Thanksgiving: the one day a year where it’s socially acceptable to wear stretchy pants at the dinner table and argue about football. But what if, between the mashed potatoes and the pie, you squeezed in a conversation that could save your family future headaches?
Yes, I’m suggesting we talk about estate planning. Don’t roll your eyes yet—it’s more interesting than it sounds, I promise.
Why Thanksgiving is the Perfect Time
Think about it: everyone’s gathered in one place, mellowed out by carbs, and (hopefully) in a good mood. It’s the perfect opportunity to “talk more than turkey” and tackle those big questions about the future. Sure, it might feel awkward to bring up wills and legacies when the sweet potato casserole is still warm, but it’s a lot less awkward than sorting it all out during a crisis.
How to Bring It Up Without Causing a Fork Fight
Not sure how to steer the conversation without turning dinner into a courtroom drama? Try these lighthearted openers:
- Make it personal: “I just finished updating my estate plan, and honestly, it feels great to know I’m not leaving a mess for you all.”
- Ask for Help: “I need your help with something more important than figuring out how to reheat leftovers without drying them out.”
- Tell a Story: “You remember Aunt Mary’s estate fiasco, right? Let’s make sure to avoid that.”
- Future Planning with a Twist: “Let’s all agree now—no one fights over Grandma’s tea pot, okay?”
- Keep It Playful: “This isn’t about waiting for anyone to kick the bucket. It’s about making sure we know who gets the bucket!”
If you want to really spice things up, bring The Death Deck to the table. It’s like Cards Against Humanity, but for estate planning—a guaranteed conversation starter, complete with laughs.
Key Questions to Get the Ball Rolling
Once the conversation is flowing (and everyone’s too full to run away), consider sprinkling in some practical questions:
- When was the last time you updated your will, financial power of attorney, or healthcare directive? Where are they stored?
- Where are all important documents kept?
- Do you have a list of your current assets and liabilities?
- What banks and institutions hold your accounts?
- When the time comes, how can immediate expenses be managed?
- How is your digital footprint managed, including passwords and online accounts?
- Have you set up any online planning tools for digital assets, like Apple’s Legacy Contact or Google’s Inactive Account Manager?
- Does anyone have access to your phone and computer?
- How do you feel about managing the upkeep of your current home?
- What are your thoughts on decluttering and getting rid of some belongings?
These kinds of questions might feel tricky to ask at first, but they often lead to deeper conversations about family values, memories, and what matters most—topics that are surprisingly heartwarming once you get started.
The Bigger Picture
This Thanksgiving, as you share family stories and laughter, take a moment to also talk about how you can preserve those memories and make the future a little easier for everyone.
Because at the end of the day, planning isn’t just about paperwork—it’s about creating peace of mind for the people you love most.
Wishing you a warm and meaningful Thanksgiving,
Rachel
