What’s the Worst Job You’ve Ever Had?

A while ago my husband and I were telling our daughter’s about the worst job we’ve ever had. My husband worked at the Albertson’s deli in high school. The worst part of the job was cleaning out the deep fryer. Every night. Gross.

My first job was at The Gap in high school circa 1993. I would later work as a receptionist, a server in multiple restaurants, a painting teacher at Sundance Resort, I sold pest control door-to-door in Hawaii, worked for a tech start up after college, then motherhood and this blog has been my main gig for quite a while now.

But there is one job that easily stands out as the worst job I ever had. But in some ways it was also the best. Let me explain.

The summer of 1995 I graduated high school and had finally quit The Gap a few months earlier. Three weeks into my last summer before college and I couldn’t find a job anywhere! This was pre-internet, so we’re talking pounding the pavement, temp agencies and eventually the classified ads in the newspaper, and that’s when I saw it: deliver newspapers for the Denver Post for $175 a week. The money wasn’t great, but I was desperate. And besides, how hard could it be?

Turns out it wasn’t that hard, but it was pretty sketchy. This was not little Timmy’s paper route being delivered on bike around the neighborhood. Here’s how it went:

The paper had to be delivered before 6am. Sometime around midnight I would show up to this warehouse where I’d pick up my stack of papers (depends on how many people are on your route) and spend an hour or so folding all of them. Yes they go from being stacked, to being folded and held with a rubber band. If it was raining, then I also had to slide them into a little plastic cover. Once all my papers were folded and loaded into my car, I would start delivering.

My route was divided up by homes and an apartment complex. Each house/apartment had a specific way they wanted their paper delivered: In the basket under the mailbox, on the front step, on the driveway. There was even one apartment on the 3rd floor that asked for their paper to be thrown all the way to their balcony. That one usually took a couple tries. This was the only strict part of the job (and the papers being delivered before 6)–the papers had to be delivered to their appointed spot or I’d hear about it.

Also, there were the Sunday papers. Sunday’s were a BEAST. The papers were HUGE. Loading and folding them took forever and delivering them, even longer. Not only that, but the Sunday paper took over my entire car–nothing or no one else could fit in there when I was delivering the ol’ Sunday papes.

Now in some ways this job was perfect for me. Ever the night owl, the hours were perfect. It was super easy for me to stay up every night (and fun since I was allowed to be out all hours) and work for a few hours each day. I loved coming home and falling dead asleep at 6 and then waking up around noon or 1 and still having the entire day! I could sleep until noon on a regular day, so it really felt like I was even more productive than ever. I could also bring friends with me on my route. I loved the super casual, laid back nature of the job and again, the hours were great.

However, it was not the safest job. I would NEVER EVER let one of my daughters deliver newspapers by herself in the middle of the night. Like, NEVER. (And to my recollection there were no other young girls at the warehouse, and few women in general.) I liked delivering to the houses because for the most part I could stay in the car. Yes I sometimes had to make sure the paper was on the front step or whatever, but most people were cool and just had their paper in the driveway. This particular neighborhood wasn’t super sketchy, but it was a little sketch. I was always looking over my shoulder and keeping an eye out for anything out of the ordinary. But I hated delivering to the apartment buildings as I was out of my car most of the time, running around this complex in the middle of the night. One night as I was throwing a paper onto a balcony I heard a male voice out of the dark ask, “Do you want to come inside for a drink?” Remember this is 2 or 3 in the morning. I sheepishly said a quick no thanks while running back to my car. Another night as I was in the parking lot of the complex there was a car full of dudes, and another car full of dudes behind that car. Luckily I was still in my car at this time, but I got nervous so instead of delivering the paper I decided to drive around for a minute. Well these two cars started following me. Two cars FULL of dudes. I drove ALL over town and they followed. I still remember the slight panic I felt worrying that they would try to box me in. I kept driving. I didn’t know where the police department was or I would have driven there, but I also didn’t want to go home and have them follow me and know where I lived…so I just kept driving. They eventually stopped following me.

At that point I went home and I waited until the sun came up, around 5 and then went back and delivered to the apartments. And every night after that’s what I did. I delivered my houses, came home for an hour or two and read–and then went back out and delivered to the apartments in the daylight. In hindsight I’m surprised I didn’t quit after that.

There were some nice people who worked at the warehouse, many of whom were just trying to make ends meet. I’ll never forget one couple and their two young kids (aproximate ages 2 + 4) that I saw there night after night doing the paper route together as a family. However, there were also some unsavory characters in this line of work and when a guy I was friendly with flashed me his giant knife one night, I tried to keep my head down and stay to myself. And let’s not forget the time I got a flat tire at 3am on a random side street and I changed it myself. Good times!

So tell me, did anyone else ever have a job as stupid as mine? And by stupid I mean kinda dangerous and risky? If not risky, please tell me about the worst job you ever had and how you finally got out of it.