Tell an Embarrassing Office Story and Win File Folders with Attitude

As a WorkAwesome reader, you may have noticed that we love to talk about office life, and we love to find the humor in it. For example, Michelle Burleson’s Taboo but True: Rules of the Loo outlines the bathroom etiquette all the other stuffy career sites were too scared to talk about. (After all, we don’t talk about the process of expelling waste; professionals don’t need to do that.)

That’s why we want your stories, and we’re willing to reward you handsomely for them. Well, at least some of you, and it depends on your definition of handsomely. But we’ll get to that in a moment. Here’s what we want:

  • Write about the most embarrassing office incident of your career in 600 words or less.
  • Leave the story as a comment on this post, leaving your real name and email address. Your email address will not be publicly viewable, but if you use a fake one, we can’t contact you if you win.
  • I’ll spend a good half-day in the office reading funny stories, and my boss won’t be able to do anything about it.
  • Then I’ll pick the three funniest, and they’ll win. I’ll publish them in a follow-up post.
  • The three winners will be contacted regarding their prize, which is…

File Folders with Attitude from ThinkGeek

Sick of being smirked at by your co-workers since the embarrassing incident you’re about to tell me about? These File Folders with Attitude are perfect for getting back at the world (or at least your co-workers) with some attitude. At least you’ll feel a whole lot tougher.


Best of all, you can put paper in them.


  • Employees and contractors of Envato past or present are not allowed to enter.
  • I select the winners at my sole discretion and based on how much my belly laugh irritates fellow Envato workers. I’m particularly looking to annoy Skellie. My decision is final.
  • Entries close at 9AM on the 17th of November, Australian Eastern Standard Time. If you can’t figure out when that is in your timezone, I suggest using Google. Or going back to school.
  • You must be 18 or above to enter. We’ll be sending security teams to the winner’s homes to ensure that you haven’t told a fib about your age.

Go on. Embarrass yourself publicly, and you might be lucky enough to receive $8 worth of cardboard!

Popular search terms for this article:

an embarrassing incident, file folders with attitude

Joel Falconer is the co-founder of public relations company Methodic Studios, publishes the gaming blog StartFrag, and is an editor at leading technology news site The Next Web. You can follow him on Twitter.


  1. Phil Davis on the 3rd November

    I probably should keep this one on the DL but I’m feeling reckless.

    About 8 month’s ago the entire design department accidentally received an email from a hiring manager regarding an attractive female employee who shall henceforth be referred to as Rose. The email was unprofessional, crude, slightly misogynistic and thus needless to say very inappropriate. The notorious reply all button had struck once again. Terror, suppressed giggling, and awkward glances roamed the cubicles.

    Unfortunately this was not what made the situation embarrassing. Rose was one of the very few employees who did not know about the email circulating the office, and I was one of the few employees who did not know that Rose did not know about the email. Well as luck would have it I was assigned to work with Rose on a small project. I was determined to let my mature, and professional attitude reek from the very ground I would trod. Class and respect would ooze from the very pores of my flesh and…well… you get the point. At any rate things were going smoothly, and I assumed this was a direct result of my high level of swag. Alas, as all good things come to an end my relationship with Rose was about to take a turn for the worse. I have calculated that 97.31% of all bad things happen as a result of not signing out of your email inbox, and as the laws of gravity hold the universe together so to so the laws of email privacy hold our relationships together. As Rose’s eyes “accidentally” meandered across my laptop monitor she spotter her name in a Subject line. Then, she asked me to open it. What happened next is much to graphic for online content. But rest sure that many awkward explanations followed.
    Like a disturbance in the force my swag was gone. I was a vulnerable lamb in the midst of a furious wolf. Rest assured I fought valiantly against an onslaught of questions but in the end I succumbed. A victim of a crime I had nothing to do with.

    Many have been in situations similar to mine, but few have lived to tell about them. Take heed my little ducklings. Protect your passwords, guard against all spyware, and most importantly…Never stay automatically logged in to anything…EVER! If you heed my warnings you shall live long and awkward free lives.

