Taking Creative Risks: Writing Prompts to Build Creative Courage
Use this week’s prompts to explore vulnerability, experimentation, and growth through creative writing and reflective journaling. And join us for the second week of July’s Creative Courage series.
July Theme: Creative Courage
Big Question: What does it take to begin, risk, and share what you create?
Week 2: Taking Creative Risks
Taking Creative Risks
Welcome back to our July series, Creative Courage.
Last week, we focused on Beginning Before You Feel Ready and explored the idea that creative confidence often follows action, not the other way around. If you’ve spent time writing from those prompts, and exploring their dialogues, you’ve already practiced one of the hardest parts of creating anything: simply beginning.
This week, we’re taking the next step in this creative journey by allowing ourselves to be a little more vulnerable with ourselves and our writing and experiment a little.
Creating something is an act of courage. And taking a creative risk with what you create is another.
But taking creative risks doesn’t have to feel intimidating or unpleasant, and can even be fun, as long as you remember that they don’t always need to include dramatic changes or upheavals to your current style of work, unless that’s what you’re interested in accomplishing.
Taking creative risks can entail trying a new writing style, exploring an unfamiliar genre, writing honestly about something you’ve never said aloud, or allowing yourself to write a first draft without worrying about whether it’s ‘good’ or not.
Taking creative risks is also how our creativity evolves and expands. It’s where new ideas emerge, unexpected voices appear (usually the kind we want to listen to), and we begin discovering what our work is truly capable of becoming.
Throughout July, we’re exploring one guiding question: What does it take to begin, risk, and share what you create?
This week’s prompts invite you to experiment, challenge yourself, and lean into uncertainty with curiosity instead of fear so that you can take some creative risks.
You don’t need every attempted draft to succeed. You only need to get curious about what you can accomplish with the willingness to try.
You’ll see my response to one of the creative prompts in tomorrow’s post, and my response to one of the reflective prompts on Wednesday.
I hope to see what you come up with for one of these prompts in this week’s Drafters Workshop chat thread soon too, so we can discuss further what it means to take creative risks and build creative courage.
General Tips for Every Prompt
Before you begin writing, remember that these prompts are invitations, not assignments. There isn’t a single ‘right’ way to respond. The goal this week is to practice taking creative risks by exploring ideas with curiosity rather than judgment.
As you write, keep these tips in mind:
Trust your first instinct. Your initial idea is often more original than the one you talk yourself into later.
Resist the urge to edit as you go. Let your ideas unfold naturally before deciding what works and what doesn’t.
Take one small creative risk. Try an unfamiliar point of view, experiment with dialogue, choose an unexpected ending, or write about something you’ve been hesitant to explore.
Allow imperfection. Growth happens through experimentation, not flawless first drafts.
Follow your curiosity. If your writing starts leading you somewhere unexpected, give yourself permission to follow that path.
Focus on progress instead of perfection. Every sentence you write strengthens your creative practice, even if it doesn’t end up in a finished piece.
Be honest. Whether you’re writing fiction or reflecting on your own experiences, authenticity often creates the strongest connection between your readers and you.
Challenge your comfort zone. If a prompt feels just a little intimidating, it may be pointing toward something meaningful to explore.
Remember there are no failed attempts. Every draft teaches you something, even if the lesson isn’t immediately obvious.
Celebrate showing up. Creative courage isn’t measured by writing the perfect story but by your willingness to begin, experiment, and keep going.
This week’s invitation: Choose curiosity over certainty. Take one creative risk, no matter how small, and see where it leads.
Quick Note: While I will always encourage writers to write to the extent of their heart’s content, I would suggest starting with one prompt from each section first. Select the creative prompt and reflective prompt that seem to really speak to you first, then see where those writing experiences lead you before attempting to complete the rest of the prompts. If you end up completing all or most of the prompts after that, that’s amazing! But if you don’t, that’s perfectly fine too. You won’t run out of opportunities to see prompts like this because there will be another post of prompts available next Saturday when this one is auto-archived.
Creative Writing Prompts About Taking Creative Risks
1. The Risk Worth Taking
Write about a character choosing something uncertain over something safe. What are they hoping to gain? What are they afraid of losing? Show the moment they decide to leap.
Focus On:
Internal conflict
Emotional stakes
Character motivation
Personal transformation
Skills to Practice:
Building tension before a major decision
Showing emotion through actions and dialogue
Raising meaningful stakes without overexplaining
Tip: The most compelling risks aren’t always life-changing, they’re emotionally meaningful to the character.
2. The Version Nobody Has Seen
Write a scene where someone reveals a hidden part of themselves. It could be a secret dream, an unexpected talent, a painful truth, or a side they’ve carefully protected from others.
Focus On:
Vulnerability
Authentic relationships
Emotional honesty
Trust between characters
Skills to Practice:
Writing natural dialogue
Creating emotional subtext
Revealing character traits gradually
Tip: Sometimes what a character almost says reveals more than what they finally admit.
