Time to Rock Your Imagination, Ontario: The Annual Hype for the Toronto Star Short Story Contest and Some Creative Writing Advice

I love storytelling.

I've been a storyteller before I even knew how to write. I remember gathering in a circle with my cousins and sharing sweeping and imaginative adventure tales. I'm sure many of the stories were heavily influenced by my obsession with Star Wars and He-man and the Masters of the Universe, but I eventually expanded into different types of stories.

One of the reasons that I shifted this site to a movie focus and have hosted with Scott Martin the movie review podcast, The Movie Breakdown is my love for the creative process in storytelling. I have always been fascinated by digging into how a story was made, and I also love analyzing what makes it work. Movies are such a fascinating form of storytelling, because it uses so many creative forms to craft and express the story to a viewer. 

I have not hidden the fact that I want to grow the readership of this site and expand the listeners of The Movie Breakdown to the point where it can be a significant part of my income. I absolutely love diving deep into all aspects of a creative work and exploring the history of how a story was formed.

But my true first love and what I've always wanted to make a living doing is being a novelist and storyteller. It is the dream that still holds tight to my heart even now as a 44-year-old. Recently, my kids have been getting me to tell fantasy stories to them on long car rides, and they have proven to be better at remembering where I left off since the last time that I was telling it. I love immersing them into a new world and getting them excited about what will happen next. I also do have a few unfinished manuscripts that need to be refined and completed, and I have countless more ideas that can be crafted into full length novels. 

Not all stories are best told in the form of a novel. I know many of my ideas are better suited in other mediums or formats or lengths. As a long-time Stephen King fan, I do have a soft spot for the short story, and some of my favourite Stephen King books are his short story anthologies (if you include his novella collections, he has 11 of these anthology books).

A short story is also a great way to enter the world of fiction, because it isn't as daunting or time consuming as the novel. If you're like me and have always had the dream of having your fictional work published, then short story contests are a great way to break into the world of fiction publishing.

If you are a resident of Ontario, then January and February are a great time for you to chase that dream, because one of the biggest and most lucrative short story contests begins.

The long-time readers of the site know that I love to declare the start of the Toronto Star Short Story Contest. With that declaration, I announce that once again that I will be entering the contest and crafting an original short story over the next two months.

Here you can learn all about the contest details here.

The stand-out details is that first place gets a $5, 000.00 cash prize, tuition for a Humber writing program, and the story gets published in a Saturday edition of the paper. The second place gets $2,000.00 plus published in a Saturday paper, and the third gets $1,000.00 plus published in a Saturday paper. I haven't really seen any other contest with prizes of that level, especially one where there is no entry fee. The deadline for the story needs to be mailed by traditional post and received by March 1st.

The biggest challenge for me is that the word count is a maximum of 2,500 words, which may be a decent number of words for an article or a university essay but is easy to blow through when telling a story. I usually need a good portion of the two months to just chop away and focus my story down to the required word count. This may not be a challenge for everyone, but I find it much easier to craft a longform story rather than a concise tale that is in and out in under 2,500 words.

A writer obviously wants to craft a tale that has twist and turns, and one that is compelling and unique while creating characters that the readers connect with on the journey, and all that is tough with such a small word count. If you have read a lot of short story collections, you will notice that most of them stretch far past the 2,500 word count. I don't think many Stephen King short stories end anywhere near that word count, but rather surpass several thousand words.

What is my advice for nailing 2,500 words?

I find that it works best to imagine a scene or a snapshot from a bigger story. You don't have much space to build-up and develop your characters, so the reader needs to learn about them by how they react to the situation and event rather than providing background. It works best to stick with around two characters, since there isn't much room to develop more. If you really want more characters, then they should just exist for the purpose to develop your main characters. The characters should engage in a single event or scene, such as a lawyer coming home to discover a surprise or a wronged person confronting the former friend. You should jump right into the event, and it works best if it is in a single location and if the conflict can lead quickly to a solution. You should think smaller scale, but with interesting characters and a brisk pace, then you can still blow away and resonate with the reader.

