8 Creative Writing Challenges to Fire Your Imagination

Creative Writing Summer School - typewriter

Do you want to hone your creative writing skills?

Then you probably already know that the key to scintillating dialogue, brilliant prose and beautiful poetry is many long hours of practice. Like any skill from playing the violin to running marathons, the more time you put into practising your writing, the better it will become. And writing the same things in the same style and the same genre that you always do will only get you so far; trying something challenging, rather than something comfortable, is the best way to make progress.
But trying to figure out what form that challenge might be can be trickier. It’s all very well to decide to challenge yourself, but sitting down in front of your laptop – or notepad, if you’re a traditionalist – and expecting a challenge to emerge can be a little optimistic. That’s why, in this article, we’ve taken a look at some fun and interesting creative writing challenges that will put your abilities to the test, and maybe help you develop as a writer at the same time.

1. Try the challenge of National Novel Writing Month

Every November, tens of thousands of people across the world take part in the National Novel Writing Month – usually shortened to NaNoWriMo. It’s a challenge to write a 50,000-word novel – so about the length of Of Mice And Men – in thirty days. There’s no reward if you win, except the satisfaction of having written a novel, and adulation among the large online community of writers who gather every year to take part.
It’s worth noting that if you have a brilliant idea for what may well become the defining novel of the 21st century, NaNoWriMo is probably not the occasion to write it. NaNoWriMo novels are seldom good (though there are some exceptions – a few, heavily edited, have made it into publication). Writing approximately 2,000 words every day doesn’t usually result in good prose. More often, in fact, writers resort to lengthy dream sequences, elaborate descriptions of extraneous details, very long conversations of little significance, and various other devices to eke every little bit of word count out of their plots as they possibly can – up to and including characters with very long names who refuse to be referred to by any abbreviated version. This is not high-quality fiction.
You might not think it’s worth bothering if you aren’t even going to write anything good, but that’s not the point of NaNoWriMo. Instead, it gets you into the habit of writing regularly. It may cure any fears you have of facing an empty page. It’ll give you a sense of word count, and just what you can do with those 2,000 words allotted to you every day. And even if most of what you write is dreadful, chances are one or two good passages will sneak in there somewhere.

2. Write a daily microfiction

If you can’t imagine that you’d ever have time to write 2,000 words in any given day, don’t worry. One way of practising your writing that’s also much more sustainable long-term is to write a daily piece of microfiction. Task yourself with writing something that forms a complete whole every day (or every week, if daily is unmanageable). It might be only be a couple of hundred words long – or even less – but the challenge here is to create something regularly that stands on its own. In some ways, this is harder than NaNoWriMo’s punishing word count; in NaNoWriMo you don’t have to come up with a fresh idea each day, but instead you can just pick up where you left off. If you write microfiction, you don’t have this option.
So what might your new idea each day be? That’s up to you. You might decide to fictionalise a brief encounter you observed between friends at the lockers in school, or rewrite a fairytale, or see if you can compose a Shakespearean sonnet. The content doesn’t really matter; it’s the exercise of trying to come up with something new daily that really counts. Once you’ve been doing this for a couple of weeks, you’ll notice that you’re starting to see the world a little differently – you’ll be looking for inspiration for the day’s microfiction wherever you go, and hopefully you’ll be finding it too.

3. Write in the style of a famous author but on a different topic

If coming up with ideas or tackling a blank page don’t bother you, perhaps you’re interested in trying out a challenge that will stretch your technical skills as well as your creative flair. One idea that’s a popular exercise among creative writing classes is to write in the style of a famous author, but choose a different topic. You’d need to take an author with a very distinctive style – such as Virginia Woolf, PG Wodehouse or Jane Austen – and write about a completely different topic to their preferred subject. Could you write a short detective story in the style of Austen? A horror story in the style of Wodehouse? A romantic comedy in the style of Woolf? You can surely think of combinations of your own.
This tests more skills than you might realise. First, you have to take a close look at the writing of the author you’re trying to imitate. What aspects of their style are most distinctive? Are there any words or phrases that they overuse? When they describe a person or a setting, what do they focus on first? Looking at these traits will also help you identify them in your own writing. Trying to apply them to a different genre makes it more of a challenge, as you genuinely have to imitate style instead of just aping the same content. And if you write with a group of friends, you can all try this challenge and see if you can guess afterwards which author each of you chose.