3. The Rule Breaker
Write about a character who breaks an important rule. The rule could be personal, cultural, professional, magical, or moral. Explore both the decision they make, and its consequences.
Focus On:
Cause and effect
Moral complexity
Conflict
Consequences
Skills to Practice:
Creating believable motivations
Building suspense
Exploring emotional and external consequences
Tip: Readers connect most with broken rules that force characters to confront who they are and who they want to be.
4. The Impossible Choice
Write a scene where every available option has at least one undesirable consequence. Instead of searching for a perfect answer, allow the tension to come from choosing between two or more imperfect options.
Focus On:
Ethical dilemmas
Emotional tension
Personal values
Decision-making
Skills to Practice:
Weighing competing priorities
Writing layered conflict
Revealing a character through difficult choices
Tip: Every difficult decision should teach readers something about the character making it.
5. The Second Version
Choose a paragraph you’ve written before and rewrite it in a completely different style.
You might make it:
humorous instead of serious.
poetic instead of direct.
minimalist instead of descriptive.
first-person instead of third-person.
fast-paced instead of reflective.
Focus On:
Creative experimentation
Voice
Perspective
Flexibility
Skills to Practice:
Developing multiple and different writing styles
Letting go of attachments to first drafts
Discovering new creative possibilities
Tip: The goal isn’t to improve the paragraph, it’s to discover something new by approaching it differently.
Reflective Journaling Prompts About Creative Courage
6. What creative risk have you taken that changed you?
Focus On:
A moment when you stepped outside your comfort zone
How taking that risk affected your confidence or creativity
What you learned about yourself afterward
Skills to Practice:
Personal reflection
Honest storytelling
Identifying growth through experience
Tip: Sometimes the greatest transformation comes from the act of trying, regardless of the outcome.
7. What risks are you afraid to take?
Focus On:
Creative opportunities you’ve avoided
Fears that may be influencing your choices
What taking one small step forward could look like
Skills to Practice:
Self-awareness
Emotional honesty
Recognizing limiting beliefs
Tip: Fear often points toward the places where growth is waiting.
8. Do you value originality more than perfection?
Focus On:
Your definition of originality
Times when perfectionism held you back
How embracing imperfection might change your creative process
Skills to Practice:
Critical thinking
Clarifying personal values
Reflective writing
Tip: Original work often begins where perfection ends.
9. When has discomfort helped you grow?
Focus On:
A challenging creative experience
What felt uncomfortable in the moment
How the experience shaped your perspective later
Skills to Practice:
Finding meaning through reflection
Connecting experiences to personal growth
Writing with authenticity
Tip: Looking back often reveals growth that wasn’t visible while you were experiencing it.
10. What would your creative work look like if you stopped trying to impress others?
Focus On:
The work you’d create solely for yourself
External expectations that influence your creativity
Ways authenticity could reshape your creative voice
Skills to Practice:
Vision-setting
Authentic self-expression
Creative exploration
Tip: Imagine creating as if no one were grading, comparing, or judging your work. What changes?
Join the Conversation
Every creative risk has the potential to reveal the next story you need to tell, in a way that only you can tell it.
Maybe your next creative risk involves trying a new genre, writing from a different point of view, sharing something deeply personal, or simply allowing yourself to write without editing every sentence as you write.
Whatever your next creative risk entails, I’d love to hear about it. And so would the rest of this writing community we’re growing.
Share one of your responses in the comments or join our community chat to discuss this week’s prompts, encourage fellow writers, exchange ideas, and celebrate the creative risks you’re taking.
You never know whose courage might begin with reading your comment or story next, and vice versa!
QUESTION OF THE WEEK: What’s one creative risk you’ve taken—or one you’re ready to take this week? Share your response in the comments or chat and encourage another writer along the way.
And try to remember that creative courage isn’t about eliminating fear. It’s about making space for curiosity alongside it. Each draft, experiment, and vulnerable sentence becomes part of your creative journey, whether or not it turns out exactly as you imagined.
I’m so glad you’re here and look forward to engaging with you this week about creative risks and courage.
Please don’t forget to like and share this post if you enjoyed it so others can enjoy it too. Thank you!
Continue Exploring July’s Creative Courage Theme
ICYM Week 1: Beginning Before You Feel Ready
Beginning Before You Feel Ready: Writing Prompts
Do writers need to feel ready before they begin a new project?
Beginnings and endings are linked in a lot of ways…
Why Beginning Feels So Difficult, But Doesn’t Have to Be
Books That Made Me Want to Write and Take Creative Risks
Consider going more in depth with this month’s theme with July’s Creative Courage Writing Collection.
The writing collection is designed to help you explore creative courage from different angles: discovering your voice, strengthening your craft, experimenting with new approaches, and reflecting on the writer you are becoming.
The free Drafts writing prompts posts that will be published every Saturday this month (like this one) will explore the outward side of creative courage—beginning, risking, and sharing— and should complement this collection quite well, which invites you to go much deeper into the internal work of creativity with 30 guided writing prompts and craft exercises, reflections, as well as three options for guided monthly writing challenges for those who want to go even further than that.