Real-Life Nightmare Bosses

Real-Life Nightmare Bosses: Stories of Bosses That Put Movie Villains to Shame

Ultimately, there is only one thing that can make or break your job: BOSSES! And nothing can be WORSE than having a really bad one. You can probably deal with difficult coworkers or less salary but your day to day functioning at work can get exhausting with a horrible boss. Users on Reddit share their stories of the worst bosses they've ever had—and surprisingly, many found ways to navigate these challenges, and in some cases, even succeeded in getting them fire from their high power. Get ready to cringe with stories of awful bosses who were just the difficult and worst ones. 

1. The Staycation Permission

I worked for a boss who denied my 'unplanned vacation' as I wanted to go visit by grandma because she was on her deathbed. Because of such attitude, I decided to quit immediately. It was quite unexpected because until that incident happened, she was very laid back and pretty cool. When I asked her if I could take a weekend off to visit my grandmother she flipped and immediately lectured me on how I need to 'plan' my ‘trip’ better.

2. See You In The Line Of Unemployment 

Once, my boss held the back of my neck and told me that, 'If you ever say I am wrong in front of a customer again, I will literally beat your ass.' I straightway went to the General Manager and told him about the same and my supervisor was fired from his duties within 5 minutes.

3. Beach Is The Beginning, So Is The End.

My boss motivated the team by stating that if any team hit the goal for sales, the incentive would be a trip to Cancun and then canceled the trip. However, then two people decided to quit and I took up the job offered by a competitor organization and within less than a year, the company closed, declaring bankruptcy. Karma is seriously a Beach!

4. Aren’t They Cute When They Are Cheap?

I got to know that my boss had fired each and every high school worker after 3 months because they have to pay minimum wage after 90 days, by law. She was a complete jerk, she might as well have paid a bit less during the initial 90 day window.

5. Show Me The Money For The Camera

I recorded a video on my cell phone of my boss stealing money from the safe and keeping it in her wallet. I knew she was doing it and knew the moment when it came out that money was missing she'd blame it on me. She was so dumb because she didn't even notice or realize that she should stop doing that while I was standing with my phone facing her, literally 10 feet away. 

6. Resolve Instead Of Increasing The Issue

One Boss that I worked with added a poster stating, 'Complaining is like vomiting. You feel better but everyone around you feels sick.' The confidence was pretty bad already but it was very mean of him to take a shot at us and disappoint the staff instead of doing something positive.

7. Sweet Money

I had switched to a new job and was waiting for my bonus. For about 90 days, I was open to expressing myself in different ways I would not have otherwise. I figured out that my trip period was not approved and normally I would have asked about it but decided if I can see how it plays out. Two weeks prior to my leave, my manager called me to inform me that it was denied.

However, I was not so upset but said that I would leave anyway. She tried to pressurize me every way under the sun which only made me laugh at her. Everybody was surprised when I left her office happy because they could hear her. I straight away headed to my desk to print my resignation and gave it to her. I also received my bonus, got my vacation, and also got an extra two weeks paid because they discovered I was offered by a competitor and they didn't want me to share any information.

8. Bosses' Mini Version

My Boss had her 8 year old daughter move around in the office and report to her who wasn't working. I was simply fired because the daughter must have lied or did not have a sense of time. She told her mum that I was talking to a friend for 30 minutes whereas I actually took a break by his desk to tell him 'Hi' as I headed to the washroom. This was just one example of many many horrible things done.

9. Might As Well Have Focused On Tasks On To-Do

The CEO of the organization I worked for praised me in front of everybody for completing a task my boss struggled with. As a revenge to that, my boss sent in all his tasks to overwhelm me with work and I found his work quite manageable which was then again noticed by the CEO so he fired my manager and gave me his office.

10. Breaking News: Employees Are Not Your Slaves

I was a small programmer from a bunch of large number of programmers working on a project. We had a deadline in few months and they over-promised to the client and then asked us all to work extra hard to meet the headline, and asked us to work 50+ hours weeks, which of course must of us did while there were 70-80 hour weeks to meet this deadline.

