13 Writing Challenges to Sharpen Your Writing Skills
By: Linda Caroll
Tags: Inspiration, Writing, Advice, Creativity, Writing Tips

I

noticed an interesting thing when my daughter was in art school. If the teacher brought in a model and said “draw this” the students got to work immediately.

If the teacher said “draw something from nature” they’d think a few minutes, and then get drawing.

But if the teacher just said “draw something,” they’d all get that deer in the headlights look. Writer’s block is the writer’s equivalent of that.

Turns out constraints make it easier to draw. Or write.

With writing, there’s an additional bonus to constraints. They sharpen your writing skills. Without a constraint, it’s easy to just write like the internet is your journal, blathering and rambling. We’ve all done it.

13 Writing Challenges to Sharpen Your Writing Skills and Break Through Writer’s Block

If you’re feeling stuck, here’s some writing challenges to get you writing.

If you’re up to a challenge, pick some of the more daunting ones.

#2, #5, #11 and #13 will push your skills, that’s a promise!

1. Shorten your longest story to 500 words

Look in your stories list and find the longest story you’ve written. Rewrite it so it’s 500 words or less without losing the point of the piece. Also, you need it to be different enough that it won’t trigger duplicate content flags.

2. Double your shortest story without fluff.

Look in your stories list again and find the shortest piece you’ve written. Revisit that topic, but make it twice as long without fluff. Again, you need it to be different enough that it won’t trigger duplicate content flags.

3. Write a how-to guide a child could understand

Think of something you know how to do. Write a how to guide that’s simple enough for a young adult to understand but interesting enough that an adult won’t roll their eyes reading it. The more unusual the thing, the better. :)

4. Start with a random sentence from a book

Grab a book from your bookshelf. Open it at random and point your finger at the page. Type out that sentence. Close the book. The story can go anywhere you want, but start with that sentence.

5. Write a post that’s entirely dialogue

Dialogue is hard! Think of an interesting experience you’ve had, or make up a fictional story. Doesn’t matter if it’s real or imagined. All that matters is that the entire piece is dialogue.

6. Start with a photograph

Go to unsplash, pixabay, pexels or piqsels and type in some odd searches. Try things like surreal landscape or bizarre people or surreal woman. Find an image that you like. Now write something inspired by that image.

7. Write about a random tidbit on Wikipedia.

Go to Wikipedia’s home page and click “Random article” in the sidebar. Write 500 words about whatever topic comes up. Don’t copy and paste. Just let the topic inspire you to write something.

8. Borrow a story

Think of a great story someone told you long ago. Maybe a story one of your parents or grandparents used to tell, something that happened to them decades ago. Retell the story in your own words.

9. You can’t make this stuff up!

What’s the stupidest way you’ve ever hurt yourself? Write the story. Make it at least 500 words, and the longer you can make it, the better.

10. In this room…

Think back to your childhood home. Think of a room in that home. Okay? Got one? What’s the first memory that comes to mind from that room? Write about it in at least 500 words. Don’t just spit out a sentence. Tell the story.

11. Word Salad Beginnings

This one will surprise you if you try it. It’s real simple. Write the first word that comes to mind. Then write another random word, unrelated to the first word. Do a fourth and a fifth. Just keep writing random unconnected words.

Hit the return key whenever you feel like it. A weird thing will happen. Here’s why. When you typing words that aren’t even related to each other, you free up your creativity and end up making surprising connections.

12. Play Devil’s Advocate

Not that the devil needs any advocates, as Seth Godin says. Take a controversial topic and write a piece that covers both sides. For and against. Why and why not. You’ll need to figure out how to make it readable. Will it be two characters? A debate? The angel and the devil on your shoulder?

It’s been said that a rare skill is being able to see both sides of an issue with equal weight. That type of objectivity enhances writing. I dare you.

13. Absolutely Bizarre

Go to this random headline creator and hit the “randomize” button until you find one you like. Or use this one, which is mashups of real headlines.

Then write the story in 500 words or more. Stupid as it sounds, this one will push creative buttons like little else because you aren’t tasked with “thinking of an idea” — instead you need to come up with a story to go with a bizarre title. It’s like weight lifting for the right brain. Have fun!