10 Creative Writing Challenges to Stretch Your Imagination

Even the most creative of writers hit a wall sometimes. And let’s be honest, sometimes that wall feels like the wall is made of 10 feet of solid concrete, and there’s not even a ladder in sight.

So, whether you’re running a writing workshop, planning a classroom activity, or simply trying to spark your own creativity, quick challenges can help shift the energy and get ideas flowing again.

Here are 10 creative writing challenges that work for anyone - writers, teachers, students, or anyone who’s ever stared at a blank page wondering where to start.

Challenge 1: What 3 Things?

This idea is loosely inspired by the what3words app, which splits the world into tiny squares and gives each one a unique three-word address. But instead of finding a location, you’re finding a story.

Pick three random words and weave them into a narrative. You could use your home’s three-word address from the app, use a random word generator, or just pick three words that feel right (or totally wrong, sometimes that’s even better).

If you want ready-made printable versions of this challenge, you can grab my full set of 30 story starters here!

Challenge 2: Genre Swap

Genre Swap is a brilliant way to shake up a predictable story, or breathe new life into a familiar plot.

The idea is simple: take a story, character, or even just a rough plot you already know, and retell it in a completely different genre.

You could take Romeo and Juliet and reimagine it as a dystopian rebellion between rival city-states.
Or flip The Great Gatsby into a psychological thriller about obsession and identity. You could even take a well-known movie plot, like Jurassic Park and retell it as a tense political drama.

It forces you to rethink setting, character motivation, tone, and structure, which often leads to surprisingly original results.

This challenge works brilliantly whether you’re writing for yourself or guiding students. It helps deepen understanding of genre conventions and opens up creative possibilities you might not have considered otherwise.

And sometimes, stepping sideways into a different genre is exactly what a story needs to find its real heart.

Challenge 3: Character by Object

Character by Object is a simple but incredibly powerful way to build richer, more believable characters.

Start with a single object - literally anything. A cracked trophy. A worn ballet shoe. A half-melted candle. A broken watch. A handwritten note stuffed into a coat pocket.

The idea is to imagine:
◆ Who owns this?
◆ Why do they keep it?
◆ What story does it tell about them?

The object doesn't have to be obvious or sentimental. In fact, the more random or everyday it is, the better as it forces deeper, more layered thinking.

This method is something I use a lot in my own teaching. If you want a simple way to try it, I shared one of my favourite activities here in The Shoe Lesson - it’s always one of the most fun and engaging writing exercises for students (and myself!).

I also built this concept into my Creative Writing Boxes, where each box includes small physical objects designed to spark stories and character ideas in new, unexpected ways.

Because sometimes the most ordinary things (a feather, a postcard, a key) can unlock the most extraordinary stories.

Challenge 4: Genre Mashup

If you ever feel like a story idea is a little too predictable, a Genre Mashup might be exactly what you need.

The challenge is simple: take two genres that don’t usually belong together, and fuse them into one story.

Imagine:
◆ A detective noir set in a whimsical fantasy kingdom.
◆ A romantic comedy unfolding during a zombie apocalypse.
◆ A historical drama where time travel is casually part of everyday life.

The goal isn’t to make it ridiculous (unless you want to). It’s about using the expectations of each genre, and then twisting them together in ways that surprise you.

Genre mashups push you to think outside neat storytelling boxes. They open up new emotional tones, new conflicts, new character dynamics - and often lead to worlds and plots you never would have thought of otherwise.

This challenge works just as well for quick writing sprints as it does for full-length projects. If you’re teaching, it’s a brilliant way to show students how genre shapes story expectations and how they can break those rules creatively.

Challenge 5: Opposite Day

Opposite Day flips your characters' instincts and forces you (and them) out of comfortable patterns.

The idea: take a character (any character) and have them act against their natural instincts or expected behaviour.

Imagine:
◆ A fearless hero who freezes up at a crucial moment.
◆ A villain who risks everything to save a stranger.
◆ A lifelong sceptic who suddenly believes in miracles.

