MY WORST DAY JOB: I Was A Crazy NYC Millionaire's Personal Assistant

the devil wears prada personal assistant nyc

Photo: YouTube/anamour2009

“I really don’t care what I do!” I say with the kind of disdain that only a 22-year-old stuffed from too many unlimited salad and breadsticks from the Olive Garden that her parents just bought her, can say. “It’s just a job to pay the bills till I can support myself doing what I love!”I’m home for winter break, and my parents just asked me if I’d given any thought to what kind of job I’d like to get when I graduate in a few months. My BFA in drama taught me many things: comedia dell’arte circus skills, basic fencing, and how to naturally speak in iambic pentameter. Unfortunately none of these are actual job skills people look for. Besides, as you and your friends say with all the weariness of a person who’s never seen the inside of a free clinic, “I just could never work behind a desk all the day!”

The irony is that unless you’re a bike messenger, waitress, or babysitter, you will definitely end up behind a desk all day, and doing grunt work for people who do things like tuck their button down shirts into jeans and says things like “oh bummer” as they check their Blackberry when being told someone’s grandmother just died.

I’ve always felt grateful for having a job and being able to support myself, but I’ve realised along the way that these just for now jobs tend to affect you more than you realise they will. In honour of all the people graduating now who didn’t choose the most linear paths to career success, but who still believe in themselves, here are some of my crappiest day jobs.

1. The Box

I had just moved to New York, and was searching Craigslist for waitressing jobs when I found it. It was to be a “Cigarette Girl” at this new bar called The Box. The only other time I’d ever heard the term “cigarette girl” was on an episode of The Flintstones; in a flashback episode where Wilma and Betty were working as cigarette girls the night they met Fred and Barney. Encouraged by how well it worked for them, I sent in my resume and got an interview!

I wore my best business casual, brought the standard copies of my resume and showed up at The Box. I sat down with the manager and explained that while I wasn’t a smoker myself, I was very familiar with the different brands and would research them in case the customers had any questions, and that my experience with salesmanship was limited to girl scout cookies, but I was a fast learner.

She looked completely confused, then explained “Oh no. You wouldn’t be selling actual cigarettes. A cigarette girl is just a term for someone who sells things table to table at bars.”

Oh no. I’m interviewing to be that old lady who walks into restaurants trying to sell flowers or glow-in-the-dark bracelets?

“The job is selling high-end sex toys table to table.”

She took out a velvet lined briefcase like a villain from an ’80s movie and showed me a silver plated vibrator and silk restraints, should people suddenly be in the mood for aggressive love-making during the show. She went in another room and then showed me the uniform that was required. And by uniform, I mean something a Prohibition-era sex worker would wear.

“So, the job would be… selling sex toys table to table while wearing lingerie?”

Somewhere in the Midwest, my Dad felt an unexplainable pain in his heart at that very moment. I didn’t take that job. Even I had my limits.

2. Staffing Firm

I’m somehow working in sales at a staffing firm downtown, where I had originally interviewed to be a temp. My job consists of being on the phone all day trying to sell, and wearing a mandatory pin to client meetings that says “I Love My Job!”

One day I’m sitting at my desk writing out holiday cards for my prospective clients, when the owner of the company, who’s in her sixties, and dressed meticulously with the most perfect hair I’ve ever seen, walks up to me.

“Do you feel like you have good handwriting, Michelle?”

“I do… yes. I think my handwriting is definitely…legible.” (The last time anyone questioned my handwriting, I was wearing a Rainbow Bright T-shirt because it was the late ’80s. And in fairness, cursive uppercase Q’s are not easy.)

“Ok… just checking. I figured you may not have the same perfect handwriting your colleague has, since I know you didn’t go to Catholic school, where the nuns are very precise about meticulous handwriting.” (Between this and her comment yesterday—”Oh Michelle, this Bernie Madoff business is so awful. How is your… community taking it?”—I am thinking she might not be the biggest Seinfeld fan, if you catch my drift.)

“Michelle, I remember when I first came back from maternity leave in the seventies, I was exhausted all the time, and a colleague pulled me aside and told me I looked tired.”

She looked at me pointedly. (Is she implying I remind her of someone going through post-partum depression?)

“When you leave your apartment in the morning, you need to look at yourself in the mirror and say, ‘Do I look like an adult woman going to work?'”

I looked down at myself, and said weakly “Are you saying you don’t like my outfit?”

She was.

“Umm, ok. I’m sorry you feel that way, I thought this was nice…”

I needed to defend myself and show her that I’m a professional woman not to be trifled with.

“My outfit today is actually from …The Gap.

In that moment, I learned something crucial, in life and in business: Namedropping The Gap will never get you anywhere; no one respects The Gap.

3. Personal Assistant

Tip for any young men or women: If you see a job on Craigslist that asks you to send along a photo of yourself along with your resume, prepare for this to be the worst job you’ve ever had. Do you know who has to send in photos with their resumes? Hookers, girls who live with men for free rent in exchange for being forced to walk around nude, and people who see postings for “Actors wanted for personal assistant work! Make $$$ while pursuing your dreams!”

Read the rest at The Billfold >
This story was originally published by The Billfold.

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