If you're in a position of power, you never really want to fire someone—but sometimes an employee leaves you with no other choice. These bosses share stories of workers whose behavior finally crossed the line.
1. Hey, Sleepyhead
I never hovered over my employees, and I usually gave them plenty of freedom in how they handled their work. But when a new contract-to-hire employee kept disappearing from his desk for long stretches, I decided to look into it.
Using my admin access, I signed into his computer to see what he had been doing. I checked his email, and sure enough, I found a message where he told a woman that he parked in the basement away from everyone so he could go nap in his car.
The next day, I went downstairs and found him asleep in the car. I tapped on the window and asked for his door keycard. The look on his face was like a kid caught red-handed. He knew he’d been found out.
2. Bye For Now
I was managing a call center in the early 2000s, back when we still dialed numbers by hand from paper call sheets. I had a new employee who, after several days, still hadn’t convinced a single person to complete a survey. So I decided to listen in.
His first call went to voicemail. On the second call, someone answered: “Hello?”
My employee quietly muttered, “I know where you live, you coward.” I couldn’t believe it. Out of the hundreds of calls he had made, I happened to catch that one on my second try. I called him into my office and said, “You can’t work here anymore.”
When he asked why, I said, “Because you just said, ‘I know where you live, you coward.’” The expression on his face told me everything.
3. A Real Head Scratcher…
I hired a young man who was, to put it mildly, extremely impressed with himself. He had attended top schools and had clearly been very sheltered by his parents. I picked him from a large pool of strong economics graduates.
The first warning sign came in his first week, when he made a point of bragging to his former employer about his new position.
After six months, he had become a real problem. His work was poor, and he would audibly complain whenever he was asked to do anything routine. He also started quietly insulting the people paying his salary—namely me—and was careless enough to print and circulate those emails in the office, where my assistant often found them.
My favorite was the email where he described what a terrible person I was, how much money I made, and how I drove around admiring myself in my Porsche—when in reality I drove a 1978 Toyota Corolla.
On the anniversary of his eagerly awaited performance review, which also happened to be the night before his fancy overseas trip, I asked him to stay late and come into my office.
I calmly handed him the stack of emails my assistant had collected and said, “You left these on the printer. Enjoy your holiday, and don’t bother coming back.”
4. Taking Care Of Business
I once hired a guy who was completely convinced he was the smartest person in every room, when in truth he was not very bright. Still, I needed staff for the yogurt shop I owned, so I kept him on and made sure only to schedule him when I was there.
One time, a group of his friends came in right after one of his shifts, and I could tell trouble was coming. They all had loyalty punch cards, which I’m sure he had given them and filled out himself, so I had to give them whatever they wanted for free. That was strike one.
Another time, I had to leave while he was working. When I came back, nothing had been entered into the register for a full hour, even though the till had been opened more than a dozen times. That was clearly theft, and strike two.
So I sat him down, and since he thought he was destined for great things, I said, “I think it’s time I make you vice president.” His eyes lit up instantly.
“Yep,” I said, “you’re VP of garbage collection. Now go change all the trash bags and clean up the parking lot.”
He just sat there, frozen, so I added, “And I’m only going to need you for about an hour a week from now on.” The confused look on his face was unforgettable.
5. Swim For Your Life
I was the head lifeguard at a summer camp, and one of the staff members was new. Usually we all knew each other because most of us had worked there for years. I was stunned to realize this new guy must have faked his certification. It was honestly painful to watch.
He couldn’t swim a quarter mile, couldn’t dive below three meters, and clearly didn’t know what he was doing. During training, he nearly drowned me while I was acting as the practice victim. He had me in a headlock with my face underwater, and I had to start hitting him just to get free.
Then one day, a child actually started drowning, and this new employee just stood there. One of the lifeguards-in-training began yelling and jumped in to help. Of course, the trainee got pulled under by the struggling child, and the new guy was still just standing there doing nothing.
As a trainee, that person was only supposed to use reach-or-throw techniques, but because of a separate frustrating situation, they were the only guard on the dock at that moment. A friend and I heard the shouting, ran over, and jumped in fully clothed.
We pulled both of them out, and then the new guy said something that completely stunned me.
He said, “Sorry, I took a bunch of stuff earlier, so I’m really out of it.” I fired him on the spot in front of the whole class. I told him to gather his things and wait by the side of the road. Then I called my boss and the authorities, who came and took him away.
6. Completely Unhinged
One time, I saw an employee shove his girlfriend into a wall in the break room, and I immediately said, “What the heck? You can’t do that.” He told me it was none of my business. Unfortunately for him, I was both of their supervisor, so it absolutely was my business.
After about five minutes of threats from him, I locked myself and his girlfriend in an office and called the police. Then I came back out and tried to calm him down until I saw the officers pulling into the lot. Around that same moment, he ripped off his shirt, threw it at me, and yelled, “Meet me outside if you’re a real man!” before storming out.
