35 Workers Who Outsmarted Their Toxic Bosses By Following The Rules Too Well

Rules are necessary to keep any larger organization functioning well. It’s impossible to meet deadlines, innovate, and provide quality products and services if you don’t have discipline. That being said, there are limits…

Too much of a good thing, like order at work, can be horrible for your bottom line and your staff. Some bosses are so obsessively controlling people’s behavior and dress codes that it stifles creativity, beats down company morale, and pushes away top talent. And life’s too short to deal with petty tyrants.

In a witty AskReddit thread overflowing with creativity, workers shared the most out-of-the-box ways that they pushed back against micromanaging, toxic bosses who tried to regulate everything about them. Scroll down for some awesome inspiration the next time you have to deal with a robotic, dictatorial manager.

#1

My brother in law worked for UPS for 17 years. He was a bit of a joker and was constantly getting in trouble for coming to work with crazy hair colors, or cornrows (he was a big Italian guy and was told it wasn’t appropriate). It was always something. But they couldn’t say anything about him wearing sunglasses. So his little rebellion was he would wear the most outrageous sunglasses he could think of. Ones shaped like giant red lips, guitars with the stems sticking up, purple ones with rhinestone hearts on them. Anything for a laugh. After a while people knew him by his glasses. If some one said they lived in a certain area I would say, “Oh my brother in law is your UPS man, the guy with the crazy glasses.” and their reply would almost always be something like,”Oooooh John. Yeah I love that guy, he’s hilarious.” He passed away 4 years ago, he was hit by a drunk driver while he was out walking one night. When we attended his funeral all of the guys from work came dress in their browns with crazy sunglasses on. His best friend gave his eulogy wearing a pair of neon green glasses three times the size of his face and the pastor even borrowed John’s guitar glasses when he went up to speak. After his funeral we counted, he had over 200 different pairs. What started as him being a pain in the bum to his boss ended as a tribute to his character in life of always wanting to make some one else smile.

35 Workers Who Outsmarted Their Toxic Bosses By Following The Rules Too Well

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#2

When I was working at an OfficeMax about 10 years ago, I was the only employee who didn’t smoke. Needless to say, everyone in the building took a 15 min smoke break 2-3 times a shift, and I got squat. One day, I asked the manager if I could have a “Clean Air Break”, and he was confused. I explained that since smokers can have their 15 min breaks 2-3 times a shift, I should be able to step outside and do the same without having to smoke. Irked my manager, but he knew he had to let me to avoid any discrimination.

35 Workers Who Outsmarted Their Toxic Bosses By Following The Rules Too Well

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#3

While I was in the Navy it was recommended that I get a extensive surgery on my ankle. My command felt that I “didn’t deserve a bunch of time off for a surgery” so they said they would approve it but none of the convalescent leave. They refused to sign ANY paperwork.

First thing I did was hit them with the regulation stating that they were required to respond to all requests within a certain amount of time (3 days I think). They responded with a “no”. So then I had Navy legal draw up paperwork (with accordance to regulations) that my command would be responsible for 100% of my medical care if they did not abide by doctors orders. I then let them know that would mean that ALL of my medical care would then be handled by civilians and the command would be responsible for paying the bill out of their budget.

They approved my surgery, convalescent leave, and convalescent leave extension.

35 Workers Who Outsmarted Their Toxic Bosses By Following The Rules Too Well

Image source: anon, Pixabay/Pexels

#4

At a former workplace, the dress code was changed. Men were no longer allowed to wear shorts. Women could wear skirts. I started wearing a kilt, because skirts were ok in the rulebook.

35 Workers Who Outsmarted Their Toxic Bosses By Following The Rules Too Well

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#5

I used to work for this small town, twice weekly newspaper. The editor/publisher, mayor, county commissioner and a few other people were skimming tax dollars. When I confronted my boss about it, he told me he’d blackball me if I said anything.

So I went to the local television station, tipped them off and they uncovered the story. When they won their awards, my name was added to the list of reporters.

I still can’t get a job as a journalist, but darn if it didn’t feel good.

35 Workers Who Outsmarted Their Toxic Bosses By Following The Rules Too Well

Image source: anon, Suzy Hazelwood/Pexels

#6

Company dress code allows women to wear open-toed shoes, so long as they are leather. The dress code does not allow men to do the same. A few years back, I started wearing leather sandals during the warmer months. A few managers mentioned to me that I was in violation of the dress code and I pointed out that my shoes would be considered acceptable if I were a woman and that it’s gender discrimination to deny me the ability to wear something that is considered ok on someone of the other gender. Haven’t heard any comments or problems since.

