They strutted in with buzzwords, PowerPoints, and coffee breath... but beneath that blazer? Nothing but hot air and LinkedIn lies. We’re talking ego, unraveling in real time. Respect, evaporating like yesterday’s coffee.
These bosses talked the talk, but couldn’t manage a group chat, let alone a department. You’ve seen it. You’ve lived it. And now? You get to laugh about it.
Get ready for the juiciest stories. Grab your popcorn, your PTO request, and a front-row seat. Slide in. It’s payback time.
1
Trending on Twitter... for All the Wrong Reasons
“My boss made everyone at the office send tweets for 2 straight hours using the same hashtag so we could... trend on Twitter worldwide.”
2
Nepotism at Its Worst
“My boss was shooting up heroin and nodding off on the line. I babysit my 38-year-old manager whose parents own the store and do nothing. Yay for nepotism!”
3
When 27 Lanes Still Wasn’t Enough for Thanksgiving Madness
“I was working at a grocery store the day before Thanksgiving. We had all 27 lanes open and it was still really busy. Boss: ‘Open up another lane.’ My Co-worker: ‘But, we have them all open.’ Boss: ‘Well... get another one open’.”
4
Skincare Boss Doesn’t Believe in Germs Outside Hospitals
“My former boss thought staph infections only happen in hospitals, ignoring that they exist everywhere. For someone running a skin care clinic, that’s just clueless. I quit soon after.”
5
One Man, 30 Angled Posts, and No Sense of Symmetry
“My boss messed up by cutting angled fence posts all facing the same way instead of uniformly in or out. He realized it, called himself an idiot, and we spent a whole day fixing it.”
6
The World’s Worst Cover-Up
“My ex-boss regularly ditched work, claiming her son was sick but actually partying and hitting casinos. She even posted pics and rants about skipping work… on Facebook, where she’d added her entire staff and her own boss.”
7
Spy Thriller or Just My Job?
“My paranoid boss bought a new house and told me to set up utilities and cable, but I wasn’t allowed to give the cable company his address. So I had to arrange services for a location I wasn’t allowed to reveal.”
8
“Itam” Gate: The Supervisor Who Misspelled “Item” Everywhere
“I once had a graphic artist supervisor that created all the images for a shopping site spelling the word "item" as "itam". When I brought this to his attention, he responded by looking up the word to validate my report of misspelling. English was his first language.”
9
The Mayo Incident: When the Boss Blamed Reality Itself
“My boss got mad searching for mayonnaise while holding it in his hand, then blamed someone else for leaving it out.”
10
One Man’s Guide to Not Running a Business
“My boss lost contracts, only hired unpaid interns with false promises, paid felons under minimum wage for skilled work, and pocketed a $100k investor loan instead of investing it.”
11
Fired for Reading Harry Potter: The Morality Police in the Break Room
“The owner wanted to fire me just because I was reading a Harry Potter book on my break, calling it “unapproved and immoral.” He even made a termination form for it. The manager stopped him, explaining that’s illegal and a lawsuit waiting to happen.”
12
We Spammed the Entire Internet, Got Banned from All of It
“My boss forced us to spam every news aggregator site known to man and incidentally us got banned from most, if not all of them.”
13
The Boss Who Thinks Google Is a Fad
“One day he goes: ‘Are we still using that SEO thing?’”
14
Made the Website Better. Got Yelled at Because ‘Now They Need an App?!’
“I redesigned his website's CSS so that it would be more responsive, and when I walked over to show him, he literally got p*ssed. Like, genuinely p*ssed; and yelled at me something along the lines of: ‘NOW PEOPLE ARE GONNA HAVE TO DOWNLOAD AN APP TO BE ABLE TO SEE OUR SITE?’”
15
“Can’t You Just Go Open Source?” When Your Boss Doesn’t Understand Software
“My boss made me install Windows on a computer and when I asked him for the activation key, or a means to pay for one (it was a bootlegged version). He, with absolute no hints of doubt in his voice, yelled: ‘Can't you just go open source?’”
16
The Great Contractor Heist: Loans, Lies & Legal Limbo
“My boss exaggerated income to get loans, stiffed small contractors, illegally seized tenant property to resell, and ran the company bankrupt.”
17
Facebook Help Desk: Just a Boomer and a 25-Year-Old Wizard
“I'm the only person in my office (of 15 women all 25+ years older than me) who knows how to work a computer. Today I spent my entire lunch break showing my "boss" how to block game requests on Facebook.”
18
You’re Fired! (Oops, CC’d the Employee...)
"My boss sent an email to a supervisor recommending her to fire an employee… She accidentally CC'd said employee along with other employees.”
19
Still Can’t Save a File in 2025: The Boss Stuck in 1998
“My boss doesn’t know how to save a document and attach it in an email. She's been here longer than I've been alive.”
20
The Doctor Who Played Charades Instead of Doing His Job
“I worked with a doctor who’d just touch whatever he wanted you to fetch instead of grabbing it himself: like touching a stapler, walking away, and expecting me to bring it. Completely lazy.”
21
The Sergeant Who Did Nothing While I Ran the Army
“My First Sergeant did zero work and just used me to answer all questions in meetings. The Sergeant Major even told him to leave and talked to me like I was the real First Sergeant. He got mad, punished me for “disloyalty,” but I wasn’t the problem. Eventually, the CSM bypassed him entirely and emailed me directly.”
22
She Fired Me With Fake Paperwork, Then I Fired Back with Facts
“My district manager fired me unfairly and claimed I falsified paperwork to deny my unemployment. At the review, she tried to prove I “padded” records, but I showed she made a $50 accounting error. When she suggested illegal bookkeeping to fix it, the panel called her out and said they'd report her.”
23
Doritos for Equilibrium: Snack-Based Medical Advice from a CEO
“My boss said to me one day: ‘Could you please get me some Cooler Ranch Doritos? I have a headache and the mustard in the chips balances out my equilibrium’.”
24
Boss Logic: Save Gas by Freezing Employees, Ignore Tires Leaking Fuel
"My boss refused to warm up vans at -15°C to save gas but ignored that all our vans have low tire pressure, which wastes way more fuel. She won’t pay to fix tires because it takes an hour.”
25
Corporate Word Salad: “Work Overtime, But Make It Up Later”
“My boss said to me: ‘I cant get through to communications’, ‘You can work overtime, but you will have to make it up’.”
26
Quarterly Reports? You Mean... Four Times a Year?
“My boss asked me: ‘How often are we supposed to get quarterly reports?’, ‘How do you re-send a voicemail?’”
27
The Developer Who Became a Designer by Yelling
“The CEO insisted I design ads even though I’m a developer, not a designer. He kept yelling at me to “make the van look fast,” demanding more speed effects until I just made it yellow to please him.”
28
My Boss Bought Everything… Including a Wife
“My boss bought tons of useless stuff online daily and reportedly “bought” his wife from South America.”
29
Pirate Bay CEO: Running a Company on Floppy Disks and Broken Dreams
“My boss used pirated, ancient software on terrible computers and refused to buy decent equipment, opting for broken junk instead.”
30
“Just Spin It, Baby!” The Blender Boss Who Thought Physics Was Optional
“My boss thought removing the mixing blade head and just spinning the shaft would fix the overheating. When I said it wouldn’t mix properly, he insisted it worked because the batch stayed cool, even cranked the RPM higher. Surprise: the batch failed QA.”
