Career & Money

26 Women on Their Worst Career Mistakes


Work mistakes are a special kind of stressful. If you’re scared of making one or knee-deep in one or still shivering from a weird email you got last month, allow the below story, originally published in February of 2018, to be the Tums to your emotional indigestion.

I’ve never made a career blunder dastardly enough to get me fired, but I’ve made plenty of small ones I subsequently mulled over for weeks on end, like Everlasting Gobstoppers that never failed to run out of stress juice. I think work mistakes feel particularly anxiety-inducing because unlike disappointing a parent or friend or even yourself, disappointing a colleague — especially a hierarchical superior — can have immediate, rippling consequences for an entire business that depends on its employees to keep it running. Those are high stakes!

The thing about messing up, though, is that literally everyone does it. Your capacity for failure doesn’t mean you are terrible or special — it just means you are human and ordinary. But I know that’s easy to forget in a moment of crisis, so to buoy all of us with the comfort of solidarity in those moments, I asked a whole bunch of women to tell me about their worst (or best, or funniest, or most memorable) career mistakes. Enjoy them below, and add yours in the comments if you have one.

During my first college job interview, when asked why I wanted the job, I said, “Because I want to make money.” My subconscious totally took over!

Hannah, 21

“I was managing Instagram for a young brand that was taken very seriously at my corporate company. Every piece of content we posted ran through at least four rounds of back and forth, down to the most minor retouching notes for what was meant to be a ‘casual’ shot. In a time of social media spontaneity and sharing content in the now, we did nothing of the sort and it was an absolute nightmare. One sunny afternoon, I was rummaging through my purse when I realized that I had left my Polly-O string cheese snack in there to marinate all morning long. I thought it would be hilarious to post the discovery on my personal account, bouncing the cheese against my desk for the full effect. I penned a witty little caption, clicked send and posted the video onto my account. Roughly four minutes later, checking back to see if anyone had replied to my story, I quite literally dropped my phone in horror. Not only had I posted to the brand’s account, but it was our debut story so Instagram SENT A NOTIFICATION TO ALL OF OUR FOLLOWERS TO COME CHECK IT OUT!!!!! After an immediate delete and a mild panic attack, a coworker talked me down from the situation. Her main piece of advice? If someone had seen it, I would’ve already known. Turns out she was right, and I never heard anything from anyone in the company about it. Long live The Great String Cheese Incident of 2016.”

Paige, 30

In my first months working at my first job, I accidentally sold the director’s personal suit in a sample sale. When he (quite understandably) demanded to know where it was, all of my new colleagues said it was a group mistake and wouldn’t let me go down alone.

Elle, 25

“I am a French stylist assistant based in Paris and worked for two years at Vogue Russia (but the office is in Paris). They like their assistants to be really discreet and quiet, not spontaneous or funny in any way. So I learned to be as discreet as possible when on set and at the office. Then I got the job of my dreams: assistant to the editor-in-chief of French Vogue. I was so excited! But after a month, I got fired because I was too discreet and not funny enough, according to my boss. So basically I learned that I have to be myself in any situation and be really adaptable to any people I work with from now on.”

Annabelle, 23

My first job was in a bakery. The first day, I dropped a knife and tried to catch it with my foot. I ended up cutting my own toe off. From that day on, I never wore slippers to work.

Betty-Marie, 18

“I took my job as an executive assistant right out of college, and the learning curve has been wildly steeper than I could have ever expected. An integral part of said learning curve is the seemingly never-ending stream of mistakes — scheduling errors, lunch order misunderstandings, travel plans gone wrong, etc. Most recently, and potentially my worst to date, were flights booked for the wrong day, a mistake that was only caught as my boss was heading out the door for the airport. As stressful and anxiety-producing as the fiasco was, it gave me a much-needed opportunity to stop and review my mindfulness practices at work and at home. I completely restructured my organizational methods, developed better communication structures with my boss and have started working out daily. Though I will most likely have stress dreams about that mistake for a while, I do (begrudgingly) appreciate the incredibly helpful changes that have been made as a result.”

Liz, 23

I fell hard for a coworker and dated him for nearly two years. It ended very, very badly, and then I was let go. Never, ever linking work with romance again.