    Hitherto, and Forevermore,
    Phil Davis

  2. Richard Collett on the 4th November

    A techno-illiterate client once popped in with the photos for his website stored on his camera.

    Cue me, in the middle of the office, going straight to slideshow view of all the photos with my boss behind me and the client next to me:

    Some amateur shots of the accommodation
    Some amateur shots of the surroundings
    Some amateur shots of the local wildlife
    Some amateur shots of his wife in the shower…

    Lesson learned: Double check with the client that it’s ok to look via slideshow view at the photos on his camera, and confirm that he’s looked at the contents recently to be on the safe side…

  3. Tylor on the 4th November

    At our office, we have a small toaster oven that employees may use to cook their lunches in. I was finishing heating up some leftovers (Asian stir-fry) in a little glass bowl, when I realized that (after cooking for a good twenty minutes) it was going to be too hot to touch.

    Looking around for something to use, and finding out that we didn’t have any oven-mits or rags available, I decided that a paper towel would be sufficient. I ripped off a good sized piece and wrapped my hand around in it. With the makeshift mitten, I reached to grab my cooking bowl out of the little oven.

    It took only one loose piece of towel, poking up on the top, to touch the red hot coils of the oven. Suddenly it burst into flames and I was sanding there, in shock, holding the ball of fire. I quickly managed to put it out but was left startled and extremely embarrassed!

  4. Hi, call me Bob. I'm new here and I just pooped my pants. on the 4th November

    Got my first big job and apartment in the city in April of 2005. I didn’t know what to expect and only knew 1 person so you can assume that I was pretty nervous. The night before I had a hard time sleeping and my stomach was anxious, but I was ready to take on the word, dark suit and all.

    After getting through the HR paperwork, I met my boss who mentioned that she had to leave to meet a client that afternoon and the other remaining members of our team were out of the office on vacation, business, etc (I worked on a team of 4). She offered to make it up by taking me to lunch when she returned.

    So I decided to venture out downtown to try and find some lunch on my own and get the lay of the land. I wasn’t too familiar with my surroundings and Arby’s was a familiar, slow-roasted friend from my past. Little did I know that this Arby’s was one of the most foul restaurants in all of the area.

    After eating lunch, I decided I better use the restroom before heading back. I had a little gas so I did what every self respecting man would do and tried to help it out. As I pushed the door to the restroom, a shart (urban dictionary it) of career crippling consequences let loose into my new navy blue suit. I nervously jumped into the stall to assess the situation (btw, the lock did not work on the door). As I looked down in horror, I came to a cross-road. I would be meeting many other members of the organization later that day and I could either pull them up and hope for the best and be referenced as the poop guy for the rest of my time there or maybe I could commando it. I decided to take the road less followed. I pulled off the underwear, gently folded them up into a square and placed them behind the basin of the toilet (this place didn’t even have trashcans in the johns). I commandoed it across the street to Macy’s, bought one pair of underwear, changed in the fitting rooms and was back in the hour allotted to me for lunch.

    To this day, I’ve never been back to Arby’s.

  5. Lisa Nguyen on the 4th November

    Early in my young career I was in charge of pulling off a reception for Executive MBA students (think the next Fortune 500 CEOs). I was cool and collected wearing a black evening dress. This dress was just no ordinary dress – it was sheer fabric placed delicately over a black sheath. After the awards ceremony I turned to grab the elevator for one of the high level executives in attendance.

    Little did I know that the sheath of my dress had slowly ridden up and static had taken over. My entire backside was now facing the award ceremony.

    It was a good thing I had the fashionable instinct to at least wear black underwear and not hot pink.

