I can think of a million things more enjoyable than having to tell someone that you are taking away their source of income and potentially jeopardizing their livelihood for good. These next few stories (although rather entertaining) support my theory - firing someone does not seem fun.
(Content has been edited for clarity).
Just Leave

“My boyfriend fired a lady in her 50’s at Walgreens because instead of patiently going through this customer’s intense coupon book, she became extremely frustrated and just told the customer to leave. So she essentially allowed a woman to walk out of Walgreens with upwards of $200 all because she was too lazy to enter her coupons.
Oh, and she was also a closing manager.”
‘That’s Messed Up, I Quit’

“My absolute favorite was a guy my boss hired who was ‘an absolute whiz’ in the shipping department. He’d find people on the golf course, talk with them while golfing, and hire them.
The guy comes in and I learn he’s been hired with a quick phone call to my general manager so I get all his paperwork filled out and send it over to human resources. I gave him a good orientation on the company rules, break times, lunch, etc. then walked him back to shipping. Jake is my manager back there and a good guy. He’s not the fastest, but he shows up every day, does an adequate job, almost never makes a mistake and if he does, he fixes it without being a little suck about it.
I hand off the new guy and go back to work.
A little over an hour later it’s break time and I go see how the new guy is doing. I stop in with Jake and he says the new guy is out back and says nothing more.
I find the new guy out back smoking a bowl. He looks up at me, clearly stoned and says ‘Hey computer dude! What’s happ’n?’
Me: Come on up front. I need to fill out some paperwork on you. I’m letting you go for violating our policy – the policy I read to you about 90 minutes ago.
Him: Dude, that’s messed up. I quit.”
‘I Had To Tell My Best Friend He Was Fired’

“I fired my best friend in high school. He knew it was coming though. The night before we had been hanging out at the arcade (it was in the 80’s), and when we went to leave, his car wouldn’t start. He was scheduled to work the next day, and told me that night he wouldn’t be in as he had to work on his car.
The next day came, I’m opening the restaurant and he didn’t show up. I called the manager and she said he’s fired, so I called him and told him.
He picked me up after work and we hung out some more. Easiest firing ever.”
‘I Told Her To Take Her Other Offer’

“I ‘fired’ this girl without the permission of my company once. Essentially I had been told to hold on to a freelancer through the holiday push, utilizing her desire to get a full-time role to ask her to sacrifice her own Christmas to make up for all the extra work of the season (e-commerce). I was informed that we weren’t going to offer her a full-time job, though, and I knew she had another full-time offer with the other company she was freelancing for.
She’d been holding out to work at my company and was at risk of losing the other offer while she was waiting to see what my company would do. Of course they hadn’t told her they weren’t going to hire her, they instead asked me to imply that she would get an offer with a good enough holiday push. They were going to say any amount of work she did wasn’t enough to get the offer and let her lose a real offer in the meantime.
I essentially pulled her into an office and told her it was in her best interest to accept the other offer and to quit on the spot. I was pulled into a room with the CEO and some others to justify why she’d quit after talking to me, but I just couldn’t have it on my conscience. She took the other job and we made it through the holidays without her. I managed the team she was freelancing for, so I absorbed most of that extra work, but I’m so glad I chased her away instead of lying to her.”
Always Leave With A Bang

“I fired a guy at my work who was just way too timid. The guy avoided confrontation like the plague and just couldn’t get his work done on time because of being too afraid to ask for help. Even after numerous chances to improve and being put on a ‘Performance Improvement Plan’ for 12 weeks with copious amounts of retraining, he just couldn’t bring his work up to scratch. He was such a nice guy and it really pained me to have to fire him as we knew he relied on his job. For you information, anyone that thinks firing people is fun … it’s the worst thing you can do – it sucks hard.
When I delivered the news that he was fired and thanked him for his service and whatever else he calmly stood up, put on his jacket, walked to the door and flipped me the bird, then left and didn’t say a word.
Part of me wanted to rehire him just for that.”
‘Three Cops Ended Up In The Parking Lot’

