Shoulded to Death

Shoulded to Death

October 08, 2026•5 min read


About this Video:
I’ve spent most of my life trying to solve things.

Somebody brought me a problem, I gave them a plan. Somebody was struggling, I handed them a list. I thought that was helpful. And sometimes it probably was.

But lately I’ve started noticing something I couldn’t hear before.

I read a conversation from a woman who had retired because of her health, lost her last parent, and didn’t know who she was anymore without work and colleagues. She got thirteen replies. Almost every one gave her something to do: take a class, get a job, join a club, travel, find a hobby.

Then I read a caregiver forum where someone described walking home alone after losing the people they used to walk with. There were eight replies. Almost none offered advice. They simply said, in one way or another, “Me too.”

That difference stopped me.

Some problems look solvable from the outside. When they do, we reach for the lever. We give people homework.

But sometimes there is no lever.

I’ve been the clipboard guy for forty years. I even made lists at home to keep myself moving. And somewhere in the last year, I stopped making them. Only after I stopped did I realize how much of my life had been organized around solving, fixing, and moving on.

I hear the difference most clearly when somebody says, “I know what you’re going through.”

No, you don’t. And I don’t know what you’re going through either.

But I can say, “I appreciate what you’re going through.”

That leaves room for a conversation.

Maybe that’s the lesson I’m still learning: sometimes people don’t need a solution. They need somebody willing to sit beside them while there isn’t one.

Transcript:
I read 13 replies to a woman who says she was disappearing. 13. I counted them twice because I didn’t believe the number. She was 65, retired for health. Her last parent had just died, and she wrote that she didn’t know who she was anymore without work and colleagues to go back to.

Here’s what she got back: a Shakespeare course, a part-time job, a stand-up comedy class, an Oculus headset, a book club, Rhodes Scholar, an Airbnb in Italy. Retiring to something, not from something

Not one person said, “Me too.”

So I ran the same count in a different room, a forum caring for a parent or a spouse at home. Somebody there had written about walking home from the store alone, counting backward. Four of us used to walk this, then three, then two, now one

Eight replies. One of them had any advice in it. The other seven were just company.

Every day, I feel this way. Yes, it’s just me and my mom. Same fear, two rooms. Thirteen to nothing one way, seven to one the other.

Here’s what I think is going on, and it isn’t that one room is kinder. The retirement conversation lives on personal finance forums, optimization rooms, full of people who are good at solving things. The caregiver room runs on the opposite premise. Everybody there knows nothing can be fixed. Take away the lever and all that’s left is company.

So it isn’t about compassion. It’s about whether your problem looks solvable from the outside.

And that’s the rotten luck of this one. It does look solvable. Just make new friends. That’s exactly why you get a syllabus instead of a chair

Now I have to turn this around because it belongs on me. I handed out to-do lists for forty years. Somebody brought me a grief, I gave them a plan. It’s what I had.

I was a list guy at home too. Thirty, forty items. I’d finish five. They were self-defense. I got a love of bright, shiny objects, and the list was the fence.

And then somewhere in the last nine or ten months, I stopped making them. I didn’t notice until recently. I sat there and asked myself if I should start again. I’ve got things I need to do. I don’t. The thought of it gives me the heebie-jeebies.

Here’s the part I didn’t see coming. It was only after I stopped making lists that I started noticing what everybody was handing me. Forty years I couldn’t hear it. You can’t hear a list being handed to you while you’re busy writing one out

‘The place I hear it worst is cancer. Somebody finds out, and they say, “I know what you’re going through.” And then comes the cousin or the wife or the father. You don’t know what I’m going through. I don’t know what you’re going through either.

I don’t remember where I got this. One day, I just started saying it differently. I appreciate what you’re going through. If I know what you’re going through, there’s not much room for conversation. If I appreciate what you’re going through, there’s a lot of room. That’s the only thing in this whole piece I’m sure of.

So tell me about a time you said a true thing out loud, got handed homework, and if you’re honest, tell me about a time you were the one holding the clipboard. I was that guy for forty years. I only just put it down.

Comments are open, and I’ll be reading them, and I’ll ask you a question instead of telling you what to try.

Hey, this is Josh. You’re at The Long Strange Trip. I’m glad you’re here. And boy, I hope to see you back here next week.

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