What he didn’t realize was that the police were already coming around the corner, and they detained him the second he stepped outside. While they were handcuffing him, I leaned out the door and said, “Just so you know, you’re fired. We’ll mail your final check.” He was crying in the back of the car while they spoke with his girlfriend.
It was incredibly satisfying. As it turned out, he also had warrants out for his arrest, so that was an extra surprise. And for anyone wondering, the last I heard, they were still together.
7. Got Your Back
I once hired someone I thought might be a hidden gem—a 40-year-old youth pastor with some cleaning experience. I was only 23 at the time and in my first management role, and people had already warned me it might be difficult managing someone much older than me.
At first, things seemed fine while I walked him through the job. He came across as decent enough, but whenever I showed him little tips or explained the standards we were supposed to follow, his responses started to feel borderline disrespectful. Then later that morning, I asked if he had cleaned one specific part of the bathroom that was supposed to be done.
He replied, “I wasn’t born yesterday, man.” That caught me off guard, and when I checked, he obviously hadn’t done it. I let it go, but near the end of the morning he was just sitting on his phone because he said he was “finished,” instead of helping me with the rest of the work.
I really can’t stand when people have no sense of teamwork or basic courtesy. I had been completely polite to him, and all I got back was attitude. The last task of the shift was taking the trash to the dumpster, so I walked him out there and asked, “So, how are you liking the job?”
He said, “The job is fine. It’s just you, man… your mannerisms.”
By that point, after a long shift, I was done. I laughed and looked him straight in the eye and asked what exactly I had done wrong. He kept going on about how disrespectful I was and how I didn’t say “please” and “thank you” enough. The more examples he gave, the harder it was for me not to laugh, which made him even more upset.
The next day, I told my boss what had happened, and my boss told him it wasn’t going to work out. The guy responded by sending a long email claiming my boss smelled like alcohol when they first met and that I was an awful manager. My boss was a former heavy drinker, so that hit him hard.
It was the first time I’d ever heard my boss swear that much while venting about someone. Needless to say, I never saw the youth pastor again. On the bright side, my boss and I ended up bonding over the whole thing, and he eventually gave me a pretty significant raise and a part-time “counseling role,” which basically means he vents to me now. I don’t mind it.
8. Plot Twist
I once fired a guy by telling him he was clearly too talented to be working under me and should really be running his own kitchen. He found another job afterward and actually thanked me for it.
9. Special Delivery
I worked at a pizza place in a college town, and we had a delivery driver—let’s call him “Derrick.” The manager was also named Derrick. Driver Derrick sold illegal substances on the side. Nothing major, and he wasn’t obvious about it, but most of the kitchen staff knew.
One day, another driver called in on his day off and asked to speak with Derrick. Manager Derrick answered the phone and said, “Thanks for calling Pizza Place, how can I help you?”
The caller goes, “Yo, Derrick! Where’s the weed at?” Wrong Derrick. Click.
Driver Derrick finished the rest of his shift, and then Manager Derrick brought him into the office and fired him. Driver Derrick was actually a nice guy and pretty well liked, so word spread fast.
The idiot who made the call and asked that on the phone got fired too, although not many people cared much about him. The whole thing became one of those legendary Pizza Place stories people kept repeating for years.
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10. Shine On You Crazy Diamond
One summer, I managed the mowing crew at a large park. A few of the guys clearly liked to get high, but honestly, I didn’t care much as long as the grass got cut. Then there was one kid who was assigned to mow the strip along the road outside the park.
He headed out on the mower at 8:00 in the morning, and by noon he still hadn’t come back. By 4:00, I was getting concerned. I took the pickup out and saw that he had mowed all the way along the road and kept going right past the park entrance toward the highway on-ramp. I followed the trail of freshly cut grass for about 30 kilometers before I finally found him sitting on the side of the highway.
He had just kept mowing until the tractor ran out of diesel. I found him still holding the steering wheel, smiling ear to ear, listening to Pink Floyd. Whatever he was on must have been strong, but I still had to fire him.
11. Mixed Emotions
This one was easy for me. All I had to say was, “Welcome back. You’re fired,” after an employee missed four shifts in a row without giving any notice.
12. Yikes!
I found out my assistant manager had a serious substance problem. She was taking money from the registers and using substances in the bathrooms on a regular basis. But somehow, that wasn’t even the worst part.
One morning, she was involved in a hit-and-run at 4:00 a.m. and then came straight to work.
Around noon, police officers showed up, put her in handcuffs, and took her to the station. As they were leading her out, she told the other employee to lie to me and say she was sick in the bathroom if I called. Thankfully, that employee called me instead. I came in, sent that person home, and worked with HR to figure out what to do next.
