planning.

Many times when one doesn’t do estate planning, a significant portion of the estate’s value can be lost to attorney and court fees.  Plus, it is hard to know who to trust when so much is going on with a loved one just passing.

Key Topics to Discuss

When engaging in estate planning conversations, it is essential to cover certain key topics that will ensure a comprehensive and well-rounded plan.

Before we start our list, estate planning is for everyone over the age of 18.  Single or married, divorced, young, old, etc., etc. and etc. if you are of sound legal mind, estate planning is almost certainly something for you.  Protect your choices and the assets you and your family have worked hard for across life.

Here are seven important estate planning topics to discuss with your family during Thanksgiving:

  1. The Importance of Having a Will

Start the conversation by discussing the significance of having a will. A Gallup News poll found that less than half of adults in the U.S. have a will that outlines how their assets should be distributed after their passing1. Explain the implications of not having a will, which can result in a lengthy and costly probate process. Encourage your loved ones to consider drafting a will and discuss the importance of choosing an executor for the estate.

  1. Identifying and Organizing Assets

Help your family members compile a comprehensive list of their assets, including physical and digital assets, bank accounts, life insurance policies, and retirement plans. Emphasize the importance of keeping this information organized and easily accessible to the executor of the will or the trustee of any trusts.  You can save and share any or all of this in your Gentreo Digital Vault,

  1. Selecting Powers of Attorney

Discuss the significance of selecting powers of attorney for financial and healthcare decisions. Explain the role of a power of attorney in managing one’s financial and legal affairs in the event of incapacitation. Encourage your loved ones to choose a trusted individual who can make important decisions on their behalf.  If you need to learn more about a financial power of attorney, visit Gentreo’s Learning Center, Or to learn about a health care power of attorney, often called a health care proxy, which includes a living will, visit

  1. Exploring Trusts as a Management Tool

Introduce the concept of trusts as a valuable estate planning tool. Explain how trusts can help avoid probate, keep information from going public, can protect assets, and can often provide for the smooth transfer of wealth. Discuss living trusts, and their benefits. Here is a good tool for learning the difference of a trust versus a will,

  1. Think about Planning for Long-Term Healthcare

Long-term healthcare is a critical aspect of estate planning, especially for aging family members. Discuss the various options available for long-term care, such as in-home care, assisted living, or nursing homes. Encourage your loved ones to plan ahead and consider factors such as healthcare costs, insurance coverage, and the potential need for Medicaid.

Navigating the Discussion with Sensitivity

When discussing estate planning, it is crucial to approach the conversation with empathy, understanding, and respect for individual comfort levels. Here are some tips for navigating the discussion with sensitivity:

  1. Focus on Family Values and Legacy

Frame the conversation around the preservation of family values and the desire to leave a lasting legacy. Emphasize that estate planning is an opportunity to ensure that their wishes and intentions are carried out, providing peace of mind for both the individual and their loved ones.

  1. Avoid Pressuring or Judging

Avoid pressuring or judging your family members’ decisions or lack thereof. Respect that everyone may have different priorities, concerns, or reservations about discussing estate planning. Create a safe space for open and honest dialogue where each person feels heard and respected.

  1. Offer Support and Assistance

Demonstrate your willingness to support and assist your family members throughout the estate planning process. Assure them that your intention is to help and alleviate any burdens they may face.

  1. Revisit the Conversation

Estate planning is an ongoing process, and it is essential to revisit the conversation periodically. Encourage your family members to regularly review and update their estate plans to reflect any changes in their financial situation, family dynamics, or personal preferences. Remind them that estate planning is a dynamic and evolving process.  This is why Gentreo allows unlimited updates when ever desired.


Thanksgiving provides a valuable opportunity to engage in meaningful conversations about estate planning with your loved ones. By initiating open and respectful dialogue, discussing key topics, and navigating the discussion with sensitivity, you can help ensure that your family is prepared for the future and that their financial and legacy wishes are fulfilled. Remember, estate planning is a continuous journey, and the support and guidance of trusted professionals can make all the difference in creating a comprehensive and effective plan. Start the conversation this Thanksgiving and empower your family to secure their financial future.

And, one last thought, It is important to emphasize the emotional and financial benefits of estate planning, such as providing for loved ones, avoiding family conflicts, and leaving a lasting legacy. The tone should always be empathetic, reassuring, and informative, ensuring that your family feels empowered and supported in their estate planning journey.


  1. NASDAQ, “Statistics on Wealth and Inheritance,” source 2


Don’t wait until it’s too late; start your estate planning journey with Gentreo today. By doing so, you’ll not only protect your loved ones but also gain the peace of mind that comes with knowing your legacy is secure.  Click here to join now



Recent Posts:

old man completing document

Common Reasons for a Medicaid Denial

Applying for Medicaid can be complicated. While applications may seem straightforward, there are many hidden pitfalls where you could be denied Medicaid benefits or result in extensive delays being approved.

Read More »