  6. Esteban Carpio on the 4th November

    At one of my first (real) jobs, I worked as an environmental issues assistant to the HS&E country manager, and his boss, the regional HS&E (Health, Safety & Environment) manager in an oil services company.
    One of my first days in the company, during a whole day meeting where all country HS&E staff was present, we decided to stop for lunch, and then, as part of my newbie assignments, I had to waiter everyone and order everything they wanted for lunch. So I started taking note at everyone’s menu, they started asking me politely for whatever they wanted to eat and when the turn came for my boss’s boss to order (regional HS&E Manager, who was paying for lunch with his corporate card) he replied to my surprise: “Just a bag of popcorn, please”, I doubted so I double checked and he confirmed, or that’s what I believed that moment, that he actually just wanted “a bag of popcorn, please”. Then with all the menu ready to order I passed the list to the secretary who made the order; one hour later the food arrived and everyone started taking out what they had asked for and started eating, I waited for everyone to take their stuff from the bag until finally the only two things left were my lunch and the boss’s popcorn bag. He stared confusedly at both items and yelled: “Where’s my lunch?!” and I told him: “You told me you just wanted a popcorn bag!” and everyone in the room started to laugh out loud! “Now I get it” he told me, “I haven’t explained you yet, a popcorn bag means the usual for me”; while everyone in the meeting room was still laughing big time, he left the room, payed the bill with his corporate card and went home for his lunch. Huge embarrassment, but I guess it’s a lot easier to tell “the usual for me” than trying to understand what “a bag of popcorn means”

  7. Ash on the 4th November

    My very first job was as an Office Assistant with a prestigious advertising company. My role involved various office duties but mostly mediocre ones like getting groceries for the office, photocopying, running errands etc.

    One day I was sent to go pick up the CEO’s Porsche 911 from the repair shop. ‘No problem’ I thought until I got there and discovered it was a manual drive with me only being able to drive an automatic. I rang up my boss in a panic and she quickly dismissed it saying ‘It’s easy’ and ‘I don’t have time for this. Just drive the damn thing back here’.

    So I managed to crawl my way out of the repair shop, slowly crawl my way across town (stalling the car many times in the process) and make it to the parking lot at my work. Just as I thought ‘Victory! I’ve done it!’ I put the car into the wrong gear and slammed the car into the parking lot / office wall. Everyone in the office rushed out to see what had made so much noise and all raised their hands to their mouths in horror when they saw me in the CEO’s Porsche all smashed up.

    I wasn’t fired and he had insurance so it was OK in the end. I did use the opportunity to remind my boss to never, ever make me drive a manual car for work again though.

  8. Scott Cowley on the 4th November

    Once I accidentally tripped our director at the top of the stairs as we were headed to lunch, causing her to take a good, long tumble down. As if that weren’t enough, some other guys were on their way up the stairs (windy staircase) on their way back from lunch and she crashed into them like a bowling ball, knocking one to the ground. Everyone ended up alright, but she never let me forget it.

  9. Steve Spatucci on the 5th November

    When I’d just started my first real job, I was invited to a meeting with my manager and a bunch other senior managers from various departments. My role was to design the project, and I was the most junior person in the meeting by far.

    My manager arrived a few minutes after I did, and since the seats next to me had filled, he wound up sitting directly across from me. The meeting got underway, and I started taking notes on a ruled notepad I used for everything.

    About twenty minutes into the meeting I had a question, so I leaned forward – notepad in hand – and started talking to the room. I felt like I was being professional, turning left and right to address each of the the different managers.

    I didn’t notice the strange looks I was getting until I saw my manager opening his eyes very, very wide in some type of warning signal to me. I stopped mid-question, and my manager gracefully interjected a “…what Steve was asking was…” and took over for me.

    It was only a minute later, when everyone’s attention was diverted to a projector screen, that my boss silently directed me to flip over the notepad. It turned out that I’d used the back of the pad – an entire 8.5 x 11″ sheet of paper – to draw a very detailed, fully-inked rendition of Wolverine. His mask was half ripped off, his head tilted back in a rage-induced scream, claws above his head, bloody from some unforeseen enemy he’d just dispatched. It was a very detailed, very violent illustration.

    Realizing that I’d been holding this in front of me as I spoke – inadvertently displaying it to everyone in the room as I thought I was being professional – gave me the chills. My boss just let his eyes fall to the table and slowly shook his head from side to side. For the rest of the time I was at that company, I always made sure to check the back pages of my notepads before going into meetings – or I’d just grab a fresh one from the supply closet. That was always the safest way to go.

  10. Suzanne Earley on the 5th November

    Ooh, Lordy, where to start?

