People Share Stories About the Worst Bosses They’ve Ever Worked For

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Bosses are who we turn to if there’s a problem at work, but they’re also the people who discipline us when we don’t do what we’re supposed to. Sometimes though, they go above and beyond and not in a good way; some bosses are so horrible that they’ve made their employees quit, get into trouble, cry and literally want to give up on life.

They’re insensitive, care only about themselves and never admit when they’re wrong. And we have some stories that show just how bad these men and women can get. If you’d like to read about some of the things people have gone through with some of the worst bosses in the world, just keep scrolling.

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41. Banning People From Making Friends

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Our boss actively tried to ban friendships. If co-workers became friendly, she would schedule them so they would NEVER see each other. “You’re here to work! Not to socialize!” She also banned everyone from coming into the workplace when they were not working. It was a pub. She banned socializing in a pub.

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She became insanely paranoid when she learned four people were in a WhatsApp group. She said the only reason people who work together set up group chats is because they wanted to talk trash about her. She was actually kind of right.

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40. “Who Are You? I Don’t Work Here”

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I worked at an amusement park, and one man wanted his child to go on a ride despite not having any tickets. The man was screaming at me for 15 minutes when I saw my boss walking by. I told the customer he could talk to the manager and proceeded to call my boss over.

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My boss looked at me and said, “Who are you? I don’t work here.” He began to laugh and walked away. I had to deal with that angry customer without any help.

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39. My Boss, The Culprit

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I’m a lifeguard and I usually put my lunch with my name on it in the lifeguard station’s fridge. When I went on my lunch break, my food would disappear.

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Thanks to some fellow guards and a video camera, I soon found out that the culprit was none other than my boss, who had been stealing my food for the past two weeks.

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38. An Emergency is an “Unplanned Vacation”

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I had a boss who refused to let me take an “unplanned vacation” to see my grandma on her deathbed. I quit on the spot.

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It was strange because up until that incident, she was really cool and laid back. But when I asked for the weekend off to go visit my dying grandmother, she snapped and lectured me about how I needed to “plan” my “vacation” better.

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37. No To Christmas Party, Yes to Vacation

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Our boss canceled the Christmas party and Christmas bonuses for the whole company because we “didn’t have the money for it.”

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I found out later that the CEO and CTO used company funds to take a week-long ski vacation in Whistler instead of doing something nice for the employees. You better believe I spread that evidence around the office.

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36. The Queen of All Evil

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I had just started working as a waitress for a restaurant. My boss had been working there for a very long time and had a great relationship with almost all our customers. In the beginning, she was very sweet and helpful, but toward the end, she became everyone’s nightmare. Little did I know, she had a history of sleeping with many customers, despite the fact that she was married.

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She also had been stalking our coworkers’ social media to find reasons why we should be fired; she was successful with about three people. She and my other boss then got into a disagreement and she decided to quit. But before she did, she badmouthed the entire management team and company to every customer she had to chance to say it to. It’s safe to say we are very happy she is gone now and my workplace is much better off without her.

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35. No Tipping

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I was working in a restaurant that switched from fast food to half full service, so I would refill water, bus dishes, etc. but customers would order food at the counter and carry the tray to their table. Once we switched, customers would occasionally leave tips out on the tables for us, which was awesome since we were doing twice as much work with no pay raise.

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But then the manager put signs on all the tables saying “no tipping.” Maybe it had something to do with taxes or payroll, I don’t know, but at the time, it just felt like a huge crap move.

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34. The Flirtatious Texts and Photos

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I once worked for a woman who would send me to get her some bubbly in exchange for her working my shift. She would give me various retail bags to put them in so I could sneak in what I had bought for her. On the plus side, she offered to buy me whatever I wanted!

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To top it off, she would flirtatiously text her boyfriend and leave her phone openly lying around. On more than one occasion I would see text or photos that would downright make me cringe!

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33. It Was “Accident”

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We had a bathroom at our store that our boss liked to keep to herself and didn’t want to share with the customers, so she always had a sign to close it off saying it was ‘broken.’ One day, a customer shopping asked me if she could use the bathroom; I was prepared to tell her, no, but then she pointed out that she was pregnant and that she had to go so bad that she was about to urinate herself. My boss wasn’t in yet so I let the customer use the bathroom.

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As soon as she walked out from the bathroom, though, my boss, with perfect timing, got to work. She found out it was me and yelled and screamed at me in a store full of customers. I had never been so angry and embarrassed in my life, but had to hold my tongue. Later that day, I could still feel her hostility; she ‘accidentally’ threw something away and had me jump in the dumpster to go get it. After crying twice at work, I’m grateful to say I quit that week.

