15+ Employees who made huge mistakes on the job: 'Accidentally sent a company-wide email complaining about the boss'

Author image for Remy Millisky
Remy Millisky • Writer and Editor
Apr 12, 2026 3:15 PM EDT

We all make mistakes on the job sometimes, but it's what you do afterwards that determines your fate. 

Whether you've been at your job for 10 minutes or 10 years, you're bound to make a few mistakes here and there. As they say, you usually just make smarter mistakes as you continue through your career. It really is one of the most effective ways to learn! If there's a sign instructing you to not do something, you can accept it, or try it yourself, and find out exactly why you're being warned away from something. 

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  • Some of these employees had 0 common sense. Seemingly using their worst judgement, they made some very questionable choices. For example — what would you do if you ordered some very specific jeans and got them stolen… only to find that your coworker is now wearing them around the office! That actually happened to someone, and that's not even the wildest story. 

  • Young construction worker worries about what her colleagues are doing.
    via Yunus Tuğ

    Young construction worker worries about what her colleagues are doing.

    The image does not depict the actual subjects of the story. Subjects are models.

  • This must've been the best day in the office ever

    DueBeaa Accidentally sent a company-wide email complaining about the boss instead of just to a friend. Total chaos for a day.
    via DueBeaa
  • laxpanther Construction crew meeting with our workers comp insurance rep, going over company safety policies in our shop. One guy decides. he can't be idle and needs to do some work. Decides to change a broken plug on an extension cord, which by itself isn't an approved repair, definitely not by someone who isn't an
    via laxpanther
  • electrician. But anyway. Proceeds to cut the busted end off WHILE THE CORD IS PLUGGED IN. Big spark, shorts it out and the inspector is just like what the f are you doing?
    via laxpanther

  • The hypocrisy!

    sitewolf My now-former CEO once sent an email to all staff admonishing people for using Al incorrectly while obviously using Al to create the email, with the typical bullet-pointed layout but also forgetting to remove an 'insert image here' placeholder.
    via sitewolf
  • May not be the dumbest thing, but one I laughed at the hardest; just a taste of why she's my 'now-former' CEO
    via sitewolf

  • Absolutely wild thing to steal when you could choose literally any other item

    spot_coffee Vouchered three pounds of frozen shrimp from a Friday night shoplifting arrest. Put the frozen shrimp in the property locker, which is not opened until late Monday morning. It was August and the property room is not air conditioned. That is just one of many dumb things he has done.
    via spot_coffee

  • Insane!

    ChiefNunley At a buy here car lot, the new girl used a customer debit to order pants with sparkley bot pockets off Amazon. Had it delivered to her dads. A few days later the customer comes in and knows everything, including that it was shipped to her house. And my coworker?
    via ChiefNunley
  • Yeah she was wearing the jeans. It was hilarious. She didn't get fired for a few more weeks though when she got caught stealing a cash payment.
    via ChiefNunley

  • Goodness gracious

    annoyed_meows Told me he was swing trading his entire 401k. He timed it wrong. Stopped talking to me about investing after that lol (I told him I'd never do that)
    via annoyed_meows

  • Bro couldn't keep his mouth closed

    Queen_Andromeda Ex coworker now. Told all of the guys at work that he was quitting. Not by turning in his two weeks but by just packing up and clocking out.
    via Queen_Andromeda
  • He also blabbed that he'd take company tools with him. Word got back to our supervisor and said supervisor made him hand over the company tools before firing him. He has a stay at home wife and at least one kid to take care of. I still don't know what he was thinking
    via Queen_Andromeda

  • This might be the dimmest way you could possibly end up losing your job

    markmcminn 6 figure IT job - gave gf his password to keep him logged in while working remotely to go to the store to get pork rinds. She proceeded to mistyped it 3. times before logging back in, which alerted infosec to message via teams and she
    via markmcminn

  • What were either of them thinking??

    just straight up said her bf gave her his password to keep him logged in while he went to the store and she mistyped it a few times. Fired.
    via markmcminn
  • Precipice_01 HVAC here. I had a coworker who did side jobs on his own time. We carry phones that are company provided, which is typical.
    via Precipice_01
  • One day, he and I are talking after packing up on a job and his phone rings, he answered it with his typical side job spiel. His face goes pale, and he hangs up. I ask what happened, and he tells me it was our boss who called him. Answering the phone with his side job hello had just gotten him fired.
    via Precipice_01

  • Ever wondered what happens when you get too comfy in your role? This. This right here.

