Kim and I are currently in the process of estate planning. We both completed simple wills about a decade ago, but things have changed. And now that we’re older we’re trying to get more sophisticated with our plans. We’re establishing a trust. We’re creating advance directives for healthcare. Et cetera.

This is proving much more difficult for me than I’d expected. I don’t want to think about some of these things. Completing a will? No problem. But thinking any farther than that is proving problematic.

I can now see how my cousin Nick felt. In February 2022, when it became clear that he had only weeks to live, I had to pester him and pester him to complete his will. He didn’t want to do it. He told me that thinking about it felt like an admission that death was imminent. Things were complicated too by his indecisiveness. I went with him to notarize one version of his will, which — fortunately — he revoked and replaced. There may have been other versions.

Now I’m experiencing similar indecision, and sometimes about basic things!

Take beneficiaries, for instance. Designating a primary beneficiary is non-difficult. If I die before Kim, she gets my stuff. But what happens if we die together? Or what happens if she dies first? It would be easy if either of us had children. But we don’t.

Should I designate my brothers as secondary beneficiaries? My nieces and nephews? Kim’s nieces and nephews? My ex-wife? My college? A charitable organization?

On some level, it doesn’t really matter. If I’m dead, I don’t care who gets my stuff. Yet at the same time I know I have a chance to improve the world in some fashion. I ought to do that.

This decision — which should be stupidly simple — has kept me stymied for a week. I’m not joking. My gut tells me to designate Kris as my secondary beneficiary. I spent 23 years with her and she knows me better than anyone besides Kim. But she has plenty. And isn’t it a little weird to leave your estate to an ex? I don’t know.

It’s also tough to answer some of the questions on the advance directive. What if I’m in a vegetative state? No extraordinary measures, I guess, although it feels like I’m betraying my future self in a way. What if I’m terminal, like my cousin Nick was, and likely to die in a couple of months? Nick wanted all available treatments to sustain his life but it didn’t make a bit of difference in the end. The cancer was going to kill him no matter what. Would I want to fight like he did? Or would I rather say, “Drug me up. Turn on some anime. Let me drift away.”

And who do I want as my secondary (and tertiary!) health-care representative? Again, Kim is first. But who is second? My brothers? My ex-wife? Honestly, I trust Kris more than anyone…but I also don’t want to saddle her with this sort of thing. (In this case, the health-care representatives must sign off that they agree to take the responsibility, so this will remove part of the dilemma.)

What about our animals? For us, our pets are very much like children. I know, I know: Many people find this annoying. So what? It’s just how it is for us. If Kim and I were both gone, we’d want our beasts — especially the dog — to have good homes.

All of this is to say: I see now why so many people put off planning for death. Nobody wants to think about their own demise, of course, but it’s also tough to answer some of the questions. At what point do I want doctors to stop trying to save me? Who do I want to get my stuff? Who do I want to make decisions for me if Kim isn’t there to do it?

I don’t know. I don’t know. I don’t know. At least by writing about it I’ve been able to delay making decisions by half an hour…

6 Replies to “Advance directive.”

  1. J.D. Roth says:

    Well, Kris has agreed to serve as backup health-care representative and beneficiary, so that’s one less thing I have to think about.

  2. J.D. Roth says:

    “I do not want life-sustaining procedures if I cannot be supported and be able to engage in the following ways:


    __ Express my needs
    __ Be free from long-term severe pain and suffering
    __ Know who I am and who I am with
    __ Live without being hooked up to mechanical life support
    __ Participate in activities that are important to me”

    I can imagine so many edge cases! This is almost impossible for me to complete. 🙁

  3. Erin says:

    My spouse & I recently struggled with some of these questions as well. We don’t have kids either, which really does complicate things. We were almost completely stumped when it came to choosing our secondary executor & medical POA. Ultimately, we each decided on one of my sisters & chose to designate a salary of sorts for her handling things, if that’s how life pans out. That helped me feel a lot less like a burden. She declined the salary when we told her about it, but it’s written into our documentation regardless because she deserves to get paid for all the time she’ll spend in probate, etc. Again, more for my peace of mind than anything. I felt kinda gross even asking anyone to hold this role in my life, but I also didn’t want to just leave it up to my extended family without any sort of structure – that’s worse for them. As for our financial legacy, we decided to split it equally between our siblings if we go at the same time, each receiving an equal share, after our charitable giving. They can then choose to keep it or distribute it to their children. But this way we don’t have to choose family favorites or keep adjusting our wills every time a new niece or nephew is added to the family.

  4. veronica says:

    Lucky you. I have no spouse/partner and no children. Makes this task infinitely harder.

  5. Amanda says:

    The book Being Mortal might help you think about what kinds of medical interventions you want.

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