your 10 most cringe-worthy career mistakes

Whether it’s inventing a non-existent coworker, poorly timed flatulence, or accidentally asking the boss how much he makes, we’ve all made mistakes in our careers that have haunted and shamed us for years afterward.

I recently asked readers to share their most cringe-worthy career mistakes, and oh did you deliver. (Those three above are among the stories you shared.) I’ve compiled the 10 most embarrassing.

1. Asked the boss for his salary

In my previous career in advertising, I asked my boss how much he made while our whole department was out at a social gathering. Everyone stopped talking and stared at me, and I didn’t realize till then that it was a major faux pas. My boss just said, “We don’t talk about that.”

2. Beanbags and puppies

I was interviewing for a job at a small publishing house. I was still in college and had never had an interview beyond “Can you wait tables? Good. You’re hired.” The interviewer asked me what kind of office environment I preferred to work in. I said something like “Oh…my dream office environment would have bean bags instead of chairs, lap desks that we could use on the floor, and office dogs to play with.” I remember there was a silence, and then the rest of the interview moved surprisingly quickly. It was on the way home that I realized that my idea of “office environment” probably wasn’t what they were looking for. D’oh.

3. Name confusion

I had a coworker named Joaquin. At the time, I spoke zero Spanish, and didn’t know how to pronounce it. I didn’t make the connection when other co-workers talked about “Wakeen.” For months, I honestly thought I had two different co-workers, Joaquin (pronounced JOE-a-kwin) and Wakeen. In my head, I assigned them different personalities and areas of responsibility and everything. I sent emails saying, “We should get Wakeen to look into this” and talked about what Joe-a-kwin had been working on, and no one said anything, including poor Joaquin. I wanted to die when I finally put it together.

4. Mistimed flatulence

I was only in my job for about a year when I had to present a marketing plan to all my colleagues in my department. Near the end of the presentation, I was cruising along when someone made a joke and we all laughed.
Then I farted. And everyone started to laugh as if I would laugh it off, but I didn’t. I just pretended it was my shoe squeaking. Then came the red face, the stammering speech, the rush to finish things and the long, awkward silence for the rest of the presentation.

5. Locked in the office

One day, a coworker came into my office, told a dramatic story, slammed the door to illustrate some point in the story…and apparently slammed it so hard it broke the lock and we couldn’t get out. I was due to present an important report to my boss, but I was too embarrassed to confess to her that I was locked in my office, so we spent a good half an hour trying to figure it out from the inside, and then calling building security, who basically had to take the lock apart from the outside. When my boss finally came by to find out where the report, my coworker, and I were, the whole thing was revealed.

Fortunately, she thought it was hilarious, but did say several times, “Um, you could have just called me and we probably would have gotten you out of there sooner.”

6. Outsourcing your own job

My boss had asked me to do some follow-up phone calls, inviting donors to a gala for a client of ours. I felt awkward making these phone calls, and after a few, I was over it. I asked my friend (who had recently lost her job) if she wanted to make the calls, pretending to be me. I offered to pay her and take her out to dinner. I headed to the pool and took a secret day off.

She called one donor who was actually a close family friend of mine. I didn’t realize he was on the list. They small talked for about five minutes, him thinking it was me. When my friend eventually ask if he and his wife could come to the gala, he got confused – his wife had recently passed away. I even went to the funeral! My friend acted as if she just found out, saying she was so sorry to hear about his loss. I was absolutely mortified when she filled me in later.

7. Slightly too comfortable

I was fresh out of college and was unbelievably green. I had to moved to San Francisco and was hunting for a job. I interviewed with an incredibly cool advertising agency for an admin position. They loved me and invited me back for a second interview to meet the whole office. I showed up in the early 90′s version of skinny jeans tucked into soft-sided “slouch” cowboy boots, was chewing gum, and put my feet up on the conference table. (Gads, I’m cringing just remembering it).

8. “Any great ideas?”

At my first job after college, I knew nothing but was full of enthusiasm. I attended a meeting where the sales team spoke in a slew of acronyms and things I didn’t understand, but I was too shy to ask anyone for clarification. The CEO then stops me in the break room after the meeting, and asked, “Get some great ideas at the meeting?” and I responded with an enthusiastic “Yes!” As he waited for me to elaborate on what those ideas actually were, I froze. The voice in my head kept saying “say SOMETHING” but I couldn’t think of a thing. He waited a few minutes, then sighed and shuffled out of the break room. I ran into him a few years later, after I’d long left that job, and he said “Hey, E.R., have any ideas from that meeting?!” Yes, it really was as bad as I had remembered.

9. Several extra zeros

At my very first job, I had to put in an order for color/glossy/laminated/everything-you-can-think-of copies at a copy store. My manager asked for 300 — I ordered 30,000. And I didn’t realize the error until I went into the store to pick up and the person handed me several boxes filled with paper. And then the bill confirmed it.

