Published May 8, 2026
Many years ago, I was on the team at Fidelity Investments that built the firm’s digital estate planning tool. As the team’s researcher, my role was to interview people to understand their estate-planning needs and test the usability of early designs.
Given the topic, the interviews tended to be intimate. Research participants frequently would open up about their family dynamics, money, legacy, and mental and physical health challenges. It was an honor and a privilege to be trusted with their stories.
One 2016 interview stands out in particular. The participant was a woman in her 60s, and we were testing the usability of the advance directive part of the tool, the part that asks people about their wishes for end-of-life medical care.
The participant, who had been lively and gregarious up to this point, froze.
My job was to observe and probe, so after a period of silence, I asked what was on her mind. She hesitated, gathered her thoughts, then said something to the effect of, “I don’t think anyone should be asking questions like this. I don’t want to think about these things. This is inappropriate.”
Roger. Data collected.
We moved on, and the rest of the session resumed its friendlier tone.
Over the years, I conducted hundreds of interviews, and I had the honor of listening to many, many intimate stories about people’s financial lives. But that session stands out. I think of it often, especially now that my work supports people organizing their estates and those coping with practical estate settlement tasks while grieving.
Grappling with our own mortality is scary and uncomfortable. And honestly? It’s totally avoidable. Nobody has to create an advance directive. So why bother?
Here’s why: if we opt out of grappling with, deciding, and documenting our wishes for end of life, the work doesn’t just disappear. It gets passed on to those we love most.
And if you think it’s hard to decide whether you yourself should receive invasive—often painful—life-saving medical treatment, try to imagine making that decision on behalf of the person you love the most. Imagine that you have no idea what they would want for themselves.
Brutal, right?
If you don’t do the end-of-life planning work yourself—and it is hard work, there is no sugarcoating that—you relinquish control over your own medical decisions if you’re ever unable to communicate them. You also place an immense burden on your family members to guess correctly. It can create conflict among loved ones and lead to lasting guilt and regrets.
Creating an advance directive, and making sure your loved ones know where to find it, is an act of profound generosity.
One version of an advance directive is The Five Wishes. It goes beyond the basic things that are included in a boilerplate legal document to include emotional and spiritual needs.
If it’s time to get your affairs in order and you need help or an accountability partner, you know where to find me.
I’m just about finished designing the Undermountain Partners Estate Organization Kit. It includes The Five Wishes plus custom worksheets for financial assets, real estate, devices & digital accounts—and much more.
Getting your affairs organized is extremely procrastinate-able. I walk you through the kit in small batches so it gets done. I’m also here to listen to your stories, just like back in my research days.
At the end of the process, you’ll know you’ve made your loved ones’ future job easier by putting the important information they’ll need in one place.
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