Gratitude, Gatherings, and Generational Conversations

Estate Planning at Thanksgiving

Thanksgiving is a time for connection, reflection, and the occasional spirited debate over who gets the last slice of pie. Thanksgiving is also an opportunity to tackle important family conversations, including estate planning. While discussing topics like wills, powers of attorney, and inheritance might not feel as warm and fuzzy as sharing recipes, these discussions are deeply tied to the values of gratitude and care that define this holiday.

Whether you’re a Baby Boomer looking to ensure your legacy is secure or a Gen-Xer balancing care for your children and aging parents, Thanksgiving can be the perfect time to talk about estate planning—if approached thoughtfully.

Why Thanksgiving?

Thanksgiving is unique in its ability to bring multiple generations together in one room. For many families, it’s the only time all year when everyone is seated at the same table. This makes it an ideal moment to:

• Share your wishes: Whether you’re a parent or an adult child, estate planning is about ensuring your wishes are honored.

• Open the lines of communication: It’s easier to discuss sensitive topics in person, where tone and intention are clearer.

• Strengthen family bonds: Addressing estate planning now helps avoid misunderstandings or conflicts later.

Breaking the Ice: How to Start the Conversation

Starting a conversation about estate planning can feel awkward, but with the right approach, it doesn’t have to be. Here are some tips to ease into the topic:

1. Focus on Gratitude and Legacy

Baby Boomers are often motivated by leaving a legacy, while Gen-Xers value security and preparedness. Frame the conversation around these shared values. For example:

• “I’ve been thinking about how thankful I am for our family and how important it is to me that we’re all taken care of. Have you thought about how we can ensure everyone is supported, no matter what happens?”

2. Use Stories as an Entry Point

Personal anecdotes can soften the edges of the discussion. Share a story about someone you know who didn’t have an estate plan—or who did—and the impact it had:

• “A friend’s family went through a tough time because there wasn’t a plan in place. It made me realize how important it is to have these conversations before it’s too late.”

3. Emphasize Care, Not Control

For Gen-Xers managing the “sandwich generation” responsibilities of caring for kids and aging parents, estate planning is about creating stability. Boomers, on the other hand, might be concerned about relinquishing control. Reassure them:

• “This isn’t about making decisions for you. It’s about making sure your wishes are honored and that we all avoid unnecessary stress later on.”

Topics to Cover: A Checklist for the Conversation

Once the ice is broken, consider discussing these key topics:

1. Wills and Trusts

For Boomers: Do you have a will or trust in place? If so, is it up to date?
For Gen-Xers: Have you created a will to protect your minor children and ensure guardianship is assigned?

2. Powers of Attorney and Healthcare Directives

Boomers: Who will make decisions for you if you can’t?
Gen-Xers: Have you named someone to act on your behalf in an emergency?

3. Beneficiary Designations

Double-check that life insurance policies, retirement accounts, and other assets have the correct beneficiaries listed.

4. Long-Term Care Planning

Boomers: Have you thought about how you’d like to handle aging in place or assisted living?
Gen-Xers: Do you have a plan in place for your parents and yourself?

5. Open Communication About Finances

Discuss how to share necessary financial information—such as account locations or passwords—without overstepping boundaries.

Overcoming Resistance

It’s not uncommon for family members to shy away from these conversations. Here’s how to address common concerns:

• “I don’t want to think about dying.”
  Frame the discussion as a way to celebrate life:
  “This is about ensuring the love and care you’ve built continues no matter what.”

• “I don’t want to burden my kids.”
  Reassure them:
  “Having a plan reduces the burden—it prevents us from having to make difficult decisions during a tough time.”

• “It’s too complicated.”
  Simplify the process:
  “We can start small. Let’s just make sure the basics are covered and go from there.”

Creating a Plan for Action

After the conversation, follow up with actionable steps:

1. Schedule a Family Meeting
   If Thanksgiving isn’t the right time to get into the details, agree to have a dedicated family meeting within the next few months.

2. Consult a Professional
   Encourage your family to work with an estate planning attorney. As a professional, I often guide families through these conversations and help tailor plans to their unique needs.

3. Review and Update Plans Regularly
   Life changes—so should your estate plan. Use Thanksgiving as a yearly reminder to review your documents.

The Gift of Preparedness

For both Gen-Xers and Boomers, estate planning is an act of love. It’s a way to care for your family even when you’re not there to do so in person. And what better time to start than during a holiday dedicated to gratitude?

This Thanksgiving, as you pass the mashed potatoes and share family stories, consider adding estate planning to the menu. It’s a conversation that ensures the traditions, values, and care you’ve built will carry on for generations to come.

Contact Us

When you are ready to begin your estate planning, give us a call. We would love to help you and your family get your affairs in order.