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How to Start the Holiday Conversation No One Wants to Have

With Thanksgiving and Christmas just around the corner, families will gather in homes to eat, drink and talk turkey. If you find yourself at a loss for what to chat about this year, we’ve got just the thing. We want you to discuss two topics: death and money.


That’s probably not the turkey talk you had in mind. But hear us out.

It’s true: Discussing end-of-life plans may be the most awkward memory you make this holiday season. But it’s a sincere act of love than can bring your family closer together at one of the most meaningful times of year.

Here are two questions to get you started.

Question 1: Do You Have an Estate Plan?

Let’s get one thing straight: This isn’t about what’s in it for you when mom and dad die. The goal is to create understanding so you and your siblings can responsibly—and respectfully—honor your parents’ vision for the future.

A basic estate plan includes the following components:

  • Last will and testament: More than just who gets what, a will outlines the legacy your parents want to leave behind.
  • Power of attorney: A power of attorney puts someone in charge if your parents can’t make financial or medical decisions on their own.
  • Living will: Also called a healthcare directive, a living will documents your parents’ wishes for end-of-life care options like life support and organ donation.

Reviewing these instructions as a family not only enables your parents to explain the why behind their choices. It also eliminates surprises so you don’t have to deal with drama in the midst of the grieving process.

Question 2: Can You Afford Long-Term Care?

Experts estimate that 70% of people age 65 and older will need long-term care at some point. Many folks think Medicare will cover nursing home or at-home care expenses in their golden years. Sadly, that’s not the case.

No more money fights! Get on the same page with your money!

A recent Merrill Lynch study found that two-thirds of older adults have done nothing to avoid staying with family if they can’t live on their own anymore. With yearly costs in the tens of thousands of dollars, a plan is a must. Otherwise, it won’t take long for the nursing home bills to deplete your parents’ nest egg—and maybe even put a dent in yours.

Long-term care insurance enables your parents’ retirement income to stretch further so they can enjoy a better quality of life in their golden years. Dave recommends long-term care insurance for anyone 60 or older, because the probability of having to stay in a nursing home increases dramatically at that age. A trustworthy insurance professional can walk you through all the options and help you find an affordable plan that gives your whole family more peace of mind.

Dos and Don’ts for Keeping It Positive

Now that we’ve covered what to talk about, let’s dig into the how. The following tips will help you steer the conversation in the right direction.

  • Don’t bring it up mid-feast. This isn’t a pass-the-turkey kind of conversation. Save it for after dinner when the kids have run off to play and the grown-ups can retire to the den for a more relaxed conversation.
  • Do approach the topic gently. Ask your parents to help you understand their wishes and assure them you have their best interests in mind. The goal is to ensure everyone’s on the same page when it comes to your family legacy.
  • Do recognize it’s their decision. You may encounter what Dave calls “powdered butt syndrome.” Once someone has powdered your butt, they don’t want your advice on money! Acknowledge the awkwardness up front and lead with love instead of your inner control freak.
  • Don’t limit it to just one meeting. You can’t solve the world’s problems in one sitting, and the same goes for sensitive family issues. Look at it as the start of an ongoing dialogue and schedule regular family meetings to keep the communication lines open.

The conversation won’t be easy, but it will be worth it. When it’s all said and done, the future will feel a lot less scary for everyone, and you can breathe a sigh of relief knowing you’ve loved your parents well.

Ramsey Solutions

About the author

Ramsey Solutions

Ramsey Solutions has been committed to helping people regain control of their money, build wealth, grow their leadership skills, and enhance their lives through personal development since 1992. Millions of people have used our financial advice through 22 books (including 12 national bestsellers) published by Ramsey Press, as well as two syndicated radio shows and 10 podcasts, which have over 17 million weekly listeners.