Unfortunately, there’s no shortage of bad bosses. Some simply aren’t meant to be supervisors. But some make conditions at work so unbearable, their employees would rather resign and live off their emergency funds. In fact, 44% of workers who’ve left a job said a boss was the primary reason they quit, according to a survey by human resources software company BambooHR.
It might seem extreme to give up a steady paycheck to avoid dealing with a bad boss. But if you only knew what some employees have had to endure, you’d probably understand why they would want to quit — or maybe even find a new gig where they can work from home.
Click through to learn what it’s like to work with a bad boss and read about some of the worst things managers have made their employees do.
Last updated: Dec. 11, 2020
Change a Wedding Date
There are bad bosses. Then there are bosses who are so bad that they ask you to reschedule the biggest day of your life, as Rich* from the blog PF Geeks discovered. “I honestly wish this wasn’t a true story,” Rich said. “I once had a boss ask me to change our wedding date.”
He had just started a new job out of college and wanted to make a good impression on his boss. So when she asked him to reschedule his wedding, he didn’t know how to say no. Then she asked him to postpone his honeymoon.
“We ended up getting married on a Sunday, and I was back in the office on Tuesday,” Rich said. However, he’s actually somewhat thankful for her out-of-line request because it led him to discover the FIRE movement. Now, he and his wife are on a path toward financial independence and early retirement.
Wear Orange Prison-Like Jumpsuits
When it comes to country clubs, you likely expect the members — and even the staff — to dress a certain way. The last thing you’d expect is for the employees to look like they stepped off the set of “Orange Is the New Black.” But that’s exactly how Molly McCaffrey’s boss wanted her and the others working in the golf pro shop at a country club to dress while she was working there one summer in high school.
Her boss made the employees wear full-length orange jumpsuits – even in the 100-degree heat. “They looked like orange prison jumpsuits,” said Molly, who now is an author. “We revolted after a few weeks and went back to golf attire.”
Pose For an Awkward Group Photo
Some might consider getting to play golf for a work event a great job perk. But Josh* doesn’t have fond memories of the time when he, his female boss and two colleagues teamed up for a charity golf tournament. It was his first job out of college, and he was 25 years old.
After the tournament, his boss made him pick her up for a team photo of their golf foursome. “I was definitely uncomfortable grabbing her midsection and bare legs to hoist her for the photo,” Josh said. “The other guys weren’t really providing much support.”
Do Something Completely Outside the Job Description
Plenty of workers occasionally have to do things outside of their job descriptions. But some bosses take advantage of employees by asking them to tackle tasks that are in no way related to their jobs. This happened to Catherine Alford, a personal finance blogger, when she landed her first job out of college working at a museum.
She was hired as an educator to teach history lessons in schools. “However, the museum was underfunded, so one day the head of the museum asked me to rake leaves outside because he had no one else to do it,” Alford said. She wanted to be a team player, so she ended up raking leaves for four hours, which left her hands covered in blisters.
“I told my dad about it, and he made me go back to work and tell them I wouldn’t do that again,” Alford said. “It was hard to do but a good lesson to learn the difference between being a team player and being taken advantage of.”
Get a Doctor’s Note for a Single Sick Day
You might remember needing a doctor’s note when you were sick and had to miss a day of high school. But it’s probably not something you’ve been asked to do in an office setting. That’s why Chris was so surprised when his boss asked him to produce a doctor’s note to prove he had actually been sick.
Shortly after starting his new job, Chris had gotten food poisoning and needed to take a couple of days off work to recover. To get the doctor’s note his boss wanted, he had to collect a sample of the “effects” of his food poisoning — to put it politely — and take it to a lab for testing.
“Keeping the container clean on the outside and filled with enough sample on the inside was a task that required the purchasing of latex gloves and a strong stomach,” he said. Needless to say, he didn’t stay at that job long.
Share a Hotel Room — and a Bed — With Colleagues
Slumber parties can be fun when you’re a kid, but it’s not something you’re likely to do as an adult — especially not with colleagues. But that’s pretty much what Emma Johnson’s boss had planned for her and other reporters at the newspaper where she worked when she was in her early 20s.
“One newspaper editor expected reporters on a business trip to not only share hotel rooms but beds!” said Johnson, a journalist and author. When she refused to bunk with colleagues, a female senior editor took her aside and said that it was an honor that she was even invited on the trip — and not only was it not a scandal to share beds, it was necessary.
Johnson didn’t cave. “I didn’t go,” she said.
Decorate a Christmas Tree
Asking an employee to decorate a Christmas tree might seem tame compared with some of the other nightmarish things bosses have done. But when made mandatory, the task certainly can offend employees who don’t celebrate Christmas, as it did Risa*.
While in her early 20s, Risa had been hired for a job at a law school. Shortly after she started work in December, her boss asked her to decorate the office Christmas tree. “As I stood in front of the tree with a box of tinsel and ornaments puzzling over what to do, I finally told my boss that I was Jewish and had never decorated a tree before,” Risa said. “I asked her how you do tinsel. She was astonished.”