“I had a repairman working for me who had some anger issues.
He’d stopped making his daily runs, and was turning in false trip reports. I called him into my office to discuss the situation with him, and it rapidly turned into him yelling at me, including phrases like ‘you’re not my dad!’ – weird. I know.
Anyway, my boss came in to try to calm him down, and told him to go home, and then come back the next morning to discuss the situation.
As soon as the repairman was gone, I told my boss that I was firing him if he came back. My boss told me that he’d take care of it because the thing would get too messy if I did it (which may have been accurate at that time). I was instructed to stay home the next morning so that the boss could talk to him.
I came in at around 10:30 AM, and there were three cop cars in our parking lot, and as I walked up to the building, our repo man was being dragged out in cuffs and cursed out one of our salespeople who just happened to be walking by.
When I got inside, I found the boss’ office thoroughly trashed, with chairs and paperwork everywhere.
I’m sure glad that I wasn’t there to make things messy.
The repo man called another manager who was a friend of mine looking for a job the next week.”
‘You Are All Imbeciles!’

“This one guy couldn’t finish projects. He worked hard (sort of) but he could not finish anything he started. He would have like 12 open projects and I’d yell at him over and over again that he had to just finish ONE.
So, finally I document everything and I gave him a 90 days notice to close these 12 projects. 30 days go by and he just keeps starting new work but not finishing anything. Then we come up on 60 days and I look and he hasn’t completed anything, and now he’s up to 16 open projects. Clearly the guy has some mental block about finishing work.
So a month early I call him in with human resources and I spread out everything in front of him and tell him it’s over.
He completely loses it. He has a full panic attack in front of me, crying, shouting, flailing his arms. He was like a muppet. He looked and sounded like a muppet.
So in the middle of all this, he tells me that I don’t understand anything that needs to be done in this work. I tell him that if I don’t understand it, then it’s probably best that he leave because then he can start his own company and do this on his own, but I remind him that the customer is not happy with him.
Then he tells me that our customer we were supporting doesn’t know anything about what they’re doing.
So I asked him if our company also didn’t know what we were doing?
To which he says, ‘right!’
‘The customer doesn’t know what we’re doing?’
‘Darn Right!’, he said.
‘Out of all of us, who is the only person who knows what’s really happening here?’
‘ME!’, he shouts. ‘ME ME ME’. I’m the only person here who isn’t an imbecile.
I responded along the lines of, then you should be happy not to have to deal with us anymore.
Of course, his intelligence was never in question, it was only his ability to finish projects. But the way he shouted ‘I’m the only one here who isn’t an imbecile, was just wow.”
‘I Have No Idea What You’re Talking About’

“I used to manage a pizzeria. I had a shift leader that told me he needed to leave because his son went to the emergency room. This was like 10 minutes into his shift. I let him leave and closed the store myself. His wife came in to pick up his paycheck a few days later and I asked if everything was okay with their son after the ER visit. She had no idea what I was talking about. So, I fired him 10 minutes into his next shift.
Here’s a pro tip for all of you out there, make sure you get your significant other(s) on board when telling your boss your kid went to the emergency room to skip out of work.
The dude was generally a crappy employee, to begin with, but I didn’t think he would stoop that low. He admitted he lied when I called him out on it, only after that was he fired. And another thing, make sure you give an excuse that doesn’t merit a follow-up question because a toddler in the emergency room certainly does.”
‘Miami Vice Was Based On My Life’

