My Boss Is A Karen

February 18, 2022 | Melissa Gervais

My Boss Is A Karen


Workers don’t quit their jobs, they quit their bosses. It only takes one bad boss to ruin the workplace, and when that happens, it can feel nothing short of life-draining. Fortunately, not every employee feels compelled to keep their head down in those situations. These employees clapped back against their awful higher-ups in such a way that it left everyone suddenly wondering: Who’s the boss, now?


1. It Was Over The Top

Here's the scoop: My supervisor is a real piece of work. His favorite pastime during his shift is strolling around, demanding everyone tucks in their shirts. He's also generally a nightmare to deal with. 

A couple of days ago, on my birthday, I came into the office and my friend shouted, “Happy birthday!” loud enough for the whole office, including my boss, to hear.

Turning towards me, I thought my boss was about to wish me a happy birthday. But nope—his words hit me like a train. What he said was, “Yeah, could you tuck your shirt in please?” He even acted it out with his hands, miming tucking in a shirt. I responded, “Sure, I'll just drop off my stuff at my desk and then tuck it in.”

So, I made the seven-second trek to my desk to offload my stuff. But before I could blink, my boss was behind me, snappishly repeating, “Tuck your shirt in!” After hurriedly tucking it in and as he briskly passed me, I said, “My bad, I just needed to put my stuff down.” But he seemed not to hear me and carried on, strutting around as if he'd scored a victory. But, I was about to turn the tables.

In record time, I whipped out my HR manual and scoured it for the shirt-tucking rule. My eyes WIDENED. To my surprise, all shirts had to be tucked in...except Hawaiian or guayabera shirts. 

Off to Walmart, I went, picked up a stack of 10 of the loudest Hawaiian shirts I could find, and wore one to work the next day. My boss gave me the once over and glared, but he couldn't say a thing.

Whirling away from me, the moment of victory was sweet. When my curious coworkers asked about my eye-catching attire, I joyfully shared my little loophole discovery. The next thing you knew, half the office was donning Hawaiian shirts, driving my boss up the wall yet perfectly by company policy.

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2. The Relieving Of The Guard

I used to work in a waterpark, and we had this boss who was not the kindest, especially to the lead lifeguards stationed at the tallest slide. She wouldn't let them take bathroom breaks. One day, a lifeguard near the top frantically signalled via radio that he really needed to use the restroom, but she didn't allow this. 

Now, it's worth mentioning that every so often, the boss would permit these lead guards to slide down, mainly to check for any stranded tubes on the way.

Caught in a tough spot, one of the lead guards feared he might embarrass himself by having an accident in front of all the guests. Left with no other choice and pressed for time, he decided to address his problem in an eyebrow-raising way—he used a cat litter bucket from the janitor's closet, meant for cleaning up when a guest gets sick.

Afterward, he rode down the slide, using the water to clean up a bit. He left an unpleasant surprise in the bucket for our unyielding supervisor to deal with.

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3. They Turned On A Dime

During my time in the Navy, a medical professional recommended that I undergo a significant surgery on my ankle. Unexpectedly, my superiors agreed to the operation but rejected the necessary recovery time, saying I didn't warrant the downtime following the procedure. 

Strange, right? They declined to authorize any paperwork associated with this, prompting me to swiftly dispute their choice. They weren't prepared for my response. I initially confronted them with a rule, stipulating that they were obliged to answer all requests within a set timeframe (around three days, I believe). 

Yet their reply remained a firm "no," so I engaged the aid of Naval lawyers, who crafted official paperwork based on all relevant regulations. This legally binding notice declared that if my superiors failed to follow the doctor's directives, they would be liable for the full cost of my medical treatment. 

I also informed them that this could result in the management of all my healthcare being shifted to civilian providers, with the bill landing on their budget. This finally caught their attention: They authorized not only my surgery but also the recuperation leave and its extension.

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4. You Never Know Who’s Listening

I had a job at a grocery store, and our boss, Rob, was incredibly unpleasant. He graded us poorly on our evaluations to avoid increasing our wages, and he frequently abandoned his post which even the other managers found puzzling. He was dismissive and disrespectful to us all. 

He was always bossing us around but achieved less than any of us. Then one day, my patience ran out. An elderly lady fell down in the parking lot right in front of me. I quickly asked a fellow shopper to stay with her while I hurried inside to inform the store manager, seek help from a pharmacy worker, and grab a water bottle from our lounge.

 Once everything was sorted and emergency services were called, I even assisted her back to her car. After the incident, I got a customer compliment (you can exchange these for a free sandwich if the manager approves). But Rob denied me this reward. His exact words had me fuming: "It's not extraordinary; it's your duty.” 

I was so irritated that I punched out for a break and bought my lunch. While in line, a cashier mentioned the incident and sarcastically referred to Rob as the "hero" of the day.

In response, I joked, "Yeah, more like Rob the major jerk." Little did I know who was standing behind me, until I turned around. It was a regular customer, known throughout the store for his autism and remarkable memory for verbal phrases. I bolted out of the store, convinced I'd lost my job.

Fortunately, he didn’t mention my comment to anyone, saving my position. But here's the twist: For the next few months, every time this customer ran into Rob, he would say "Rob the major jerk" for everyone to hear. The first time it occurred, Rob was taken aback and looked like a deer caught in the headlights.

Naturally, I couldn't help but burst into laughter. Luckily, all of the other bystanders joined in, so my reaction didn't stand out. Even though it was unintended, it was probably one of the funniest moments I've ever witnessed...and I got to see it unfold three different times.

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5. Music Is Food For The Soul

Once upon a time, I was part of a team in a corporate kitchen where the General Manager wasn't a fan of our music selection. His choice to combat this? Blasting children's tunes. To his surprise, we all ended up belting out these tunes enthusiastically, and we triumphed in our little musical standoff. 

Later, we found ourselves in another kitchen, this one closed off, equipped with surround sound. The same picky GM once again tried to govern our music with strict rules, not appreciative of our choices.

Unbeknownst to him, we'd devised a flawless scheme to really bother him. We simply reverted to the kids' music—for an entire week, no less! The takeaway? Don't underestimate the rebellious spirit of a motley crew of kitchen staffers belting out tunes like "Banana Phone" in resistance against unnecessary restrictions—You jerk!