Sell Shoddy Products
It’s tough to sell a product when you know it’s no good, but for Ben*, that’s what his boss made him do. Ben’s job was to sell an email marketing software program to a client even though the program wouldn’t be ready by the time the customer needed it. Ben knew it wasn’t the best solution for the customer and that it was an incredibly overpriced product.
“The boss assured me it would be ready and made the impression that if I didn’t sell it, then my job would be in jeopardy,” Ben said. “I unwillingly sold it with hopes that my intuition was wrong, but it was right, like usual, and the client ended up mad and with a crappy email software.” After that, Ben found another job and learned to trust his intuition, he said.
Do Something Unethical
While working in the insurance industry, Michelle* had a boss who asked her to find an artist to create some designs for a side project he was working on. When she gave him the bill for the designs, he said the company should pay for it. When she reminded him that the work was for his side business, he denied that he’d said that.
Worried about being part of a fraudulent setup, Michelle called the president of the company that night and said she needed to speak with him the next day. Fortunately, when she told him and the human resources department that her boss wanted to use company money to pay for his own project, they believed her and fired her boss. “What I found out later is that he was going to take all of these designs and start his own competing company,” she said. “And I wasn’t going to be a part of that.”
Go To a Drunk Customer’s Home To Remove a Clothing Security Tag
One night when, Laura* was working the late shift at a department store, she got a call from a customer who’d purchased an expensive pair of jeans earlier that day and discovered that the security tag was still attached. He wanted to wear the jeans that night but couldn’t come to the store because he’d been drinking at his bachelor party.
Laura, who was a department supervisor, apologized for the error and said the store would refund him 50% of the price he paid. But she said he would have to come to the store for them to remove the tag and give him a refund. He kept calling and calling until Laura’s manager intervened. Her manager said that she needed to go to the customer’s house and remove the security tag herself.
“I said, ‘We don’t even know who he is, and it’s late, and it’s dark outside, and it’s a group of very drunk guys having a party! I am not comfortable doing that,” Laura said. “She didn’t care, said it was my job, and I had to do it because the other two managers — both men — had kids they needed to get home to, so it was on me.”
So Laura went. The drunk guys at the party were obnoxious and a few tried to grope her. “I got out of there as fast as I could, and when I got back in my car, I started crying,” Laura said.
Come Running to a Cow Bell
While working at a television station selling local airtime for advertisers, Kym* had a boss who treated her and her colleagues like animals — literally.
“My general manager at the time wanted salespeople to gather together for on-the-spot meetings when he rang a cowbell,” she said. “Yes, a grown man rang a cowbell and expected other adults to come running to it. I put in my notice the following week.”
Take On an Extra, Unpaid Duty as a Chauffeur
While in college, Amanda worked as an instructor at a fitness studio. Not only did she teach classes, but she also became her supervisor’s chauffeur. Her boss was in her late 30s — and had had her license suspended for six months due to a recent DUI. She was also going through a divorce and didn’t want her husband to find out about the DUI. So, she asked Amanda to take her to work and pick up her two kids from school every day. “I didn’t say no, but I really wanted to say no,” Amanda said.
Her boss took it to an extreme one early Sunday morning when she called Amanda to pick her up after a late night of partying. She had gone home with a man and didn’t want to be there when he woke up. So she was wandering the streets, not knowing where she was, but insisted Amanda pick her up.
“For the next 20 minutes, I’m driving around in my pajamas,” Amanda said. “She’s describing her surroundings. She kept describing a church. I remember her finding a church and waiting, hoping I would get there before people started showing up for church.”
Train an Intern for a Position the Employee Wanted
While working on Wall Street in graduate school, Sandy had a boss who abused her power on several occasions. For example, she made Sandy* stand in front of her glass office door to block the view of others while she put pantyhose on … because she didn’t want to go to the bathroom to do it. This boss also made Sandy go to her apartment, get the pillow from her bed and mail it to the hotel where she was staying.
The absolute worst, Sandy said, was when her boss made her train an intern for a position she wanted but didn’t get because she supposedly needed more training for it. “You know, the one I trained the intern on how to do,” she said. The intern happened to be the child of her boss’s friend.
Pick Up a Colleague’s Dead Dog
Sometimes a boss recognizes the error in their ways, as Jeannine Grasso once did. One of her employees had gone home for lunch and discovered that the family dog had died. She called Grasso and was hysterical because her parents were out of town and she didn’t know what to do. So Grasso asserted her authority to get help in dealing with the situation.
“I asked, and kind of strong-armed one of the male staff members to come with me over to her house, wrap up the deceased dog in a rug and carry him to the back of her van so she could drive him to her vet,” Jeannine said. “I hope I didn’t scar the male staff member for life.”
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Katie Wudel contributed to the reporting of this article.
*Last name has been withheld upon request.