Stumbling From Job to Job

I started working when I was 14 years old. That’s more than a decade ago!

When I think back on all of the different jobs I’ve had, it makes me think of that scene at the beginning of Wayne’s World where he points to a bulletin board full of hairnets and name tags. Like, that’s me, too.


But in today’s world it’s not weird for someone to have worked a dozen different jobs, unlike decades ago when our grandparents devoted themselves to one company for their entire lives. That’s just not realistic any more.

And as someone who craves a job that inspires them, that fills them with joy and passion, I don’t mind working the odd job to support myself while I aim to get there.

So, here are the jobs I’ve stumbled from in the last dozen years.

Job #1 – Banquet Waitress

My mom got me a job as a banquet waitress through an old college friend who owned a catering business.  This was the first job I ever had, and I actually really enjoyed it. Mostly for the free food, but the tips were good and the shifts were short.

My mom would drag my older sister and I out on Friday and Saturday evenings around 5 p.m. to the Newfoundland Club here in Cambridge where we would help unload the catering truck, serve the food, clear the tables and pack up all the dirty dishes at the end of the night. It was an easy gig and since we usually got done around 9 p.m. I still had time to hangout with my friends after work.

We were busiest around Christmas time and in the spring for the wedding season. The way this gig operated was you would call in on Wednesday to see if there was an event that weekend and if they needed your help. By the time I was 15 I sort of just slowly stopped calling to go to work. Because, honestly, what 15-year-old wants to spend every weekend night working?

Job #2 – General Labourer/Office Assistant

My parents started their own business when I was 16 years old. They had a drywall contracting business or something. I’m not 100 per cent sure because I was too preoccupied with my own life at the time (damn selfish teenagers).

But they did give me a job that summer that paid $10 an hour, back when minimum wage was about $7 an hour. I felt rich!

My stepdad would wake me up at 6am Monday to Friday and drive me to the construction site for 7 a.m. and we would work there until around 3 p.m. There I would haul garbage away from where the guys were installing drywall, and throw it down the garbage shoot. When I wasn’t doing that I was standing around pretending to be helpful, or actually being helpful by staying out of the way.

On days my stepdad didn’t need me to stand around or throw out garbage, I would help my mom in the office. She taught me how to do bookkeeping, file properly and all that fun office stuff. I liked that job much better because my mom didn’t make me start work until 10 a.m.

But then the summer ended and so did my job.

Job #3 – Sales Associate

Fall of 2006, 16 years old and in a very dark place. Some how I managed to get a job at a liquidation store stocking shelves. They didn’t want to put me on cash register duty, probably because I was a negative bitch but I worked fast putting items away and keeping the aisles clean.

I was in such a bad place back then mentally that I don’t remember much about this job, just endless wandering and misery, a terrible Christmas playlist and wondering how everybody managed to work that much while still in school.

I got fired from this job twice. Which I realize I shouldn’t admit on the internet, but it was over a decade ago and the person I was back then is not the person I am now. As a result of depression, too much partying and whatever else was going on back then, I also dropped out of school at the same time and basically went into hiding.

Not good.

Job #4 – Bookkeeper

Remember I said my mom taught me how to do bookkeeping? So when I was 18 I had a one-year-old daughter and didn’t want to go to work outside of my home until she was a bit older.

At this point my parents didn’t have their drywall company any more, but my mom did have a bookkeeping business so she would send me work to do at home and pay me for it.

I found bookkeeping kind of fun, as long as I didn’t have to spend more than a few hours a week on it. And it’s helped me manage my money better as an entrepreneur now.

Eventually, I decided to get a part-time job.

grocery store clerk

Job #5 – Photo Lab Technician

This was honestly one of my favourite jobs ever!

When I was 19 and my daughter was two years old, I asked my friend if the grocery store he worked at was hiring. They were and he put a good word in for me. Obviously I got the job and started working right before the holiday season.

Since most of my coworkers were still in high school I got the best shifts and a good amount of hours. I worked 8 a.m. to 1 p.m. most week days and the odd weekend evening. It was the best!

My job was to open the photo lab in the morning and process the photos while the full-time lady downstairs was in charge of customer service. It was heaven, like seriously. I loved the company I worked for, I had benefits, the perfect work schedule and I loved my coworkers.

But then the damn photo lab closed down because, who woulda thunk it, less and less people started bringing in film cameras to get developed. The company shut down the lab and brought in a few extra digital photo kiosks to replace me.

Job #6 – Cashier

Since I was in a union, they couldn’t technically lay me off without offering me a cashier position first. I didn’t want to take the lay off so I switched to front end and became a cashier.

Worst. Job. Ever.

I lasted a couple months until I found a new department at the grocery store to transfer to.

Job #7 – Seafood Clerk

The only department that was hiring was the seafood department. Now, I don’t eat seafood because I don’t like it, but anything had to be better than being a cashier so I took a leap of faith and transferred.

And, what d’ya know, being a seafood clerk really wasn’t that bad!

Eventually I got used to the smell (although my friends and family never did), and because it was such a small department I got to work all by myself (the besssst) and was still getting a fair amount of hours during the day.

