When I first moved to Chicago over 15 years ago, the only job I could find was basically being IT for rich people. I would go to their houses, setup backups, fix wifi, replace hard drives, that sort of thing. We were all background checked and vetted, whatever.

Coming from a farming town to Chicago I had never encountered rich like this. Rich people to me were people who bought new Toyota Camrys every 3-4 years. These were live in nanny, live in maid, chef cooks dinner 3-4 nights a week kind of rich I was working for.

For those unaware, how these households work is the wife runs the household and often has an assistant who is effectively your boss. You are warned to NEVER bother the husband EVER, that he worked “in finance” and was very tired when he got home. In practice it was never an issue, these men didn’t even seem to register my existence. I could be sitting at his desk and he would turn off the lights in the office.

I have a million stories of these people, but today I can’t get Mrs. French (not her name) out of my head. I remember her for humiliating me in a way that will always kinda linger with me. Her and her daughter used to pay my hourly fee to have me do things like “wait in line for the new phone” or go buy printer paper and put it in their printer. One day I mentioned casually to her daughter I was going to be moving kinda close to them. I had gotten a sweet deal on an apartment.

I knew I fucked up immediately. The daughter ran to the mom and they both looked upset. The next day they scheduled me again. It’s snowing, Chicago, etc. I made $25,000 a year plus a per trip fee and had zero wiggle room. I got to the house, side door and the assistant informed me I needed to wait for the owner “to be ready”.

Fine, I sit outside while snow falls. Hour 1 passes, I try again. Wait some more. Hour 2, I get insistent. “If you leave we will cancel our contract with your company.” I’ll get fired if they do that, so I sit down again. Hour 3 turns into 4 into 5.

I’m freezing out here, hands shaking. Finally the assistant comes to the door. “Oh, we forgot you were out here. You can go for today.” Then I look up and there they are. The mom and daughter are looking right at me grinning ear to ear. Everyone is staring at me.

Idk why it’s in my head today but that scene is burned into my memory.