Not surprisingly, she keyed my car on her way out. When she came back for her next shift, I got the satisfaction of saying, “You’re fired.”
13. That Escalated Quickly
I used to manage a T-shirt shop. One employee had been rehired after leaving many years earlier. Since she’d been gone for more than five years, she didn’t get her old seniority back, and she was very unhappy about it.
One night, I was working alone and the store was absolutely packed. I didn’t have time to tag the last 10 or so shirts in my inventory pile before it was time to clock out. So I left a note on the counter for the rehired employee asking her to finish tagging them. As a sales associate, that was part of her job.
The next day, she sent me a long four-part text message. In it, she directly threatened to hurt me if I ever left her work like that again. She also went on about how it wasn’t her job to do mine if I was feeling lazy, and accused me of taking her position.
She even explained in detail how the extra 10 minutes it took to tag the shirts completely ruined her flow. On its own, that would have been enough for a formal warning.
But since this wasn’t her first outburst or her first time making threats, I followed up her text with a phone call that went like this: “Hey S, I just forwarded your message to [boss’s name], and you won’t have to worry about being in that situation again. You’re fired.” I won’t lie—it felt pretty good.
14. Up In The Air: The Prequel
At a job I had back in 2003, I was once sent to a city I had never even visited before with instructions to fire the entire crew, then hire and train a brand-new one. I had never met any of those people in my life. No one even told me why they were being let go.
All I knew was that I was making $20 an hour, which was good money at the time, to do it. I felt awful. I felt like the worst person imaginable. One woman cried and said she would lose her apartment without that job. I never want to do anything like that again.
It didn’t matter that it wasn’t my decision. It still felt like my fault, and I hated that feeling. Some people can handle that kind of thing. I can’t. Unlike George Clooney’s character in *Up in the Air*, I had no training for it.
Hiring people? Sure, I was good at that. Training a crew? No problem. Firing people was completely new to me. I didn’t even know that was part of the assignment until after the flight had already been booked. I felt tricked into it.
I was only 20 at the time, so I couldn’t even rent a car. Imagine being at work and seeing some kid step out of a cab, introduce himself, and then awkwardly tell everyone they no longer had jobs. It was a nightmare.
15. Caught In The Act
I used to do mechanical maintenance at a brewery in New Zealand while I was studying. Out of nowhere, a chain on one of the conveyors kept slipping off, and it was a real pain to put back on.
Whenever it happened, the packaging line usually had to be shut down, and the staff would get sent home early with pay. We couldn’t figure out why it kept happening, so we decided to install a camera. That’s when we found out what was really going on.
It turned out one employee was jamming a metal bar between the chain and the drive sprocket because he didn’t feel like working a full day. Unfortunately for him, he didn’t know about the camera, and we caught the whole thing on video.
16. That Was Too Easy
One of my employees was selling illegal substances during her shifts at my internet cafe. I had my night guy come in with me. He went behind the counter, and I asked her to step outside and talk with me. She said, “Who’s going to watch the till?” I told her the night guy would.
We went outside, and I asked her if I could buy an ounce from her. She said, “Just a sec, I’ll get you some.” I said, “Hey, don’t worry about it.” She looked at me, confused, and said, “What?” I just smiled because she had basically handed me the proof herself.
I said, “You’re fired.”
17. Slow And Steady…
My most satisfying “You’re fired” moment was with an employee who had worked in our family business for about four years. For three of those years, he had been quietly stealing money from us.
We finally switched to a new accounting system, and he kept doing it. The old system only gave us weak evidence, but the new one was solid. Once we added up everything he had taken, it came out to just under the threshold for the most serious theft charge in our state.
So we sat on it for a day or two, trying to decide what to do. By the time we finally acted, he had stolen enough to cross that line. We got all of our money back, but as far as I know, he still has a record because of it.
18. Timing Is Everything
I had an employee who struggled with addiction. He also thought he was slick enough to steal merchandise and sell it behind the store. I sat through six tapes of security footage, and in one of them, you can clearly see him snorting something off one of the boxes in the storeroom and then nodding off for fifteen minutes.
After that, it was only a matter of time. In a scene that felt like it came straight out of a movie, I told him he was fired just as the authorities were putting him in handcuffs. The best part was that I got a pay raise and an award for uncovering the source of the theft inside the store.
19. Bonus Points
I work at a residential facility for at-risk youth. One time, I caught the supervisor sleeping with a teenager in the program. I told the supervisor to go home and wait for the authorities. But the facility tried to cover it up, so I called law enforcement, Child Protective Services, and two other government agencies on both the employee and the owners of the facility—a four-way firing.
20. Damage Control
I used to be a manager at Journeys, the shoe store in the mall, and I always liked to be very direct when I was firing teenagers and people in their early twenties. I’d start by telling them that because I had been fired before, I already knew what they were going to do.
