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.

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.

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?