Retiring Well: Life-Giving Conversations about Death

Retiring Well: Life-Giving Conversations about Death

Charlie Jordan, CPA, CFP®, CeFT®  | Partner | Lead Advisor

"If end-of-life discussions were an experimental drug, the FDA would approve it."

― Atul Gawande,  Being Mortal: Medicine and What Matters in the End

In April, I shared an article about the heightened urgency of reviewing your estate documents in light of the current pandemic. If you have not done that yet, you can review those recommendations here:

While ensuring your documents and your household are in order is a critical step, it's only one part in the process of "finishing well." A fruitful and often ignored step is engaging in conversations with our family and friends about our thoughts and wishes for our living and dying. Here are recommendations for the who, what, when, where & why of end-of-life discussions.

Why is this important?
As with many things, its good practice to start with "why?". Death is an emotional and often fearful topic to discuss, and one most would prefer to avoid. But, having this conversation has real benefits. In her recent book  The Art of Dying Well: A Practical Guide to a Good End of Life, Katy Butler remarks, "In the years I've spent listening to hundreds of people's stories of good and difficult declines and deaths, I've learned one thing: people who are willing to contemplate their aging, vulnerability, and mortality often live better lives in old age and illness, and experience better deaths, than those who don't." There are other benefits from these conversations, such as easier probate court processes to reduced family disputes following a loved one's passing. Merely taking some guesswork off the table for your heirs can have an encouraging effect during the grieving process.

Who needs to be involved?
You should primarily engage those who will have decision-making or fiduciary responsibility for your health, financial affairs, and overall care. For baby boomers, this is often your adult children. In today's multi-generational families, that could also include your grandchildren or even your aging parents. Additionally, according to Gawande, conversations with your medical providers have been proven to impact well-being late in life and reduce invasive, costly, and unnecessary medical procedures. Finally, your financial and other advisors can lighten the administrative burden during stressful times for your family if you have advanced conversations.

When do we do it?
Retirement author Mitch Anthony says, "It is better to prepare than to repair." The same sentiment applies to conversations about dying. First, you want to have them while you can. None of us are guaranteed another day. Trying to guess intentions or "fix" a disorganized estate is incredibly stressful for your loved ones. Second, you want to have them while there is time to make changes to plans or documents. Diminished mental capacity can happen quickly, and you don't want to wish you had that time back. Finally, you want to reap the benefits mentioned above for as long as you can.

What do we talk about?
Most conversations about death focus on funeral logistics, estate flows, and personal property. These are undoubtedly essential details. But, while they reflect the letter, they don't quite capture the spirit of the message. A great option to get started is to simply tell stories. Tell your family stories of your childhood, how you met your spouse, what your first job was like, the good times, the hard times, etc. Then tell them why those things matter to you and who you have become. If you are the audience, ask probing questions. These moments can be so precious for multiple generations to hear what is important to you and your family. Meaningful talks about principles, values, and other non-financial matters create lasting memories for all involved.

It's normal for this to be an awkward thing to get started. One of my favorite resources that can assist is The Conversation Project (, a website dedicated to helping people talk about their wishes and end of life care. The site also includes a "Starter Kit" to speak openly about what matters most before a medical crisis occurs.

Where do we do this?
Ideally, this would take place in a relaxed and controlled environment: around the kitchen table on a quiet evening after dinner, relaxing on the sofa on a lazy Sunday afternoon, etc. But, in our current normal, you may have to opt for a virtual meeting. If you don't see your family often or are unable to do so right now, schedule some family Zoom or FaceTime chats. Be intentional, and let your family know this discussion is important to you. The free version of Zoom allows you to have 40 minutes uninterrupted. Open a bottle of wine and enjoy a good chat. Perhaps you could include a front porch virtual background for good measure.

Talking about death is awkward and difficult. Those that do, however, testify to a cathartic experience. It's one that can bring clarity, focus, and intentional relationship-building. Those are things for which it's worth being uncomfortable.

Have more questions about life-giving conversations? Click here

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