 Long live Raffi! Long live Raffi!

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6. Knee-Jerk Reaction

I once held a job at the Jaws ride in Universal Studios, Florida. My outfit consisted of a plain blue T-shirt, jeans, or jean shorts, white socks, and matching white shoes. However, we girls had an “unofficial” uniform, often opting for jean shorts and tall, white knee socks. 

During one summer, I managed to snag a position working both the Jaws ride and the Jungle Cruise ride at Walt Disney World. As a Disney fan, I was excited about the opportunity but quickly found their excessive rules to be suffocating.

While working at the Jungle Cruise, my uniform was a khaki shirt and shorts, or pants, paired with white socks, and brown shoes. On a particular day, I found myself without any regular-sized socks for the Jungle Cruise ride. As a solution, I wore my tall white socks from Jaws, which looked utterly absurd with my jungle outfit.

As I arrived at work, one of my managers lost his cool. He objected, stating my socks weren't in line with “The Disney Look.” He insisted that I roll my socks down. This made it look as though I had mini white flotation devices around my ankles, which was even more conspicuous.

Though it annoyed me, I found a way to get my revenge. I returned home and dug through my Disney Look guidebook, looking for any sock related rules. I discovered that socks only had to cover the ankle bone; there was no rule about a height limit. In essence, I could have paired my khaki shorts with white tights if I chose. 

Emboldened by this, I decided to wear my knee-highs again, in a tiny rebellion. When the same manager saw me, he understandably went ballistic. He hauled me into his office, intending to write me up. However, I brought my copy of The Disney Look, showing him that while my choice was strange, it was perfectly acceptable. 

I asserted my rights to continue wearing the tall socks. And I did. It may have looked silly, but I didn't mind. I wasn't thrilled with my experience at Disney, but at least I had the satisfaction of expressing a tiny bit of freedom: I could wear my socks any way I wanted.

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7. Condominium Scheme

Back in my high school days, I sported a shirt from a teen education website encouraging the use of protection. After only a few hours of parading around in it, I found myself being summoned to the principal's office. They accused me of endorsing inappropriate activity. 

I countered, arguing that my intentions were to promote safe sex and avoid unintended pregnancies. But, despite my argument, I was defeated and given an ultimatum: change my shirt or leave school.

Instead of walking out, I devised a crafty alternative. I simply slapped a post-it over the 'M' in 'condoms' and spent the rest of the day playfully pestering teachers about my great deal on free lakeside condominiums, or 'condos' for short.

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8. The Bright Side Of Life

For 17 years, my brother-in-law was an employee at UPS. A natural prankster, he was often in hot water for coming to work sporting wild hair dyes or braided hair (which, as a big Italian guy, his bosses didn't consider suitable). 

There was always something. However, he later discovered that his bosses couldn't reprimand him for wearing sunglasses. So, in his own unique way, he resisted conformity by wearing the wildest sunglasses he could find.

Red-lip-shaped sunglasses, guitar-shaped ones with raised stems, purple ones decked out with rhinestone hearts… He wore them for the sheer joy of a good laugh. Over time, he was identified by his eyewear. 

Whenever someone mentioned they lived in a specific neighborhood, I would say, "Oh, my brother-in-law is your UPS guy, the guy with the wacky glasses." The usual response was invariably, "Ohhh, John! Absolutely, I recognize him. He's such a fun guy." Then came a major plot twist...

Unfortunately, he was tragically hit by a tipsy driver while out for a walk four years ago. At his funeral, we were deeply moved by the respect his colleagues displayed for him—all his workmates came wearing their brown uniforms and outlandish shades. 

His closest friend delivered the eulogy with neon green glasses perched on his nose, three sizes too big for his face. Even the pastor donned John's guitar-shaped glasses during his address.

After the service, we tallied more than 200 pairs of peculiar sunglasses in his collection. What began as a sort of rebellion against his boss grew into a wholehearted tribute to his uplifting personality in life—his primary goal always was to bring a smile to someone else's face.

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9. Sorry, Not Sorry

I used to be an employee at a television station where the management was truly terrible. I would vent my frustrations to my pals consistently. Over time, curiosity brewed with some folks on Facebook about my work, so I'd respond honestly, aware of the risk of getting canned for badmouthing the company. 

That's when I started combing through the HR manual, discovering I couldn't be sacked if I didn't specifically mention the company's name. Fast forward to a month later, I hit my tipping point and couldn't endure the job any longer. 

I did the unthinkable—I vented on Facebook about the horrors of my job without calling out the company directly. Next day, my superiors fired me. I happily left that place and headed straight to a lawyer's office. After it all, I ended up with a check for $17,800—precisely my annual salary. It was quite a satisfying feeling.

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10. A Moment Worth Dyeing For

During my high school years, I went on an uncommon out-of-state field trip with a small group of students and teachers. Although I was an honor student, I was also a bit of a rebel, often seen sporting baggy clothes, midnight-blue hair, and opaque contact lenses. 

However, for this trip, we were told to dress "appropriately" as there were planned activities shortly after our flight. So, I switched my opaque contacts for transparent ones and dressed rather conservatively. 

The only defiance left was my bold blue hair. On reaching the airport, just about to take our flight, one teacher who knew me well, spotted my blue hair. She looked at me in surprise and asked, "Are you serious?"

Curious, I asked her what she meant. She then proceeded to point out my "unnatural" hair color, arguing that it was distracting and reflected negatively upon the school. To provide some context, my hair had been a spectrum of colors for months, including vibrant shades like hot pink and sky-blue.

Additionally, a hairstylist friend had dyed my hair with a semi-permanent dye, so the blue wasn't going anywhere anytime soon. Despite this, the teacher suggested to the school principal that I should go home and change my hair to a more "natural" color. 

However, the principal, who I got along with well, included me in the conversation and asked for my opinion. I defended myself by pointing out that the teacher's own hair color, garish orange-blonde, was far from natural too.

In the end, I proceeded with the trip and, to my amusement, the rural folks we met found my urban odd-colored hair quite enjoyable.