“Let’s call him Jeff. Jeff was a freaking nut case. I’m certain he spent the entire 80’s doing some hardcore substances and bad karate.
I didn’t hire Jeff. My boss did. I was his direct manager. Jeff didn’t have a house, he lived in a recreational vehicle which he ended up parking on the property. Cool, whatever. So I started to train Jeff on his daily duties of the shop. This is where living in an R.V starts to make some sense. On days it was me, another employee and Jeff. We had a moment to rest as our busy time ended. So I sit at my desk and start doing paperwork. While my great employee and Jeff started to talk.
Jeff started his story along the lines of, ‘you ever watch Miami vice?’. The Another employee Jay says, ‘yeah I’ve seen it’. ‘That was based on me man. I was Miami Vice undercover. I’ve seen some crap man’, Jeff says to him. I glance up from my desk and see him walking over to the mop bucket and picking up the mop. He then starts screeching and doing the worst moves I’ve ever seen with it. Like some cracked out white ninja that had forgotten anything he’d ever learned about anything. I see Jay trying his hardest not to laugh. I follow suit and also try not to laugh. I get a grip and ask, ‘why aren’t you a cop anymore?’. To which he replied ‘because it was a bunch of politics and I was a loose cannon’, he said as he put the mop back. I followed with, ‘you don’t say’. Then listened as he told his story about riding a motorcycle in circa 1980’s Miami as he was trying to take down a crime lord.
My boss did this sort of thing. He’d hire people, anyone really, then hand them over to me to train and manage. He had an ability to pick out the most absurd people in the state.
And well, Jeff lasted a good…two weeks. I came in to watch the previous night’s tapes (I had to review them daily in order to ensure no theft had happened – due to employees stealing a lot). There he was, Jeff and all his ‘Vice’ glory, standing in a hallway in the middle of the night, doing his crack karate with a mop stick. He then went on patrol with it in the parking lot. Some customers complained and I let him go. Jeff flipped out like you’d think. Cops were called and we ended up banning him from the property as he would sneak on every night and sabotage things but that’s another story for another time.
As it turned out…my boss hired, I trained and fired the ones that couldn’t make the cut.
Also Jeff, I guess didn’t have a bathroom in his R.V. So he did his business in a five-gallon bucket. We kept finding them on the property after we fired him. Jay found one, didn’t know what was in it and went to throw it away. Now, we really didn’t know what they were at this point. He goes to toss it in the dumpster and the lid came off. Coating Jay in crap and urine. I was right by him when the smell hit me. He starts puking, I start puking and I send him home for a long weekend. That wasn’t just it though.
Jeff had loosened the lug nuts to the company truck. I did a pre-trip on the truck Friday before I drove it. I locked it and came in on Monday. I had to make parts run and do another pre-trip. I found the front tire’s lugs were loose and pry marks on the door to the shop. There were no cameras outside the shop, just on the front lot. So we called the cops and he was banned. He came back the next night and I was there. I had to call the cops and we were told to get a court order to keep him off. The cop said that right in front of him. I guess that got through to him and we didn’t have a problem with him. I did see him about 5 years later in town and he came and shook my hand and apologized. After he left, I went to the bathroom and washed my hands for 3 minutes straight.
The buckets man, they haunt me.”
‘Nice To Meet You, You’re Fired’

“Several years ago I was a bank branch manager. I was being transferred to another branch across town and had to fire a teller on my first day in the branch. About a month before, the teller had cashed out a bad check for a few thousand dollars, he didn’t check the correct I.D and let the money walk out the door. Shortly after, before the mistake was found out, he was in a car accident and had to miss a few weeks of work. He was due to return to work the same day as my first day in the branch. My regional manager had told me about the situation, but they couldn’t fire him because he hadn’t been back to work since they found out. So, that morning, I came in, said nice to meet you, come sit down, you’re fired.”
Life’s Just Not Fair

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“In our deli shop, we had a girl named Jesse, who worked for us for about 8 months before she realized she wasn’t going to get the experience pay a trash human resources representation promised her and decided to get another job. But she wanted to stay on board with one foot in the door, just in case what she had didn’t pan out so well, so she asked to work one day a week. This was fine by us, she was a good worker and we could use the extra help, so she decided to work Sunday evenings.
It soon became clear that Jesse really wasn’t feeling it. Her work ethic dipped, she spent more time on her phone, and she called off. One night she asked to go home early, and when a manager wouldn’t let her because the rest of the staff would suffer for it she just left anyways. The next week she came back and we told her she couldn’t behave like that, it’s unfair to her coworkers, but she blew us off like it was no big deal. And the week after that, she didn’t show up at all. We called her and she didn’t answer, so we assumed she was finally done. I told management to make moves to terminate her (we usually don’t bother with formalities, but I was a bit miffed at how she had so easily disrespected her coworkers and quite frankly tired of her b.s).
Almost two whole months pass without any mention of Jesse, when suddenly one day I get a call from the front office. ‘Um, Jesse’s here asking for an override to clock in’. I go up front and yep, there she stands in her uniform, ready to clock in. I burst out laughing and told her she doesn’t work here anymore, and to my great shock, she’s actually pissed off! She says the deal was she would work Sundays. ‘Uh, yeah, and you haven’t called or shown for the last 8 in a row’. She tried to call the union, who told her that more than 3 no call no shows in a row is a voluntary quit, we were free to terminate her and she couldn’t fight it after the third week. She got so flushed and angry and said ‘That’s not fair! I didn’t know that!’
Watching her storm off was pretty satisfying. Learning she had her hours cut from her new job and wanted to come back from a co-worker close to her was even better.
Folks, moving on up is great, but don’t burn your bridges.”
‘I’m Crapping And Vomiting Everywhere’