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32. The Boss With Trust Issues

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I worked at a grocery store and booked a day off three months prior because it was my high school grad. I was told,  “Graduations can’t be on a Tuesday and if I didn’t show up to work, I would be fired.”

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The same guy also texted me after I called in sick for the first time, saying, “Nice try faking being sick. I better see a doctor’s note on Monday.” I got a doctor’s note and had to spend $20 on it.

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31. It’s Unhealthy to be a Vegetarian

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I once had a boss who would lecture me if I ever looked tired and blame it on the fact that I was a vegetarian. Then she would spend the following hour explaining why she didn’t agree with my lifestyle.

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She believed it was ‘unhealthy’ to be a vegetarian and was never shy about making me feel bad for my choice. Needless to say, I didn’t last long at that job!

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30. The Total Jerk

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Most people don’t like serving, but my boss was a total jerk. His moods changed within minutes. Sometimes he was tolerable, other times he yelled at his employees in front of customers, threw plates through the kitchen window at the cooks, and barked at customers when they asked where to sit. 

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He also told me that I should smile more (but never said the same to the male staff) and insinuated that I look better with makeup. He also fired someone for taking out the garbage too early. He was such a jerk. Needless to say, I found another job and quit within five months.

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29. Matchy Underwear Contract

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Our old supervisor would pick on certain members of staff and give them disciplinaries for silly, made up reasons. One guy (overweight and a bit scruffy) was disciplined for wearing grey scruffy boxers that you could see when he bent down.

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She claimed it was in his contract that he had to wear black underwear to match our work uniform colors. At the same time, she always has a thong half way up her back.

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28. What a Nice Response!

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About a week ago, I had to email my old boss to get some tax stuff. After about a week, they still hadn’t responded.

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So, I sent them another email asking if she had received my last email. The response was priceless! “I am vomiting. Thanks for the email. I will get back to you.”

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27. An Unusual Assist Request

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I worked for the federal government. My boss wanted me to assist him with stealing a $2,800 laptop for his daughter to take to college so he could save some money (he was paid about $168k a year).

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I refused and he fired me. I filed a complaint which was promptly ignored by his superiors. I lost a $100k-a-year job because of this sociopath. What makes it worse is that he was shortly thereafter caught stealing from the government, but was not fired because he had been there for more than 25 years and his boss “did not want to ruin his career.”

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26. This is So RUDE!

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My boss used to tell me and another coworker that he hadn’t showered in days and wanted us to make sure clients didn’t get close to him at events.

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He also fired the girl who was in her third trimester of pregnancy three days before her maternity leave was supposed to start.

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25. No Exemption

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The summer after my senior year of high school, I worked at a day camp that was run by my school district. It was a very popular job for students in my high school and there were maybe a dozen employees who were in my graduating class. In mid-July, a classmate of mine passed away (he had been fighting cancer since he was in the second grade, and a number of us had been by his side the 10 years since) and the funeral was on a weekday. Our boss wouldn’t let us go. He flat-out refused to allow any of us to miss work to attend the funeral.

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After several meetings, pleas, and finally [all of us threatening] to quit mid-summer, he agreed to allow us to go. As an apology, he rented a bus to take us all there and bring us back (also so he could make sure we weren’t out too long). The hour and a half we were gone was deducted from our paychecks.

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24. My Words Don’t Matter

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I was the only female manager at an independent college bookstore. I was hired as the merchandise manager, but I was never allowed to order any merchandise for the store because the general manager would never let me have any say or take any of my suggestions of what to order.

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He would constantly undermine me by asking the sales associates what they thought of a product rather than consulting me, even though I was hired to do that job! I was told multiple times I wasn’t very creative and that I would never get a raise! 

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23. She Got Away Scot-Free

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I once worked at a company where the CIO (Chief Information Officer) sideswiped a woman’s car as she pulled into a parking space. The woman whose car was hit got out and stood beside her car to see what damage was done. The CIO got out of her Mercedes and brushed right past the woman without so much as speaking to her. She completely ignored her and walked away. Even with witnesses.

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The woman that had her car damaged had to go to the HR department and the company cut her a check for damages (the actual business paid for it – not the CIO); she got away scot-free without ever admitting anything or paying a thing.

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22. Girls To Entertain, Guys To Do His Work

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I worked at a liquor store and the store manager was the biggest loser I’ve ever known. He hired two kinds of people: pretty girls to entertain him, and guys to do his work for him.

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He was a disgusting slob and NO girl he hired EVER wanted to touch him. He threatened to fire me behind my back to one of my other coworkers (in an effort to intimidate the coworker). I caught wind of it and reported it to the district manager and he changed his tune real quick after that.