    When I first went to London, I was in a crap admin job (dictaphone typing, filing, etc) at a Chartered Surveyors office. The day after I started, the whole team went to lunch, leaving me to answer the phones.

    Phone rings:
    Me: good afternoon, XYZ Company
    Caller: edguivr hggsykj udgv. Ggdd my farm jjkdh Kent hgdtuv dyjbf?
    Me: [what the f…?] Uh, sorry sir, could you repeat that?
    Caller: (repeats gibberish)

    all I’m getting is “my farm” and “Kent”, I literally cannot understand ANYTHING else this older, (presumably) English fellow is saying.

    Me: sorry, who did you want to speak to?
    Caller: (more gibberish, getting cranky now)
    Me: thank you sir, I’ll leave a message.

    Now what? 50 surveyors in the building, and I have to go door-to-door after lunch, asking each of them if they had a client with a farm. In Kent. His name? No idea, sorry… Number? No, I didn’t catch it (because you gave me the shit phone with no caller ID on it), sorry…

    No one knew anything. 3 weeks later, I was called into a meeting to explain to the senior Surveyors why on earth I hadn’t passed on a message from Lord Bbbb. Oh. Shite.

    Because I couldn’t understand him when he rang, no one had called him back. Offended, Lord Bbbb had taken his £2million business elsewhere.

    I was summarily dismissed.

  11. Natalie on the 6th November

    I was having technical difficulties and was sharing my screen with an outside contractor. Sadly, I had forgotten to sign off AIM (this was a couple of years ago).

    My (female) friend IMed me with the question: What size underwear do you wear?

    I’m pretty sure the IT guy could see how red my face was.

    Just as a side note, my friend was asking because I was a bridesmaid in her wedding, and she got us all cute underwear with “Bridesmaid” embroidered on the butt. Hence the question…just thought I’d clarify.

  12. Tanja on the 9th November

    Two little stories:

    It was one of the first days of my very first job. At that time I was a shy person and terrified by the possibility to do anything wrong. So this very day I had to call a customer to get some informations about a topic which was also new to me. I took about 20 minutes to figure out what to say and how to say it and told it to myself a few times until I finally gabbed the phone (his name “Smith”, my name “Henderson”):

    He: Hello, company xyz, Smith?
    Me: Good morning Mr. Henderson… eeeh
    – silence –
    He: Did we marry? Sadly, I can’t remember. Or is it an offer? (laughing) Have to ask my wife first…

    Hehehehe, I needed a few moments until I remembered what I wanted to say.


    I didnt see that an important customer was sitting in the room as I stepped in to tell the secretary that one of the toilets is out of order… Unfortunately I said it in a very colloquial form and added some malediction 😀

    But luckily he had enough humor, so he just smiled, waved to me and said “Nice day today, isnt it?”.

  13. Chris Offner on the 11th November

    I’d been hunting for jobs, and found one at a local community college in Texas; things were going well. I just graduated with my degree in Graphic Design, and things were looking up when I had met with the coordinator of the Student Activities department. We completed the interview, and everything had gone well. I got the job, and met me coworkers that share my office. One of them, I’ll call “S” (in her early 40’s), sits right behind me, while the others are nearby, in clear eyes view.

    “S” is a competent user of Windows Live Messenger, and was chatting with a friend of hers over matters foreign to me. “Girls…gosh” I was thinking, but my photoshop project had reached a halt. I needed a bit more information before I could proceed. I turned around to ask her a question, and we got in a heated conversation about working here, and problems that we face, when I notice her monitor blinking. My eyes wandered around the room, and finally made their way to her monitor. Her friend, (who’s name I could see) had sent her an instant message, “He’s just jealous because he doesn’t have a big cock like this one”. I tried to act coy, but she noticed that I was looking behind her, and when she turned around to see what I was looking at, she exited the Instant Messaging window as fast as she could and we both started laughing hysterically for the better part of 10 minutes. She explained to me that her friend had tried to send a picture of a “well-endowed” man to her husband, and it had never gone through. She was interpreting his lack of response as anger, and was explaining her point to “S”.

    Needless to say, I now ask if I can turn around before I ask her any questions face to face.

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