    Fritzo2162 We hired this guy to our help desk and he got WAY too comfortable. He wasn't great at his job, but we gave him a lot of slack hoping he would grow into the role.
    via Fritzo2162
  • We had some weird smell going on in the office for a week while he was out and ended up tracking to a sandwich he left in his desk drawer. The boss came and wanted to talk to him about it when he returned, and he had his work board open on one board and Netflix opened on the other with an earbud in
    via Fritzo2162
  • his ear. His boss started speaking, and the guy put his finger up with a "One sec" motion, put his hand on his earbud so he could hear the show he was watching better for a few seconds, then paused the show to say "What's up?" He was shocked he was fired that afternoon.
    via Fritzo2162
  • Office worker squats down to pick up numerous binders she dropped on the floor.
    via Andrej Lišakov

    Office worker squats down to pick up numerous binders she dropped on the floor.

    The image does not depict the actual subjects of the story. Subjects are models.

  • This is a lesson some folks learn the hard way

    Sean20636 During an "Open Forum" employees were encouraged to provide honest feedback on a topic. He did. He was immediately fired.
    via Sean20636

    Never assume that your employer actually wants honest feedback, because they probably don't want to hear that. And also, never ever presume that an "anonymous" survey is actually so. There's like a 9 out of 10 chance they can trace it back to you! 

  • Bold move

    No_Organization_... Steal a co-worker's coat then wear it to work on another day.
    via No_Organization_9879

  • How odd

    MrSpindles We laid off a temp and he kept coming back even though he wasn't getting paid. We repeatedly tried to explain to him that he wasn't being paid and shouldn't even be in the building but he had this bizarre idea that if he worked for free for long enough they'd take him back on.
    via MrSpindles

  • He just had to satisfy his curiosity

    NighthawkUnicorn I heard this second hand so I'm not sure of all the ins and outs. Apprentice was told to flip a lever on a machine, hold it for 3 seconds, only 3 seconds, no more than 3 seconds, and then let go.
    via NighthawkUnicorn
  • Colleague goes around the other side. Tells the apprentice to flip the switch. and hold for 3 seconds. Machine powers on, starts grinding and shaking and smoking. Colleague is panicking trying to figure out what's going on. Comes to discover apprentice is holding the lever on and not letting go.
    via NighthawkUnicorn
  • Colleague grabs apprentice's arm and pulls away from the lever, shutting the machine off. He asks why he didn't let go after 3 seconds as told. Apprentice says "I wanted to see what would happen"
    via NighthawkUnicorn

  • This is what you do just before you quit

    Dry-Club2898 Someone decided to reheat leftover fish in the breakroom microwave for 10 minutes. The smell was so biological and aggressive that we had to evacuate the office and hire professional cleaners
    via Dry-Club2898
  • CatPartyElvis Told a girl to go vacuum the side room at a restaurant I worked at, 20 minutes later she still wasn't back so I checked on her. She was using the vacuum like a broom. She had never used one before so I showed her how to tilt it back. She also told me chipmunks were baby squirrels.
    via CatPartyElvis

  • Bro left his brain at home that day

    Blue_Ascent My boss asked for a number between 1 and 10. Coworker said 11.
    via Blue_Ascent

  • They.... didn't have the time??

    redbeancat I was on opening shift for a retail store. I came in to see the previous day's takings on a stool in the middle of the (very messy) shop floor. My coworker said they didn't have time to put it in the safe during closing. I told
    via redbeancat
  • management and my coworker got mad at me as "I can't afford to be fired as I have a mortgage". Well if job security is so important to you, do your job properly.
    via redbeancat

  • Big oops

    _devmanoharrr Turned off the power strip to "save electricity"... took down the entire office network.
    via _devmanoharrr

  • The fire department letting out the longest sigh as they extinguish the cookie blaze

    GoldenFrank Grocery Store. Couple of teen cashiers bought a cookie dough roll for break and thought they could cook it in the microwave? Just put the entire log on a plate and kept going assuming it would eventually turn into a giant cookie loaf? The fire department disagreed but didn't seem too surprised.
    via GoldenFrank
  • slow_cars_fast Not my coworker, but relayed by a friend. So, homeboy is an admin on the systems at the employer, managing servers and whatnot. This gives him near unlimited access to pretty much anything. One day, he's working on the HR system and decides it's a good idea to see how his
    via slow_cars_fast
  • salary stacks up against his peers. He finds out that he's the lowest paid person in the group and proceeds to take this new-found information to HR to complain, expecting to get a raise. Not only is he not given a raise, but he's fired and escorted out of the building.
    via slow_cars_fast
  • chewedgummieb... Back when cell calls were charged by the minute, we had someone in security that would call toll based numbers on every cell phone that was turned into lost and found, tuck them away and let them stay on the call until they ran de d.
    via chewedgummiebears
  • The security station was on camera too so he knew he was being filmed, but thought he would never get caught. After a few complaints were made about cell phone bills and the timing of their lost phones, he was walked out but not after doing it to a dozen or so phones.
    via chewedgummiebears
  • Office worker holds his neck while a closed laptop sits in front of him, as he contemplates his mistakes.
    via Getty Images

    Office worker holds his neck while a closed laptop sits in front of him, as he contemplates his mistakes.

    The image does not depict the actual subjects of the story. Subjects are models.

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