Many of us had that boss—the one who makes you question your career choices, your sanity, and sometimes, the very concept of humanity. From the micromanaging overlord to the boss who takes credit for your work while forgetting your name, the world of terrible bosses is as vast as it is painfully relatable.
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At the first team meeting of the year, the boss announced his plan to “personally guide” our New Year’s resolutions. He handed out forms where we had to list goals like “improve performance”. We thought it was harmless until he started yelling, “Are you living up to your resolution today?”
One brave coworker wrote, “My resolution is to quit micromanagement.” The boss put him on probation for “negativity,” claiming, “We can’t start the year with that kind of energy.”
Our boss got obsessed with stopping office snack thieves. He installed a camera aimed at the donut box, but donuts still vanished. HR launched an investigation, only to find out the boss was eating them himself during midnight work binges. He claimed he forgot every time!
Every time someone requested vacation, their PTO mysteriously disappeared from the system. After weeks of frustration, we found out the boss had been reallocating our days to extend his personal vacations. He didn’t think we’d notice. Spoiler: we did.
The boss declared a sunrise hike on January 1st to “start the year with positivity.” Attendance was optional, but he reminded us that “optional means highly recommended.” We dragged ourselves there, only to find him decked out in full hiking gear... but with no clue where the trail began.
After three hours of wandering, someone checked Google Maps and realized we were going in circles. The boss got bored and called an Uber from the trailhead, leaving us to find our way back.
Our office plants started disappearing, one by one. We blamed a rival team, but the truth came out when the boss’s Instagram showed his apartment full of office plants. He said it was to ‘liven up his Zoom background.’
It was supposed to be a normal project update, but halfway through, the boss’s ex, Sarah, walked in late. After a snarky back-and-forth, Sarah dropped the bomb about “personal vacation days in Cabo” and how the project was delayed because Dave (the boss) spent weeks rebranding the cover page.
Things escalated until they were both crying, with Sarah accusing him of calling her at 3 a.m. and Dave shouting about her leaving him for Gary in marketing. The project? Still no idea if it got approved, but we’re definitely due for an HR meeting.
Our boss hated open spaces, so she started building a ‘desk fortress’ using whiteboards and fake plants. By the end of the week, her office looked like a jungle fort, and we weren’t allowed to enter without ‘clearance.’
For office Secret Santa, the boss set a $10 limit but gave everyone $100 gifts. We were suspicious until he started demanding reimbursements with a spreadsheet. Turns out, he forgot to budget for his yacht party and thought we’d ‘chip in.’
The boss decided coffee breaks wasted too much time, so he banned coffee machines. Employees revolted, sneaking in thermoses and setting up a covert coffee club. The boss found out and called an emergency meeting—only to beg for a cup because he couldn’t stay awake.
In an effort to “build morale,” the boss asked us to decorate the office for New Year’s. We assumed balloons and streamers. He expected a full-on Times Square replica, complete with a countdown ball.
When we didn’t meet his standards, he canceled the New Year’s bonuses, saying, “You didn’t commit to the theme.” He used the bonus money to rent a fog machine and laser lights for his office.
The boss decided the office chairs were “too cushy” and downgraded them to cheaper models. We all suffered through back pain while he kept his fancy ergonomic throne. A week later, an anonymous tip led finance to discover he’d billed the chair budget to his personal expense account for a new gaming setup.
His excuse was, “It’s technically work-related; I strategize while gaming.”
The boss created a new “Employee of the Week” award, but instead of basing it on performance, he gave it to whoever “seemed like they needed a win.”
Our boss booked a motivational speaker for a team seminar. The speaker turned out to be his college roommate, who only talked about “manifesting success” through loud chanting. By the end, the boss was leading the chant while we quietly slipped out to check emails.
The “speaker” charged $5,000, which the boss later admitted went toward his friend’s new startup.
Sometimes, if you don’t laugh, you’ll cry into your coffee during yet another mandatory meeting about synergy.
