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How to improve your writing skills (and win stuff at the same time)

by Rebecca Douglas
01 May 2019

I’ve never really approached things the ‘normal’ way, and the start of my writing career was no different. I was at uni, studying for a maths and computer science degree, but I’d secretly always wanted to write for magazines.

English was one of my majors, but writing professionally seemed like such a pipe dream. Between full-time uni and a part-time job (sometimes more than one), I had barely enough time to turn around twice. I possessed neither the hours in the day nor the confidence to start pitching publications.

One activity I could squeeze in between coding programs and penning essays were a couple of minutes at my computer to enter competitions. I decided at worst it’d be a bit of fun, at best I might land myself a few freebies.

How I used my writing skills to win

I homed in on contests asking entrants to answer a question in ’25 words or less’ (or ‘fewer’, if you’re a grammar pedant), such as why they’d like to win a Gold Coast holiday. I figured it was a good way to practice both my writing and editing skills, albeit on a tiny, tiny scale. It also cuts down on the number of people vying for the prize – not everyone can be bothered conjuring up something witty.

I found these comps on TV channel, radio station and magazine websites, on chip packets at the supermarket, and, well, everywhere I looked once I tuned into them. I especially enjoyed using the free-to-join Australian Competitions Club website, which lists every imaginable contest.

My first win was a $200 Kookai clothing voucher. Spurred on, I kept entering and other prizes soon landed in my letterbox – from CDs, movie tickets, and magazine subscriptions to big-ticket items like trips to Japan and Melbourne, a $1,000 Westfield shopping spree, and even a year’s supply of toilet paper (I kid you not).

I also sent 12 reader letters to Madison magazine in the space of 12 months. Seven were published and one of them took out the monthly prize – a Chloe perfume pack. Even more valuable, I became hooked on the high of seeing my words in print, in a real-life glossy.

These wins gave me enormous self-assurance, knowing someone had read my words and actually liked them enough to pick them out of a large number of entries. The hobby also encouraged me to try new experiences that fuelled my creativity – my wins included a personal shopping session, a stunt driving course, advance screenings of movies, and front-row tickets to a fashion parade.

Entering competitions is a lot like pitching stories

I’ve now been freelance writing for nine years. Like entering competitions, pitching is a numbers game. The more you send out, the more success you’re likely to have. An unexpected benefit of my comping is I’ve developed quite a philosophical view of dealing with rejected pitches – I usually just shrug my shoulders and keep trying, confident that something good will be on the horizon.

Freelance writing these days has largely crowded out my time spent entering contests, but I still send in the odd entry here and there for some light relief, especially when I’m stuck on a drier, making-the-money type of writing job.

Over the years, I’ve figured out how to craft my entries based on what seems to yield the best results.

My top tips for winning

Be poetic: I must admit, poetry has never been my cup of tea, but free stuff is a powerful motivator. Besides, a simple haiku, limerick or four-line stanza is pretty easy to conjure up. You can also go wild with similes, lists, alliteration, puns, puzzles, jokes, recipes and whatever else fits in the word limit.

Mention the brand: I often mention the brand and/or prize in my entries. You know how humans have been scientifically proven to respond well to someone saying their name? Companies like to feel this warm fuzzy as well.

Be upbeat: As a general rule, portraying a happy and energetic image works well, and if you can make the judges laugh, all the better. Look at it from their point of view – they want a likeable brand ambassador, especially if they’ll be featuring your entry and/or photo on their company’s social media.

Be honest: Sometimes, it’s not appropriate to answer the contest question with a glib quip. A brutally and beautifully honest anecdote can come up a winner, particularly if it’s unique, yet relatable.

Be original: The judges will often be reading hundreds, if not thousands, of entries. If a joke or word association is obvious to you, it’ll probably be obvious to other entrants as well, and the judges will grow sick of seeing it. Come up with an idea out of left field that is unique, yet oddly perfect. Like coming up with a dynamite pitch, that’s the trick.

How to write a winning entry

So how exactly do you craft a killer “25 words or less” entry? Firstly, I sit down and brainstorm words and ideas surrounding the topic, looking for an offbeat take. I cross out anything too obvious and often come up with a poem in either the ABCB or AABB rhyming scheme.

For example, here’s one I wrote to score a signed Jamie Oliver cookbook from the Penguin Books website. Entrants were asked: “What is your favourite Jamie Oliver recipe and why?”. My answer was:

Jamie’s steak sandwich is the best ever,
Cooking his recipe’s a worthwhile endeavour,
His sanga is hearty and unpretentious,
Because he’s arty and conscientious!

It’s certainly not Shakespeare, but I came away with the prize.

For a website called Life.Styled. offering a LUSH Cosmetics pack for the best answer to “Describe why you deserve a Lush-scious Christmas”, I wrote this winning entry:

I’d love to go ballistic,
It’d be such a rush,
To relax in soapy goodness,
Thanks to Life.Styled. and Lush!

Remember to keep to the word limit, editing out any pesky extra words like ‘that’ and ‘so’, ensuring every syllable earns its place in your entry. Give it a go and you never know your luck, you could score yourself a well-deserved holiday or a bath bomb or two.

Have you ever used your writing skills to win something?

Rebecca Douglas

Rebecca Douglas is an award-winning freelance writer based in Adelaide. Her work has been published by ELLE, Frankie, CHOICE, Good Health, MiNDFOOD, The Big Issue, The Sydney Morning Herald, The Australian, and an assortment of other lovely places. She also writes fiction and essays, mostly about fairness, feminism and the future. She has appeared as a panellist and commentator on writing and other topics for outlets such as the Emerging Writers' Festival, SA Writers' Centre, The Morning Show and Radio 6PR (Perth). Find her on Twitter and LinkedIn.

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