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21. The Complete Insensitive

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One of my managers was a complete brat. A friend of mine who I worked with had a miscarriage and called in to tell our manager she wouldn’t be in because she lost her baby and was about to go into surgery later that day.

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Well, our manager told her, “Well you know you work tomorrow right? You need to come in or find someone to cover your shift.” She was completely insensitive to my friend’s situation and later that day, my friend’s mom went up there and went off on her in front of EVERYONE. She deserved completely deserved it.

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20. Very Unappreciative

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My boss would try to change my set schedule at the last minute and would be angry when I couldn’t change my plans suddenly. 

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During busier times of the year, I would end up working longer hours and was never recognized or compensated for it. 

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19. Some People Just Can’t Take Constructive Feedback

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My company had an (anonymous) employee survey this past year and when the results (which reflected negatively on the GM/manager) were revealed, everyone had to sit through a four-hour meeting where, line by line, our GM asked “Why do 50% of you feel this way” or “why do 60% of you not like this?” No one really spoke up (it was supposed to be anonymous) so we were told that if we felt that way, this is why our feelings were wrong.

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By the end of the four hours, most of us were like, “Was that supposed to deter us from rating negatively next year…” So we really didn’t have to sit through a 4-hour meeting about how we’re not right in feeling the way we did?

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18. Band-Aid for A Bruise

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I had work the morning after I had been hurt, and when my boss came in, she noticed a red mark on my neck. I guess she thought it was a hickey and told me I was a brat and to put on a turtleneck or cover it with makeup.

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When I tried to speak, she shut me down, telling me how it was disgusting and I was a disgrace. I started crying and asked if I could leave for the day. She said if I left I was fired. I told her I didn’t have a turtleneck and I am allergic to makeup, so she gave me a Band-Aid.

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17. Karma is a Witch!

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My boss seemed like a dream at first. We talked about our weekends, lives, boyfriends, etc. My first indication that something was up was when I saw that the schedules were missing names of people who were supposed to be working at my job. When I asked her what happened with the previous employees, she gave me some crazy stories about why they left. I let it slide, but shortly after, she started showing up less and less and putting her workload on me, on top of mine.

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My shift was usually from 9 a.m. to 7 p.m., and a lot of the time, I was told to stay later at the last minute. I got a 15-minute lunch if I was lucky, and a lot of the time, I went without one. I ended up quitting, and months after, I got a call from the government because I had done my taxes and apparently she had not put me (or anyone else) as an employee. She ended up in quite a bit of trouble.

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16. It’s Too Personal

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My boss called me into her office one day because she wanted to ‘catch up.’ We started talking, and before I knew it, she was calling me an idiot and trash.

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She then started to bring up my personal history of being adopted. She told me I had to get the heck over it and let go of all the demons that are swirling around my head. She also told me that it was going to become mandatory that I start going to church. When I started getting upset, she told me to get over it and get out of her office and go back to work. I should also mention that my boss is my aunt.

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15. The ‘Naughty Dog’ Lover

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I worked at a children’s clothing store at the mall in college. My boss was nuts, but I kept working there because the hours were good. She walked in every day yelling, “Are you freaking kidding me!” Once, she came in an hour late and said it was because her boyfriend was being a ‘naughty dog.'” 

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Another time, she asked my male coworker what a certain infection looked like, just assuming he would know. My friend was unemployed and desperate for a job, so I got her an interview. She came in and my boss was on the phone crying. She had just got a phone call from her doctor saying that she did indeed have disease she had asked my coworker about.  

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14. Her Hobby is Making Us Cry

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An ex-boss of mine used to breathe down our necks about everything. When she used to discipline us, there wasn’t one person that didn’t cry. Of course, we all followed the rules, but if you didn’t do it her way, it was a no go and she’d get very angry.

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She’d watch you to make sure that you were doing your job right. When you did something wrong, she’d lay into you, start yelling, thus making a person cry. She disciplined me one time when I barely did anything wrong, and she hoped to make me cry, but she never did. Everyone was so beyond happy when she finally left. This woman was definitely the biggest control freak I’ve ever met.

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13. The Crazy Manipulator

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My boss was so paranoid that she would complain to HR that her employees did not have her back and looked for ways to force them to leave the company.

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And if that did not work, her favorite ploy was to fire an employee for a single event of actual or construed wrongdoing; this worked even when the employee(s) in question had stellar performance records. Luckily, I survived her crazy manipulation and have moved on.

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12. Fashion Show at Work

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One time I walked into my boss’ office to find him shirtless. 