“You’re going to tell your friends and family it was a misunderstanding, or that I’m a jerk, or anything else that takes the blame off you,” I’d say. “You’ll point the finger somewhere else, but I want to make it very clear to you, just like someone once made clear to me, that you are 100% the reason you got yourself fired.”
21. Relax, It’s FedEx
I used to manage a FedEx office and had just been transferred to a new location. It was open 24 hours, so someone always had to be on duty. During my first week or two, I was getting used to how everything worked when I noticed the overnight tasks weren’t being finished.
So I looked into it more closely and found something pretty surprising. The main overnight employee would spend the first couple of hours doing part of his work, then sit down at one of the computers and browse the internet.
About an hour before the opener arrived, he’d start straightening things up and doing a few small tasks to make it seem like he’d done more than he actually had. The next day, I checked the security footage and watched him sit there for five of the eight hours on his shift.
Then I went back through footage from most of the previous week and saw the same pattern. After that, I checked the browser history: Reddit. I fired him the next day. He didn’t argue. He knew he had been a really poor employee.
22. Hello, Goodbye
My dad told me about a new employee who showed up about an hour late three out of five days during her first week. On the third day, he asked why it was taking her so long to get to work. She said, “Oh, there was a lot of traffic coming from my hometown this morning.”
What she didn’t realize was that she lived in the same town as we did. My dad replied, “That’s interesting, because I live there too and had no trouble getting here.” By the end of the day, she was on her way out carrying her things in a box.
ANTONI SHKRABA production ,Pexels
23. Let This Sink In
I once told an employee who was performing very poorly to take a paid day off and think about whether the job was really a good fit for him. When I called him after the day off, he said, “This is definitely the right place for me.” I told him to take one more day and think it over again.
Eventually, he understood what I was getting at and realized I was giving him a chance to resign before being fired.
24. Meet The New Boss…
This happened during my first week at a new job. I was a manager, but one of the employees assumed I was an intern, so he started complaining about management—which meant me—and bragging about how he slept on the job.
One day, while he was playing World of Warcraft on his laptop in the break room, I asked if he ever got in trouble for it. He told me the game was just a distraction and that he was actually watching explicit videos.
He switched screens to prove he was serious, then told me to stay quiet and not tell the new department manager. I told him I was the new department manager and that he was fired. Then I went straight to HR.
25. Fill ’Er Up!
I heard this story from one of my favorite bosses. The main person in it was especially unpleasant—creepy toward women and remarkably good at making everyone dislike him.
He got hired as a driver on a reasonably well-funded movie project, and my friend hadn’t wanted to bring him on, but he had managed to get support from some of the higher-ups. During production, my friend told him to fill up one of the production cars with diesel and drive it back to the office.
He stopped at a gas station to do it. The car had lost its diesel cap, and someone had replaced it with a cheap plastic one that just said “fuel.” So this guy forced the pump in without noticing it didn’t fit correctly and filled the tank.
Then he drove the car back to the office, which was more than an hour away. For anyone who doesn’t know, putting regular gas in a diesel car is a very bad idea. The engine damage ended up costing five figures, and it was traced back to him. If he had just admitted the mistake, he probably would have been okay. If he had apologized, he likely would have been forgiven.
But when he was called into the office, he stormed in acting aggressive, cursing at everyone nearby, and trying to blame my friend. He handled it so badly that he was fired on the spot.
26. The Best Movie Ever
As the manager of a movie theater, I made sure security cameras covered the important parts of the business. I had one employee who would roll his eyes and argue with me every time I asked him to do something. I needed a legitimate reason to let him go.
One day, I gave him a task and then went back to my office. My assistant manager was watching the cameras and told me that as soon as I turned around, the employee made a rude hand gesture behind my back. I pulled up the footage and called him into my office.
I played the clip for him, and then I fired him. Honestly, it felt great to finally be done dealing with him.
27. To A Tee
I got my boss fired. I worked at a restaurant, and every month we ordered uniforms and retail shirts that we sold to customers. I put everything away neatly, but the next day I noticed all the retail shirts were gone.
When I asked my boss about it, he acted strange and said he had handed them out to the crew. I didn’t push it, because he was my boss. The next day, though, he called me in and wrote me up for checking my email on a work computer. The company rule was basically not to visit any website you wouldn’t want your mother to see.
That’s when I started thinking he was trying to build a case to fire me. So I asked around to see if any of the crew had actually gotten shirts. None of them had. That made me suspicious.
I checked the security footage from the day before and saw my boss leaving with a large trash bag full of something.
I called our district manager, and then, on a hunch, I looked on eBay. Sure enough, someone was selling our company’s retail shirts. I checked the invoice, and the quantity matched exactly what was listed online. I called the district manager back, and he told me to come in for opening because he needed me to work a double.
