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Working for eccentric bosses sounds fun, and you certainly have stories that entertain, but actually being there is stressful because you never know when they’re going to snap and start screaming or grab you. Plus, most people aren’t eccentric in the cool way like they wear funny hats and give out didgeridoos as presents to encourage an impromptu amateur concert at the Christmas party. Most oddball bosses are going to be unpredictable in their expectations and therefore impossible to please. Had a manager at my previous job that really, really tried his best to be everyone’s BFF. He loved giving pep talks and thought he could raise our abysmal morale by being Mr. Positivity (note: morale was low because we were always buried in work and paid shit). He’d crack jokes, randomly burst into John Kelly Nice Swing Bitch Vintage Shirt song and sneak up behind you to yell “you’re doing a great job!” . Unfortunately, he was also super incompetent at his job. He relied heavily on a junior colleague for help with technical stuff (they practically did his whole job for him), and spent days working on paperwork that should really only take an hour or two. If you had a problem, his answer was usually either to stare blankly at you until you left or to say “think positive and it’ll work itself out!” Thing he did I hated the most: whenever people would apply to work at the company, he’d print out the stack of resumes, sit at his desk and read aloud all of the parts he found “funny.” He’d laugh at people for working at McDonald’s or other fast food places. He loved finding grammar mistakes and making fun of them. If someone had a cringe-y objective statement, he’d guffaw over that too. This was all done loudly, and it was a open office so you couldn’t avoid hearing it. That definitely lowered morale too.
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