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11. Out To Lunch

Back in the days when I worked at a McDonalds in Pennsylvania, it was common for managers to stay clocked in during lunch breaks. Essentially, this meant if there was a sudden influx of customers, you were expected to ditch your break and rush to assist. 

By state regulations, however, we were qualified for a peaceful off-the-clock lunch break. But enough was enough. One day, I decided to cheerfully clock out, sit down, and enjoy my meal.

Just then, the owner walked in. He swiftly inquired why I wasn't assisting given the customer surge. I made my rights known to him and surprisingly, I was left undisturbed for the rest of my break. In fact, others began to follow suit, adopting this new break structure.

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12. He Nailed It At The Eleventh Hour

At the company I previously worked for, positive feedback was practically nonexistent. Once, a colleague even proposed, “Can’t we say something kind just for once?" The blunt response to that was, “That’s not our job here!”

 For five exhausting years, I opposed this toxicity until, finally, some colleagues who had long-standing personal grievances against me got promoted and assembled a case to oust me from my position.

Thankfully, another colleague clued me in on their shifty intentions. This allowed me to start job hunting and secure a new position before I was officially let go. The plan was to confront me on a Tuesday at 11 A.M., but thankfully I received my new job offer at nine. 

I handed in a simple resignation that said, “I am stepping down from my position.” I also declined an exit interview and showed them state and federal laws proving that I was not obliged to participate.

Although they were eager to get rid of me, it outraged them that I had acted first. To my surprise, their plans for me were even more insidious than I’d initially thought—they intended to place me under a doomed-to-fail improvement plan so they could use my skills throughout the summer season. 

Instead, I took the sneaky route—I turned in my resignation dated to take effect later, knowing they wouldn’t want me on the premises another second. I also anticipated they would have to pay me until the resignation date, which meant I would receive my annual profit-sharing distribution. 

Now, I am working fewer hours and earning more, surrounded by colleagues I genuinely like. On the other hand, my former company laid off 10 percent of their workforce and cut the remaining staffers' pay by 30 percent.

They got what they deserved.

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13. Yay, Or Neigh?

Our previous CEO was quite a difficult person. He implemented a controversial policy—no dogs or cats were permitted inside the office, a break from our prior pet-friendly environment. Our team lead was completely against this decision. In an act of defiance, he showed up one day with a surprising companion—a tiny horse!

Predictably, he lost his job over the stunt a week later. The funny side of it all still brings smiles. However, once we found a new CEO, he rejoined us. Currently, our kind hearted new CEO even encourages us to have dog races at work.

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14. He Paid For It In The End

In the past, when I juggled school and a job, I often got to work from college 10 to 20 minutes before my shift. My supervisor sometimes would need a hand with a task— stowing something or picking up the phone—before I officially started. But within a few months, this "now and then" became a "daily" routine.

After going along with this for several weeks (still marking time at the usual 3 pm), I thought it only fair to get paid for those extra minutes I was putting in each day. When I gathered the courage to address this, less than an hour into my shift, my boss exploded at me. 

He tossed the employee handbook at me, loudly declaring that I was only permitted to clock in five minutes before or after my shift. So, I decided to push back, albeit subtly. From that day on, I made a point of checking in exactly five minutes after my shift was due to start, no matter how early I arrived. 

Fast forward three months, and karma caught up with my boss—he was let go. He had it coming.

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15. It Suited Him Just Fine

Back in the early 80s, my dad worked at a post office. One crazy hot day, the indoor temperature soared to around 85°F, and to make it worse, there were no fans. Despite the soaring heat, men weren't allowed to wear shorts. But my dad, hoping to keep cool, came to work in knee-length shorts. 

This didn't go down well with his boss who promptly sent him home to change. His boss probably thought that would be it, but little did he know, my dad had a clever idea up his sleeve. He made a comeback wearing my great-grandfather's outfit from the late 1800s which included a top hat. 

His boss couldn't help but question whether he wasn't too warm in that suit, but my dad just breezily insisted he was completely comfortable.

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16. Good Thing She Maid It Out

Being a nanny is odd when your employer is a mom who lacks genuine supervisory experience. When I first became employed, my then-boss didn't seem awful. However, as time went by, she continually added more tasks to my plate. 

Suddenly, I wasn't just looking after the baby anymore—I was also acting as their housekeeper, but without a pay raise. Eventually, it felt like I was her personal assistant.

With her newfound authority, she took full advantage, and not in a good way. Being just 19 at the time, it was challenging for me to realize the extent of the worsening situation, as nothing happened abruptly. I was eventually let go. Then, the day after she dismissed me, she strangely inquired about my whereabouts. 

By then, the job had worsened...I was handling everything in their house, from minding the baby to washing the mom’s personal garments. She even provided me a "uniform", which I would be criticized for if not maintained well. The same rule applied to her beauty regimen requirements. 

Then, while expecting her second child, she proposed that I become a wet nurse for them. Following my dismissal, I never returned, and she was so upset that she confronted me at my home.

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17. "Missteaks" Were Made

While my boss was away at a conference for a few weeks, a colleague and I hatched an ingenious plan: a George Foreman grill for the office. Every day for over a month, we'd pop over to the deli, grab a feast for lunch—burgers, lamb chops, pork, steaks—you name it. But when the boss returned, he was less than thrilled. 

"I don't want that thing in the office," he declared. So, we moved our grill to the communal kitchen area of our floor, where we had a rented suite.

Yet, our boss was irate about that too and protested, "I DON'T WANT IT ON THIS FLOOR!" Hence, we relocated it once more to the underground car park, sneakily using the power outlet near his parking space while he was out for lunch. Despite our sneakiest efforts, our plan was exposed rather in a grand fashion. 

One day, he caught us—burgers in hand, huddled over our tiny grill—as he returned from lunch along with an associate (who was also in the car with him).

Imagine his surprise witnessing three IT guys crouching in a dimly lit underground car park, grilling burgers on the floor. Needless to say, it didn't end well. 

If he hadn't directly said, "Take that home, or I will smash it and toss it in the bin," our backup plan would've been the church parking electricity supply located across from our building (directly in view of his office).

