Important Family Conversations for Thanksgiving Weekend

by Charles Rotblut | November 27, 2025

My sister and I, along with my wife, took a cruise with my parents earlier this month to celebrate their 90th birthdays. We are very lucky to have parents that are both alive and mobile. My wife previously lost both her father and mother, and we have many friends who have lost their parents too.

If you have older parents, spend time with them this holiday. If you can’t physically be with them, call them. The same goes for those of you who are older. Spend time with children, grandchildren and great-grandchildren, if you are fortunate to have them.

Use the holiday to celebrate Thanksgiving and be thankful for the food and company.

Then, over the weekend (not on Thanksgiving), take some time to talk to your family about late(r)-in-life care, estate plans, finances and related issues. Use the time spent with them (whether in person or on FaceTime, Zoom, etc.) to discuss these important topics. Doing so will help those tasked with making important decisions feel comfortable that they can make the right ones.

Here’s a checklist based on my wife’s and my personal experience of taking care of her parents and talking with mine.

  • The Location of Key Documents: One of the most helpful things my late father-in-law did was show me where he stored things. It is critical that your children know where to find key estate documents, powers of attorney, the house title, your military ID and discharge papers (if applicable), and other related documents.
  • An Inventory of Financial Accounts: Even if you don’t feel comfortable sharing details about all your finances, provide a list of every account you do have. My parents have done this. It will make it easier for someone you trust to step in when the time comes. Plus, when it’s time to settle your estate, the list will help your heirs. (After my mother-in-law died, I found a credit card in her purse that neither my wife nor I knew she had.)
  • Your Investing Strategy: One of the biggest gifts you can give is the lessons you’ve learned as an investor. Furthermore, don’t assume the person you trust to step in on your behalf will necessarily know the decisions you want them to make. Both my father and my father-in-law, when he was alive, have had conversations with me about investing.
  • Advance Directives: Speaking from personal experience, tell those you love what you want regarding medical care. Be specific about your preferences, be it possible medical intervention, ending all care beyond what’s needed to bring comfort or something in the middle. This discussion also provides the opportunity to share diseases and ailments that are in your family history.
  • Wishes Regarding Care: As you grow older, do you want to age in place for as long as is feasible or move into a retirement community? If you want the latter, do you have preferences regarding location? As you discuss your desires, understand that we middle-aged children often worry about our parents’ safety—especially when it comes to stairs.
  • Final Arrangements: No one likes to think about their demise, but advance planning will help your loved ones. Preplanned funerals certainly helped my wife with her parents’ arrangements. Other helpful information includes who to contact, where you want your obituary to run (if so desired), which clergy (if any) you want involved, and what you want on your tombstone/marker or any wishes regarding your ashes.
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