The team on the weirdest jobs they've ever had

By: Jessica Mach on January 22, 2019

We’ve all needed a job at one point or another. And because meeting one’s needs rarely happens without at least some degree of compromise, it’s no surprise that most of us have taken on at least one job that was, well, loveless — and sometimes even outright weird.

All of us at are pretty happy with what we’re doing now, but this wasn’t always the case. We’ve each done our fair share of sad, creepy and perplexing jobs, and today, we’re sharing our experiences. Maybe you can commiserate.

Assassinating coat check

The year was 2004 and I must have been on the verge of turning 17. I spent the entire year obsessing over Kill Bill Vol 1. and 2. I was convinced I could become an assassin or a professional mixed-martial arts fighter. I had raw potential, all I needed was a teacher. A sensei, if you will. To find one, I turned to my mother's copy of the Yellow Pages (the print version). I found an ad for a gym called Crazy Bob's House of Death located in the Forest Hill neighbourhood of Toronto (where Drake is from). I was immediately intrigued.

Unfortunately, when I made it to the House of Death, located in the basement of a very respectable-looking detached house, I found out I couldn't even do a somersault properly. Crazy Bob, a nice gent in his early thirties, saw potential in me as a coat check girl. He recommended me to his friend, who owned a restaurant-nightclub at Yonge and Eglinton. It no longer exists, but a scene from the movie American Psycho was shot there. The one where Christian Bale's character tries to break up with his girlfriend played by Reese Witherspoon.

Anyway, I wasn't great at working the coat check. I mixed up coats, caused huge lines to form, and was constantly on the verge of tears. I shouldn't have been there in the first place because it was a nightclub and I was underage. Anyway, one night I met the members of B-44 and some cast members of Degrassi: The Next Generation (not Drake, though). I probably got fired.

— Alex 

Fun biblical nudes 

After grad school, I applied for 67 jobs and only went on three interviews in six months. So, imagine how elated I was when I finally got a job offer. I was going to be paid $40K a year! In dirt-cheap Montreal! I could stop buying groceries on credit!

The job was at a small insurance office, and until I actually started working, it didn’t occur to me that I actually knew… nothing about insurance. Another bad sign was that the girl who trained me was firm about one, peculiar point: I had to write down every single thing I did at the office. I wrote her off as unfashionably scrupulous. Later, I realized it was because the broker liked to gaslight us.

Other bad signs: I opened a drawer under the colour printer one day and found a stack of large, high-quality photographs of the broker and a bunch of other guys, naked. My coworker later told me they were “reenacting the crucifixion of Christ.” The broker had been inducted into a pyramid scheme before I started, and the leader of the scheme had disappeared. So he made my coworker, an office assistant, “track him down” because he didn’t want to hire a private investigator. He’d call me from a beach in like, Maine, where he was antiquing, and yell at me to move tens of thousands of dollars around his accounts without explaining what exactly I was doing. He also made my coworker place a Craigslist ad for a 19th-century rose gold chandelier with hawks emanating from multiple angles.

Anyways I quit after six months, moved to Toronto, and was unemployed again for another 10. Being 25 should be illegal.

— Jessica 

No startup capital? Just steal 

My sister and I used to sell golf balls when we were in our tweens. It wasn't a formal business — you could say we were entrepreneurs, but really I just needed money to buy video games. It all started when we were hanging out by a creek that ran through a golf course near our house (we didn’t have a lot of adult supervision in our youth). We noticed stray golf balls kept being shot into the water. So every weekend, my sister and I would roll up our pants, wade into the muddy creek waters and scoop up golf balls covered in algae. We cleaned them up and displayed our wares in egg cartons near a putting green — but just off the golf course property to avoid security telling us to scram. “50 cents for a golf ball!“ we shouted to balding men in slacks.

This went on for two summers and we sold hundreds of golf balls. Titleist, Nike, TaylorMade — we had all the best brands. It was a profitable business and we eventually made enough money to invest in a golf ball retriever — no more risking tetanus by going barefoot into the creek.

Unfortunately, the next summer, the course owners built a fence to keep us out. At first it couldn't stop our entreprenuerial spirit — we dug a hole under it, crawled under the fence every morning, and continued to sell golf balls. But security kept chasing us off and more golfers started turning hostile after they caught on to the fact that we were selling them back their own stuff. Our business formally shut down in 1998.

— John

Pay your journalists in designer handbags

The job posting sounded harmless enough: “Journalist (for Aesthetic Medicine Magazine).” A Google search confirmed the existence of this cosmetic surgery magazine. The confusing part, though, was that it was based in the U.K. That should have been the first red flag.

Never mind the moral quandary that should have stopped me from applying to write about cosmetic surgery. (I was fresh out of school, and would have taken any job with the word “writer,” “journalist,” or “editor” in the title.) Why was a Toronto agency hiring for a British magazine? Things crystallized at the interview, when a magazine with a completely different name — one I’d not seen anywhere in the job posting — was put in front of me. It was a magazine about “aesthetic medicine,” but that was not its title. This should have been the second red flag.

I got the job, which lasted all of two months. On my second day, I was told not to come in because the rest of the team was shooting a movie off-site. I asked if I’d be paid for the mandated day off. The next morning, my boss pulled me aside and reamed me out for “asking him for money.” I suppose I often asked him for money — like every two weeks or so, when I was legally supposed to get paid but couldn’t cash my cheque until he was certain it wouldn’t bounce. Red flags three, four, and five.

There was also the $200 pantsuit from Melanie Lyne we were expected to buy; the designer handbags he promised to buy us; oh, and the office dog, a black Chihuahua mix, that repeatedly had seizures in the middle of the floor.

… Are the red flags on fire yet?

One day, he threatened to fire all of us if we didn’t finish an assignment by the time he returned. We walked out that afternoon and told him we quit. As we cheersed over tequila shots at a nearby patio, we each received a text message from him telling us we were fired.

I never did get the pantsuit. Or the handbag. Just a Ministry of Labour file and the relief that this job will never appear on my resumé.

— Lisa 

Bad, bad, bad, bad, bad

Before I figured out what I wanted to do in life, a friend of mine was working promo jobs and I wanted to give it a shot. For the most part, I liked it. I got to work with a number of well-known brands and meet new people.

The jobs and hours though weren't always my favourite. For example, one night I had to wander around King Street West in Toronto until 1:30 a.m. handing out free cover for a club — I would have much rather been in the club with my friends than approaching strangers with free cover, but, it paid well.

Another time, I had to wash people's dishes in a popular downtown area to promote cleaning products. I hate washing my own dishes as is, so imagine having to wash them for a full day straight for OTHER people!

One of the oddest promo jobs I had to do involved wearing a witch hat and a tiny, black dress that showed way too much skin and walk around downtown in broad daylight promoting a movie (luckily I wasn't alone for this one).

Finally, and probably my least favourite, I had to promote gas cards at various gas stations. It was uncomfortable to bother people while they pumped gas, and payment was never on time.

— Nicole