FJ readers share the most ridiculous requests their bosses have made

“Did you want the monthly report done before or after I picked up your dog from the vet?”

Climbing the corporate ladder is often regarded as simply needing to pay your dues. In most roles, there are certain things as a junior you’re expected to put up with, no questions asked. But sometimes there comes a point where the requests tip over into the absurd (aka Miranda Priestly’s infamous request for the unpublished Harry Potter manuscript).

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When you’re really trying to make a good first impression (or you simply don’t have any other options), the question arises of just how far you’re willing to go to stay in your boss’s good books and keep your job – whether it was picking up dry cleaning, working on a weekend or taking their pet to the groomer. Below, FJ readers the most ridiculous requests their bosses have made.

Hillary*, 33, she/her

I was the executive assistant at a tech company, and had worked there for a little under a year. One of the VPs I supported asked me to check the full moon schedule for the next three years and manually enter the moon phases into his calendar, specifically the date of each full moon. Oh, and to also set a reminder the week prior to the full moon.

Anjali*, 26, she/her

I worked for a large eCommerce activewear brand, lasting about two years. My boss more or less asked me to get filler in my top lip to match my bottom.

Lauren*, 25, she/her

I didn’t think my fashion magazine internship would involve me steaming my boss’s undies before a work event but I didn’t question it. They were Miu Miu to be fair.

Nourh*, 35, she/her

I’m a freelance makeup artist. I can’t tell you how many times I’ve been hired as a makeup artist (the only profession I advertise myself as) and arrive on set to find they haven’t booked a hairstylist, and they ask me to do that as well. It makes for a very awkward conversation with the producer and a bad experience for the models.

Nothing tops the time I showed up for a commercial shoot (for a big tech company) and was asked to do the hair and dress the models, too because they hadn’t hired a stylist. To make matters worse, one talent wasn’t fit for wardrobe properly and I was blamed. I spent the whole shoot looking after hair, makeup and wardrobe. It was ridiculous.

Annabelle*, 25, she/her

I worked as lead designer for a start-up label, which was my first major break in the fashion industry. I was beyond excited when I landed the job and even got a company car – though that excitement changed pretty quickly.

My old boss was one of those startup founders who believed ‘professional boundaries’ were more of a loose suggestion than an actual workplace concept. Personal and professional were fully merged in her mind. There was no line. There wasn’t even a blurry line. There was just me, in a company car, somehow becoming an unpaid family chauffeur.

It started innocently enough with, “Can you quickly drive me to my cosmetic appointment?”.
And by cosmetic appointment, I mean a thread lift. Which, if you’re unfamiliar, is where they insert biodegradable sutures into your face and literally pull it upward.

Then suddenly it escalated to:
“Can you pick up my daughter and bring her to the office?”
followed by
“Can you drive my sister home after work?”. Mind you, the company car was intended for factory visits and stock runs. Not for me to become Uber Family Premium.

Saying no to my boss was never really an option. There was yes or there was being dragged into a meeting room and spoken at for forty-five minutes about loyalty, flexibility and the importance of supporting the business.

Every day, my role moved further away from fashion and closer toward executive suburban errand runner. What made it even better was that after losing hours to these deeply non-business-related tasks, I’d then get questioned on productivity. Emails not sent, stock not processed, work delayed.

And I remember sitting there thinking, with absolutely none of the courage to say it out loud, “Did you want the monthly report done before or after I picked up your dog from the vet?”.

Charis*, 24, she/her

I work in marketing, and at this point, I’d been there somewhere between four and six months. It was in 2022. My male boss was looking to buy a new suit for an event and said to me and another female of the same age (the only people in the office at the time) if we could measure his inseam because we’d both previously worked retail. Mind you, I worked in jewellery… no seams involved.

Tayla*, 27, she/her

I’ve worked as a social media manager for two and a half years (I’m still there). One time, I was asked not to wash my hair for as long as possible. I lasted 31 days. It was horrible, but it brought in so much business. It got 90 million views online and I got a huge promotion, so I’d do it again in a heartbeat.

Bridget*, 31, she/her

I worked as a nanny for a while for a couple of years. I became really close with their two young kids, and the mum in particular but the lines just became too blurred. We’d arrange to catch up for coffee outside of my work hours and I’d somehow end up wrangling all the kids and spending half a day helping feed and entertain them.

She would ask for my recommendations for clothing brands and end up buying all the same things, or places I liked for dinner and then ask me to book them for her. I’d end up running her errands, buying her husband his birthday present, getting dry cleaning, even cooking dinners for her extended family. I felt like I’d blinked and somehow become her personal assistant.

Sienna*, 26, she/her

I worked for a female fashion brand in 2016. The owner used to leave her kids with the store’s casuals at our Westfield stores to babysit. And she wouldn’t come back to pick them up even after the shop had closed.

*Names have been changed for privacy.

For more stories about difficult bosses, try this.