Alexandra, 31

“My biggest career mistake (can you call it a mistake if you learned something from it?) was staying almost two years in a marketing job that was so far away from where I wanted to go professionally. At the time, I took it out of financial need and felt it was something temporary, but I ended up getting comfortable. I ended up leaving it in order to explore and find my place. It wasn’t easy, but it was definitely worth it. I learned to never settle, follow my bliss, get out there and knock on many doors, even if it’s just for a short conversation. … You will be surprised where the connections you make along the way can lead you.”

Michelle, 26

On the first day of my first job out of college, my new boss was extending her arm to point to my office but I thought it was a hug, so I went for it. And I haven’t really recovered from it. I have just repressed it until right now.

Abbey, 21

“While working as a long-term child protective caseworker, I had a child in foster care with a pre-adoptive family. The biological mother would float in and out of contact with the agency, without a permanent address or way to locate/contact her. There was not an identified father. On one occasion, the mother made contact with me and agreed to come to court and surrender her parental rights, with conditions. She wanted four annual visits and progress reports on her child. In an effort to achieve permanency for this child, I had a 15-minute phone conversation with the adoptive parents encouraging them to agree with the mother’s desires. They reluctantly agreed. At the time, I thought this was great casework because I had achieved permanency for a child.

However, I did not realize the burden placed on the adoptive parents to facilitate four annual visits and provide progress reports to the biological mother. As I continued my career, I realized that such important decisions should not be brokered by telephone — families need time to process and evaluate if they can accommodate having contact with biological parents until the child is of age. At the time, I did find permanency for a child in foster care, but at what cost? I’ve learned to look at a case from all sides and to facilitate decisions that benefit all involved. I am now a supervisor in the adoption unit.”

Michelle, 45

The first that comes to mind is knocking a huge crystal vase off a shelf at a high-fashion magazine (and then awkwardly trying to clean it up with my hands and cutting myself while my coworkers watched in silence).

Emily, 25

“I recently got a new boss. He’s pretty awful (I promise this isn’t hyperbole). He was describing these nonsensical templates to me and they were very backwards and made no sense. So, as any mature professional woman would do, I Slacked my coworker, saying, ‘What a fucking waste of time,’ and yup, I sent it to him instead. Luckily, he wasn’t at his desk so I immediately deleted it (thanks, Slack!) but then he got the notification on his phone (fuck you, Slack) and messaged me he didn’t know you could delete Slack messages until now. So yeah, that was a pretty low low and very embarrassing. I acted confident. I tried to play it off and apologized for deleting it. Obviously, I should have just told him what I had done and why. I learned it’s better to be honest when you fuck up instead of covering something up, but also, sometimes it’s necessary to play the policy game and put on a good face and tell someone what they want to hear. Even though he’s a shitty manager and sucks, he’s still my boss at the end of the day, and I need to respect that and use that to my advantage. You can’t get anywhere if your manager doesn’t have your back.”

Emma, 28

One time, after I quit my job, I went and begged for it back. I’m talking ugly crying and pleading. I didn’t get the job back, but in hindsight it all worked out for the best! I learned that you have to leave the past behind you and move forward with life even if it’s scary!

Sarah, 20

“On the second day of a job that I was so excited to land, I put the coffee mug (that they gave me on my first day) in the office microwave to heat up some coffee. I didn’t realize it was metal and that metal can’t go in the microwave so…I started a fire. Someone I didn’t know from the accounting department had to put the fire out because I was practically useless.”

Carson, 27

I didn’t file my vacations properly so they were filed as absences and I received a $3.50 salary last month.

Sabrina, 23

“I stayed with a manager who refused to give me metrics and a pathway for growth, both skill- and money-wise. I spent a year stagnating financially after that, and though I did learn and it wasn’t a complete waste, I was shocked when I started job hunting and discovered I was way more valuable than the amount my employer was paying me suggested. I’ll strive for girl bosses forever now. The moral of this story is don’t let anyone sell you short!”