Once the deadline was close and we met the promises, they gave as another one they wanted to be met. And another, people were tired cause they had lives to lead and scaled back to their hours. Most of the programmers were still working 50-60 hours a week but not more than that. Once they realized we were not killing ourselves on their project anymore, there was an all hands meeting where the managers told that they were let down in our professionalism because very few employees were now working more than 50 hours a week.

Later, it got even worse and one of our workers stood up and said, 'Look, I have three kids and I drive an hour to work everyday and taking care of the family by getting presents for Christmas, writing the cards, apart from decorating and cleaning the house for everybody for the holidays — I have a really had time reaching 50 hours already.'

Manager just stared at her, smirked and said, 'If it isn't Christmas, then it would be Easter, or Memorial Day, or because it's summer and it's nice out. You will always have an excuse.' There was dead silence in the room. When we left that meeting, we did not exchange any words but each and every staff on the project just put in 50 hours, a week of work after that.

When it was the time for Christmas—raise and bonus time! Every worker on the project got a 1/2 percent raise, the managers got a 5 figure bonus and we were quite pissed. After Christmas, came the pain as in the first year of the week, four programmers had better jobs lined up and quit. Three more the following week. Five the next. It was a series of domino effect. 

For over three months after the Holidays, we took away 3-5 programmers every single week, It lead to such a point where the managers had to schedule a meeting every Monday at 11 to decide about the week's resignations and rearrangement of staff that was surviving. SCREW THEM!

11. Calm Down, Soldier

When I passed out from the Army and joined the Air Force National Guard in my home state. After leaving for my base 20 minutes later for the first time, I received a call from a Sergeant First Class from the Army Reserve informing me that his system shows my name had been pulled from the reserve pool to deploy to Iraq within three months and congratulated me.

I informed him that, I had just returned from deployment before:

1) I had just returned from deployment before stepping out and I and was still guaranteed more than three months stateside

2) I was recruited with the Air Guard and was therefore exempt. He was pissed and he then raised his tone of voice and said: 'Well you better get that paperwork to me ASAP because my system says you are going.'

I said I signed a contract that binds me to that not the system. I said, it is not my job to update to ensure your system for you. I mentioned the name of the organization I was associated with, the city and state it was in be it my recruiter's name, rank and personal phone number. Then I said: 'Now you have several different ways to contact who you need to in order to get your system updated.' I straight up then I hung up on him.

12. Welcome to the Carnival

Many years back, at my new job I was informed that the office would be re-organized in the new year and my designation will be shuffled to a new group. Exactly one month later, we are busy running a major year-end event and things are going to the garbage. Everything needs entire co-ordination between groups across multiple divisions and it came to a grinding halt with a lady in my office.

She was not prepared sufficiently and the process was lagging behind the planned schedule which was a huge problem. She also had a major meltdown and walked out of the office screaming at everyone and any guesses on who is my new supervisor, now?

13. Lunatic At Head Of It

I worked for the maintenance of the ice rink and one rule for everyone who knew how ice rink works is if the Zamboni doors open, you get out of the ice. Some idiot ignored that it was open and was standing at the doorway and was going to take a last slap-shot. The puck bounced off the glass and hit me in the head.

It was fine but I had to report it to the boss as we had to fill the incident report for events like this. My boss asked, 'Are you okay?' to which I replied I feel okay then he said, 'Well, we don't really have to report it then, do we?' I was completely shocked and I reminded him about the procedure but it seemed pretty clear to me that he didn't want to do it.

Since he would nit do it, I sent an email describing the incident to the administration because I felt there should be proper documentation/paper trail, in case, god-forbid, I ended up having a brain hemorrhage or something a few days later. By the time by next shift arrived, my boss was fired.

14. A Plan That Can Never Disappoint

The management we worked for had purchased a manufacturing plant and fired everybody. Later, they tried to hire them back for less than $2 and yes you guessed it right, it did not go well.

15. Out Of Your Price Range, Sir

A week after the official switch, my boss sold the company. The new owners called me to do a task and I told them that my consulting fees were $120/hr. Surely they did not consider me worthy, unfortunate for them.

16. Inputs From the Receptionists Will Not Be Tolerated

At my previous job at a marketing firm, the owner, president went for an hour rant towards the client by calling them 'stupid', 'ungrateful'. 'idiots' with a bunch of swears. It began as the client who was a dentist presented my boss with ideas that came from her receptionist. I could not believe what he was uttering from his mouth.

