Sex, Rx, and the 20-Year Conversation:

Why the "Hard Talks" Aren’t Actually That Hard

I ain’t scared to talk about it: Sex, Rx (the prescribed ones, anyway), Death, and the "20-Year Conversation."

In the clinical world, these topics are often treated like a secret code nobody wants to crack. They’re taboo. But I find that interesting because the #1 piece of writing I’ve ever put out was about end-of-life decisions. I was overwhelmed by how many people reached out to say, "Finally, someone is actually talking about this."

I’ve yet to have one of these conversations where the person was actually uncomfortable. Maybe it’s my approach. Or maybe it’s because a lot of the folks I’m talking to were the hippies and rockers of their day—they spent their youth breaking rules, and now they realize that the "polite silence" of their parents' generation actually did more harm than good.

The Problem with Silence

Back in the day, the culture was different. You didn’t talk about sex because parents thought it was "giving permission." You didn’t talk about death because people felt like it was "giving up."

It reminds me of how we used to handle suicide, and the old myth that if you asked someone if they were suicidal, you’d "put the idea in their head." We know better now. We know that bringing the dark stuff into the light is the only way to manage it.

Most people are actually relieved to have these "Hard Talks." They aren't hard; they just need a prompt because it wasn't common practice for them. But there are damn good reasons to do it:

  1. It ensures a person's wishes are respected.

  2. It ends family conflict before it starts.

  3. It stops five different relatives from guessing what they "think" you would have wanted when you can no longer speak for yourself.

The "20-Year Conversation" Script

If you’re a caregiver and you’re struggling to bring this up, don’t make it about today. Frame it as the 20-Year Conversation. Ask your person:

"If in 20 years you were in a position where you couldn't speak for yourself, what would a 'good' ending look like for you—even if nothing about it was actually good? Who would you want making the calls?"

Let them know the answers can change any time. You’re just looking for a bit of guidance now so you don't have to guess later.

Why the "Who" Matters (The Army Buddy Rule)

The goal isn't to be perfect; it's to take the pressure off the caregiver. And sometimes, the right person for one job isn't the right person for another.

Take me, for example. If I’m in a traumatic situation and it comes down to a "quality of life" call, I love my wife, but I wouldn't want her to have to pull that trigger. I think my old Army buddy would be a better judge of what I’d consider an "acceptable" life. He knows the "Street Rules" I live by.

However—I’m still leaving my wife in full control of the money. I wouldn't trust that Army buddy with my wife OR my bank account!

For the "Already In It" Caregivers

If you’re caring for someone with a chronic progressive illness, things tend to slide inch-by-inch. If you’ve already passed the point where they can have this talk, here is my suggestion: Take the 20-Year Perspective anyway.

Ask yourself: "If I could have had this talk with them 20 years ago, back when they were at their clearest and strongest, what do I believe they would have wanted?"

Let that be your North Star. If you look at it through that lens, you cannot make the wrong decision. You are doing the best you can with what you’ve got.

If you are the sole person responsible and this weight falls on you, I’m sorry. It’s heavy. All you can do is your best, so please show yourself some grace. Ultimately, there is no "clean" right or wrong when you are acting on their behalf with love.


Need a place to record these wishes? The UnMedical Brain has a specific section for "Emergency at a Glance" and "Comfort Focused Care" to make sure the story stays straight when things get loud.

I hope you, your family, and your person are happy, healthy, loved, and safe. And remember — if a clown like me can do it, you’ll be fine (if not better).


Disclaimer: I am not writing this from the perspective of a medical professional. The information in this article is for general caregiver support and educational purposes only. It should not be taken as medical advice, diagnosis, or treatment. Always consult a qualified healthcare provider with questions about your loved one’s health or recovery.


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Who I Am — James. No Scrubs. No Jargon. Just UnMedical.