5 Estate Planning Conversations Worth Having This Thanksgiving

Thanksgiving brings multiple generations together, making it a natural moment to talk about the future in a way that feels warm and human. We asked members of the Trust & Will Advisor Contributor Panel to share simple conversation starters families can use at the table and how to keep the tone caring, not clinical. Here’s what they had to say.

“What stories do you want to remember 50 years from now?”

Advisor Ryan L. Goldschmitt, WMCP, Founder of Geminus Wealth Partners suggests starting with legacy, not logistics. Estate planning often focuses on documents and beneficiaries, but what really lasts are the stories and values that define a family.

He recommends asking loved ones, “What stories do you want remembered 50 years from now?” Then capture those stories with a short video, a handwritten note about what matters most, or a new family tradition that keeps the story alive.

Estate planning isn’t just about preserving what exists. It’s about creating something new that keeps your family connected long after you’re gone.

“What traditions do we have that you’d want to see continue in the years ahead?”

For Charles Thomas III, CFP®, Founder of Intrepid Eagle Finance, the best conversations start with appreciation. People often assume gatherings are automatic, yet when a dish or ritual is missing, everyone feels it.

This simple question surfaces what matters most and makes it easy to bridge into, “How can we make sure this continues even when things change?” It naturally opens the door to talking about guardianship, caregiving, and how family resources support shared experiences.

“If we won the lottery, what family legacy would you like to leave?”

Karl Leonard Hicks, CFP®, AEP®, Founder of Leonard Financial Group, encourages families to think bigger. He asks,“If we won the lottery, what family legacy would you like to leave? If money were no object, what would you want to be remembered for in our family?”

This question moves the discussion beyond possessions and into purpose. As Karl explains, estate planning isn’t only about passing wealth efficiently, but it’s also about building a cohesive family by sharing morals, beliefs, and values.

“Hey, just curious, do we know who’s in charge of what if something unexpected happens?”

Bob Chitrathorn, CFP®, CPFA®, Co-Founder & CFO of Simplified Wealth Management, believes that the best time to talk about serious topics is when everyone’s together and at ease. Thanksgiving offers that perfect moment. The key players are in one place, the mood is good, and you can bring it up casually over pie, not like a board meeting.

He’s seen families torn apart because no one knew what the plan was, or worse, because there was no plan at all. “One honest question, served with a side of mashed potatoes, might just be the most loving thing you bring to the table,” Bob says.

“Can we normalize the topic?”

For Al Faber, CFP®, Founder of DIWY Financial Planning, holidays are the perfect time to normalize estate planning. For too long, it’s been seen as something only the wealthy talk about, but everyone has wishes that deserve to be documented.

“I remind clients: it’s not just about death,” he explains. “It’s about incapacity, accidents, and ensuring your loved ones know your wishes. The more we make these discussions part of everyday family life, the more peace and protection we build for the future.”

A soft reminder for every family

These conversation starters aren’t about paperwork. No, they’re about people. The more you bring legacy into everyday life, the easier these talks become.

Ready to start your own estate plan and put those wishes in writing so your family can act with clarity, not guesswork?

Create or update your estate plan with Trust & Will, invite loved ones to collaborate where appropriate, and review your documents after major life events. Start today to protect what matters most.

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