Plot Twists Short Stories & Freak Workplace Novels

On my third day at the company, my supervisor suddenly patted me on the head. “Anna! I saw you won the lottery! I’m giving you a chance to make a good impression. The day after tomorrow, I’ll get everyone together for a private party aboard the luxury yacht Black Pearl. It’ll be your treat, of course!” Before I could even decline, Sarah was already rattling on. "There are over a dozen people in our department. We'll need at least ten bottles of XO, Australian and Boston lobster for everyone to pick from, and we all need terrace suites." “You can afford a little thing like that, can’t you, Miss Moneybags?” I frantically tried to explain that the ticket was one I'd bought for someone else. I didn't have any money at all. But Sarah just shot me a look of pure contempt and walked away. That night, the work group chat exploded. She announced to the entire group, "To celebrate Anna winning the lottery, we're having a blowout bash on the Black Pearl the night after tomorrow! Everyone sign up!" Over fifty people jumped on the list within seconds. Even the cleaning lady signed up with her three grandchildren in tow. "Oh my God, our parties are usually just drinking beer in someone's apartment. We've never been on a luxury yacht! Thank you, Sarah!" Sarah's private message came through. "Anna, I noticed the account you used to claim the lottery ends in 0663. The club booking is already confirmed. We're counting on you, Miss Moneybaaags~" I stared at the booking screenshot she sent, breaking into a cold sweat. That lottery ticket was one I'd claimed on behalf of the company's CEO!

The 3 PM all-hands meeting was already underway when Audrey Mitchell, the CEO's wife, shoved the door open, her expression cold as ice. She marched straight at me and slammed a photograph onto my laptop keyboard. It was taken in a luxury hotel lobby. A young woman was trying to wrap her arm around Benjamin Mitchell, our CEO, while he held his hands up in a gesture of resistance. "Dylan, is this your girlfriend?" More than a hundred people packed into the conference room, collectively holding their breath. The room went dead silent. Beside me, my intern, Zoe Brooks, slowly pushed back her chair and stood up. She turned to look at me. Her eyes were red. "Dylan, last month in the break room, I heard you say it," she stammered, her voice trembling, "You said if you sent your girlfriend to Mr. Mitchell's hotel room, that director promotion would be yours. I thought you were just making a sick joke. I had no idea you'd actually go through with it." Benjamin stepped out from the shadow of the projector screen, his face hardened with righteous anger. "I’m a married man," he declared, adjusting his jacket as he scanned the room, "I shut her down on the spot. I have ethics, people." Audrey never broke eye contact with me, completely ignoring her husband's speech. "Are you going to explain yourself," she asked, her voice dropping an octave, "or should I do it for you?" My mind went completely blank. The side profile, the jawline, the soft sweep of hair—it was undeniably my girlfriend. Except there was one massive problem. How on earth did my digital, code-based AI girlfriend end up as the CEO's lover?

I walked back into the office after the Labor Day weekend and found myself trending online. One employee had posted under their real name, complaining that the company never organized team-building events, and that a long weekend like this was exactly the kind of time we should be setting aside to bring the staff closer together. Plenty of other employees had piled on in the comments. The internet tore into me, insisting I had no idea how to run a company. What none of them knew was that I hadn't skipped team-building to save money. I'd folded every dollar of that budget into everyone's bonus instead, and I paid out even more around the holidays. As far as I was concerned, people came to work to earn a living, not to make friends. Cash in hand beat everything else. Since the crowd felt so strongly about it, I decided to give the people what they wanted. The next day, I posted a notice to the company group chat. [Starting today, we'll hold team-building every Monday, Wednesday, and Sunday evening. Location: the grill stand outside the office. Anyone who misses it without a valid excuse will be marked absent and docked pay.] The moment employees read it, the outrage was instant. "Monday, Wednesday, and Sunday are already our worst days! How are we supposed to come in the next morning after staying up half the night?" I just smiled and answered, "Don't say the boss doesn't care. Nothing warms the heart like a late-night team dinner."

My supervisor, Jessica Lawson, spotted me coming and going from a multimillion-dollar oceanfront estate in the Hamptons. She decided I'd landed a wealthy man and was about to marry into money. That same night, she dropped the estate's location into the company group chat and invited everyone to a department party there. "Emma Bennett is hosting at her oceanfront estate this weekend. Bring your families. Everyone in the department is invited!" I patiently explained that I was just a part-time caretaker. "My job is literally walking the owner's dog." But the group chat went feral. Everyone ignored me and started placing orders. "Remember to open the Romanée-Conti early so it has time to breathe." "Pick me up in the Lamborghini that day. Ferraris just aren't my vibe." In under ten minutes, more than fifty people had signed up. Jessica tagged me directly. "The catering bill is going under your name. Make us proud, and don't embarrass the boss." I gave a humorless laugh at the endless sign-up list. Richard Hale, the estate's owner, was a boxer who stood nearly six foot six and was built like The Rock. The last thief who trespassed on his property is still in a coma.

