The Gift of Conversation: Talking Estate Planning Over Thanksgiving
The Thanksgiving holiday has always been a time for sharing space — stories, laughter, fixing your parents’ tech issues while you’re staying with them, and taking a good cousin walk. And let’s be honest, it’s also often a little awkward. This year, consider adding something new to the Thanksgiving menu: a conversation about estate planning.
If you're a woman in your 30s to 50s, chances are your parents are entering or already well into their retirement years. And while they may seem as vibrant as ever, the reality is that without proper estate planning documents, a medical emergency or sudden incapacity could leave you making impossible decisions without guidance — or fighting through probate court when you should be grieving. These documents must be drafted and signed while someone still has mental capacity to avoid a complicated, time-consuming court process.
I see it in my practice far too often: adult children who never had the conversation suddenly facing crisis without the legal tools they need. The good news? Thanksgiving, with its built-in family gathering, offers a natural opportunity to start this crucial dialogue.
Why Now Matters
Northern Virginia families tend to be mobile — adult children often live states away from aging parents. This distance makes advance planning even more critical. Without the right documents, you may not be able to access medical information, handle financial decisions, or honor your parents' wishes when it matters most.
And let’s be honest: these conversations don’t get easier with time. They get harder as parents age and health issues emerge, when emotions run higher and options narrow.
I recently had this talk with my own mother. Even though she had a will and funeral arrangements, she didn’t have a Power of Attorney or Advance Medical Directive. I had no idea and I was so relieved I asked.
Setting the Stage
The key is to approach this conversation with love, not alarm. You’re not suggesting your parents are declining — you’re showing that you care about honoring their wishes and protecting the family.
Choose your moment wisely. Not during the chaos of meal prep or when everyone’s settling in for football. Find a quiet moment with some privacy.
Start with your own planning. Try something like:
“Mom and Dad, I’ve been working on my own estate plan, and it made me wonder — do you have a will, power of attorney, or advance medical directive?”
This approach normalizes the conversation. It positions you as seeking guidance, not implying anything about their health. And if you haven’t started your own documents yet… well, maybe it’s time for everyone to get things in order together.
The Essential Documents
Keep the focus on the key elements without overwhelming them:
Power of Attorney (Finances): Who will manage bills, banking, and property if they can’t — whether due to travel, illness, or cognitive issues?
Advance Medical Directive: What are their preferences for end-of-life care?
Who should make medical decisions if they can’t?
Last Will and Testament: How should assets be distributed? Who will serve as executor?
Keep it conversational with helpful, non-threatening questions:
"Where do you keep your important documents?”
“Can we create a list together of what financial accounts someone would need to know about to manage your life?”
“Can we create a list of logins and passwords for accounts someone would need access to be really helpful."
“Can we create trusted contacts for your digital assets so that I can have access if something happens?”
"Do you have an attorney you trust, or would you like help finding someone?"
"Have you all discussed this together, would you want to?"
If they're truly not ready, don't push. Plant the seed and revisit after the holidays. Sometimes it takes multiple conversations.
Your Next Steps
If your parents don't have documents or they are decades old (pre-dating major life changes like moves, divorces, or deaths), encourage them to meet with an estate planning attorney in early 2026. Virginia law has specific requirements, and DIY documents often miss critical protections.
This Thanksgiving, as you count your blessings, give yourself and your parents the blessing of preparedness. It's not a comfortable conversation, but it's a loving one—and that's what the holidays are really about.
SEE ALSO: Family First Law Group Named Alexandria Chamber's Small Business of the Year
