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3 Essential Questions to Ask Your Parents This Holiday Season

Writer's picture: Travis GasperTravis Gasper

The holidays are a time for connection, reflection, and family traditions. They’re also a rare opportunity to have meaningful conversations with loved ones about their wishes for the future. While these discussions can feel uncomfortable, asking the right questions now can save your family from confusion and heartache later. Here are three essential questions to ask your parents this holiday season:


1.What do you want your end-of-life experience to look like if you are ill?


  • Why It’s Important: This question is about more than life support or medical interventions—it’s about understanding what matters most to your parents in their final days. Whether it’s being surrounded by family, staying in their home, or making specific medical decisions, this insight ensures their wishes are honored.

  • How to Approach It: Use empathy and focus on their values. For example, you might say, “I want to make sure I honor your wishes. What would be most important to you if you became seriously ill?”


2. What do you hope any money you leave us will accomplish?


  • Why It’s Important: Inheritance can be a sensitive topic, but understanding your parents’ intentions helps ensure their values guide your decisions. It’s also a chance to explore not just what they want the money to achieve but what concerns they might have about its use.

  • How to Approach It: Keep the tone curious and caring. You could ask, “What impact would you love for your money to have on our lives? Is there anything you’d hate to see happen with it?”


3. If you became incapacitated, would you want to stay at home or go to a nursing home?


  • Why It’s Important: Deciding between in-home care and a nursing home can be emotionally and financially overwhelming. Understanding your parents’ preference allows you to plan accordingly and make decisions that align with their comfort and values.

  • How to Approach It: Be specific and thoughtful. For example, ask, “If something happened where you couldn’t care for yourself, would you prefer to stay at home or consider a nursing home? What kind of care would make you feel comfortable?”


Planning for the Future Is About More Than Paperwork

These questions aren’t easy to ask, but they’re essential. Estate planning is about more than drafting documents—it’s about listening to your loved ones’ wishes and ensuring they feel understood and protected. This holiday season, start the conversations that will bring peace of mind to your entire family.

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