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18. Petty Officer

There was a time during my army stint when I parked my car at the military base ATM. Four men came closer, and one of them joked about my car, "Is that junk heap really yours? Probably should call a tow truck." I didn't even glance back and shot back, "Forget you and your tow truck." 

I had no clue who this guy was; he'd vanished by the time I collected my cash. But trouble came knocking the very next day. My squad leader questioned me, asking if I'd used rude language against Staff Sergeant "P". 

I admitted I likely had. So, three other witnesses were interrogated, and they confirmed I'd indeed insulted a staff sergeant and a tow truck. They let me scrutinize the statements attesting to my ill behavior before making my own, likely to clarify that lying was a futile effort. 

Luckily, while scrutinizing the statements, I discovered a handy little detail—only one of them knew the man was Sergeant "P" as he was in civilian attire; he was off duty.

So in my statement, I depicted an "excessively offensive and confrontational civilian, unknown to me," behaving irrationally. I shared how I "responded jovially to avoid further argument." Thanks to the statements I'd read, I could brilliantly incorporate this into the unadorned facts the others had delivered.

In the military, the UCMJ (Uniform Code) doesn't recognize an act as "disrespecting a non-commissioned officer." There's only "insubordination," and that only applies when the officer is in uniform. With that, everyone decided it was best to brush off the incident since Sergeant "P" would suffer more significant consequences. 

Just like that, the issue disappeared. "P" persisted in annoying me whenever he could, so whenever I saw him in casual wear, I'd yell, "Hey, 'P,' forget you!" My squad leader eventually requested that I stop acquiesced, as he asked as a personal favor. Even if it ended, it offered some chuckles for a time.

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19. Sandal Scandal

The business I'm employed at permits women to wear open-toed shoes, but only if they're made of leather. Interestingly, the same rule doesn't apply to men. A couple of years ago, during the summertime, I started donning leather sandals. 

This move raised some eyebrows among the management, and they told me I wasn't following the dress code.

In response, I calmly highlighted that if I were a woman, my choice of footwear would be deemed completely acceptable. So, denying me the privilege—purely based on my gender—amounted to unfair treatment. Ever since that conversation, I have not been bothered or received any comments regarding my footwear.

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20. Found The Loophole

Back when I was an employee at Best Buy, the company's dress code required us to wear black shoes and trousers, add a belt, and sport a neatly tucked-in blue shirt. But as someone on the heavier side, bending down to sort DVDs on the lower shelves often meant an untucked shirt and a belt digging uncomfortably into my stomach.

 Sounds like a trivial issue, right?

Regardless, my boss would often give me a hard time about my untucked shirt, and eventually, she started nagging about my missing belt too. Curious, I looked over our dress code and found this unique rule: "Wear a belt if your pants have belt loops." 

Inspired by this, I came up with a clever workaround—I took an Exacto knife and snipped off all the belt loops from my pants. The next day at work, my boss spotted me yet again without a belt and demanded, "WHERE'S YOUR BELT?" I swiftly shot back with a triumphant grin, "WHERE'S MY BELT LOOPS?" 

Trust me, it was one of my most memorable moments there.

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21. It Shaved Him Some Time

During my tenure at Big 5, we had a certain dress code which men had to adhere to. It specified that men should either be clean-shaven or have a mustache but no other facial hair like beards, goatees, or sideburns. 

Being someone who loathed daily shaving but also didn't look good sporting just a mustache—giving off a creepy or '80s adult film star vibe—I found myself in a dilemma.

In the end, my solution didn't exactly thrill my managers. I decided to grow the largest, most outlandish Hulk Hogan-inspired mustache imaginable and wore it with a sense of pride throughout my time at the company. A personal victory, indeed!

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22. She Got A Kick Out Of It

I'm employed at Home Depot, where it's a requirement to wear steel-toe boots. These shoes typically set you back more than $100, and unfortunately, the company doesn't cover the cost. As a woman earning minimum wage, locating a suitable pair was no easy task. However, I seized this challenge as a chance for some sly retaliation.

Since the company didn't specify any particular color, I shopped around and purchased steel-toe boots that were a dazzling combination of bright white and green, even matching laces included.

Their notable lack of style is what first catches my co-workers' attention when they see me.

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23. From Zero To Hero

In my previous retail job, they had this requirement: 70% of every sale had to be linked to the store's membership program. I discovered a surprisingly simple workaround to this rule that really got under the store managers' skin.

My solution? I ensured that my shifts showed a perfect record—a 100% membership signup rate—by only processing a single customer's purchase during my entire workday. Of course, this was only if they either used their existing store membership or agreed to sign up for one.

Then, on any random day, I'd process a non-member's transaction, causing my track record to drop to 0%.

When the store managers would confront me about my sudden dive to zero, I'd explain that I had maintained a flawless record the entire week, and had only made one sale that day, and the customer wasn't interested in the membership. 

The frustrating part for them was, they couldn't justify berating me for a single non-member sale or for only processing a single customer on other days since my record still showed a perfect 100% success rate.

Needless to say, my actions drove them up the wall, but on paper, I was doing a stellar job.

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24. Shoe Boss

Once upon a time, I was an assistant manager at a lingerie shop, which meant I had to dress well and convey a professional image. Other staff members usually wore high heels, but at the end of their shifts, they would frequently complain about their sore feet. 

My strategy was to wear stylish yet comfortable flats, steering clear of the discomfort brought by towering heels. To my surprise, my manager was rather miffed about my choice of footwear, wrongly insisting that heels were part of the dress code. Instantly, I got suspicious.

So, I fact-checked the dress code, pointing out that it did not specify the necessity of high heels—it simply asked for proper work attire. However, she refused to accept this and claimed the dress code was outdated. At that moment, I had had enough.

I suggested that if the dress code was indeed outdated, it was her responsibility to provide an updated one. Eventually, this dispute reached the regional headquarters, and the provincial manager tried to persuade me to comply and wear heels. 

My response was clear—if they wanted me to wear heels, they’d need to pay me significantly more than the current wage to compromise my foot health.

As one might expect, I didn't get a raise, but interestingly, no one insisted on me wearing heels at work ever after.

