From Cupcakes to Porn: Every Job I Had in My 20's

Reading and listening to other people’s stories have helped me feel less alone. So as I close the twenties and turn thirty, something that’s supposed to be big and important, I’d like to reflect on lessons learned in different chapters of my life. Some of these will be funny, most of them will be reflective and thoughtful. I’m writing them in hopes that other people relate and feel less alone. Or maybe, at the very least, you’ll be entertained.

I’m a millennial stereotype in a lot of ways. I like avocados (but I’m Cuban, so this shouldn’t be counted against me). I’m on various forms of social media. I’ve had a million jobs. I surf to work (let’s make this a new millennial stereotype as our generation gets older).

When I graduated from college in December of 2010, I needed a job FAST and the market was terrible. I had graduated a semester early just so I could get a head start on my career — having to go from my college graduation in cap and gown to iO to perform in opening night of my sketch troupe’s show. I felt like I was really about to work my ass off, but I was released into one of the worst job markets in U.S. history armed with a theater degree and intermediate computer skills.

After about four months of job searching, I walked into a local cupcake shop and asked if they were hiring. It was my last resort after having worked temporarily at my friend’s sports marketing company, getting fired from a super stuffy temp job that didn’t want me to wear nail polish where clients would call asking to speak to a man (I would tell them no and transfer them to a woman on staff, so it isn’t hard to guess why I was fired), and being left off the schedule at the daycare I was working at because my boss was an improviser who was mad at me for not booking her on the improvised musical that I was only the assistant producer for. Post-college life wasn’t going great.

To make everything worse, I suddenly got super sick with a mysterious virus. When I went to the doctor only days before he seemed unbothered, shrugging off all the symptoms I had been experiencing for almost two weeks. After some blood work, he nonchalantly told me, “I don’t know what this is. It’s like mono, but in your stomach.”

I asked what I should do. I was down twelve pounds on my five-foot-one frame because saltine crackers were the only food I could eat that wouldn’t make me vomit. “I don’t know. It should pass, I guess. If it doesn’t, let me know.”

So with this mystery illness I dragged my tired, sick, and broke self into a cupcake shop, despite the fact that all of the sweet treats were a little nauseating at the time. I had never worked in a restaurant before — something I was nervous about when I walked in. But I was desperate. I really needed to start making money, even minimum wage plus tips money, and hopefully I could secure a job before I withered away from “mono in my stomach”. Seriously if any doctors are reading this: what did I have???

“Are you hiring?” I asked, carrying a neat folder filled with my resumes.

The lanky manager and the woman behind the counter exchanged a look with each other and told me to sit down. I handed them a resume, but the manager took it from me without even glancing down to see what my name was.

They sat down with me and said, “Sooooo who would win in a fight: a robot or a monkey?”

That was the first question in the spontaneous job interview. I decided to go with it and confidently gave my answer: “It would depend on the monkey.”

“Bingo!” the woman said. I figured this answer would buy me a little time to give a more definitive answer. They then talked about types of monkeys with each other while I listened, almost like I was watching two people in a play. It felt like Nichols and May were performing a show just for me while they debated whether a Rhesus monkey could pry apart a robot with its tiny hands. The manager then mentioned that there are different types of robots, too.

“Is a toaster a robot?” He asked like it was some kind of philosophical question we were supposed to discuss, like he was the Socrates of kitchen robotics. They still weren’t reading my resume.

The woman then said, “Moving on. If you could meet any historical figure and…you know…who would it be?”

The manager looked at her incredulously. “What do you mean by ‘you know’?”

This moment revealed to me that they hadn’t discussed these questions ahead of time. This was all on the fly and she had taken a jarring left turn.

She explained that she, obviously, had meant having sex with a historical figure. This was a job interview.

“Why have sex?” The manager asked. “Can’t they just hang out?” He then turned to me. “What historical figure would you hang out with?”

“Or have sex with,” she mumbled.

As a history lover, I was disappointed that my brain went blank. Harriet Tubman, Flannery O’Connor, Abraham Lincoln, Frida Kahlo, Nefertiti — so many people! But at the time? I couldn’t think of a single interesting person.

“I don’t know…” I began and quickly reminded myself that this was a job interview and that my answer was somehow reflective of my ability to serve coffee and cupcakes. “John Lennon.”

He was probably 25th on my list in real life because he would probably be insufferable to me after about ten minutes of conversation. I’m sure after he rambled about world peace or Yoko, I’d make up an excuse about having to leave our hang sesh early. But the answer made the manager happy.

“Hell yeah!” he said. “Hey — Beatles or Rolling Stones?”

“I like them both.”

“I like the Stones. Do you like pop music?” my prospective boss asked.

I nodded.

“We play a lot of pop music here so you have to love it,” he said.

I took note of the fact that Elvis was currently playing in the bakery. Pop music’s definition must have been pretty loose and not subject to modernity.

