Those #firstsevenjobs — yours?

By Caitlin Kelly


Off on the train, hi-ho…


A little late to this party, but those of you on Twitter might have seen this popular hashtag, where people share their first seven jobs.

It’s been really interesting to see all the odd and unlikely things people do to earn money…tank driver, fishmonger, clown, pipeline surveyor, funeral musician.

It was also interesting to see how many of the jobs were fairly low-level/low-wage until people hit a well-paid professional career, and it seemed like a longer, slower trajectory for the Americans who tweeted, maybe because so many go on to graduate school, maybe because some just didn’t need — or couldn’t get — a better position sooner.


Here are the first seven ways I tried to make money, (and you’ll quickly see a pattern!):


  • Made and sold home-made bead necklaces on a street corner in a chi-chi shopping area of Toronto. I was 12.
  • Made and sold home-made envelopes (magazine pages, with an address label). I was 15.
  • Lifeguard at various Toronto swimming pools, public and private. Ages 15 to 18.
  • Waitress (very briefly!)
  • Busgirl (even worse)
  • Sold my photos on the street. Age 19
  • Sold my articles to national magazines and newspaper. Age 19.


One of my first national magazine stories…I entered an animal testing lab. Grim and gruesome. But it was part of my job as a reporter


I soon learned that:


  • I like to sell
  • I like to talking to strangers
  • I’m not scared of selling or of speaking to strangers
  • I like seeing how people respond to my creativity
  • I like it even more when they pay me for it!
  • Lifeguarding is really, really, really, boring — until or unless (which never happened) someone is in serious trouble
  • Waitressing and bussing tables demands huge physical stamina, patience and a shit-ton of emotional labor
  • I prefer being paid to challenge and question authority (journalism) than kow-towing to bosses and customers (service work)


The world of work can appear terrifying, impenetrable, overwhelming. No matter how hard you work or whatever degree(s) you earn or your stellar marks/GPA, you can still hit a wall, or many.

There are many people out there insisting you follow your passion, without regard to — you know, money.

Just because you like making cupcakes/walking your dog/playing the banjo doesn’t mean you can earn a decent living from it.

The challenge for everyone, from first job to last, is finding steady work we enjoy, (at least much of the time), and that uses our skills and emotional intelligence.

Working for income is such a potent blend of drive, determination, talent, sheer get-this-shit-done-now, emotional labor, (i.e. sucking up, being nice to people even when — especially when — you’re being badly paid and treated like crap, as in retail and foodservice), management draaaaaaamas, finding smart/kind (if you’re lucky) co-workers, bosses and clients…

A job can look perfect on paper and then you start and….ohhhhh, shit…It’s not.

Or, yay! It really is.

I’ve spent much of my career as a journalist working freelance, i.e. without any paid sick days or paid vacation, without a boss or co-workers or raises or promotions or bonuses or commission. Whatever I earn has to come through my efforts and skills, and, when it works, the generosity of my networks who refer me on to their contacts.

Some years have been terrific, others much less so.

I do enjoy working in/with/on a team, as one does in a newsroom or magazine. I enjoy, and I miss, the camaraderie and the mix of smarts and energy.

But I also treasure autonomy, being able to plan and manage my own time, (and time off — Americans with staff jobs are terrified to ask for or use their skimpy vacation days) –and to pick and choose work that makes sense to me, intellectually if not always financially.

malled cover HIGH
My second book, published in 2011

I’ve had three well-paid staff jobs at major daily newspapers, in Toronto at the Globe and Mail, (Canada’s best), the Montreal Gazette and the New York Daily News.

I loved the first, enjoyed aspects of the second and barely survived the third; daily American newspapers, now struggling mightily and shedding staff like autumn leaves, are highly specific cultures, some welcoming, some less so.

I’ve also worked as a senior editor and editor in chief of a few magazines, work I enjoyed less, as it was totally desk-bound.


What were some of your first jobs — and what did they teach you?


10 thoughts on “Those #firstsevenjobs — yours?

  1. My first job was as a cashier in Woolco department store. I was 16 and worked part-time two evenings a week and ALL DAY Saturday from 10 am to 10 pm (wow). The job taught me lots of things – how to interact with the public, Customer Service, how to handle money and be responsible, and how to work in a team. I loved it. But what I especially loved was earning my own money and not being dépendent on my parents for pocket money.