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25. Bet This Threw Her For A Loop

About half a decade ago, I was employed at Petsmart, specifically in the "Pet Hotel" section. This is where we would care for animals while their human 'pet parents' were away on holiday. 

Although my work was hidden from the customers and my interactions were only with dogs and cats, my strict manager would always give me a hard time for not wearing a belt. One particular day, she became exceptionally upset with me because I had shown up belt-less, even though I was covering for a sick colleague at the last minute.

What I did next left her utterly surprised. I grabbed a dog leash, threaded it through the loops on my trousers, and announced, "Looks like I do have a belt now."

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26. Taking A Breather

About a decade ago, I was part of the OfficeMax workforce, and intriguingly, the only non-smoker in the entire crew. As such, while my colleagues jumped at two to three 15-minute smoking breaks every shift, I had no comparable privilege. However, I was soon going to level the playing field. 

One day, I casually approached our manager and inquired about a "clean air break." At first, he was baffled, so I clarified my request. Since all the smokers were allowed two or three quarter-hour breaks each shift, I believed I should have the same opportunity to step out, smoke-free. 

Even though the proposal clearly irritated my manager, he recognized that it was fair, and so he reluctantly permitted my "clean air breaks" to avoid any potential claims of discrimination.

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27. All Wired Up

I'm part of the food industry where rules are often tweaked. One day, they implemented a policy that demanded all employees to tuck in their hair ensuring it doesn't graze their collars. My hair is long, but it's always neatly braided and we wear caps anyway. 

Out of the blue, two hours before my shift was about to wrap up, I was informed about this new policy. They sternly told me I was violating health codes and demanded instant action.

I nicely pointed out that I was not in the wrong, but it was merely a store procedure. I agreed to style my hair up for the next shift. I figured it wasn't an unreasonable expectation—given the time I'd need to fix my hair and gather the necessities like hairspray, bobby pins, etc. 

To my dismay, their response was "Insufficient! Do it NOW!!!" This fueled my resentment. I clocked out for a break, headed to a shop, and picked up some elastic bands and flower-patterned wire. Subsequently, I fashioned my hair into eight braids, each interwoven with wire, and jutted them out in various directions. 

When my supervisor laid his eyes on me, he freaked out. I simply responded: "Well, my hair isn't touching my collar, is it?"

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28. They Had A Right To "Bare" Arms

I'm in my last year of high school, and a group of senior lads decided to launch "Tank Top Tuesday." Essentially, every Tuesday, around half the senior boys came to school in tank tops. There was no ban on tank tops at our school, the only rule being that the strap should be at least two inches wide. 

We didn't foresee any issues, especially since tank tops were a common sight among the school's female students. However, following the first Tank Top Tuesday, the school hit us with an unexpected surprise—it put a ban on boys wearing tank tops. 

When we inquired about the new rule, they said the issue was the distraction of visible armpit hair, which supposedly hindered the learning environment. Our response seemed to cause our teachers a headache. On the next Tank Top Tuesday, we all arrived at school in tank tops, but with our underarm hair neatly shaved off.

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29. He Sub-Dude His Boss

In the naval service, it's a rule to always have a white T-shirt underneath your uniform. I used to have a head supervisor who was religiously ensuring our T-shirts could always be seen. After rummaging through the uniform guidelines, I discovered we were allowed to throw on a V-neck tee with our working attire. 

So, I did. Of course, it didn't take him long to notice.

When I informed him of the rule permitting it, he seemed taken by surprise. All he could utter was, "Score one for the team," before he sauntered off. Afterward, he scrutinized me for any breaches of the rules he could pick out. Being a smart-mouth rarely pays off, at least not in the modern Navy.

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30. This Principal Got Schooled

Even though my family and I don't share the Pentecostal faith, I attended a Pentecostal School. They wanted me to constantly trim my hair, and I had a fondness for growing my hair and sideburns long. One alarming day, the school made an alarming demand: I either shave off my sideburns or they'd do it for me. 

To counteract this, I informed the principal about my wish for a tattoo. She instantly disallowed it, explaining that the school's policies aligned with biblical principles. To support these rules, she cited Leviticus 19:28, "Do not cut your bodies for the dead or put tattoo marks on yourselves. I am the LORD."

This prompted me to ask her to consider the verse preceding it, this read: "Do not cut the hair at the sides of your head or clip off the edges of your beard." As a result, I was allowed to keep my sideburns.

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31. There’s No Shaving Face Now, Stesha

I used to work at an all-American food chain. I had this incredibly unreasonable manager who always used to send me home if I showed up with the slightest stubble. Mind you, I was a busboy and barely interacted with the guests, hence I couldn't figure out why she had such an issue with my Wolverine-style facial hair. 

After all, the rule allowed a clean-shaved look or full-grown facial hair, be it a beard, mustache or goatee. Her reaction to what I did later was priceless.

One time, I took a week off and spent that duration growing a phenomenal beard. The day I got back to work, my first task was showcasing my splendid beard. Hope you liked it, Stesha.

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32. They Made No Concessions

I'm employed at a local cinema and it seems like because I'm a female, I'm always stationed at the snack bar. Annoyingly, one of our bosses even refers to us as "confectionery ladies," which is pretty absurd. Part of our uniform includes these pointless visors and boy, are they irritating. 

For the longest time, I tried to dodge wearing it until one day, the most senior manager got so steamed up about it he threatened to discipline me. But I spotted one key inconsistency—and it would eventually tip the scales in my favor. 

The guys working with us were never forced to don the visors when they assisted at the snack bar, and the excuse being that "they don't have as much hair as we girls do." Taken aback by this reasoning, I decided to get a pixie cut. It cracks me up now whenever that old-school boss attempts to pick on me.

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33. She Earned Her Stripes

At my job, we have "casual" days with a specific dress style: No jeans, no T-shirts, and definitely no sneakers. In short, casual days basically mean "men not wearing ties," but apart from that, it's business as usual. 

So, I had a fun way of responding. A typical casual day outfit for me would be zebra-striped pants in black and white, a shirt with horizontal black and white stripes, a vertically striped jacket, a black and white scarf, and towering four-inch platform heels.