The two of them looked at each other, grinning. Despite that errant question, this all felt like it was planned and that I was just a pawn in their bizarre hiring game. I expected them to tell me that this was all a prank and to send me off with a jobless cupcake to thank me for my time. They then looked back at me at the same time. It was as if they were communicating telepathically to each other.

“Let’s frost a cupcake,” the woman said.

They stood up from the table and led me behind the counter. They had not yet asked me about my work experience. They didn’t notice my lack of food service skills, but it wasn’t necessary. I was already behind the counter with a bare vanilla cupcake in front of me.

The woman picked up the tube of frosting and showed me her technique.

“Start on the edge here on the outside and then circle in like this,” she said as she did as quickly and perfectly as possible. I had never frosted a cupcake like this before. I had only ever basted them with a spoon in my own kitchen. I gave it my best shot — it was pretty messy, frosting spiraling off the sides of the cake.

The manager held the cupcake up to inspect it. “Not terrible,” he said. “So. Doing anything tomorrow?”

And just like that I was hired, without the ability to even eat the cupcakes for another two weeks until my stomach mono passed.

I only worked there for about four weeks, however. In my desperation, I had hooked up with a temp agency (if you pictured having sex with a temp agency, congratulations, you’re wrong). It was at a time when every young person working in Chicago was trying to work at a certain online coupon factory and one day the temp agency asked if I wanted to work there. How could I say no? It almost seemed like a nEtWoRkiNg opportunity because every other improviser in Chicago was there. It seemed fun!

But so was the minimum wage cupcake job. Of course, I wasn’t going to turn down the temp job to work at a cupcake shop. I had a college degree! This is what we’re supposed to do. Offices, computers, paperwork…until I obviously was discovered and became a star. The college dream.

It. Sucked. I temped in that one office for 18 months where they began telling us they were developing computer technology that could do the job we were doing, so they weren’t going to hire us. One day my boss told me the computer got some information I had missed.

I looked at him blankly and said, “So you’re telling me the computer that is supposed to be better than me IS, in fact, better than me?”

He nodded sheepishly. “Yeah, I guess I am. Good work.”

I quit that job to work in a school despite having ZERO qualifications. A Catholic school that a friend of mine was working at needed someone ASAP. A teacher’s aide quit only a week before school started. In my job interview the principal asked me if I was Catholic and when I said “yes” she wrote that down and circled it. She didn’t even give me a background test. The Lord had already done that for us.

If you can believe it, a year after I worked at the school — a job that was really not for me — I was back at a temp position at the coupon factory. A different one this time. One that ended up hiring me on, but one that also had bosses in blazers that were younger than me. And remember, I was only 24. It was hard to respect people I wanted to give swirlies to.

After that I was a celebrity chef’s personal assistant, a dog walker, a nanny, a customer service representative at a gift basket company in Queens and a daycare receptionist. All until I finally realized that I could just quit. Not quit and find a new shitty job. I could quit it all and just write.

I started feeling bad about my work history as some peers or family members had relatively stable jobs. I was worried that I would never find something like that, but that wasn’t what I wanted anyway. I was simply projecting what I thought other people wanted for me. I wanted to earn a living as a writer. That was it.

During this time I had started getting my writing published. It began small at first with some 300-word history pieces on a friend’s website. But it grew over the years. I kept writing at all these day jobs, sneaking away to research and write essays or just plain blowing off work to blatantly write on the job. One day I had an interview for a…um…adult entertainment website.

Hear me out. It isn’t porn. It is just a website that is like IMDB, but only for nudity in movies. You have likely heard of it. The company didn’t hire me then and there, but six months later they asked me to freelance for them.

I then spent two years freelance writing for a living. One year was super difficult with me never fully knowing where the next paycheck would come from, asking to borrow money and taking strange odd-jobs to make rent (I once had to fill bean bag chairs with tiny little beads for four hours). The following year, however, everything changed. Between building relationships with clients and getting my name out there, I was suddenly being asked to write and it ruled. I even got to write trivia for a video game and suddenly the little adult entertainment website that could asked me to join them for realsies. I had actually done it. My goal when I graduated college was to be a writer and while the road was winding and bumpy, it happened.

Like with my cupcake job stint, I never intended to work here specifically. I answered a Craigslist post and wasn’t even sure if it was real. I could have shown up to the interview and it was a man behind a camera telling me to wear a bikini and shave my legs. Who knows what could have happened? But I took some chances, I went for jobs I never really saw myself having and I took enormous leaps of faith. That’s how you become a writer, or anything creative really. You have to take chances and you never really stop taking chances. To stop taking chances it to be complacent and complacency flies in the face of creativity. So take a risk. Apply for something stupid. Quit what makes you miserable. Put yourself out there.

At the very least you might learn how to frost a cupcake.

Stephanie is a writer and comedian whose work has been featured on Reductress, Slate, The Weekly Humorist, The AV Club, Mental Floss, Atlas Obscura and more.

Get the Medium app

A button that says 'Download on the App Store', and if clicked it will lead you to the iOS App store
A button that says 'Get it on, Google Play', and if clicked it will lead you to the Google Play store