It doesn’t have to be dramatic. Sometimes the most interesting shifts are small: A loyal friend who chooses self-interest once. A quiet character who finally snaps.

Opposite Day challenges you to think about your characters' core traits and how flexible (or fragile) they really are. It often leads to more layered, human characters, because real people don’t behave consistently all the time either.

If you're teaching creative writing, this is also a great way to discuss character arcs and growth.
If you're writing for yourself, it’s a fun exercise in character psychology, and sometimes it unlocks better plot twists, too!

Challenge 6: Switched Settings

Switched Settings is a great way to force your characters to grow - or fall apart.

Take an ordinary character and throw them into an extreme or unfamiliar environment.
A small-town baker stranded on Mars. A retired sailor waking up in a futuristic underwater city. A lawyer lost in a crumbling medieval kingdom.

It pushes you to rethink their strengths, weaknesses, and assumptions.

Whether you’re teaching world-building or just looking to shake up your own writing, a new setting can reveal sides of a character you didn’t even know were there.

Challenge 7: The Last Object Left

The Last Object Left is a simple setup that instantly builds emotional depth.

The challenge: your character can only save one item from a burning house. What do they grab? Why?

It forces you to think about priorities, attachments, and backstory without info-dumping.
Whether you're writing solo or guiding a class, it’s a powerful way to reveal what really matters to a character.

Challenge 8: Genre Expectations Subverted

Genre Expectations Subverted is all about taking what readers think they know and flipping it.

Start by thinking about the usual “rules” of a genre, and then flip them. You end up with a horror story where fear is defeated by kindness. A detective story where the mystery is never solved. A fantasy quest where the hero decides not to save the world.

It forces you to question why certain patterns feel so familiar and whether breaking them can reveal something deeper about your characters or themes.

For students, it’s a great way to teach critical thinking about genre conventions. For writers, it’s a fast way to surprise yourself (and your readers) without needing complicated twists.

Sometimes the most powerful stories are the ones that refuse to follow the rules.

Challenge 9: Story in Reverse

Story in Reverse challenges you to rethink how stories are built by starting at the end.

Instead of following a plot from beginning to end, you write the final scene first. Then you work backwards, step by step, asking: how did we get here?

For example, you might end with: "And that’s how I ended up owning a lighthouse." Your job is to trace the decisions, accidents, and twists that led to that moment.

It’s a brilliant way to focus on causality, character motivation, and the domino effect of small choices.
For students, it’s a great reminder that every ending is made up of hundreds of invisible turning points.
For writers, it often leads to stronger plots because you can’t rely on coincidence or filler when you’re working backwards.

Challenge 10: Unlikely Friendships

Unlikely Friendships is all about character chemistry, the kind you didn’t plan for, but can’t stop writing once it clicks.

The challenge: pair two characters who would never normally work together. A ghost and a teenage hacker. A washed-up magician and a cynical scientist. A runaway royal and a detective who doesn’t believe in destiny.

The bigger the clash in personalities, goals, or worldviews, the better. Conflict drives the story forward - but so does unexpected understanding.

For students, it’s a great way to explore dialogue, tension, and character growth. For writers, it can unlock new layers of humour, conflict, and emotional depth that wouldn’t have emerged otherwise.

But also, because sometimes, the best stories are the ones where even the characters are surprised they’re on the same side.

Final Thoughts

Creativity doesn’t always come from waiting for inspiration to strike, sometimes it comes from giving yourself permission to play.

Challenges like these aren’t about writing perfectly. They’re about taking risks, stretching your imagination, and seeing where unexpected ideas lead.

Whether you’re planning lessons, running workshops, or just trying to get back into your own writing flow, setting small challenges can make a huge difference.

If you’d like even more inspiration in the form of ready-to-go writing prompts, you can join the Daily Prompts waitlist here. You’ll automatically get 31 free prompts sent straight to your inbox to test them out, with no pressure to subscribe, just pure writing inspiration when you need it.