I also had this stunning, completely appropriate blouse in vibrant neon green, neon orange, and chartreuse, that looked fantastic when paired with my understated turquoise skirt and multi-colored, striped knee-high socks. Technically, I wasn't violating any dress code rules. 

The administrative ladies would gaze at my outfit near the elevators, whispering amongst themselves about my unusual dressing sense. Their condescending looks seemed to say, "She obviously doesn't understand." Well, let's just say I have a feeling they were the ones who really didn't "get it."

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34. Vacation, Or Power Move?

I was employed in a struggling IT department. At the time, our company was merging with another, forcing a drastic 50% budget cut for our department, which led to me having to let go of six team members. Incredibly, we were still expected to cover the same workload or face disciplinary action. 

This led to me working practically round the clock, pulling 80-hour weeks for nearly three months, until I reached my breaking point. I was on the verge of throwing in the towel, job lined up or not, because I felt my health was slipping and it seemed the company couldn't care less. 

However, just a day before handing in my notice, I happened to re-read the staff handbook and found an interesting rule about resignations—it said an exiting employee could take any unspent vacation time right away, because the company wouldn't pay it out later.

In their view, it was a misguided way to save money. The following morning, I stepped into my boss's office, left my laptop, blackberry, and office keys on his desk, and declared, "I'm stepping down, and I appreciate everything. Goodbye." He was initially taken aback, and then asked when my last day would be. 

I replied smilingly, "Well, right now. I'll be off in five minutes. According to our HR policy, I'm going to take the 10 vacation days accrued in my account, which is essentially two weeks."

His reaction was priceless; his jaw nearly hit the floor. Immediately, he was on the line with HR, while I merrily started to pack up my things. My abrupt departure clearly ruffled his feathers, but the HR team confirmed the policy.

 Indeed, I left five minutes later, claiming my due vacation pay over the next two weeks. I learned soon after my departure, the policy was swiftly amended.

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35. Stocking Fees

I do my job in a bank, and their fashion rules insist that we ladies MUST sport socks or nylons with our shoes. I operate behind the counter, so absolutely no one notices our legs! 

Plus, is anyone genuinely curious to confirm that I wear underwear beneath my skirt?! They totally underestimated me. So now, every time I wear a dress or skirt to work, I pair it with my knee-high boots.

If ever people ask, "Hey, where are your nylons?" I'll hoist my foot on a chair, unzip my boot, and present them a surprise: "Socks."

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36. Not Lovin’ It

Probably my least favorite boss was at a McDonald's where I worked. Initially, we had a young manager for about 10 months, then they introduced another from a different store. During his first week, everything was smooth. But then, he inexplicably moved a teen girl from her usual post at drive-thru to grill cooking.

One day, she unintentionally splattered grease onto her shirt. This made the manager extremely furious—and his reaction was uncalled for. His harsh words were, "You look like a pig. Either tidy up or leave." Upset, she left in tears. 

The following day, another young worker, visibly fatigued from a three-hour marathon shift, asked for a water break. The manager refused. So the youngster suggested he would drink from the backroom sink.

The manager warned him with a threat of sending him home if he did so. Upon hearing this, I couldn't hold my anger. I firmly told him off and walked out. I never returned. Word later reached me that the manager was dismissed about a month later.

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37. Living Well Is The Best Revenge

Once, I worked at Comcast with the dream of climbing the corporate ladder. Being new to the professional world, I thought assisting my boss would help pave my way upwards. I undertook all her tasks, from arranging meetings to handling paperwork, while she engaged in games on her iPad.

This setup was our norm until one day I lost my cool with a client, which was out of character for me. I admitted my mistake and was ready to face the music. Still, my boss took this as an opportunity to chastise me publicly before higher management.

She replayed my mistake over a ninety-minute period, pausing periodically with remarks like, "How could you?" By the end of the session, I was distraught, and she capitalized on my vulnerability, using it as leverage to prove my incompetence while making herself appear the good boss who was guiding me.

I was then issued a final notice; another mistake within the given year would terminate my job. Human Resources and colleagues from management were of no help once I was isolated from the rest because of this incident. My supervisor, however, continued to demand that I do her work.

This episode led to a lot of emotional turmoil for me, followed by intense anger. Yet, I chose to channel my anger towards my progress. I overturned my situation by returning to school to earn my degree while managing an internship alongside my full-time job at Comcast.

As a student and an intern, I prioritized my responsibilities over fulfilling my boss's requests, excusing myself from late-night work and additional reports by citing school work and internship duties. I also started maintaining a minimum distance with her, replying only to work-related queries and ignoring unnecessary group mails.

This went on throughout my probation period during which I intentionally kept my sales figures low, not enough to get me fired but significant enough to prove my disinterest. This did impact my commission, but the goal was bigger.

Towards the end of my probation, I switched to a new boss and raised my sales effort, which resulted in soaring numbers. Upper management couldn't help but recognize and compare this sudden improvement with the poor performance under my previous supervisor. 

The satisfaction of having given her the taste of her own medicine was priceless. On completing a year of probation, I handed over my resignation notice. During the exit interview, I shared the growth journey I had embarked upon during the last year except for the intentional lower sales part. 

I also revealed that my aspirations to become a better person were aimed at defeating Comcast and that I had planned to quit only post-probation.

Worst Co-workers FactsShutterstock

38. They Needed To Pay Up

I once held a position where my client accidentally revealed what they were spending for my services. Shockingly, they'd pay more in one month than what I'd receive in a year! So, I approached my boss asking for an increase in my pay but was informed there simply weren’t any funds available. 

I then gave them a deadline of six weeks to find the resources, which was met with laughter because apparently, I wasn’t the 'ultimatum type.' Turns out, she was mistaken to underestimate me.

When I landed a superior contract and handed in my resignation, lo and behold, the higher-up, my boss's boss, suddenly counter offered with a 50% wage boost for me to stay on the team.

HR NightmaresShutterstock

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39. Blue Collared Workers

At the large, well-known architecture and engineering firm I worked for, my role had me shifting between the office and construction sites. The office's dress code was pretty strict, including dress pants, shoes, and a collared shirt. Whereas on the site, we were required to wear jeans, long-sleeve shirts and protective steel-toed boots.