“I hired an employee who was close friends with my other employee. They are in their early 20’s and have recently graduated college. Employee 1 is super responsible. So responsible in fact that I started letting her watch my home when I am out of town. Her friend, (employee 2) is fiercely intelligent, great with customers, has great sales while she is at my business but she calls in at the last minute and often always claims she has suddenly been stricken ill and is crapping herself, vomiting everywhere, so on and so forth. On numerous occasions she would pull this at the last minute resulting in me having to cancel meetings to go work, family obligations, or close my business for that day.
The last straw was a during a major shopping holiday. She agreed to work, and it was a short shift – maybe 4 hours. She started calling me and texting me at 4 am which I didn’t respond to because I was asleep. From 4 am to 9:45, I had 15 texts telling me she has been stricken ill and she was ‘crapping on herself and vomiting everywhere’. I called her back, I’m furious because I am 99.9% certain she was faking. I fired her and told her to give the key back to employee #1. 30 minutes after I got off the phone with her she started posting Facebook pictures of her night out drinking downtown. Later, employee 1 (who now has a real job and whom I consider a friend) tells me that her friend was just hungover that day and didn’t want to come it. She said she wasn’t even sick. Since then, she has called me asking for her job back.”
Pick Up Your Slack

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“I worked in fast food for years from high school through college and was in management for a majority of the time.
As a manager, I fired way too many people to count. Most of them just didn’t want to do the basics stuff like show up on time and at least try and to do a good job.
Over the years, I was asked to help clean up a few stores. I usually went in and found out who was busting their bottom to pick up other people’s slack. I would give that person a good raise and either fire or cut the hours of the slackers and the store would take off in a positive direction. The guys busting their behinds have more money and are happy and the customers are getting better service and are happy. The moral of the entire store goes up. The owner is happy because he is saving labor and seeing more revenue. Happy owners tend to give out more perks for everyone. So firing the bad apples was pretty easy as it made a lot more people happy.
What amazed me is the parents that would get their kid fired. We had a schedule and everyone had to put in time off. Parents would call in and say their kid wasn’t going to be there because they JUST decided to go out of town that weekend. They thought the job was some sort of after-school club.”
‘Stop Falling Asleep’

“We had a ‘starving, stifled artist’ type millennial who worked for us. The typical self-entitled kid who played the race card a lot. The funny thing is, he was working security so it wasn’t really a hard or demanding position. We worked nights but he thought that sleeping during the day was wasteful so he wouldn’t get much sleep at all. So it turned into him sleeping on breaks, sleeping on his lunch, and then falling sleep where ever he could put his head. So I was constantly waking him up when he didn’t check back in from breaks or his lunches and finding him out cold, where a hard shake was needed to wake him.
Over time, this got old, then we started to write him up. Three of those and it was termination time. Except at our level, we couldn’t terminate so it was a ‘suspended pending investigation’ then human resources would call them the next day and make it official.
So I had to wake him up 3 times when he was 45 minutes late getting back from his lunch. We get him into the office, and as we are doing the paperwork for his suspension, he falls asleep and falls into me (we’re at the corner of my desk with him beside it). I put my hand on his forehead and push him back into his chair, he wakes up and accuses me of assault. We had the camera and audio along with 2 others in the office watching this. He falls asleep 2 more times and I push him off of me and back into his chair each time.
So we got the papers signed, he got all irritable and we showed him to the door. Five minutes later we have a guest telling us there is a car horn going off solid in the parking lot. Sure enough, he fell asleep at the wheel. So we get him a cab ride home and that was it.
For the record, he had no health issues, he just refused to sleep during the day because cool people never did that.”