4. Write a piece designed to evoke emotion

This exercise is another creative writing class staple, and for good reason. After all, the point of most fiction is to evoke emotion, but that can sometimes get forgotten in the process of getting the plot from a to b. It’s worth practising writing to evoke emotion for the simple reason that if your reader is feeling something – whether that’s fear, amusement, sympathy, tension or excitement – they’re unlikely to be getting bored. Sometimes, amateur writers focus excessively on crafting beautiful prose for the reader to admire – but if you’re sitting back and looking at how elegant the writing style is, you’re unlikely to be fully immersed in the story. Focusing on the emotional impact of your writing can bring the effect it has on the reader back to the fore.
You can pick almost any emotion that writing might evoke for this, though if you’d like to test how well you’ve succeeded, picking an emotion that’s more obvious – like amusement – can work better when you give your work to a reader. Try to evoke the emotion more by your style than by the content of your writing. You could even try writing the same outline of a scene twice over, but evoking different emotions each time – for instance, you could write a burglary scene first as frightening, then as funny.

5. Write the same narrative in a different form

When Douglas Adams wrote The Hitchhiker’s Guide to the Galaxy, he initially wrote it as a radio play. Then he turned it into a series of novels. Then at various points, and with varying degrees of involvement from Adams, it was produced as a stage play, a text-based computer game, a TV series, a film, a comic book and probably some more variations besides. It’s a story that proves to have been remarkably adaptable to different forms. Other stories, as anyone who’s seen a really bad film adaptation of their favourite novel will know, aren’t necessarily so adaptable.
That’s why another great way to challenge yourself as a writer is to take a story – perhaps an idea, perhaps something you’ve already written – and try it out in a different form. Could it work as a poem? As a stage play? As a film script? Trying to think about what’s needed to tell the story within the restrictions of each form can spark your imagination in all kinds of interesting ways, and you might even discover abilities in a form of storytelling that you hadn’t previously explored.

6. Put together a story from elements that don’t fit together

If you’re struggling to come up with any ideas at all, one way both to challenge yourself and possibly spark your creativity is to pick an assortment of unrelated words or concepts and try to see how you can assemble a story from them. So that might be “revolution – teacup – elephant – catastrophe” or “umbrella – suffragette – chimney – adventure” (the latter could turn into Mary Poppins!). How you construct the story is then entirely up to you, but hopefully even these couple of examples are giving you ideas.
Try not to string together just a series of objects, but instead include abstract ideas to give the story some depth. You might want to look around you for everyday items, peruse newspaper headlines for concepts that imply action (you might find war, protests, betrayal, espionage… none of them pleasing headlines, but all great material for fiction), or look at a completed crossword for some entirely random ideas. And try to think outside the box when you come up with an idea – you might not think that ‘gun’ and ‘dragon’ belong in the same story, for instance, but it could make for an interesting narrative if you do find a way to fit them together.

7. Create a prompt from an unusual restriction

If you tried writing in the style of a different author, you’ve probably already started spotting not only the distinctive things that they do as a writer, but also those features in your own writing. Perhaps when you introduce a character, you can’t help but include a lengthy description of their clothes, or you rely heavily on free indirect speech. These features aren’t necessarily bad things – in fact, they can be a positive aspect of your own personal style – but nonetheless a great way of challenging yourself can be to stop doing them.
The greater the restriction, the greater the challenge – so if you’re prone to describing characters by their clothes, try describing them without including any visual features at all. You can build up an interesting and vibrant picture of a person by describing their smell, or the timbre of their voice. Think about the image that’s conjured by a smell of sweat and engine oil, and a gravelly voice, to get an impression of how this restriction can enhance your writing by forcing you to focus on things that you might not usually consider.

8. Take two characters from personal adverts and put them in a story together

If you struggle to come up with rounded characters, one place to start can be newspaper or online personal adverts. They’ve fallen out of fashion with the advent of online dating, but a few people still stick to them, and the fact that they’re now the preference of eccentrics makes them an even richer source of character inspiration.
Simply pick two adverts – preferably not for people who sound as if they’d be in any way compatible – and fling them into a story together. That might be the retired professional who describes herself as young at heart and wants to meet someone who appreciates not only her baking but also her three golden labradors, who in the course of your narrative will be thrown together with the young man who wants to meet the love of his life but will settle for someone who’ll share his interest in extreme sports. Perhaps they’ll fight crime, solve a mystery, launch a revolution or who knows what else. The great thing about using personal ads for this is that they’re short enough on detail that you’re not really inserting a real person into your story, just using real traits as a springboard for a fascinating character of your own invention.

What creative writing challenges have worked for you?