35 Workers Who Outsmarted Their Toxic Bosses By Following The Rules Too Well

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#7

I went to a Pentecostal School even though I, nor my family were Pentecostal. They made me get haircuts all the time and I liked having long hair and sideburns. One day they gave me the ultimatum: I had to shave my sideburns, or they would do it. I then told the Principle that I wanted a tattoo. I was told that I could not, because the school’s rules were Biblicaly based, and then she read Leviticus 19:28: *Do not cut your bodies for the dead or put tattoo marks on yourselves. I am the LORD.* I told her to please read the verse above, which read, *Do not cut the hair at the sides of your head or clip off the edges of your beard.* I got to keep my sideburns.

35 Workers Who Outsmarted Their Toxic Bosses By Following The Rules Too Well

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#8

Boss told me “you have to cover X this upcoming weekend, both days, since everybody else said no.” I said “How do you know I’ll say yes?” He said “you have to, there’s nobody left.” I said, “You’re wrong, I’m left. But I quit. **Now** there’s nobody left.” He was speechless, his expression was priceless, I stood there about 10 seconds and said, “I’m walking away now” and left.

Thank God this happened the day after I had (secretly) secured a better job.

Probably one of my fondest memories.

35 Workers Who Outsmarted Their Toxic Bosses By Following The Rules Too Well

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#9

Not work but school. I’m a senior in highschool, and one day a bunch of senior guys decided to start up “tank top tuesday” every tuesday about 1/2 the senior guys would come to school in a tank top. Our school had no rule about tank tops except that the straps be at least two inches thick so we didn’t anticipate any problem, especially considering girls at our school wore tank tops all the time. After the first day, the school announced that boys were no longer allowed to wear tank tops, when questioned as to why, they claimed that visible armpit hair was a distraction that inhibited learning. The following Tuesday, we all went to school wearing tank tops and sporting shaved armpits.

TL;DR- School claims guys can’t wear tank tops because armpit hair is distracting. Next day, half the senior guys show up in tank tops with shaved armpits.

35 Workers Who Outsmarted Their Toxic Bosses By Following The Rules Too Well

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#10

When I was in grade 4, pizza was sold at lunch for $1.50 a slice

I saw a business opportunity and went to the Little Caesars a stones throw away from the school and bought 10 Hot’N’Ready 5$ pizzas and sold the slices for $1.00 (1.25 on friday).

When the school told me I couldnt sell pizza on school property, I moved my office to my aunts house which was next door, so every day at lunch the kids would walk to the neighbours front yard, buy pizza and come back to school :)

I was making a tidy sum every day.

35 Workers Who Outsmarted Their Toxic Bosses By Following The Rules Too Well

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#11

When i worked at bestbuy, the dress code was black shoes, pants, belt and tucked in blue shirt. never wore a belt nor tucked my shirt in, because as a chubster, when kneeling and organizing dvds on the bottom shelf, shirt comes untucked, and the belt cuts into my belly (first world problems huh?) anyways, my boss would constantly freak on me for not having my shirt tucked in, and finally got on my case for not wearing a belt either. so i checked the dress code, found it said “belt if there are belt loops on the pants” or something, so i found an exacto knife, and cut off my belt loops. the next morning, i come in, and she says “WHERES YOUR BELT?”, i grinned at her and said “WHERES MY BELT LOOPS?” and gave her the biggest grin i could muster. one of my finest moments.

35 Workers Who Outsmarted Their Toxic Bosses By Following The Rules Too Well

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#12

Not work related, but school. In HS I wore a freecondoms.com t-shirt to school. I was called down to the principals office after 3-4 hours(my cool teachers thought it was awesome in the AM classes) and was told I was promoting abhorrent behavior. I posited that I was in fact trying to prevent unwanted pregnancies. I lost my fight and was told I had to leave if I did not have another shirt.

Rather than leaving I put a sticky note over the ‘m’ in condoms and spent the rest of the day harassing faculty about fantastic lakeside condos that I was giving away for free.

35 Workers Who Outsmarted Their Toxic Bosses By Following The Rules Too Well

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#13

My boss went away for about 3-4 weeks for a conference, and while he was away, a workmate and I had an idea… a george foreman grill, and then we’d go to the deli and grab stuff for lunch: hamburgers, lamb chops, pork, steaks etc.

