i went to sf and i'm still processing it

Tue, 28 Jul 2026 00:00:00 +0000

I just got back from a work trip to San Francisco, and I’m still kind of sitting with it.

Not in a bad way. Just… a lot.

My former SVP invited a group of us for a last-minute get-together where he grilled food for us (spoiler alert: I didn’t have a chance to try it before I needed to head to the airport to catch my flight. My coworker did, though, and let me know it was delicious). He retired earlier this year. Some of my coworkers like to say he’s actually just busy managing his investments. I overheard from one of my coworkers that the house he lives in is worth roughly $8M. Meanwhile, his wife and daughter were away in LA for a theater camp. When we arrived, his son was outside by the garage and greeted us before immediately disappearing back into the house.

At some point, as he was still preparing food for the BBQ, he said something like, “My wife would kill me if she saw the state of how I’m hosting you all. She’d be stressed that everything wasn’t already prepared in advance,” and lightly chuckled. All that, and he’s still just a guy whose wife would be mortified by his hosting. A kind and friendly giant rattling around a beautiful house, genuinely happy to see everyone.

I went in half-expecting to feel like I was visiting a different species. Instead I found just… a person.

That turned out to be kind of the theme of the whole weekend.

Everyone there is nice. Talking about their kids, their upcoming weekend. The usual stuff. Facing the same parenting anxieties as anyone else, just with more resources to throw at the friction.

Except.

One of my coworkers mentioned offhand that she doesn’t have “enough money” to build a pickleball court in her backyard yet.

I heard the words. Understood them individually. Together they just kind of… floated there.

She wasn’t being dramatic. That’s what got me. She’s still grinding at the same company, by the way. Maybe she loves it. I genuinely don’t know.

On the flight home I found myself quietly cataloging everyone. I think I was trying to peer into their lives, essentially trying on their realities to see if I had any genuine interest in them.

The retired SVP: out, done, chilling. Made it to the exit ramp.

The pickleball court person: clearly doing well, clearly still going — with her three year old son at that.

A coworker who founded something, had it work out, came back to the company anyway. He has a five year old daughter. That one made sense to me immediately.

And then there’s this other guy. Lower net worth than most people in that room, lower than mine, actually, and he spends his weekends practicing at the karting track in preparation to go to Japan this year for a 24-hour race. Because he loves it. He’s been practicing constantly.

I don’t want his exact life necessarily. But I admire him.

(I guess it’s worth noting, I don’t actually know what any of these people owe. A big house doesn’t tell you much. Loans exist. So maybe I’m cataloging vibes more than anything. However, I’m pretty dang sure my former SVP doesn’t need more money. LOL.)

I’m 26. Most of these people are in their 30s and 40s. In fact, I accidentally said “folks in their 30s”, and a couple of my coworkers thought I was accusing them of being old. I’m aware I’m in a privileged position to even be in that room, let alone to be sitting here writing about it.

I know what I’m building toward, sort of. Not the $8M house for sure. More like… freedom? The outside kind. I’m not sure exactly what that freedom looks like at the end of the day, beyond just having the ability to do my own thing whenever I want to. But I know it means not spending 8-10 hours a day staring at a screen working on problems that don’t feel like mine. The money is a means to that baseline autonomy, not the thing itself.

I think.

Somewhere in the middle of my trip, I wandered into Dandelion Chocolate. Told the store rep what my parents and in-laws liked, let him make recommendations, walked out having spent ~$300 on a few boxes without really thinking about it before running to the hotel to make it to my evening meeting.

It didn’t occur to me to look at the prices.

That’s a relatively new thing, actually. Something likely shifted since my business trip to Singapore back in 2024 and just… never fully shifted back. At least when it comes to gifts. It’s not frequent enough to stress about, and the people on the receiving end matter enough that I don’t want to be standing in a chocolate shop doing mental math about whether the nicer box is worth it.

Half a decade ago that would have felt insane.

I’m not sure exactly when that changed. I just noticed it, briefly, on my way out the door with ~$300 worth of chocolate.

No conclusions. I came home, unpacked, and now I’m writing this trying to figure out what I actually took away from this past weekend.

Still figuring out what exactly I’m after. Choosing to believe that’s fine.

…probably.

Money on Erin's Waypoint

i went to sf and i'm still processing it