Resigned to my fate, I paid with my own debit card and severely overdrew my account. I took all the boxes to a nearby alleyway and then had a complete breakdown, where I called my mom and begged her to help me cover for some of the cost. Thankfully, she did (though I had to pay her back over time, obviously) and I dumped all but 300 of the papers in the dumpster. Wiped off my face, pulled myself together, and went back into the store – where I asked if there was anyway we could separate out 300 of the orders on a new receipt for “expense purposes.” Ultimately, my boss was never the wiser. But wow, do I still get paranoid about quantities.

10. Wrong answer

I was in my early 20′s and working with a placement agency to find that perfect job that would take me out of food service. My agency contact had set up an interview for me for my dream job, the day after my birthday. Being young and not much of a responsible drinker, I partied like it was 1999. I showed up at the interview not just hung over but still drunk. The person conducting the interview asked me if I was sick, and if I was we could reschedule. I answered, “Nope, not sick, drunk.”

I did mention that I had gone out for my birthday the night before and rambled about how great my party was.
I was not hired. My placement agency stopped returning my calls and I do believe that the other agencies in town also had me on their do-not-deal-with list.
I burned a lot of bridges that day.

{ 45 comments… read them below }

  1. Kyle*

    This wasn’t exactly my mistake, though I see how I could have done it better. It was my most cringe worthy moment though.

    Last year we could actually see our merit increases before any of us were allowed to tell our employees what the increase was… This drives me crazy, so I complained to my Boss, pointing to her exactly where people can see it on our benefits website. I helped her navigate to it (over the phone) and she goes “This doesn’t show my increase, it’s the same.” There was about 8 seconds of silence when she goes “oh…”

  2. Jenny*

    Ha! Mine made the list (I was the nervous breakdown quantities chick). Not sure if I should be proud or cringe some more. ;)

    I also realized in how I wrote it that this didn’t come across – I considered my “cover up” behavior to be cringe worthy as well; while it worked out for me, it definitely wasn’t exactly best practice.

    …Even though on its own it was still a doozy.

    Ah, to be 21 again.

    1. Alyssa*

      Jenny, yours is my favorite!!! I have totally done some similar things in my professional past and had to get quite creative in order to rectify what I had done. Ah, live and learn I suppose.

    2. Josh S*

      29,700 units of glossy, color, laminated copies had to be EXPENSIVE. IIRC from my time at Kinkos back in the day, color prints are something like $1.00 each, with significant discounts as the units go up. But with lamination, I’d still think that bill would have to be in the 5-digits.

      I can’t imagine trying to foot that bill myself. How??

      1. Jenny*

        Oh, I really couldn’t foot it myself — it was a panic-induced response when I paid for it with my own debit card. And my parents helped me out (replenishing my account, creating a payment plan, etc) because I was generally very responsible; this was an anomaly.

          1. Jenny*

            I think it was four, but a very high four. If I recall, it would have been five figures, but we had some sort of company discount. Ha.

        1. Dan*

          Yes it is… Throwing 27000 sheets in the garbage makes me cringe more than the the rest. It’s extremely disrespectful of the environment.

      1. Jenny*

        Yes, I have heard of recycling and I had seven years ago as well. But when you’re young and panicked that you’re about to lose your first job due to a dumb mistake, environmental concerns aren’t necessarily your primary concern in the moment. Maybe that’s seen as selfish, but it’s a reality. I was only human.

        1. Dan*

          I might sound annoying, but I still think it’s wrong. What if a manager in a large corporation wasted a gigantic amount of resources because they were feeling sad/angry/panicked for whatever reason? That’d be acceptable? It’s the exact same issue, just on a larger scale.

          Yes it is selfish, if everybody did that kind of stuff and blame it on emotions, our world wouldn’t be doing so well. Oh wait…

          1. Ask a Manager* Post author

            No one is arguing that it wouldn’t have been better to recycle them. Rather, we’re all recognizing that it’s really common and understandable to not think about that when you’re in a panic.

          2. Jenny*


            Clearly we respond differently to different types of scenarios. I envy your ability to be completely rational no matter the circumstance.

          3. Kelly L.*

            This is a list called “Cringe-Worthy Career Mistakes,” not “Awesome Things I Did and am Really Proud Of.” You’re either missing the point or trolling.

          4. Elizabeth West*

            Relax. The environment was just fine before we got here, and after we’re gone, it will clean itself as if we never existed. I hardly think her panicked mistake is going to kill the Earth.

            And that’s what it was: a mistake. That’s what this post is about. People are supposed to learn from mistakes and judging by her answers, she obviously did.