They were basically some typical standard suggestions (bench signs, radio ads) that any layman would know about and nothing so bad that somebody deserved to get laughed at and harassed at.

17. Abusing The Power 

When I was about to be fired from my job, I decided to tell the management about all the nasty things I heard from my manager. He had issued threats against his ex-wife and her new boyfriend and basically wanted to orphan the child. He was immediately fired once the cops arrived to escort him out.

18. Wanting To Be Number One

I once had a retail manager who sent out a memo that we worked so hard and did such a great job this month that she got a bonus. We hadn't received anything. How clueless can you be?

19. Awful For Them 

Once, I worked as a service manager for a shady organization that sold and repaired expensive American vacuum cleaners. From past two years, I had been planning 6 week scuba trip with my mates and they were aware and said it is fine. When the time was close, I applied for my 6 weeks leave' and I was called in the husband/wife owners' office and told that I could only take 3 weeks. I saved the time with their permission and when I spoke about it they were rigid that 3 week was what they were prepared to authorize. I tried my best to negotiate five weeks but that was a hard no.

When I came out of the office, I wrote my resignation letter and left. I enjoyed my holidays diving the Great Barrier Reef. They called me straight for 3 months every week to come back but by then I got a good government job.

20. Letting The Seniors Walk Free 

Once at the company I worked at, the CIO (Chief Information Officer) bumped a woman's car while pulling into the parking space. The woman whose car got hit was right beside the car to see what damage had happened. Once the CIO stepped out of her Mercedes and walked past the woman without even talking to her. She straight up ignored her and walked away. 

Even with eye witnesses, the woman whose car was damaged headed straight to the HR department and the organization cut her cheques for the damage. The business paid for the damages—not the CIO. The actual business paid for it—not the CIO, she got away unpunished without even admitting anything or paying for anything.  

21. The Drama Queens’ Fall

A faculty member who was on her term was guiding while sort of controlling the lives of people on her 'drama team'. She literally made them imitate titillating acts on stage and on top of them filmed it too. I informed the Dean regarding the same and then she was fired. I saw her somewhere around town and it is safe to admit that even after 11 years, she still hates me. 

22. Assemble The Crickets

I told my boss that I was pretty disappointed of one of his hires as he had no idea about our job and asked him, 'doesn't this cheapen my knowledge and expertise'? to which he responded by saying: 'Well, let's be honest, your job doesn't really need all that, doesn't it?'

Apart from me, there were four more people with different varying fields of  skills in the meeting and it got pretty silent after that.

23. Went Down Fighting For Glory 

When I had a problem where our district manager was intentionally not rectifying my pay so it would reflect the raise I was promised. After he bailed on me I had to call the corporate HR and they came down on him like waking the Anger from Lava. He came down to my store and attacked me in front of my customers for 'not being a team player' and going over his head.

After 6 months, we were informed that our store will close and the staff will be transferred to other stores, but not me. I was told that I would never be welcomed in any company because 'I wasn't a team player' so I was laid off once the store was closed. He said that I was needed to oversee shipping of our product to other stores based on some list he had of what store gets what.

However in the end, I got my pay back. None of the stores from his precious list received what they wanted. I spent my three weeks shopping for whatever I wanted to whoever and whenever while playing my playlist with the store speakers and telling customers about a bunch of advantages that can be taken with the loopholes in the store's policies and systems.

24. What would he do? Fire me?

Having a Corner Office Is Not Equivalent of a Medical Degree

I wasn't allowed to go to the emergency room because of Jerry after I had heavy bleeding—down there I quickly worsened. I went above his supervisor and got permission to get in. Later, I called my mom and told her to meet me in the ER. The nurse from ER said he had never witnessed so much blood adding to which she also stated I would need some blood transfusions and I shall be admitted.

However, my mother called Jerry who then tells her that it is just STRESS and I needed to get back to work. Now at this point I would not even lift my head up but I can take a bus to head to work across the town.

