Loss and Underpants
- 11 minutes ago
- 3 min read

Yesterday my son Ezekiel was walking around in his underwear, complaining about having to wear pants to school. Mommy was making him. I didn't lose anything. Weird that somehow I felt like I did.
What does loss feel like?
For me it's not simply sadness. It's my chest. Short of breath. Hands a little clammy, heart beating a little faster. Oh. Like that Doechii song.
What have I actually lost? Mostly, I think it's the chance to make future memories with whoever or whatever's gone. That's not how it works with money.
When I lose money, I don't lose the chance to make future memories with money.
But that's the point, money was never the memory itself. It's simply an input into making one.
We're moving. Yesterday I drove through our old streets and felt sad. Sad in the way I normally don't. I remembered driving my kids down those same roads during COVID, them stuck to their carseats with saliva and me sneaking in audiobooks about financial history. Good years. Hard years. Our years.
But it's a strange kind of sad. We'll drive older kids down different streets, and it'll be enough. The place doesn't have to be the memory. The memory gets to move with us.
Losing my dad wasn't like that. That had a face. I still remember him reading books into a tape recorder and sending them to me at camp so I'd have his voice to fall asleep to. There's no new dad. But one day I get to record myself and send them to my kids when they go to camp.
But losing money is different. There's nothing to grieve because there was never a person or a place there to begin with, just a number that pointed at some future that hadn't happened yet. So when I lose money, the feeling doesn't resolve into sadness.
It just loops. Why didn't I do this. Why didn't I do that. If only.
I have a memory from first grade. I must have been six. In the dream I keep showing up to class in a long white t-shirt and underpants, no pants. I sit on the rug while the teacher reads, trying to figure out how to cover myself. I never figure it out. I had this dream over and over, same rug, same shirt, same underwear. It's been forty years and I still remember exactly what I was wearing.
It doesn't get solved on the rug. Pulling the shirt down doesn't work. Crossing my legs doesn't work. Nothing works, because the problem was never solvable from inside the rug. It only gets solved by standing up and leaving the room. But when you're six and anxious and sitting on that rug, you can't think of that. You just keep trying to cover yourself with a shirt that was always too short.
I'm forty-seven now. I've been replaying financial decisions, mine and other people's, for most of my adult life, and it's only in the last year that I started to notice it as a replay. Not a new decision every time, but a repeating loop, dressed up as a new one. Same rug. Same shirt.
I know just noticing it doesn't fix it. I still find myself back on the rug more than I'd like. But I know now there's a room, and a door, and that the problem was never going to get solved by pulling on a shirt that doesn't fit.
It took me forty-seven years to even type that standing up was an option. I'm still working on it.
I know there's no amount of money that gets you a new dad. A new city gets you new streets to drive your kids down. Leaving the room might not even mean standing up. It might just be sitting there, in the t-shirt and underwear, and knowing you still have some power anyway.





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