We did this every day for over a month, and when the boss got back he put a stop to it, with the exact words “I don’t want that thing inside the office”.

So we took it to the shared kitchen area on our floor (We rented a suite).

When he got angry at that, and said “I DONT WANT IT ON THIS FLOOR”, we took it down to the underground parking area and used the power outlet at his parking space while he was out at lunch. he caught us because he was coming back from lunch with a business partner (in the car with him) and we were hunched over a tiny George Foreman grill making hamburger patties. Imagine 3 IT guys, crouching on the ground like cavemen, in a poorly lit underground parking lot, cooking hamburger on the concrete floor. Yeah, it went over about as well as you would think.

If he didn’t specifically use the words “Take that home or I will break it and throw it in the trash” our next step was to use the power point in the parking lot of the church directly opposite the building (and facing his office).

35 Workers Who Outsmarted Their Toxic Bosses By Following The Rules Too Well

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#14

Used to work at a TV station. Absolutely awful management and horrible bosses. Complained about it to friends all the time. Some would even ask me on facebook about my job and I would reply- but I knew I could get fired for speaking ill of the company. So I read the HR Handbook and found out as long as I don’t specifically name the company, I can’t be fired for it. So, about a month later, I realize I can’t take this anymore and post on facebook how terrible my job is, never mentioning the company by name. They fire me a day later, I gladly walk out of that building and into a lawyer’s office- got $17,800-my yearly salary (seriously). Feelsgoodman.

35 Workers Who Outsmarted Their Toxic Bosses By Following The Rules Too Well

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#15

Back when I was working and attending classes I would go stright from campus to work, getting me there anywhere from 10-20 minutes early before my shift. On occassion my boss would ask me to help him out with something before I clock on, putting something away or answering the phone. Over the span of a couple months, this evolved from ‘occassionally’ to “every day your shift starts when you get here”.

After doing this for a couple weeks (still clocking in at my usual 3pm) I decide that if I’m working for a few extra minutes each day, I’m gonna get paid for it. I did this ONCE, and I didnt make it an hour into my shift before my boss is screaming at me and throwing down the employee handbook saying that I’m only allowed to clock in 5 minutes before and after my scheduled shift.

Needless to say, I made it a point to not check in until 5 minutes after my scheduled shift every day, no matter how early I was. Fast forward 3 months and my boss gets fired. He got what was coming to him.

35 Workers Who Outsmarted Their Toxic Bosses By Following The Rules Too Well

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#16

My father was working in a post office in the early 80’s. It was an unusually hot day with ~85°F inside. There were no fans available so it was crazy. Men weren’t allowed to wear shorts, but dad came to work wearing shorts which covered his knees and a part of his shin, figuring he was fine. He wasn’t, and his boss sent him home to change. He returned in his grandfather’s bonjour from the late 19th century. Top hat and all. The boss kept asking if it wasn’t a little hot in that suit but he said he was fine.

35 Workers Who Outsmarted Their Toxic Bosses By Following The Rules Too Well

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#17

I used to work at a lingerie store as an assistant manager so I had to dress nice and look professional. All the other girls wore huge heels and always ended up complaining about how sore their feet were at the end of their shift and I always wore flats to avoid having sore feet. They were still nice, stylish shoes, but they didn’t have towering heels on them. My manager always used to get mad at me for not wearing heels and tried to claim it was part of the dress code. I looked it up and showed her that it didn’t say anywhere that I had to wear heels, just that I had to wear acceptable work attire or something like that and she tried to tell me it was an out of date dress code or something so I would tell her that she should get an updated one then. Eventually, she brought head office into the argument and the provincial manager was trying to tell me to wear heels to work. I told them they would have to pay me more than minimum wage to ruin my feet. I did not get a raise and no one ever told me to wear heels to work again.

35 Workers Who Outsmarted Their Toxic Bosses By Following The Rules Too Well

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#18

A couple of friends of mine work at Wal-Mart. They found out that kilts are well within the dress code as long as they are the correct color. Drove their managers nuts. It’s been a year and absolutely no problems though. :).

35 Workers Who Outsmarted Their Toxic Bosses By Following The Rules Too Well

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#19

Similar to OP, but with a military swag to it.