When I got there, my boss looked confused about why I was showing up, since he was opening that day. I told him the district manager had asked me to come in, and his expression immediately changed to panic. The district manager confronted him with everything, my boss admitted it, and then he was fired.
28. Not-So-Healthy Work Environment
About a year ago, the health club company I worked for bought out another gym chain, and I was sent to one of the new locations to help turn it around. Since the old club had just been taken over, I was expected to fix all the problems there.
Our club opened at 4:00 a.m., and within a few days of me arriving, a member took a photo of the front desk employee sitting there on her phone. My boss emailed me the picture with a simple message: “Fix this.”
This was my first major management job, so I felt like I had to prove I could make tough calls. I pulled her aside and asked what had happened. She explained that she was desperately trying to find someone to take her child to school because her car had broken down. She had already gone way out of her way just to get to work by 4:00 a.m.
I felt awful, especially because my boss made it clear it was “either you or her.” I delayed it for the rest of her shift, hoping somehow the situation would just go away. It didn’t. She cried and told me her rent was due and this was her only job. She begged me to give her another chance.
Keep in mind, I barely even knew her before I was expected to fire her. I did end up letting her go, but I also connected her with a job at a friend’s restaurant where she made almost twice as much.
29. A Way With Words
I was the night manager at a Subway, and that title didn’t really come with much extra responsibility. Still, I did have the authority to fire people if there was a valid reason. There was one employee who was just extremely unhygienic.
She would come to work smelling awful and looking completely unkempt. During one shift, she upset a customer so badly that the customer ended up in tears.
That situation was terrible, but it also gave me the clear reason I needed. I told her, “We can’t keep you on anymore. Please head out, and I’ll make sure you get your pay at the end of the week.” She took it surprisingly calmly.
Prachana Thong-on, Shutterstock
30. Nepo(ish) Baby
My story takes place on a low-budget horror movie. During pre-production, I volunteered in the art department, hoping it would lead to my first real job. Other people came and went, but I stuck with it. Then, on the first day of filming, another guy joined the department.
He got in easily because his dad was dating the producer. I didn’t really like him, but I worked with him anyway. He was loud, opinionated, and constantly talking about how things should have been done differently. Since I knew he had a connection to the producer, I kept my thoughts to myself.
Two weeks into filming, one of the department heads asked me what I thought of him. Before answering, I briefly wondered what this guy had been saying about me, but I simply said we got along fine. A few days later, the same department head came back.
Apparently, the guy had been criticizing the movie’s visual effects and talking about what my team should have done instead. Again, I said everything was fine, but the department head gave me a doubtful look and said, “Because I think he treats you like a complete idiot.” Then he walked away.
As it turned out, this guy had already annoyed the first assistant director, the third assistant director, and the standby props person. The visual effects lead and both art department heads couldn’t stand him either. So when Monday came and he wasn’t anywhere on set, I asked what happened.
Apparently, he had been moved over to the film’s “viral marketing” department.
31. A Friend In Need...
I had a cashier who worked for me for about a year, and he almost never did his job. If he went out onto the sales floor, he’d tell other employees he had already finished everything and that I had sent him to help them. Then he would just follow them around, chatting and getting in the way while they tried to work.
He would also have friends come in and shop so he could “help” them, sometimes for over an hour. More than once, I caught him actively hiding. I couldn’t prove most of it, though, and my boss was constantly angry with my shift—and with me—because we needed hours of overtime every night just to catch up on all the work this kid hadn’t done.
One night, irritated and admittedly feeling a little petty, I told him he could not leave until he finished his work. He complained that his ride was outside waiting and that it would take him hours. I told him that was his problem—he should have done his job earlier—and went into the office to take care of manager duties. Then I heard voices.
I came out and found that he had let his ride into the locked, closed store, and that person was doing his work for him. I told him it was absolutely not acceptable to let anyone into the store after I had locked the doors. I escorted his friend out and locked up again. But that still wasn’t the end of it.
The moment I went back into the office, he unlocked the doors and let his friend back in. That’s when I remembered, with great satisfaction, that the front doors were on camera. I finally had solid proof to get him out of my store for good. I sent everything to corporate.
The very next day, he was fired—and my overtime problem disappeared. Good riddance.
32. Dollar Signs
I worked as a supervisor for a sign-spinning company for a long time. I was allowed to hire people, and while I technically couldn’t fire them myself, my recommendation was enough to make the person above me do it. So in practice, I basically could.
I fired people for all kinds of reasons: dirty uniforms—and I should point out that I was not strict about dress code, so you really had to push it—attendance issues, and bad attitudes. My favorite firing involved a man I’ll call Mr. Price.
Mr. Price came to one of my hiring events in Orlando, and I was desperate to fill positions in the Clermont/Groveland area. We paid $10 an hour, but at the time I could authorize a temporary raise to $12 if someone had to travel 30 miles or more.