The idea of jumping right into a quick event may be a little daunting. My suggestion is you go in expecting to write more than the maximum word count but know that in end you need to hack it away to the required word count. I have confessed on here before that I am what is known as a 'pantser.'  This means that I usually enter into a new writing project with nothing more than an idea or premise. I don't do any outlining, though sometimes I will have a few scenes or characters or moments that I plan to hit. 

This means that I don't have much of the world or characters or direction of the story figured out. I do my planning and brainstorming while writing out my story, but what this means, is that huge chunks of my story is often just for me to have background and set-up worked out in my own head. The extra swaths of words are designed to help me get more focused on the actual publishable parts of the story. A lot of my writing in the first draft is problem solving as I try to figure out my characters, and work through what will be the twists and major plot direction.

This means that if I follow my usual writing strategy and formula that my initial draft of this story will probably be at least 5k, but it will assist me in figuring out exactly what my story is supposed to be and what I need to focus on in my second draft. The second draft is when I bring the clippers, because it needs lots of trimming. I admit that this may not be a strategy that is appealing to everyone but it is what works best for me.

In a lot of ways, the way I write is just a different way of outlining and planning. I find that putting together a rigid outline and direction before I engage with the characters causes my story to feel less organic and stops me from immersing into my story. Instead, I like to have the characters lead me along and together we discover the story as it flows. At some subconscious level, the story is already there, and I am just slowly digging it out with each keystroke. But this approach means that there are huge portions of the story that is just me discovering things and moving towards the story destination rather than actual parts of the story that will be published for the reader.

My goal is to have my first draft done when February arrives, so that I then have another two weeks to trim and move around the story. It needs to be polished at least a whole week before the deadline, because its fate relies on traditional postal delivery to make the hard 5pm March 1st deadline.

As always, I expect the creative process of crafting this story to be an adventure. My brain is jammed with a multitude of ideas, but I haven't yet chosen the one that will work best for a 2,500 word story. The story may even end up very different from my initial idea. There have been numerous times that about halfway through a story that I realize it is actually about the supporting character, and my initial main character was just leading me to the true star of the tale. The story will often be uncovered as something very different then what I had started out to write, not just in plot but sometimes even genre.

The short story contest will mean three things for the site. 

The first is that this is another project that will be battling for my time (that at least I will have more devoted to writing with the kids going back to school next Tuesday). My priority remains client work and then with this tight deadline, I may have to write some shorter pieces to hit my daily posting goal for this site. 

The second is that I've always wanted the creative process to be a major part of the site. When I encounter challenges or have a big creative breakthrough or I learn something new about writing, then I'll share it here on the site. I feel the best kind of writing advice is just sharing my own creative journey.

Third is that I hope to make fiction writing a bigger part of my year with things like submitting more short stories to publications, spending more time on my manuscripts than past years, and the big one for the site, is posting stories like the serialized fiction or other creative projects that I may be compelled to write. I hope my creative writing journey this year allows for some valuable and entertaining posts.

I want to be far more honest and revealing as a writer. My hope is that sharing my own obstacles and victories and discoveries can be an aid, motivation, inspiration and assistance to other writers. I don't just want this to be a breakthrough year for my career, but I want my own possible successes or even failures provide value for other writers as well. 

The cool thing about the creative process is sharing about it often can pull out lessons and insights that have value for more than just writers or creatives, and the experience can teach about important things about all aspects of life. My hope is this exploration has something for all my readers, but I'll be happy if it even just resonates with one.

The Toronto Star Short Story Contest is here. I will share a bit over the next two months. I really hope many of you that are eligible take up the challenge. It is a great experience. If you do decide to join the contest, then please let me know, so that we can encourage and motivate each other over the next two months. Happy writing!