Cartoons Hate Her

Cartoons Hate Her

I Was The Office Sub

I really put the "sub" in "subordinate." Turns out you can be too obedient in the workplace.

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Cartoons Hate Her
Jan 26, 2026
∙ Paid
sorry for another secretary reference i apologize im so sorry

When I was twenty-three, I was working my second-ever full time job as an account manager at a failing mobile app advertisement startup in San Francisco. My boss, Vince, was a notoriously difficult fifty-five-year-old CRO. Multiple employees had quit specifically because of him and his peculiarities. I stayed around—not because I liked him, but because I was afraid nobody else would hire me. Remember, it was 2012. I know the zoomers believe the 2010s were a golden age for the economy, but college grads were literally fighting over jobs that didn’t have salaries.

Vince did not look like your typical tech C-level executive. He was a hustler of the ‘90s, with no college degree, who built his career selling floppy disks out of his van. He was desperate to get in this big “technology thing.” He didn’t know how to use Gmail or Powerpoint. But beyond all the external quirks, he was the biggest control freak I might ever meet in my life. I noticed it early on in my tenure at that company, when a client requested an insertion order contract. I sent it over, thinking nothing of it, because I had done it before. In fact, I felt pretty good about myself, this big Boss Lady with the IO—look at me! I was just like Angelica’s mom in Rugrats. But when Vince found out, he was irate. Apparently I needed his approval for all IOs. He didn’t scream at me, but he came close. I remember standing by his desk while he sat and shook his head, staring at my disgrace of an unauthorized IO. I was terrified I was about to be fired, just a few weeks into my job.

“You will never send another one like this until I tell you to,” he finally said, softly but furiously, on the brink of losing it.

“Fair enough,” I said.

“No.”

“What?”

“You don’t say ‘fair enough.’ Fair enough implies that you have control over the situation. It implies that you’re agreeing to what I’m telling you. I didn’t ask for your opinion. It’s not your choice to agree. You don’t say ‘fair enough.’ You say ‘yes.’”

Now, I should point out that Vince was much older than I am, not good looking, and I was not single. I realize now that had these conditions been met, I probably would have just…I don’t know, gotten horny? But I wasn’t thinking about sex anyway. I was thinking about work—more specifically “not getting fired.” And I realized that if I wanted to stay calm in the workplace, I needed something very specific: a person with authority telling me exactly what to do.

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