Since I needed people badly, I said anyone willing to take that location could have the raise for the weekend. He accepted, and I later found out the site was only a block from where he lived. I had already given my word, and I don’t go back on that, so I let it go.
He called out on his first day. He did show up the next day—our company had a hard time finding replacements, so people often stayed employed even after several no-calls. The following weekend, he called out again after I told him he would not be getting the $12 an hour.
For the next few weeks, Mr. Price kept showing up inconsistently. Eventually I found someone else for that area and assigned them there. Later, Mr. Price contacted me looking for work, and I told him he could have the same location. I intentionally double-booked it.
Then, at 1:30 in the morning, I got a call from Mr. Price saying his phone was about to die, so he wouldn’t be able to make it to work. That was the last straw. I told him very clearly never to contact me for work again.
33. No Child Left Behind?
I was a supervisor at a summer camp, and one time we took a field trip to a theme park. Before we left, I gave the staff a full pep talk on all the ways to avoid losing a child: buddy systems, counting the kids, having them hold a rope, and so on. The counselor in charge of the six-year-olds did none of that.
By the end of the day, I was stunned by how careless she had been. She came back 20 minutes late and missing one child. Thankfully, another counselor from a different group had found the child. I pulled her aside and said, “You had one job. If I had to choose between leaving my son with you or with a random stranger, I’d trust the stranger more, because at least for ten dollars he’d actually keep an eye on my kid.”
She cried, and I took over her group until we found someone else to replace her.
34. Spill The Beans
This wasn’t exactly a standard employer-employee situation, but I used to care for some young children who had special dietary needs—no gluten, no dairy, and limited sugar. This wasn’t about overly anxious parents; the children had real allergies, and it was extremely important that their diet be followed carefully.
Once the older child started school, and since I would soon be moving away, the parents decided to transition the kids into what looked like a very good in-home daycare. The mother and I agreed that during the transition period, I would stay there with the children at first.
At the beginning, I stayed the whole time they were there. Then I started leaving a little early, then arriving later and leaving earlier, and so on. Because of the kids’ dietary restrictions, they were sent with special snacks and treats for the week, along with a daily lunch and drink.
One day, I walked in and found the daycare provider feeding the younger child—who was nonverbal and didn’t fully understand his dietary restrictions—bites of her own sandwich and giving him milk. His older sister, who did understand that this was a problem, was telling the daycare provider that he could not have those things.
The woman completely ignored her. When I asked what she was giving him, she admitted she was feeding him gluten and dairy, but insisted that a little would not hurt him. When I told the parents, they first thought it must be a misunderstanding, but once they realized what had really happened, we immediately went to pick up the children.
We had already been worried because the boy had recently started acting differently, but we had not realized it was because his diet had changed. We had trusted this woman to take his medical needs seriously.
It was deeply satisfying to be able to say, “If you can’t take children’s needs seriously, then you have no business caring for them. You’re fired.”
35. That Got Dark
I once fired a co-supervisor for punching a 16-year-old female employee in the eye after she tossed an ice cube down his shirt. It felt satisfying to send that awful man out the door—until he went to the regional office and complained. I still can’t believe how they handled it.
Upper management ended up firing the hardworking girl he hit, saying she had caused the incident by “playing around.” To make it even worse, her mother had a serious drinking problem, and this girl was the only one supporting the family.
36. Party Pooper
At the limo company where I used to work, there was one employee who was always breaking small rules, like wearing jeans when we were supposed to wear slacks or showing up five minutes late every day. None of it was serious enough to get her fired, but it got old fast.
She also complained nonstop about how hard it was to be in college, work a job, and raise a kid. She was taking one online class. On top of that, she was always talking about drama with her child’s father. Most of her problems were self-created, but she talked about them constantly.
One day, I had already been at work almost eight hours when about six people called out for that night for different reasons. I ended up working around a 21-hour shift. That same day, this employee, who I’ll call Jennifer, called in sick. She said her daughter had lice, she had picked her up early from school, and she couldn’t leave the house until both of them were checked.
That should have been the first warning sign, since it was Saturday, but we were so overwhelmed that nobody caught it. She also knew all the limos and buses would be downtown that evening. Around 9:00 that night, things were so hectic that the owner of the company had to drive one of our party buses himself.
While driving downtown on Fifth Avenue, who does he see crossing the street in front of the bus, wearing a short gold dress? Jennifer. Naturally, he was furious. After dropping off his group, he went back to the hotel where he had seen her go in. It took a while, but eventually he found her.
She spotted him coming from far away, probably because he was a big guy, and immediately hunched down at her table, trying to hide. He walked up calmly, leaned in, and quietly said, “Hey, Jennifer… you’re fired.” Then he smiled and walked away. After hearing that story, the long shift almost felt worth it.
