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Jealous Boss Plots To Make Employee’s Life Unbearable, But Plan Miserably Backfires On Her

By Zach Brown
July 1, 2022
kurhan/Shutterstock

First Job Faults

man, adult, young
Photo by daha3131053 on Pixabay

Most people have had a terrible experience at their first job. The duties were typically awful; the shifts felt like they lasted an eternity, and the managers were usually atrocious. Crummy managers and dreadful jobs go hand-in-hand. You can’t have one without the other! Just ask our friend, “Drew.”

Drew was just a college student, but he was shaping up to be a responsible employee. He worked at an organization on his campus with a handful of other students, and they had their workflow perfected. Unfortunately, trouble started brewing when Drew’s manager was replaced with a new supervisor named “Karen.” Karen plotted to ruin Drew and the other students’ lives at work, but he wouldn’t let Karen prevail. Drew and his co-workers constructed a plan so genius it was guaranteed to humiliate Karen and strip away her credibility for a lifetime.

~

Moronic Micromanager

angry, mad, upset
Photo by RobinHiggins on Pixabay

Drew worked at a job on campus. For the most part, he loved his job and the work he was doing. His co-workers were a great team, his boss was understanding, and the tasks were easy enough. One day, his workplace took a turn for the worse when he got a new manager named “Karen.” Talk about a vibe killer! 

Karen was a micromanager to the core. In fact, micromanaging was a rule she lived by. She made massive changes to the workplace and expected busy college students to be able to keep up. Get a grip, Karen! Drew and his co-workers were troopers, and they dealt with the changes as best as possible. 

Drew took the unofficial position as “manager” to the other employees, and he knew how to advocate for them. After all, he knew how business was conducted and how the team worked best. Karen despised him for taking on the unofficial role because it was harder for her to go on a complete power trip. Despite pushback from Karen, Drew continued to call her out on foolish policy changes which only made the employees’ lives more difficult. 

Drew and the other employees had weekly one-on-one meetings with Karen to discuss ongoing and upcoming tasks. Drew was more organized than Marie Kondo, and he always went into meetings with a proper agenda. He updated Karen about any ongoing issues, asked questions, answered questions, and gave her time to discuss anything she’d had on her mind. 

Two weeks into Karen’s authoritarian-like changes, Karen told Drew, “What’s going on? You haven’t properly updated me all day!”

He replied, “What updates are you talking about? There hasn’t been much going on the past few days.” 

She started listing off instances where Drew “didn’t update her” when, in reality, he did.

Drew rebutted, “I have the agendas for the two previous meetings we had. Looking at the agendas, it appears we did discuss all updates.”

Yes, Drew! Come through with the receipts! 

She hastily replied, “Verbal updates are no longer acceptable. I need you to e-mail me any and all updates you have going forward.” 

Drew was extremely confused. He was a great employee and was doing exactly what Karen had told him to do. She wrote him up after the confrontation, but Drew was going to pick his battles wisely while he crafted a plan to get revenge on Karen.

~

Egregious E-Mails

Photo by Štefan Štefančík on Unsplash

After Drew’s meeting with Karen, he checked in with the rest of his colleagues. Everybody was in agreeance; the new work setup was terrible. The policies Karen put in place didn’t make sense at all, and their previous manager never went to the lengths Karen did to make them miserable. There weren’t any real rules regarding the e-mail update system, and everyone was generally confused. Drew decided the only way to move forward, was to take Karen’s “e-mail update only” rule to the extreme. 

That evening, he sent Karen a novel-length e-mail detailing every little task he did the previous two weeks. No harm, no foul, right? Drew was only doing exactly what Karen told him to. If Karen wanted to be updated every day, Drew would ensure her demands would be met.

In the following days, Drew e-mailed Karen as soon as he clocked in. The first e-mail he sent included all of his tasks for the day. As Drew began completing tasks, he updated Karen via e-mail. Stuck on something? Drew e-mailed Karen for that, too. He carbon carbon-copied her on every e-mail he sent. Finally, he sent her another at the end of the day which detailed all of the work he didn’t complete. Annoying? Yes. Time-consuming? Not at all! Drew had each e-mail in a queue patiently waiting to arrive in Karen’s mailbox. Drew being the absolute brilliant entrepreneur he is, ensured he also drafted the e-mails on company time. It was his job after all, and he was getting paid an extra hour per day simply to annoy Karen. You would do it too, for a check!

In the midst of receiving hundreds of e-mails from Drew, Karen didn’t realize he had also built a strong network. A network composed solely of her colleagues. I smell trouble brewing! 

Karen never replied to or acknowledged any of Drew’s e-mails. Everything was going according to Drew’s plan, and the sour supervisor was about to be taken down for good. 