In the Navy you must always have a white t-shirt under your uniform. I had a Senior Chief who constantly checked if your t-shirt was not visible and required that it bee seen. I checked the uniform regs and found that while in a working uniform you can wear a V-neck tee. Started wearing them and he took notice as soon as he saw me. I told him that the regs allowed it. He scowled and his only comment was, “One for the blue shirts” and walked away. Then he hammered me for every reg violation he could find. Smart people never win. At least not in today’s Navy.

35 Workers Who Outsmarted Their Toxic Bosses By Following The Rules Too Well

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#20

I worked at a Petsmart 5 or so years ago, in the “Pet Hotel” where animals were boarded while their “Pet Parents” (owners) went on vacation. Everything I did was in the back. No customers ever saw me. Just the dogs and kitties.

But my boss would always get onto me for forgetting my belt. So one day she was particularly mad at me about not having a belt despite the fact that I was picking that shift up last minute for someone who was sick. I pick up a dog leash, put it through my belt loops, and say “Well, it appears I now have a belt.”.

35 Workers Who Outsmarted Their Toxic Bosses By Following The Rules Too Well

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#21

My boss was the same way. I worked in the deli of a Hannaford and every day my boss would check to make sure my shirt was tucked. I found a loophole where if I wore one of the box-cut shirts (read: women’s shirts) I didn’t have to tuck it in. Got my three of those bad boys (girls?) and never looked back.

35 Workers Who Outsmarted Their Toxic Bosses By Following The Rules Too Well

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#22

LOL w*f people. It’s not your job, why do you care what he does?? Upvote for OP. Also at one retail store, we had to wear employee issued short sleeve shirts at work, even in winter. The clothing code stated we could wear something underneath the shirt but not over. I picked the brightest and most patterned long sleeve shirts I could find. Managers could say nothing.

Image source: KA260

#23

I work in foodservice. My job created a rule one day that one’s hair can not touch one’s collar. I have rather long hair, but I always kept it in a braid and we wear hats, anyways. I was informed of this rule about two hours before the end of my shift, and told that I HAD to comply IMMEDIATELY because I was breaking health code. I politely informed them that no, I was not. This was a store policy — but I would be happy to come in with my hair up the next day. I didn’t think this was unreasonable, it takes a while — not to mention pins/hair product/etc. to keep my hair up. Not good enough! NOW!! So I punched out for a break, bought rubber bands and floral wire, made 8 braids with the wire woven in, and stuck them in every direction. Boss saw me and began screaming. I calmly told him my hair wasn’t touching my collar.

TL;DR: Long hair not allowed to touch collar, created obnoxious hairdo within regulations.

Image source: deliverusfromEVI

#24

Again, more proof that there are millions of managers and supervisors in this country who have no business being in charge of anything.

Image source: amolad

#25

Not a job, but a school.

I went to a Catholic college and they didn’t allow members of the opposite gender to spend the night in a dorm room. I made a huge case that they were discriminating against heterosexuals, and that rule miraculously disappeared the next year.

35 Workers Who Outsmarted Their Toxic Bosses By Following The Rules Too Well

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#26

In the McDonalds I used to work at in PA it was the norm to for the managers to not clock out for their lunch breaks which meant if you had this huge rush you HAD to get up and help. Well, according to da rules of da state we were entitled to a lunch break off the clock undisturbed. Well one day I had enough and clocked out sat down and had some noms. The owner walked in and wanted to know why I wasn’t helping cause they were backed up so I put him on notice. And everyone left me alone after that and actually started doing it themselves lol.

35 Workers Who Outsmarted Their Toxic Bosses By Following The Rules Too Well

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#27

When Circuit City was still in business I worked in the warehouse. For whatever reason, they had a strict dress policy of khaki pants, this awful collar shirt that also had to be tucked in. This went for everyone, even warehouse. Like Kazin420, I discovered through an old warehouse employee guide (Shoved in a draw years ago and forgotten about) That as long as Warehouse employees had khaki colored shorts, with no cargo pockets, and a t shirt with a Circuit City logo there would be no problem.

Circuit City stopped making Circuit City t shirts long before I started, but thanks to a local Salvation Army, I was able to pick up, two Circuit City T shirts, and a quick trip to Target for some shorts, and my new uniform was set. My mangers were not happy about my appearance, claiming I looked sloppy and unkempt.