37. Excuse This Interruption
My friend Chris is the executive chef at a somewhat fancy restaurant. One evening, I was walking by and saw him out back on break, so I stopped to talk. We were having a good conversation about movies and bicycles when one of his waitresses came outside.
“Chris! This is not fair! I wanted to take my break, but Audrey said she had already switched with Wendy, so I thought it wouldn’t matter, and then I went to take my break and Frank said I had to stay on the floor, and it’s all so stupid!” And she still wasn’t done.
She took a breath and kept going. “And when I got here this morning, I know I was supposed to be rolling silverware, but I had to check in back because Rodney said something about needing help when he’s not on the line because he was probably in the walk-in, but Rodney wasn’t there, so I went back up front.”
“I honestly thought the silverware was already done, but it wasn’t, so Frank yelled at me, and THAT’S why he won’t let me take my break! It’s so unfair!” She kept ranting, whining, and complaining for a full five minutes while Chris and I just stood there in silence. Eventually, she finally stopped talking.
Chris looked at her and said, “Angie, you’re fired. Turn in your apron. Your final check will be mailed to you.” We watched her face cycle through shock and panic. “But I… I just—” Chris cut her off. “I said leave the property and don’t come back. You’re done here.”
I wanted to go back to our conversation, but Chris, who was usually one of the calmest people I knew, felt the need to explain. “I put up with that for three weeks. Every single day. I have my limits.” And that was it. We went right back to talking about movies and bicycles.
38. Lowest Of The Low
I once had to fire a nurse and a nursing assistant who had threatened and hit elderly patients. I took no pleasure in firing them, but I was very relieved to walk both of them out of the building. I was glad they had been caught on camera and were no longer in a position to hurt anyone else.
39. News To Me
I have an unusual one. She was a writer, and every writer was expected to produce seven articles a day. If you stayed focused, you could finish one in about half an hour, so it wasn’t especially demanding. At some point, though, editors started noticing similarities in her work.
We found several cases where her submissions were actually old files she had pulled from the shared drive and simply changed the byline on. She was warned about it three or four times over six weeks. Every time, she said she genuinely had no idea how it happened.
She sounded so believable that we started wondering if there was some kind of technical problem. These weren’t lightly reworked pieces either; they were exact copies. Eventually, a manager dug deeper and found that over the past six months, there wasn’t a single original article submitted by her.
She had been coming to work for half a year and apparently doing who knows what. Nobody ever figured it out. When she was confronted during the firing, she cried and said she still didn’t know how it happened. People liked her too, which made the whole thing even stranger. Even though we caught her lying about months of work, it didn’t feel satisfying. It just felt unsettling.
Her behavior was so bizarre that people wondered whether something serious was wrong. A lot of people in the office had liked her and considered her a friend. In the end, she lost most of that social circle because no one could make sense of why she had done any of it.
40. What Happens In Vegas…
Our company’s new secretary and promotional model came with us to an event in Las Vegas and disappeared with some guy for the rest of the trip. She didn’t even fly home with us. When she finally showed up at work again, I got approval to fire her.
As far as I know, she ended up moving to Vegas for the guy and later started working in the adult entertainment world.
41. Food For Thought
It’s never felt good to let someone go. People depend on a steady paycheck, and when I fire someone, I’m taking away their ability to support themselves and their family. I understand that sometimes it has to happen, and I’m the one making that call because of their performance, but it should never feel satisfying.
What’s even worse is having to deal with problems another manager failed to handle. For example, when someone clearly needs to be let go because they’re underperforming, or when a manager refuses to deal with employees who have already been given plenty of warnings and chances to improve, and everyone else is expected to carry the extra load.
I’ve had to walk into a room and fire people I barely even knew because their boss didn’t have the judgment or backbone to do it.
42. No Brainer
I have a friend who works at a jewelry store and had an accountant they ended up reporting to federal authorities—for a wild reason. It turned out the accountant had faked most of her references to get the job. Then she used the company bank account to buy hundreds of dollars’ worth of adult products on Amazon.
She also used the business account to buy several plane tickets and book a bunch of hotel rooms in Europe for an upcoming vacation. They fired her pretty quickly, but then she vanished. The authorities tracked her down and sent her to jail not long after. Not her best decision.
43. Morale Booster
When I was a young manager at a large company, I was once told to fire the branch manager, assistant manager, and two other employees at one branch office. Basically, there was a love triangle happening among them, and upper management, based in another state, wanted all of them gone.
I got a call on a Sunday night and was told to meet them Monday morning with security. I also had to conduct their exit interviews, which is basically impossible right after you’ve fired someone.
The memorable part was when one employee blurted out, “I only slept with [Branch Manager] because I thought it would help the company!” I asked her what she meant, and she launched into a long, strange explanation.
