7 Employees Open up about the Worst Bosses They Have Ever Worked With

Imagine a café crumbling without its unsung hero, a cunning colleague weaving a web of deceit, a boss moonlighting as a pyramid scheme guru, promotions turning best buds into archenemies, typing up your own warning letter, facing off against workplace sexism with a twist, and a boss so outrageous, he crashes the ER to expose a “lie.”

These stories aren’t just about work; they’re wild rides through professional pandemonium, showcasing the unbelievable lengths people will go through to earn a living.

Comments have been edited for grammar and clarity.

1. I Left and the Business Fell Apart

u/VaultHawk: I worked for a small café, doing a manager’s amount of work while being paid minimum wage, and when I contracted pink eye from caring for my sister, my boss got mad at me. After that, I applied and got hired at Starbucks. His business fell apart without me there and closed within four months of me leaving.

2. She Played Me Dirty

u/madeofstarlight: I was a financial analyst excited about my job, the pay, and the benefits. I was by no means rich but would make $30,000-$40,000 a year, which would pay all my bills with a little left to save, get any extras for my child, and do my nails once a month or go out with friends. I was so happy.

My boss had the most personable girl in the department train me. And she did it incorrectly. I discovered the same thing had happened with two other people in my department. I had no idea I had errors until she had my two supervisors pull me aside.

I asked if they could train me instead. I requested retraining SOPs and asked questions when I had them. I was improving, which is what the boss asked for. She gave no benchmark, no percentage. She wrote me up because I had errors after two weeks. But everyone else did as well.

One morning, I caught the girl who trained me poorly, going through the work I hadn’t corrected or submitted and making copies to give to my boss. I knew right then that she would eventually fire me, and there was nothing I could do. It was awful.

She admitted a training issue when I was fired and said, “What do you want me to do about it?” I let her have it after that without yelling or anything. My position has been filled and vacated five times in four months.

3. The Boss Turned Pyramid Scheme Promoter

u/MartinB75: There have been so many, but I will go with the boss who started selling Amway from his office. He was pressuring his employees to buy stuff and implying that people buying from him and joining him on the pyramid would benefit (raises, extra vacation, etc.).

He also tried to get the company to purchase through his side business. I reported him, and when HR asked him if it was true, he said, “Sure is! Do you want in?” Bam, escorted out the door.

4. Our Friendship Turned Frosty after a Promotion

u/Matopus: I worked in a kitchen at a retirement home. I was the morning cook and became good friends with the evening cook (before he got promoted). Fast forward two months, our head chef retired, and he got promoted to head chef.

I was happy for him. Shortly after he got his promotion, he started to get more and more lazy. I would have to stay late in the day to ensure all the orders were put away and the rest of the staff had everything they needed for their shift.

It got to the point where he would sit outside and smoke. I found out he was sleeping with the building manager’s daughter. When the building manager tried to discipline him, her daughter stepped in, told her not to bother him if she wanted to continue seeing her grandchildren, and even demanded he get a raise.

So, I put up with it for a few months. When I told the guy that my partner was pregnant and my son was due in July, all he said was. “Oh man, that better not interfere with my birthday weekend.” Fast forward to when my partner went into labor (at 4:30 a.m.)

I called him and told him that I wouldn’t make it to work as my son was going to be born. He called me back at 5:30 a.m. asking if he was born yet, and when I told him no, he asked if I could come in for a few hours while we waited.

He had a hissy fit over the phone when I told him no and hung up. On my first day back, he called me into his office and wrote me up for missing shifts. I quit and thankfully got a new job straight away.

5. I Typed and Signed My Own Warning Letter, Courtesy of My Boss

u/knockinbootz: I worked nine years for a real winner. She used to sing my praises in the morning, then keep me two hours after work to tear me down until I was in tears, over and over again.

She would ask me to call her by her first name and then yell at me for not using her proper title and surname. She was the epitome of “Dr. Jekyll and Mr. Hyde.” She was an actual doctor. I fell behind on my filing, so she dictated a threatening letter, made me type it, and then signed it.

6. She Acted Friendly to Others and Mean to Me

u/sowhatsoplenty: A few years ago, I got a job as a bartender for a restaurant. I started my first day and met a new guy who was also hired. I got there and was sent upstairs to be a waitress.

I’d never waitressed before; I applied to be a bartender. The new guy had never worked behind a bar and had waiting experience but was told to go behind the bar.

There were two managers; the one who hired me wasn’t there, so I asked the other. She told me that the girls worked as waitresses and the guys as bartenders.

I was a bit annoyed but figured the other manager would fix it when he was there (he didn’t)! Anyway, I learned waitressing was not for me.

I was terrible at it! The female manager was getting so frustrated with me, making me more flustered and worse at my job because she constantly shouted over my shoulder.

Meanwhile, the guy at the bar who’d never poured a pint before was left alone, making mistakes, and she was also shouting at him. One night, he was left alone, and a group came in and asked for mojitos. He wasn’t taught how to make them and had no drink guides, so I jumped on the bar and helped him.

As I was helping him, the manager spotted me behind the bar, lost the plot, and started screaming at me in front of everyone; it was degrading.

What made it worse was that everybody else working there loved her, and she’d invite everyone to parties in front of me and be nicey nicey to everyone. I was fired by the other manager, whom I’d never seen, because of the feedback from the female manager.

7. My Boss Is a Monster!

u/anonymous: I was 5 months pregnant and felt terrible pain in my stomach. I drove myself to the ER. My boss didn’t believe me and said I was faking it. I told him I’d bring a doctor’s note.

The doc examined me and left, then said, “Ma’am, I know this might be alarming, but there’s no need to call your dad here…”

“But my father passed away a year ago…” I said.

“Right now, there’s a man outside claiming to be your father and demanding your medical record,” the doc explained.

I was in total shock, AND THEN A LOUD BANG!

The door to the room opened, and my boss with a red face burst in and yelled, “SHE’S FAKING IT, SHE’S NOT PREGNANT!!! DOCTOR, CALL 911 RIGHT NOW!!!” At that moment, my hubby ran into the room and forcefully ejected my boss, shouting, “YOU’RE GOING TO PAY FOR THIS!”

After giving him a few pushes, my husband called 911. The officers took the fool to the station. It then turns out that he had been keeping fraudulent accounts at work. As a result, my boss lost his job and was forced to leave the country. Karma in action.

These stories are a collection of moments that range from the absurd to the profound, all reinforcing the idea that our work lives are often stranger than fiction. So, cheers to the rollercoaster ride of employment—where every day is an episode in the greatest, most bewildering series we’re all part of.