By the time September rolls around, your students are settling into routines—but many of them may still be hesitant to open up in their writing. Can blame them? I’ve found that WAY to many prompts feel recycled, irrelevant, and plain boring.

I’ve found that if I want my kids to grow into confident, expressive writers, I have to give them prompts that make them think—ones that invite reflection, imagination, and vulnerability in a safe space. This is why I love using thoughtful and somewhat unexpected prompts in September to help students find their voice and take creative risks early on in the year. Here are 10 writing prompts that I feel go deeper than the usual back-to-school journal questions. Each one is designed to build confidence, encourage self-awareness, and give your students something worth writing about.

1. What do you wish people understood about you?

This prompt invites students to express something personal—maybe a hidden talent, a cultural tradition, or even a quiet struggle. It’s a powerful way to build empathy and voice.

2. If you could press “pause” on one part of your life and live in it a little longer, what would it be—and why?

This gets kids thinking about meaningful moments they’ve already experienced and why those moments mattered. It opens the door to rich personal narratives with emotion and detail.

3. Write a letter to someone you’ve never met but would like to.

This could be a letter to a historical figure, a future friend, a grandparent they never got to know, or even a future version of themselves. It stretches imagination and reflection.

4. Describe a place that makes you feel completely safe.

Sensory-rich and personal, this prompt builds descriptive writing skills while helping students reflect on what safety and comfort look like in their lives.

5. If your thoughts showed up like speech bubbles over your head, what would people learn about you?

This fun, creative prompt leads to surprising self-awareness and helps kids think about how they come across to others vs. what they’re really thinking.

6. Tell the story of a moment when you changed your mind.

Whether it’s about a person, an idea, or a fear, this prompt taps into real-life growth and internal reflection—two things that help students connect deeply with their writing.

7. Imagine your voice was a character. What kind of person would it be?

Is it loud and funny? Quiet and thoughtful? Brave in some moments but shy in others? This prompt builds writing voice by literally turning it into a character.

8. What’s one question you wish someone would ask you? Answer it.

It’s amazing what kids will say when given the chance to guide the conversation. This prompt allows them to reveal something they care about deeply.

9. Choose one object that means a lot to you and tell the story behind it.

From a lucky pencil to a photo or piece of jewelry, this prompt brings storytelling and emotional depth together in a powerful way.

10. If your imagination were a real place, what would it look like?

This fantasy-style prompt opens the door to descriptive, creative writing while revealing a lot about each student’s personality and interests.

September is the perfect time to help students to start breaking out of the box when it comes to writing. When you go beyond surface-level prompts and give them opportunities to reflect, imagine, and express who they are, writing becomes something they want to do—not just something they’re assigned. I have placed each one of these writing prompts on a task card that is so easy to use! Grab the set for FREE below! You can print them and have them ready to go in a pinch! Wishing you all the very best!

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If you would like to come back to these writing prompts when you’re ready to use them, feel free to pin them to one of your favorite Pinterest boards.