~

Swept Aside Supervisor

Shutterstock ID: 2057885513, Photographer: Studio Romantic

A few months later, Drew’s department at work had to organize and host an event at the college. The event planning tasks were divided among Drew’s colleagues, and he was in charge of meal planning and parking vouchers. Drew sorted out the parking tasks first, then moved on to meal planning. A week before the event, he found out a multitude of the guests attending had dietary restrictions which needed to be recognized and catered to. Drew also was made aware of how a few guests would be attending in wheelchairs. He started to panic. The venue didn’t have enough handicapped parking spots, and the venue wasn’t wheelchair accessible in the slightest. Given the extreme importance of this information, Drew elected to e-mail his manager. 

Once again, Karen ignored Drew’s e-mails. He had a gut feeling she would disregard the information, so he carbon copied the e-mail to the department in charge of parking on campus and the event guest manager. Drew had to relay the information to Karen somehow, or else she would walk into the event completely clueless. The gluten-free and nut-free meals also meant the budget for meal planning was surpassed, and he thought it would be courteous to inform Karen of the budget increase. They didn’t have any one-on-one meetings scheduled before the event, so he attempted to schedule a meeting with her. In typical Karen fashion, she ignored Drew’s request for a meeting. He attempted to contact her in every possible manner to no avail. There was nothing else Drew could do. He decided to sit back, relax, and watch the chaos at the event unfold.

~

Drew’s Radical Revenge

furious, upset, person
Photo by RobinHiggins on Pixabay

Drew absolutely despised Karen. He didn’t agree with her managing style, nor did he agree with the tactics she built to make his life difficult. Although he really hated Karen, Drew wasn’t going to allow her ignorance to affect the event or his colleagues. 

He spoke to the university facilities and secured a wheelchair ramp for the event to make the venue accessible. Drew hid the wheelchair ramp in the back room until it was needed, so it would appear it was Karen’s fault the venue was not initially accessible. He also discovered five guests with food intolerances forgot to request gluten-free or nut-free meals, so the event wasn’t required to recognize their dietary needs. Those who put in a request for special meals would rightfully receive them, and the other guests who did not would receive a reduced food offering. Drew didn’t feel a morsel of regret. Ultimately, Karen was supposed to be the person helping with these tasks but completely ignored him. 

Finally, the day of the event arrived. The guests who arrived in wheelchairs were lined up and stuck at the entry, unable to access the event. Given Drew was technically in charge of managing the event food, nobody blamed him. Karen began frantically running around the event searching for a wheelchair ramp, and her boss started to chew her out. 

In the background, Drew heard one guest complain, “There’s no food? But I am gluten intolerant!”

Only seconds passed before Karen and her boss stormed up to Drew, ready to blame him for the food mishap. Drew had prepared for this conversation, and Karen was about to be terribly humiliated in front of her own supervisor. 

~

Karen’s Dark Downfall

annoyed, woman, irate
Photo by RobinHiggins on Pixabay

Drew was now face-to-face with enraged Karen and her supervisor. 

They both questioned, “Didn’t you know we have people attending the event who cannot eat the standard meal?”

Drew replied, “Yes, I did. Actually, Karen, I e-mailed you about it, because we needed to increase the meal budget to accommodate the guests. Did you not speak to the caterers like you needed to?” 

Karen’s face turned bright red, she was finally caught. 

She muttered, “I didn’t get any of those e-mails.”

Her boss glanced at her doubtfully. Drew’s plan was finally working!

Drew clapped back, “No, I sent you the e-mails, see?” 

Karen’s supervisor asked, “Karen? Is this true?” 

Karen began profusely crying. This event was crucial to her professional development, and she completely ruined it! 

Karen whimpered, “But you didn’t send it to me. I know you didn’t. Did you?” 

Her supervisor angrily replied, “So what do you expect to do now?” 

Drew calmly said, “I will figure something out. Also, I see people in wheelchairs. What are we doing to accommodate them? I’ll take care of that, too.” 

This was his time to shine! Karen and her supervisor didn’t know Drew had already planned the event perfectly.

Drew spoke to the caterers and straightened out the special meals. Step one, complete! Next, he pulled the wheelchair ramp out of the back room and set it up at the front door. 

He walked up to the supervisor and announced, “I had facilities set up a ramp at the front door stairs, and I spoke to the caterers. The gluten-free and nut-free meals will be ready shortly.”

The supervisor gleefully replied, “Thank you so much!” 

Two days after the event, Drew had a one-on-one meeting with Karen. Surprisingly, Karen’s supervisor was also in attendance. The supervisor informed Drew his write-up had been removed, and Karen had been written up for her behavior instead. Way to go, Drew!

Karen never heckled Drew or his colleagues again, and the entire team found humor every time a gluten allergy was mentioned. 

~

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