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Office Talk: The worst boss you’ve ever had

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horrible bosses
the devil wears prada

My second job out of college was working as a jr. copywriter for a boutique advertising agency (which might explain why I like Peggy so much). It was a teeny tiny place run by a charismatic guy who also liked to write. I was living in L.A. at the time, doing something completely different, but was so excited about this opportunity and impressed by my new boss, I packed up my small car with whatever I could squeeze in and moved to San Francisco. At first, we got along smashingly. We’d toss around our ideas. He’d ask for my input on how something should be done. Sometimes we’d walk next door to Whole Foods and grab bagels together. Then a few months into working there, I started noticing his mood swings.

His bad moods went from “having a case of the Mondays” to unprofessionally aggressive. One time, to show he was upset, he punched the wall as he was walking out of my office and yelled out the F-bomb. On really bad days, he’d spend the entire day in his office just steeping in his foul mood with the door closed, while everyone else tiptoed around outside, bracing themselves for when they had to go in to ask him a question.

The last straw for me happened when we were driving back from a client meeting. He asked if I had included something in a project, and I said I was certain of it. Then he said in a cold, intense voice that still gives me chills, “If you didn’t, I swear, you better not be in the office when I find out.” How crazy is that? As soon as we got back to the office I walked out because episodes of Unsolved Mysteries started flashing through my head. He apologized that night, but it was never the same between us again. 

I feel like everyone I know has had at least one bad boss. Who was the worst one you’ve ever had? Were they too controlling, creepy, or just plain crazy? 


(Photos from The Devil Wears Prada)

Last modified: January 10, 2019