Now, picture our former VP: a short, feisty man in his 50s, with a deep-rooted Jersey accent. He had the habit of scolding anyone who dared to break the company's dress code whenever he came around. 

So one day, after returning from some on-site inspections, dirty and dusty, I found him standing at my desk. "Where's your collared shirt?" He demanded, to which I responded with surprise. I thought it was clear I had been on-site. Ignoring my confusion, he again asked "Where's your collared shirt?" 

His Jersey accent came at me louder, his finger nearly brushing against my shirt. That was when I lost my cool—and got even. Without thinking, I retorted, "Aren't you seeing my 'blue collar' or are you blind?!" I jabbed a finger at my blue T-shirt. He was left speechless, his planned response forgotten. 

After a tense silence, he shot me a glare that could curdle milk and stormed off to chew someone else out. That interaction turned me into somewhat of an office legend. However, I still ponder why I got passed up for raises and promotions during my tenure there.

Interview NightmaresShutterstock

40. Lost Wages

At the moment, I'm attempting to quit my job. I receive a fixed salary, but if I work less than 40 hours per week, my boss reduces my pay. If I exceed 40 hours per week, I only get my standard salary. A couple of weeks back, I was only able to work two days before learning I had been exposed to someone who tested positive for COVID-19. 

In no time, I started feeling unwell.

Consequently, my workplace asked me to stay home. I had a COVID test and was instructed to stay home until I got the results. When the result came back negative four days later, I breathed a sigh of relief. But a nasty surprise awaited me. 

Despite being on salary, my latest paycheck was significantly lower than it should've been, and my boss gave me no heads-up about this. Thankfully, I sought guidance from HR and they informed her that what she did was inappropriate. My boss later called to apologize, claiming ignorance about the requirement to pay me my full salary.

 Right, sure. This incident, among countless others, is pushing me to seek employment elsewhere.

Interview NightmaresShutterstock

41. They Made A Bad Call

I've been loyal to the same company for 17 years, and my work was generally appreciated. Finally, I got to work in the department I'd always longed for. The boss was enthusiastic about having me and often praised my work. Then came an evening where I was on-call, and an "emergency page" was sent to my phone, but it never rang. 

This led to the call reaching my manager. She tried texting me a couple of times, but my text notifications weren't loud enough. Needless to say, my boss was a bit annoyed the next day. I apologized for my phone malfunction and explained that if she had called me instead of texting, it could have likely worked out. 

Plus, my "backup" colleague handled the call and solved the problem effortlessly. Isn’t that the purpose of having backups? Yet, she seemed unsatisfied. She kept insisting I had messed up and warned me against future records of the same. She even recommended a backup phone. 

Can you imagine? I again apologized saying, "Look, what happened to me could happen to anyone. But, anyhow, the issue was resolved by my colleague. And the urgency of the matter was being slightly overstated."

But she wouldn’t drop it. The worst part was, she never even asked me WHY I'd missed the call. Before discussing it, she jumped to the conclusion that I was at fault and needed punishment. This incident led to souring our good relationship.

Despite my 17+ years of service and strong work ethics, things went downhill. I was regarded as an asset, well-respected by my peers, and hers too. I used to arrive early, work till late, even on my off days for urgent matters, without expecting any OT pay. My dedication to the job and the good pay were reason enough.

Fast forward a few months, my boss and I found ourselves seeking conflict resolution from an HR representative. But here's the catch—he seemed biased towards my boss. He repeatedly brought up the (very few) times I underperformed, completely ignoring the circumstances that led to it.

For instance, he’d mention, "Your supervisor shares there was an email where you responded rudely to the client. Is that true?" When I'd attempt to describe the context, he'd cut me mid-way stating, "No, answer the question. Were you rude?" 

Following my admittance, he would move on to the next complaint without giving me a chance to tell my side of the story. Eventually, I asked my boss directly, "Is this situation likely to change with you?" She sat silent, glancing at the HR representative in response.

My doubts confirmed, I tossed my security badge on the table, picked up my belongings, and announced, "I'm resigning."

As I walked out, the HR representative followed, calling out my name, "We don't want this!" I turned back, "Neither did I." Driving home that day was refreshing. Funny enough, I now work in a role where I am more valued and content.

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42. Family Matters

I'm involved in home care. My "employers" are the families I provide services to, and they usually turn out to be the reason I leave. Not because of the clients, but because of their families. One instance that stays with me is getting a verbal lashing from a mother because I wanted to take a one-week break.

For five years, I was in the service of this lady, caring for her severely disabled kid. I had already organised my holiday to fit my unpaid time off policy. However, she still insisted I should compensate for the time spent, and expressed concern over how to look after her kid in my absence. 

Just to give you an idea, I was not the only one she could rely on—there were three or four more home aides available. I clarified to her that there wasn't any need to compensate the time because I am unpaid during those periods. It was not in my hands to sort it out, and she would perhaps need to look after her own child. 

She didn't appreciate my response. Regardless, I went on my scheduled break, but upon realizing I had enough of her, I resigned thereafter. I regretted doing that to the kid, though.

That child was alright—rather pampered due to the circumstances—but otherwise, a good kid. I just couldn't bear with the mom anymore. After a week or two, I found a new job and moved on. 

Still, it's ALWAYS the families that bug me, NEVER the clients. I've had some wonderful clients. Whether I'd remain okay with them mainly depended on their families.

Bottled-Up SecretsShutterstock

43. From Three Days To Three Weeks

I used to spend my weekend nights for three years managing a restaurant. This was a tough gig, working from five in the evening till three in the morning but I loved it because I was always a night person. 

At one stage, my now wife and I took a break and decided to visit a hot spring. However, on our way back home, my leg started to hurt intensely. Before we knew it, I was rushed to the hospital and put on three different antibiotics to treat an infection.

Realising the severity, I notified work that I wouldn't be able to come in for the next three days. My Assistant General Manager okayed my leave and promised to have my shifts covered. 

