My Worst Day Jobs: I Almost Sold Sex Toys and Might Have Worked for an Arms Dealer

“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 realized along the way that these just for now jobs tend to affect you more than you realize they will. In honor 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!”

I interviewed, and a few days later I got the call. I was placed on a temporary assignment to be a personal assistant working out of someone’s home office, which was a brownstone right off Central Park. I found out that “working out of someone’s home office” is industry speak for “you will accidentally walk by your boss peeing with the door open, because that’s what people do when they’re in their own home.”

When I first got there, he sat me down for an interview in his office, where he had six monitors showing security feeds at his other homes, and every once in a while during the interview, he’d say something like “son of a bitch! It’s 10 a.m., Raul should be cleaning the tennis courts at my place in the Caymans right now!” Then he’d get on the phone, yell at someone, and a minute later we’d see Raul on the monitor running onto the tennis courts, making an apologetic motion at the camera, as he looked on. This was also a red flag, along with the fact that a majority of his property was located in tax haven countries, but I guess it’s true: Those tennis courts weren’t going to clean themselves. And I was excited by the next thing he asked me, which was if I had a working passport, in case there was last-minute international travel. I felt like Jason Bourne, but if he were a personal assistant to an eccentric millionaire.

Somehow I passed the job interview, and he told me three assignments I’d begin working on right away. He wanted me to plan a dinner party for Mayor Bloomberg (who he claimed to have friends in common with), the pool table needed to be fixed within the hour, and lastly, since he just moved into the brownstone, he wanted me to find an interior decorator student who would work for free. So I began work at my desk, with a camera above me, so he could monitor me (along with Raul) from his office next door. I was on the phone all morning; and it wasn’t going well. Apparently, most working professionals don’t feel like dropping everything to work for entitled millionaires who insist on paying them only in experience, and no actual money.

At 3 p.m. he popped his head into my office. “Let me give you a tour.” I felt like Jack Dawson at the beginning of Titanic. After showing me living room upon living room, we were in the basement.  He was about to open a door, when he slammed it shut, leaned against it and intensely said, “Do you know how to operate firearms?” I was terrified.

“No! I don’t know how to operate firearms… Why?”

“You don’t? Ok. You must never go in this room then.”

The scene in Scarface where Al Pacino defends his home with a machine gun is going through my head.

I went back to my desk to plan a dinner party that would never happen. When I Ieft work at the end of the day, I looked back at the house and thought to myself, surely there might be an easier way to support myself, and then I wondered the next time I’d be in a house that had a real dumbwaiter. I called the agency from the street and explained what just happened.

“Wow. That’s very strange” she said. “So, if you had to make an educated guess, do you think he might be an arms dealer?”

“Um, I’m not sure. My Microsoft skills are decent, but I’m really not qualified to assess arms dealers at this point. Don’t you do any type of background checks before you send your staff into people’s houses?”

“We google them first!” I needed a new job. Everyone knows that arms dealers have the worst Internet presence. That was my last day.

These are just some of my crap jobs, but more importantly, what are yours?


Michelle Markowitz is a comedy writer and storyteller in New York.  She co-hosts the comedic storytelling shows “Failing Our Twenties” and “Hookups & Hang-Ups,” and can be found online (usually talking about her love of Chipotle), and receives links to animals doing cute things at her email address. Photo: Flickr/John Pevelka


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