Even better, when the giant black dude (who hated his job, and just slept in the back, and talked on his cell phone all day) from the warehouse found out about this, he too had some old Circuit City t shirts, and joined in. Management hated us working together. I miss Circuit City.

35 Workers Who Outsmarted Their Toxic Bosses By Following The Rules Too Well

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#28

Worked at the front desk of a gym. Scanning key cards you know, being a watchdog as my boss liked to say. Only problem is when a dog gets hungry he doesn’t feel like doing much. Didn’t matter if it was a 12 hour shift or an 8 hour shift, no lunch break for the front desk, and of course no eating at the front. Well this dog happens to love sammiches, so I would tell all the people who asked me how I was doing that I was great, minus the fact that I haven’t eaten in 8 hours. I would proceed to tell them about the policy and encourage them to tell my boss to let me eat. Well after I had told enough people, I began eating my sammiches at the front. First time boss caught me mid bite and said funkybuttlovin what are you doing, I said eating my sammich. As luck would have it a daily member walks up and says you know boss you should let him eat up here, it’s not hurting anyone. Victory funkbuttlovin.

35 Workers Who Outsmarted Their Toxic Bosses By Following The Rules Too Well

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#29

At a former job, I had one particular boss who was a SoB. He asked me to join a particularly bad group (known for having to do a lot of thankless, low priority, and difficult work).

I used that company’s unique productivity/career-development tool, in conjunction with HR during a review to show him why I could not participate. HR agreed. He turned red.

Image source: SolomonGrumpy

#30

Yah my boss tried to do the whole “tuck in your shirt” bit at my work (I work at a call center too) however no where in the dress code policy it has anything about the shirt being tucked in. I asked my boss to show me where it is, and it was a no go. congrats.

35 Workers Who Outsmarted Their Toxic Bosses By Following The Rules Too Well

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#31

(This isn’t work related but happened at my old high school) I had a friend who is a year older than me, and he decided to do an experiment. He wanted to see how short short-shorts could be. He made his own jorts and every few days he would cut an inch or so off. It got to the point where he had to wear a speedo underneath otherwise people would have been able to see his balls. The only reason he stopped was because he was reported by a killjoy and told him to stop. Best experience ever. But the experiment was a success, he was testing to see if the dress-code was sexist towards girls and he proved it.

35 Workers Who Outsmarted Their Toxic Bosses By Following The Rules Too Well

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#32

Not me but a friend. Males are not allowed to wear shorts to work. Females are allowed to wear skirts. In protest he wore a kilt. He couldn’t fold it, I had to show him.

Image source: frakkingcylon

#33

Classic manager. Cuts all your pay, then is pretends to care about a menial thing such as shirt tucking so that the employees have a ‘small victory’ and care a little less about pay and are less likely to cause a stir. He’s an evil genius.

35 Workers Who Outsmarted Their Toxic Bosses By Following The Rules Too Well

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#34

Company I worked for was a large, nationally-known engineering, architectural, and surveying firm, and my position required me to work both in the office and on construction sites. Our office dress code required dress shoes, slacks, and a “collared shirt” at all times. On construction sites, we were required to wear steel-toed boots, jeans, and often long sleeve work shirts. Our former Vice President, a small Jewish man in his 50’s with a temper and a thick North-Jersey accent, used to berate people for violating company dress codes whenever he visited offices. Well, one day I was required to visit a site to perform inspections, and when I returned around midday, he was there, standing by my desk.

“Where’s your collared shirt?” he demanded.

“Excuse me?” I said, confused as I thought it was obvious to everyone that I had just come from a dirty, dusty construction site.

“Where’s your collared shirt?” he repeated, louder than before, and coming closer to jab his finger right at my shirt.

At that point, I got pissed, fired back with the first thing that came to mind: “Blue is a ‘collar’, are you blind?!?!” I snapped, pointing to my blue t-shirt.

He stood, stunned, and for the first time, had no comeback. After a moment, he gave me the biggest stink eye I’d ever seen, and stormed off to throw a temper tantrum at someone else. I was a legend for the longest time after that encounter, although to this day, I continue to wonder why I got passed over for every raise and promotion opportunity during my time there.

35 Workers Who Outsmarted Their Toxic Bosses By Following The Rules Too Well

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#35

You can’t have beer in the front seat of your car. So I went ahead and replaced the front seat with a back seat.

35 Workers Who Outsmarted Their Toxic Bosses By Following The Rules Too Well

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