Bobby, 27

I’ve been a creative copywriter for more than 10 years now, and I just realized last week that I had been misspelling “timing” the whole time (it was “timming” for me). Well, being Spanish and working in Madrid could be my excuse, but it was so embarrassing.

Claudia, 34

“I was on a call with my boss, opened Slack and typed, ‘This is so annoying’ to my best friend at work. My boss immediately asked, ‘What’s annoying?’ Turns out I had completely forgotten that my screen was shared. I quickly made up a story about spilling juice on myself and how annoyed I was about it. He definitely didn’t buy it. Lesson: Slack is dangerous, and don’t use it to critique your boss. Also don’t share your screen, ever.

Kaycie, 28

I pressed send too fast on my introduction email the first week in a new job and had not finished spelling my name in full. My name is Kimberly but it said Kimbe. It took some explaining to get people to stop calling me Kimbe.

Kimberly, 31

“I had a really important interview during the holidays and decided to take an Uber to the office near Bryant Park instead of the train, just to be safe. I completely forgot to factor in how crowded it would be because of the time of year, and I got stuck in insane traffic. Five minutes before the scheduled time of my interview, I was still a 10-minute drive away. In my panic, I somehow convinced myself that I would get there quicker by foot. I apologized to my driver, opened the door, and ran at full speed down 42nd street…in the snow…wearing heels. I showed up to the interview soaking wet, red-faced and, despite my best efforts, 20 minutes late. (But hey, I still got the job).”

Hannah, 18

I quit my job with no plan to follow my dreams, pursue adventure, etc. I was unemployed for a year. It really slowed down my progression and career. I am really frustrated and feel I didn’t quite “land on my feet.”

Alexandra, 29

“A work mistake I made was not asking enough questions about a job I was pursuing. When I first reached out, the company wasn’t actually hiring. But a couple of months went by and I had a series of calls, and they told me they had me in mind for a position that would be opening up. After months of talking to people there about myself and my strengths, I was confident they knew what type of job would be a good fit for me. I received an offer and leapt at it WITHOUT ASKING ANY QUESTIONS. What the fuck was I thinking???? I didn’t even negotiate the salary, and I took a pay cut. I was seduced by the fact that this really cool company wanted me. I got there, and it took about two hours for me to realize that I was in the wrong role for me. I tried to make it work and attempted to worm my way into a job with another department, but I was doing a terrible job because I was so out of my element. I was there for six months before going back to the exact same job I had before. It was a waste of six months, but I also learned a big lesson.”

Eleanor, 26

Week two of interning, I walked in on our managing director on the toilet. I was so stunned thinking what to do next (doh), I froze in the doorway and she had to push past me to leave the cubicle. Everyone’s human, and everyone pees and poops.

Hannah, 25

“When I was 25, I was thriving with my own little startup but was in a long-term relationship and my partner was eight years older than me. He had quit his job and was working on a food hall. Since I had PR background, I dedicated myself more toward his project, helping him build the social media, getting designers to create the logo, working on his image and the company’s [image], etc. Basically worked with him for an entire year (for free). Long story short, three weeks before the food hall opened, he dumped me after two years of being together, completely ghosting me, and a month later started going out with someone else. The truth is, it was a mistake to focus on someone else’s dream instead of my own, no matter how much I loved him!!! You should always be your own priority and dedicate yourself to advancing your career because it’s something you can fall back on when things fall apart! Happened to me!”

Andrea, 27

My biggest mistake was not having an operations agreement clearly defined in two separate business partnerships. Long story short, going into business on two separate occasions with two different people who were my “friends” left me financially, mentally and emotionally exhausted. I knew better, but I didn’t do the due diligence of writing out a contract because time was of the essence.

Erada, 32

“My work mistake was working at a jewelry story at 16 getting paid minimum wage. I had keys to the store and would open and close by myself. At 16. After two years with no raise, my parents put me on restriction until I got the courage to ask for one. Now at 32, in my career I boldly asked for a big raise after only 10 months. Because I work hard. And I deserve it. Never be ashamed to ask for something you’ve worked hard for.”

Ashlee, 32


Animation by Madeline Montoya

Harling Ross

Harling is a writer and was most recently the Brand Director at Man Repeller.

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