But, to my shock, they didn't. Instead, they gave me my first and final warning—meaning I was on thin ice and could lose my job any moment despite my years of service there. Not the sticky situation I wanted to continue with, so I handed in my three weeks notice the next day.

Hospital Wake-Up Stories FactsShutterstock

44. Management Was Super Tucked Off

Back when Circuit City was a thriving retail store, I was part of the warehouse team. They had this super strict dress code demanding khaki trousers and a not-so-flattering collared shirt, which everybody had to strictly follow, including us warehouse folks. 

But a dive into an old employee handbook revealed that the warehouse staff could wear khaki shorts without cargo pockets and a Circuit City t-shirt, and nobody would bat an eye. So, I set off to put my plan into motion. Since Circuit City hadn't produced their branded tees for ages, I found a couple at a nearby Salvation Army store. 

Throw in a quick run to Target for some shorts, and voila! I had reinvented my work get-up. When I showed up to work the next day in my updated attire, my bosses were almost comically outraged, accusing me of looking messy and disheveled.

Fun on top of this, a large fellow warehouse worker (who despised his job and used to snooze at the back and chat on his mobile all day) got wind of this. He too snagged some retro Circuit City tees and became my uniform twin. Our supervisors were not fans of this camaraderie. I surely miss my days at Circuit City.

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45. Food For Thought

The person in charge wasn't really my boss but the principal at my school. As a kid, I viewed her like a boss. I attended an Opus Dei school which was run by nuns who were incredibly strict. I despised the salads they served us. Wanting to avoid eating them, I discovered several tricks to squirrel away my food. 

After all, they always reminded us, "It's wrong to waste food considering there are millions going hungry."

Eventually, I'd reached my limit. Fed up with constantly hiding the food, my nine-year-old self decided to brazenly walk up with my tray still half full, intending to toss it all. Predictably, the nun exploded in anger. Nevertheless, I coolly responded, "I'm satiated, and overeating is a sin," before discarding it all. 

This defiance landed me in hot water.

Legendary Comebacks factsShutterstock

46. The Solution Was Hair Raising

Back at my previous school, there were strict rules for boys regarding hair length. The main dictum was that our hair shouldn't hang over our eyebrows or down to our collars. Well, being a clever chap, I found a smart way around this restriction. 

I used a bucket load of hair gel to style my hair upwards in impressive, yet audacious ways. Since my hair was always sticking up, it technically wasn't breaking the eyebrow or collar rule.

For two whole months, I went undetected, until the principal decided to change the rules. The new guidelines were supposedly tailored just for me...

Toys Of The Rich And Famous factsGetty Images

47. Found The Holes In Their Logic

About six or seven years back, when ripped jeans were trendy, my school banned jeans with big holes in them. Most teachers only worried about this rule if a hole revealed too much skin, like near the rear or groin area. But one teacher interpreted the rule to mean that any clothing with a hole was not allowed.

The teacher who was strict about this rule was my gym teacher. If she spotted you with a hole in your jeans, she'd either have you change your clothes or send you off to the vice-principal's office. I had this teacher for my second class of the day. One day, I wore my fav old, comfy jeans that had a small hole beneath one knee.

When she saw that, she freaked out and made me put on my stinky gym shorts. So, I spent the entire day smelling like sweat. I tried explaining to her the irony that my shorts showed way more skin than the jeans with the tiny hole, but she wasn't having any of it, just kept on quoting the 'no holes' rule. I had had enough.

That night, I decided to make a statement. I took an old pair of jeans that barely fit and rubbed some sandpaper on the knees until I had two decent-sized holes. The next day, I deliberately sat right up front in her class with my holed jeans, because I knew that would put me on the spot. And sure enough, she called me out.

Without a word, I calmly got up, returned to my bag and fetched a pair of scissors. While the whole class watched, I cut off the jeans at the holes, turning them into jean shorts—jorts! I sat back down quietly. The teacher was livid, but there was nothing she could say against my hole-free jorts.

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48. He Had Himself Covered

My boss approached me saying, "You need to fill in for Jo this upcoming weekend, both Saturday and Sunday since everyone else declined." I inquired, "How can you be so sure I'll agree?" His reply was, "You have no choice, there's no one else."

I retorted, making his mouth fall open in surprise. "You're mistaken; there's still me. But, I'm resigning. So now, truly, there's no one left." His stunned silence and the look on his face were truly unforgettable. I stayed there for a brief moment, then told him, "I'm leaving now," and I just walked out.

Thankfully, I had secured a better job just the day prior. This moment stands out as one of my most cherished memories.

Nightmare Co-Workers factsShutterstock

49. Their Boss Thought They Wouldn’t Notice

My best friend and I both worked at this tiny company. The person in charge was awful (imagine Miranda Priestley from The Devil Wears Prada, only with signs of early dementia). One day, my companion managed to land a fantastic new job and handed in her resignation. 

Trying to make her stay, our boss did something that truly pushed my buttons—she offered her my position. I can't understand what on earth made her think my friend would agree. It was no secret that we were buddies. Heck, we had even scheduled the same week off for a vacation together.

Naturally, my friend declined. Following that, I decided to quit just a week later, explicitly informing my boss about the reason. Of course, there were countless explanations, but that underhanded trick was the tipping point for me. Until that moment, she had no clue that I was aware of her machinations. 

The surprised expression on her face was something to behold as she desperately tried to concoct any form of denial.

HR interesting stories factsShutterstock

50. Good News And Bad News

I used to be an employee at a humble, bi-weekly newspaper in a small town. During my time there, I discovered the troubling fact that the editor, publisher, the town mayor, and the county commissioner, among others, were unlawfully dipping their fingers into the town's tax coffers. 

When I addressed this issue with my boss, he threatened to ruin my reputation if I leaked this scandal out. Little did he know, he was stirring up trouble with the wrong person.

I decided to go to the town’s television station and spill the beans. Their journalists investigated this murky affair and exposed the entire scam. When these newshounds got awarded for their groundbreaking story, my name popped up in the list of contributors, too. 

I have yet to land another job in journalism, but, boy, the sense of justice was truly gratifying.

Dark Family SecretsShutterstock

Sources:  Reddit, Quora


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