I would be tired and lose weight quickly and by that means I lost 8 pounds in a week and sleep as soon as I was home, Jerry stood his ground that it cannot be cancer. I was trying to improve from the procedure and Jerry called me to let me know that I was fired for taking off many times. After 5 days, I was diagnosed with cancer so SCREW YOU, JERRY, SCREW YOU!!

25. Disgraceful Dismissal

My ex-supervisor who I reported to immediately was a racist and male chauvinist idiot who happened to enjoy harassing me occasionally just for his share of fun. He would secretly touch me in front of everyone to see if I had the guts to say something in return and then he could then reprimand me for 'giving him attitude.' It was a tipping point for me when he grabbed and forced my hand to touch him during a pat-down.

I also planned to move to a new unit and reported his actions. It turned out that seven other women experienced the same—as there always are. He's gone now.

26. Being Suspicious? We Cannot Function Well

I used to work at a club in Miami and the owner was absolutely out of his mind, thanks to years of his substance abuse. When the housing market had crashed, people spent less but he argued that we were all stealing. Every week when we had meetings, he would give us all kinds of threats. Finally, he set up an automatic pouring system for 50k plus, and it basically looked like you're pouring drinks from a soda gun, to be honest it was super boring. 

The vibe and style we all had was all vanished and that made the sales drop even more than it was. Two weeks later, he literally ripped the system out.

27. The Classic Line: It’s Not Me It’s You

When I quit my job, I was invited to meet the CEO as he was unhappy about me leaving and wanted to understand the reason why. I told him that I wasn't paid enough and the pay rise that was out recently was not enough. He was pissed and in a condescending manner lectured me on how I could have handled this situation better. 

When I interjected, he did not appreciate that so I said, 'I am leaving and have nothing to lose and adding to that I informed him about how I had been disappointed multiple times in the past as well where I saw others getting paid more and I was being refused. I added to that by stating to him that I absolutely had no interest in begging to get paid what I already deserve.

28. Where There Will Be High Rank, There Will Be High Standards

I once worked with a boss who just hated me completely. After realizing that she was not qualified for the position and already slept with two different people at the organization, I concluded that she was a joke and just needed to be dismissed. I never really focused my attention towards her and when she would come to the building once in a blue moon, I would still ignore her.

I did not have the time to play games as I was busy. She wrote me up for coming late during 3 different times which was, 1 minute, 3 minute and 6 minutes late. Because I lived an hour from work, I came across traffic whereas I would leave home two hours early to account for this. But when the freeway is packed and clogged on side roads, there is not much I can do.

Every time I was in traffic, I updated her and she still wrote me up so she could fire me. I even planned to leave the house insanely early and she hated that. Eventually, she was fired and to this day people remember and laugh at the kind of person she was.

Apart from that, I ensured the write up was removed from my file as everyone acknowledged and recognized that she was treating many of her employees unreasonably.

29. Not Moving A Inch For Any Excuse

When my executive director was moving, he decided to take my internship student and a low-level employee to his house and help him move the furniture. When I told him that it was completely inappropriate from a liability and respect perspective, he responded saying, 'You know since I have hired you, I can also fire you, right?'

I said, go ahead and try that then I quickly then called our board, who dismissed him that week.

30. Waking Up Very Early To Outsmart The Kitchen Staff

My mother works as the Cafeteria/Kitchen Manager in school and from the last decade, the admin was trying to find a way to fire the kitchen staff and bring in new people for minimum wage. These people make great money now and their benefits are better than what my dad has working at a Dow 30 company. And for the record, she is also a part of the union.

Still, they cannot let anyone go without there being serious downfall in responsibilities. One person grows and suddenly the diary in the fridge is expired as the new person without training for $8 does not know when things need to be re-ordered. Surprise surprise, getting ready for the parental complaints,  as there won't be milk or cheese for the coming two weeks.

One of the recent strategies was to hire a 'nutritionist' who is the SIL of a high-ranking administrator. I researched about her and found her 'qualifications' are decade old with two degrees in hospitality management apart from a 'approval' from an unaccredited, unrecognized NPO. She was hired for $150,000 a year thanks to the public records.

Another recent strategy was to expel the current staff with a huge testing program on people working for the school from the past 20+ years and I never knew. Every staff member passed the three different weed-out tests excluding just one. The nutrition monster walked out of the meeting screaming when she found out about this.