            1. Flynn*

              …seriously? Only if by ‘fine after we’re gone’ you mean “there will still be a spherical rock here and eventually it will develop some new ecosystem or other”. They don’t really focus on ecology anymore at university, they focus on ‘and this is what we used to have and this is what we think we have and omg we have no idea how it will cope if X happens and we can’t change Y.’ 90% of my marine classes related to climate change and over fishing and pollution and exploitation in some way, because they so fundamentally affected everything we looked at. Handwaving away the fact that the majority of species and habitats are in danger, that the climate is changing, that idiot mining companies are trying to oil drill in insanely dangerous locations, that fishing companies are putting in ten times the resources to get the same amount of fish that they caught ten years ago, that most of this stuff is not easily fixable, is just… hugely offensive.

              (Yeah, it was a dumb panic mistake. It’s still a reasonable reaction to scream internally at the sheer waste, though).

              1. P.*

                Handwaving away the fact that the majority of species and habitats are in danger, that the climate is changing, […] is just… hugely offensive.

                Comparing all of these things to ONE instance of a young and scared person tossing out laminated papers in panic is offensive too. She said it happened 7 years ago. I think she’s being unfairly & weirdly pummeled for what should have been just a funny story.

      2. The Other Dawn*

        When people are in a panicked state of mind, they don’t always think clearly. The immediate thought for me would be, “How do I fix this gigantic f-up??!!” Worrying about recycling would be the last thing on my mind.

        1. Jamie*

          Seriously! I’d have probably panicked and quit and been working somewhere else as we speak under an assumed name with assumed fake hair and plastic surgery.

          I think Jenny was remarkably clearheaded in comparison.

      3. Elise*

        She said the paper was laminated. Laminated paper can’t be recycled (except by reusing it in some way).

  3. CK*

    Alison — I know you might not have control over this, but there’s a spellcheck typo — “shutter” for “shudder” — in the piece. But it’s great reading.

    1. fposte*

      Wakeen is my favorite employee ever. If I were Joaquin, I’d have kept Wakeen going to blame all my errors on.

      1. WorkingMom*

        Oh my gosh, I still have tears in my eyes from laughing so hard at that one!

        You should write a book of all these ridiculous things we’ve all done… hint hint Alison! :)

    2. Vicki*

      I was at a company lunch where new employees were being announced. The new employee’s name was “Jorge” (which the manager pronounced “George” as several people nearby muttered “Hoorhay” under their breath.

      1. Jamie*

        I was guilty of the opposite of this. We had an employee who spoke very little English named Jorge so I (have only seen it written) pronounced it Hoor-hay. Turns out he went by the pronunciation like George but no one told me for over a year.

        I wish people would correct others right off when they get their name wrong – I absolutely want to call someone by the name they prefer, but if your paperwork says Jose or Katherine and your ID tag says Jose or Katherine I’m going to call you Jose or Katherine …if you don’t correct me and say “actually call me Joe” or “I go by Kate.”

        Because I’m never going to presume or give people nicknames – I think that’s rude – so I go with what’s on the paperwork unless told otherwise.

      1. Amanda*

        I volunteer teaching ESL classes for recent immigrants from Spanish-speaking places. I, however, do not speak Spanish. I read your story, filed it away in the back of my mind and, as luck would have it, recently got a new student named Joaquin. Due to your post, I knew to pronounce his name Wakeen. Otherwise, I totally would have called him Joe-a-kwin, much like I spent a good four months calling another student Julia instead of HU-lia.

  4. FreeThinkerTX*

    Yay! I made the list (#7). I sent a link for the Intuit article to my dad, who reminded me of another whopper I pulled (also in San Francisco):

    I was 15 or 16, in high school, and had worked at Round Table Pizza for over a year and was tired of my dictatorial, schizophrenic boss (the owner of the franchise, a Mr. Mansoori – can’t believe I still remember his name). As a means of telling him I was quitting, I called a competitor’s pizza chain (Cybelle’s) and ordered a pizza to be delivered to Round Table. I told the guy on the phone that I’d give a $10 tip to the delivery person if they entered from the door farthest from the counter, and walked the length of the restaurant shouting, “Pizza for Michele! Cybelle’s Pizza delivery for Michele!”

    I waved from behind the counter as the driver walked past open-mouthed customers and brought the pizza to me. I told my co-workers that I’d be taking my lunch break now, and headed upstairs to the employees’ lounge. My boss was hot on my heels, screaming his head off, and yelled at me to get my things and get the “F” out of his restaurant. Which I did.

    I ate the pizza on the bus ride home.

  5. Yup*

    I’m totally inventing a workplace alter ego that I can blame for all my errors. Like my very own office Snuffleupagus. “I’m so sorry. Did Yup-with-an-umlaut delete the main server again? I hate it when she does that.”

    1. Jamie*

      Ha! That’s a great idea – I think I’m just going to start blaming everything on Jane and Bob.

      I don’t work with anyone by those names, so it’s perfect.

    2. FreeThinkerTX*

      When my brother was little he invented The Hinkle to answer for all his misdeeds. “Son, why is your room such a mess?” “The Hinkle did it.” “Who ate all the Halloween candy??” “The Hinkle did it.”

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