As a seafood clerk I was responsible for keeping the freezers stocked, and the fresh seafood display cabinets full, as well as cleaning and prepping the fish and steaming the lobsters! I felt so bad at first, sticking those poor little guys in there, hearing their bodies scream as they were literally cooked alive. And then I experienced my first lobster sale, and murdered hundreds of lobsters a day throughout that week.

Unfortunately, my husband had been laid off from work and was also only working part-time. We really depended on my income from this job, so when my hours got cut back from 27 hours a week to 8 hours I had to look for a new job.

Job #8 – Cleaner

At this point my mom was the HR manager at a cleaning company and offered me a job as a cleaner.

I only did this job for a few weeks because it was brutal!

Since I kept my job at the seafood department while working full-time as a cleaner in the evenings, I was exhausted and really missed my daughter. But basically, my responsibilities included cleaning the many, many, many cafeterias and washrooms at the RIM building where they make Blackberries. I also had to clean the front reception area and one of the laboratories! Seriously though, every time I scrub my toilet or clean my microwave I think of the nights I used to clean dozens of them over and over again.

So I quit and kept murdering lobsters for a little while longer.

Job #9 – Pharmaceutical Packager

Sounds like a fancy job, but it wasn’t.

My friend offered to put a good word in for me at the factory she worked at and before I knew it I was quitting the seafood gig and working 44 hours a week in a windowless factory. I would put pills into bottles, and then put those bottles onto a conveyor belt where they would get a label put on them, then the bottles would go into little boxes, and those little boxes would go into bigger boxes, and those big boxes onto skids.  And so it would go like that from 7 a.m. until 5 p.m. Monday to Thursday, with half days on Friday.

Despite the boring job, I had a great time joking around with my coworkers. Most of them were either Lebanese or Indian, but they were a fucking hoot! We would have dance parties as we worked, and one lady in particular was such a perv it was hilarious.

Again, I started to miss being home with my daughter and when Nick started making enough money I was able to quit.

artist assistant

Job #10 – Artist Assistant

I quit the factory job in July when I was 21. I didn’t work again until April when I came across a job advertisement on Kijiji looking for 10 youth to participate in an art project.

At this point I was once again severely depressed. I had just finished high school at the age of 22 and having a difficult time finding work. The longer I went without working, the more anxious and depressed I felt. I was also living back at home with my parents to save money.

2012 was a really weird year to be honest. So much happened outside of work, but being at the art studio from 9:30 a.m. until 4 p.m. Monday to Friday helped me stay sane.

It’s also where I met Sarah, who was one of the other youths in the program!

Other than working in the photo lab, this was my favourite job: painting and drawing all day, creative thinking, going on adventures and sketching by the river. It was a dream come true. But, as it was just a six month program it eventually ended.

With the encouragement of my art mentors, I applied for college to study journalism and it’s because of my job there that I’m now a freelance writer.

Job #11 – Photographer

I should mention that in between the art studio and working in a photography studio I also worked in a thrift store as a sales associate for a short while, worked nights at the grocery store where I had worked before making salads for a few months, was in college full-time, running two Etsy shops and my own blog, and doing an internship at the library writing tweets and press releases.

So Sarah works at a big chain store, where they have a photography studio. She knew they were hiring for the Christmas season and suggested I apply.

Since the manager knew Sarah she ended up hiring me (plus, you know, I was qualified).  I worked there for a couple of months for the holiday season. It was then that I realized I really didn’t like taking other people’s picture. I mean, I don’t mind it and I think I can do a great job, but it was so awkward. But the worst part was how much you were pushed to up-sell all the time.

Of course, the photography studio isn’t all that busy after the holiday season so most of us holiday temps were laid off around Christmas.

Job #12 – Freelance Writer

Finally, after a decade of working, I started freelance writing when I was 24 years old and in school studying journalsim.

My first writing gig was for The Young Mommy Life, a blog for young moms. Since I was a former teen mom, and current young mom, I sent Tara an email when I saw she was looking for contributors.

After that I started writing for Write.On Communications Services as a journalist. I still write for them. And now I write for multiple sites. It’s a lot of of fun, and a lot of work, but I like it.


And who knows what job I might have in the future? I hope to be able to continue working for myself, writing and creating art, taking pictures and helping people.

Because, just like Wayne from Wayne’s World, I’m committed to making a career out of my dream.


All of these jobs, as different as they are from one another, have all taught me valuable lessons that I can apply to my career today: customer service, bookkeeping, taking pictures, art and design, time management, writing and editing, and more.

What jobs have you had in the past?


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  1. hahaha the pharmaceutical packaging job reminded me of when I worked at a meat market as a meat wrapper. Boring but everyone I worked with was pretty entertaining.

  2. I’ve had like half as many jobs, this is fascinating. They’re so different! Good point though, that there’s something to take from each of them. And you wanting to be home for Sid is so heartwarming ❤️

    1. Lol! I think a lot of people have had less jobs than me. I think Sarah’s only had three so far. Before I went to school to study journalism I had no idea what I wanted to do and that definitely influenced my job stumbling lol. And a lot were temporary jobs for the holidays, too.

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