When I took my diagnosis of heart failure to my boss and asked for time off, he shot me down with two words. "Not approved." I pointed to the diagnosis. "I could drop dead at any moment." He pushed the report back to the edge of his desk. "But you're not dead yet, are you? This project is at a critical stage. Don't even think about slacking off and trying to get out of work." I stared at him for two seconds before nodding. "Fine. You win." The next day, I walked into the conference room right on time with a portable medical oxygen tank. Everything suddenly went black while I was presenting the fourth version of our proposal to the client. I had collapsed face-first onto the conference table. My boss finally froze when he saw that I was on the brink of death.

The day I got the callback for my second interview, my mother, Sara Bingley, came home with two bags. "You're about to start your job for real, and that means dressing professionally. I bought you girls a suit each, one for each of you, fair and square." Molly Pitcher happily took her bag. Inside was a fitted, deep navy suit, sharp and clearly not cheap. What landed in my hands was an ill-fitting black suit pulled from the clearance rack, so oversized the sleeves swallowed the backs of my hands. Mom smiled and touched my cheek. "Cathy, you'll still grow. I bought it big on purpose. Give it two years, and it'll fit just right. I went to I don't know how many malls just to track down that black suit." She did love me, in her way. She knew my job required a black suit, and she really had gone to several malls to find one. But she'd forgotten I was already twenty-three. No amount of growing was going to fill out a suit that oversized and that cheaply made. Both daughters were her own flesh and blood, but Molly was plainly the one she doted on. The love she gave me came measured out in careful portions. The love she gave Molly overflowed. If that was how it was going to be, then from today on, I was done being the extra one in this family.

My company let employees clock paid hours while petting the office cats, take unlimited vacation, and skip the time clock altogether. For a while, people called us a dream company. Then one of my employees posted online and accused the whole thing of being a kindness trap. He filmed the office as if it were paradise, but the caption told a different story: [Don't envy us. All of this was bought with our low pay and our youth.] The post went viral, and overnight, I became the fake-nice boss who bled his employees dry behind a mask of small kindnesses. The entire internet told my employees to run. Fine. I let them. I rolled out a new policy. Effective immediately, every flexible benefit and every trace of humane management was gone. The company entered an era of standardized management. From then on, KPIs would have the final word. The cats were banned from the office. Leave requests required layer after layer of approval. Strict KPIs meant a single bad number could cost employees part of their pay. Before long, the same employees who had torn me apart online showed up at my door and begged me to give them the dream company back.

As the Donna of the Moretti Family, I paid out of my own pocket to build a high-security school for the children of our fallen members. But the widows repaid me by dragging my name through the media. Worse, they leaked the locations of three safe houses, dealing the Family a devastating blow. They claimed the school was never a benefit at all, but a “hostage camp” where I kept their children to force them to remain loyal to the Family. While Don Lorenzo Moretti was away, they even filed an impeachment motion with the Family Council, demanding that I shut down the school and hand its operating funds directly to them. Fine. I signed the closure order that very day. But the moment the notice went out, the widows swarmed the estate gates, crying and begging me to reopen the school. Only then did they understand— What waited for their children beyond the school gates was never freedom. It was a rival Family’s hit list.

The sales department organized a team-building trip and turned it into a killer-instinct trail race, with a $30,000 prize for the winner. I volunteer with a search and rescue team, and I stayed up all night mapping the safest route with supply points along the way. The new VP they had parachuted in tore up my map right before we set out. "What's the fun in a paved trail? We take the undeveloped Wildman Gorge. That's how you show real killer instinct! "To keep anyone from cheating with GPS, everyone hands over their communication devices." I pointed at the thunderheads on the horizon and tried to stop him. Wildman Gorge floods easily, and going in without radios was suicide. Instead, he smashed my radio to pieces in front of everyone. "You're just jealous that I got to lead this thing, and you want to keep everyone from taking home the prize money, right?" For that $30,000, my coworkers lined up to call me a coward who cared nothing about the team. Fine. I took off my shell jacket and volunteered to stay at base camp at the bottom of the mountain. A storm was coming. If this pack of office wolves wanted to take on a mudslide in Wildman Gorge, I would sit there with a hot cup of tea and wish them a triumphant return.