While working on the Compass Media Careers Guide this week (plug, plug), I thought about all the jobs I did when I was still a student, before officially entering the working world full-time.
For many kids, the weekend or summer employment comes about when the parents think you’re too old to just be getting pocket money any longer, but too young to be joining LinkedIn. Frankly, even when I was still getting that weekly stipend from my mum and dad, I could have done with a bit of extra cash, but restaurants had some policy about not hiring 9-year-olds. I went through my allowance like a brush fire, and then had to turn to my younger brothers for a loan. Jacob Marley may have been dead, but Dominic and Michael Wheaton were very much alive and in business. They socked away almost every penny of what they were given, and became a fledgling Gringotts operation straight out of toddlerhood. I borrowed and repaid them until my earnings finally outpaced my spending; I was about 35.
I can’t remember which job came first, but I certainly recall the typical wise words from my elders, along the lines of “you’ll appreciate the value of a dollar when you have to earn it yourself”. I still disagree. I appreciated it so much more when it was just given to me without any effort on my part. Isn’t that what “thank you” is for? Isn’t that the very definition of appreciation?
Anyhoo, my initiation into a future career was when we were visiting our cousins in the US and one of the young ones had a paper route. I don’t know if I asked to be taken along, or if it was suggested, but one way or the other there I was, living the American dream – a little girl, riding a bicycle, helping her cousin throw rolled-up newspapers onto front lawns. It seemed so novel; we had no such service in Cayman – I’d only seen it in films. Unfortunately, I must have been distracted by something at some point, as over the handlebars I went and scraped my knee. Tears ensued. I got a dollar when we returned to the house. It was my first paycheque.
Many years had to pass after that traumatic incident (drama queen), before I could face applying for another position. I’m pretty sure my next meaningful employment was a summer stint at FedEx. Actually, just to age myself, it was still called Federal Express back then.
Those were heady days. We operated out of Elizabethan Square, when sending anything overseas other than diamond jewellery and hard drugs simply required a half-page air waybill. Where was it coming from; where was it going; what did it weigh; who was paying for shipping? Now, you’re filling in paperwork like you’re taking a convicted felon out of prison on a day trip. In late 2020, when COVID ground snail mail to a halt and we were getting birthday cards six months late from anywhere north of Little Cayman, we kids decided to send Mum and Dad (who were in the UK at the time) Christmas cards via courier. Muggins, here, volunteered to deal with the posting. I couldn’t believe the fields that had to be filled in, plus a separate customs doc for the UK, including declared values. A will was less complicated. As I had to put in the effort anyway, I lied and said that six cards had cost $100, so my parents would be impressed we’d spent so much on them. Besides, they were the ones who would have to pay the duty if it was owing, so win-win. Merry Christmas.
I really enjoyed working at FedEx, and I made it my mission to fill in the agent part of those forms at lightning speed. The ladies in the office were terrific and very helpful. Molly, Bev, Ellen Kay and Kim embraced the green newbie and showed her the ways of The Force. Even now, as a client, decades later, I am still tempted to fill in the agent section – old habits die hard. The great thing is that Ellen Kay is still there to this day. Glad to see some things don’t change.
As I entered sixth form at school, the world of fashion came calling. The late Donnie Smith, who owned Temptations (ladies clothing) and Pacesetter (mens), happily took me on, along with my friends, Betsy Leggatt and Tara Leslie. Tertius Broderick, who became owner of World Gym, worked in Pacesetter, which was right next door, so we’d go over and shoot the breeze with him when things were quiet.
While we were employed there, a fantastic opportunity came up. Donnie had the idea of running a fashion show on flights coming into Cayman. ‘Models’ would fly up to the US with suitcases full of outfits, then on the return journey, they would saunter down the aisle of the plane, showing passengers the amazing designer clothes that could be bought on the island. It all sounded very jetsetty, and the three of us were eager to sign up. Only problem was, I didn’t have my own passport. It quickly dawned on me that while my friends would be able to realise their dream of walking the runway, 30,000 feet up, I would be grounded. It was horribly disappointing, but there was nothing to be done.
So, Betsy and Tara got to fly to Tampa, Miami and other Cayman Airways destinations, exploring their inner supermodel, and I held the fort at the shop.
In fairness, their roles weren’t quite as glamorous as they sounded. For starters, there was no changing room onboard, so they either had to use the toilets or the small area at the very back where flight attendants prepped drink carts. Turbulence also kicked the excitement factor up a notch, with rough air spawning impromptu lap dances in the cabin. More than once, a model lost her balance and landed on the occupant of an aisle seat. I think the girls downplayed the joy of it when they reported back, because they knew I couldn’t go. I mean, what’s more fun than changing from one outfit into the next in one of those spacious airplane toilet cubicles?
Donnie was a very good boss, and he tried to help me improve my fashion sense, but when I showed up to work wearing a Benetton rugby-style shirt, he sadly shook his head. This one was never going to be the next Diane Von Furstenberg. That being said, I bought quite a few outfits from his store over time. In retrospect, not a great idea to be working somewhere where I was tempted to buy the goods with the money I earned. Barely any of my paycheque went into the bank.
The last significant part-time job I had, while still a student, was at Foster’s Food Fair, now just ‘Foster’s’. I started at the airport location as a cashier, and, as before, roped my friends into signing up as well, along with my sister, Gabrielle. On some nights, there would be four of us in a row with our bagging kids behind us, ready to do battle. Those boys and girls were raking it in with tips, and back then, they would offer to help a customer to their car when the grocery cart was overflowing. They’d push the cart to the client’s vehicle, help put the bags in the boot, and come back a couple of dollars richer. In the meantime, we’d have been pulling double duty on the register and doing any required bagging. It was manageable on slower weeknights, but the Saturdays were crazy, and the festive season? Don’t even… You’d think Christmas was officially peak time, but back then, the Thursday before the Easter weekend was always the busiest night of the year. You steeled yourself for a line of carts stretching back down the aisles from the start of your shift until the end. We also didn’t have barcode readers – all prices were punched in by hand. It was a job for the young, when carpal tunnel syndrome was a malady far off in the distance.
I had all my outfits from Temptations languishing in the closet, as instead of going out, I was working at Foster’s most nights. So, I decided to put them to good use. I won’t say people were mistaking me for Bianca Jagger circa Studio 54 behind the cash register, but I certainly was dressed to the nines for a time back there.
“That’ll be $53.46,” I’d say, my Jones New York sleeve dangling over the conveyor belt as I reached for the customer’s cash.
Donnie, you would have been so proud.
Of course, I’ve now been working full-time for many years, as one must do unless one falls a** backwards into a pile of money. I keep looking behind me, but no mountains of random cash have yet appeared.
In the meantime, I should thank everyone who gave me advice in those early jobs. They were great experiences and they taught me a lot.
Who knows? Maybe the modelling opportunity will come around again one day, and this time, I’ll be ready. I’ve got my passport and I’m raring to go.
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