When she finished, she asked, “So, do you understand?” I said, “Yes, I understand.” She smiled and said, “So, I’m not fired?” I said, “No, you’re definitely still fired.”
44. Happily Ever After
I once supervised a woman who was well past normal retirement age. When I became her supervisor, I knew it was probably time for her to go. It wasn’t because of her age, but because she had stopped putting in real effort.
She regularly slept at her desk, showed up late often, left early, and made frequent mistakes. When those mistakes happened, she was little to no help in fixing them. One reason we had kept her around was that she was supposed to have deep knowledge of a process we were updating. We were very mistaken.
As we worked on updating that process, we found out the hard way that she didn’t really understand it, and she didn’t care enough to learn. She knew just enough to use it, but that was all. She wasn’t pleasant to work with, and she was an even worse employee.
Honestly, when I decided to let her go, it felt like the right thing for both her and the team. That’s what made it feel satisfying. I felt like I was making a choice she couldn’t make for herself. In her mind, she still saw herself as a strong employee, but she couldn’t recognize that she had checked out years earlier.
Now that she’s retired, the team is doing better, and she seems much happier too. Letting her go turned out to be the right decision.
45. Big Baby
When I was a manager, I had a young woman working for me who was extremely scatterbrained. Thankfully, the job wasn’t very difficult, so at first it didn’t seem like a major problem. But one day, some friends came by and asked her to go somewhere with them.
She asked if she could leave early, and I said no because she was scheduled to close that day. She started crying and locked herself in the bathroom. She even called her mom to complain about what a terrible boss I was. I finally knocked on the door and told her she was free to leave—for good.
46. Um, Fries With That?
I had an employee we already suspected wasn’t doing a great job. That suspicion was confirmed when I saw her preparing a customer’s meal. My jaw honestly dropped.
She accidentally spilled a blob of ketchup on the floor. She looked at it for a second, paused, and then picked it up with her hands. After that, you can probably guess what happened next.
47. Very Dirty Work
I owned a chain of dry cleaners. Three years ago, about a month before I sold the business, I went undercover and trained with the staff as if I were a newly hired part-time employee. We didn’t want anyone in the company to know the business was being sold until everything was finalized. I was shocked by what I found.
On my first day riding along with one of the delivery drivers, he showed me how he used the company credit card to fill up the van while also putting $20 worth of gas into his own car.
When I trained with one of the store managers, she showed me how she made extra cash. She came to work with pockets full of coupons and applied one to every other cash order after the customer had already left. That earned her about an extra $10 an hour on average.
During my last few days, I was at the production plant training with the production manager. I was mainly learning about the equipment and how it was supposed to be maintained. That’s when I discovered he wasn’t doing even half of the routine maintenance required.
He was just recording that the work had been done and then throwing away brand-new filters that cost $290 each. On closing day, I walked around with the new owner and his wife and met with the staff. I introduced myself properly to everyone.
When I got to those three employees, I looked at each one and said, “You’re fired.” To say they were stunned would be putting it lightly.
48. Getting Paid To What…?
A few years ago, I was a security supervisor for the NASCAR campgrounds. After trying to reach one of my new guards on the radio for about 20 minutes, I assumed he had fallen asleep. He was supposed to be sitting in his car at a fairly remote guard post.
Naturally, I thought it might be funny, and also a good lesson, to sneak up on him and scare him a little. But when I walked up to his car, I stopped cold. He was looking at his phone and doing something completely inappropriate.
The expression on his face was a mix of horror and embarrassment. I told him, “Go back to the compound, turn in your radio, and drive home with both hands on the wheel.” I had never wanted to fire anyone before, but that time it felt completely justified.
Krakenimages.com, Shutterstock
49. Belt And Suspenders
When I had to fire one employee, she just cried. Even though she had already received three verbal warnings and three written warnings, she still tried to blame everyone around her. Then she accused me of inappropriate behavior and harassment.
Fortunately for me, the security supervisor had been standing outside the open conference room door the entire time. I was also thankful that the room where I fired her had camera surveillance.
It’s unfortunate, but that’s exactly why that workplace required a female manager to be present when a male manager was firing a female employee, and vice versa. The accusations still had to be investigated, but it didn’t take long. I’d encourage any business to have a similar policy.
50. You Deserve A Break Today
In high school, I worked at a department store. Over time, I worked my way up to weekend and night manager. I had the authority to fire people, but only for a really good reason.
I had one employee, who was the same age as me, who was often seen in her car with her boyfriend during work hours. Her breaks were supposed to be 15 minutes, but she regularly stayed out much longer.
The final straw came when she had her boyfriend call in sick for her while they were very obviously together in the parking lot. I told him, “Being busy with your personal life is not a valid sick excuse, and if she doesn’t find someone to cover her shift or come in, then she’s fired.”