    Later, once I turned 18, I started cocktail waitressing. Loved that too because I worked nights (I’m a night owl) and the tips were stupendous. I earned minimum wage but would go home with over $200 cash a night (in tips). I worked in jazz clubs, rock and roll joints, classy hotel cocktail bars (The Four Seasons in Vancouver – lots of business men on expense accounts) It was a party every night.

    Then I started working in offices as a secretary. That was good too because I enjoyed the office camaraderie, the fixed hours, lunches with the girls downtown or going out after work for drinks. The majority of my friendships, male and female alike, were all made in offices. However didn’t like the actual office work much, found it boring.

    But I’m ready to retire now. I’m the same age as you. I’m tired of working in offices. I’m sitting in one right now, typing this comment instead of finalizing a 25-page translation from French into English entitled “The Banking Financial Security Charter”. I know, boring right? But – hey – it pays the bills. And it’s another marketable skill I’ve learned. If I need to make some extra cash when I’m retired, I can fall back on freelance translating.

    1. Love your stories! It’s interesting to me how differently different sorts of work can satisfy us (or kill us.)

      Right now, very ready to leave journalism behind and trying to find a few exit strategies. The lack of $$$ and the rampant disrespect for our skills is deadly.

  2. i think it is so interesting to read this ,yours included. in albany airport right now with a bit of a travel nightmare but at least i’m in the state and it will be good to write about later. as for my first 7: landscaping and getting there by hitchhiking in high school, workout instructor with no coordination or sales prowess, temp in the foreclosure dept of a bank, accountant for a gas station, waitress, bartender, caterer……

  3. My first couple of jobs were as a child actor on stage for productions my parents were directing/choreographing. I was very VERY young (actually a baby for one of them). At the age of 10 I talked my way into an unpaid reception/cleaning job at a vet’s and discovered that not everyone was good to/with animals, but that I was the quickest administrator they’d ever seen. I also discovered I was not remotely squeamish, cleaning out the kennels and assisting during operations and animal dentistry. The worst part of that job was never the bodily fluids, but the owners. I also learned to work the till as the vet sold diet pet food, toys and collars, etc. I worked there during the school holidays for two years. In my next career phase I recorded vocals for some theatre productions from the age of about 13 and started writing lyrics for bands. I also started writing poetry around then and discovered people were willing to read what I wrote. It didn’t occur to me to try to sell it at that point. I painted a recording studio aged 15 in exchange for being taught to use a mixing desk, and worked as a runner for live and acoustic sessions at several different studios. Before I left high school I was making jewellery, props and clothing and sewed theatrical costumes for shows and ballgowns for fellow students through university on the basis that if they could draw/describe it, I could make it. I worked more admin jobs in the holidays during uni and did a couple more paid singing gigs. I spent a summer picking fruit. After music college/drama school, I juggled singing and theatre work with increasingly specialist office admin and IT training for a number of years before trying to put down some more stable roots and re-balance things toward a steady income allowing for more writing and less perfoming.

  4. I was a lifeguard from age 16 to 23 (yeah, I probably shouldn’t brag about how long I held onto it) and I absolutely loved it. I could definitely see why some people aren’t totally into it but I was able to teach swimming lessons, watch different types of swimming (diving, synchronized swimming, competitive lap swimming, water polo and others) and got to interact with a bunch of different people all the time. I think it taught me to come out of my shell, be an authority figure (as a supervisor and even as a water-safety expert) and how to clean out pools (a skill I hope not to need again).
    Thank you for the post! I really enjoyed it

    1. Thanks!

      Your life-guarding sounds terrific — and what a different perspective on it. No shame in staying with work you enjoy, right? 🙂

      I did synchro for a while when I was younger. It is SO hard!

  5. My first job (aside from babysitting) was working in a pickle factory the summer I turned 16. (It was the only employment within biking distance of my home, as we lived in the country at the time.) It was monotonous, tiring, smelly, and humbling. Later in life, I earned advanced degrees and I love my life in higher education, but I have held onto my memories of what it was like to work that job. It has often provided a bridge for working with students from working class backgrounds. It also made me have a greater appreciation for how I spend money. I worked really hard for the minimum wage, and knowing how much work it took to earn each paycheck made me more cautious about spending it.

    1. Then you must (!?) have seen Crossing Delancey, a terrific movie from 1988 about a NYC pickle man?

      I never fully grasped the brutal work it can take to earn a dollar until I worked retail — and much later in life. The stamina, the emotional labor, the numbing routine — and all for terrible terrible hourly money, not even enough to go to a movie. It made me hyper-aware of how nasty that work can be, and to fight hard for low-wage workers whenever possible.

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