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When I ran back to my desk in shock, he proceeded to strut for me in a fashion show with different jeans, asking me how they made his ‘goods’ look and if they were too tight or too loose.

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11. Get Some Quiet Shoes

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I had to walk past my boss’ office several times a day to get to my office. The floor was flagstone, and therefore one could hear when someone was coming. He could hear me, especially because I wore pumps very often.

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One day, when I got back to my computer, I had an email from him saying, “Please get some ‘quiet’ shoes with your next salary.”

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10. “The Girls’ Job”

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Our manager would often make cleaning and maintaining the sales floor a girl’s job and would never ask the male employees to do anything like that.

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Also, there was a time when a sales rep for a lingerie line came in and gave the female employees samples. The manager asked the girls later how they liked the samples in an email and in person! It was just very inappropriate.

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9. Some Gross Tasks

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I was the office manager for a farm; my boss was the 27-year-old woman who owned it. Being the office manager, you would think you’d be doing office tasks. Well, I wasn’t allowed to do office work without her because she didn’t like my handwriting and wouldn’t allow me to write on things. 

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I would constantly have to clean horse stalls in my office clothes and take care of 2,000-pound animals. She wouldn’t get out of bed until after 11 a.m. when I would start at 9 a.m. (her apartment was in the barn). Some days I would work until 2 p.m., and she wouldn’t have gotten out of bed the entire day. She would make me clean her apartment and clean up after she ate breakfast and other gross tasks.

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8. Changing Plans a Week Prior

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My boss would turn over a PR event for me (or another employee) to plan and coordinate.

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After everything was planned, she would, about a week prior to the event, without discussion, change all decisions and do it her way and if it fell flat, she would blame the person she placed in charge of the event originally.

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7. I Work, He Party

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Working at a cafe, my boss would tell me he was running to the store and would come back an hour and a half later smelling like he’d been drinking and smoking cigars.

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It turns out he had been leaving me there to do the work of two people while he was at the bar for an hour. This was after he made the schedule on a day-by-day basis and ‘forgot’ to give us our tips.

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6. The Phone Smasher

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Recently, there was a caller on the phone saying my boss did not appear for an appointment they had that day. My boss was right next to me, so I handed him the phone and said it was for him.

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He took it, yelled at me, smashed the phone against the wall and ran out of the office.

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4. Being Used in The Weirdest Ways

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One of my first jobs out of college was when my boss took me under her wing. It took me a long time to finally realize I was being used and in the weirdest ways. She made me house-sit for her for an entire week during my first month on the job, and I had to sleep there every night. It was so uncomfortable for me! 

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She would get weirdly offensive if anyone would comment on my age or physical looks. She also got personal information out of me in a strategic way, then ended up using those things to fire me nine months into the job.

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3. Paying Me To Become The Parent

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When I was in college, I worked as a nanny and they seemed like a nice family at first. The job began with me taking the kids to school in the morning; trying to be fair, I said they could pay me $10 an hour. Taking the kids to school in the morning turned into me waking up early to get them ready for school, picking them up in the middle of the day if they got out early, and essentially becoming a full-time nanny. My pay never went up, even though my responsibilities did. I was pretty much raising my boss’s kids.

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I read the parent newsletter and when the early dismissals and special days would be, helped them practice their instruments — you name it, I did it. Sometimes I would come over at 7 in the morning and my boss would tell me she didn’t need me that day (I had to walk to the apartment building in all types of weather), and sometimes on a day where I was expecting to work for one or two hours, she would ask me to work five! She was so unpredictable and so frustrating, but I needed the money so I ended up working for them for three years.

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2. “Sit Your Little Butt Down, Little Girl”

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I was a pattern maker for a large manufacturer. My boss was a glorified sewing manager who got promoted out of desperation. One day, she left us a correction to a pattern with specific details and then a verbal explanation. She purposefully kept me out of the fitting so she could have control, although I was the one ultimately doing the changes. After more than half a day of corrections, I realized the adjustments were not feasible. I investigated her notes to find the corrections were for the wrong body.

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I proceeded to explain my findings to her and offered to come in early the following day to redo what had been done wrong. She then grabbed me, pushing me into my chair, and got in my face, yelling, “Sit your little butt down, little girl, and don’t get up till you are done!!” I took a better job the following week.

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1. Well Done Self

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I once had a retail manager who sent out a memo that we worked so hard and did such a great job this month that she gets a bonus.

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That went over like a lead balloon.

Dale Cooper

Dale Cooper

Spent 10+ years in corporate finance before I realized how much more I enjoyed writing and advising people on how to achieve financial freedom. We all have different goals, what are yours?