Beginning Before You Feel Ready: Writing Prompts
Your month of creative courage begins here. We’re exploring the courage to create, one prompt, one draft, one dialogue at a time in July. Join us!
July Theme: Creative Courage
Big Question: What does it take to begin, risk, and share what you create?
Week 1: Beginning Before You Feel Ready
Over the next few weeks, I want to think about and discuss the creative courage it takes to begin a new project or practice and the risks doing those things entails, especially when it comes time to share what we create.
This week, since it’s the first week of these posts for July, we’ll start at… well, the beginning.
Beginnings can be exciting and inspiring, of course, but they can also be intimidating because they require taking risks and trusting an outcome that doesn’t exist quite yet. They require courage, in other words.
But what does courage mean in this context? And how can we make sure it stays with us not only during the beginning stages of new creative projects and practices, but the entire time we’re working on them and carrying them out? How can we kickstart our creative beginnings with the right amount of courage to keep on going?
Let’s find out by completing one or more of the following writing prompts— five to get your creative courage wheels rolling, and five to help you explore what creative courage means to you and how you can harness it.
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. And if you end up completing all or most of the prompts at that point, that’s also amazing! But if you don’t, that’s perfectly fine, 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 Prompts
1. The First Page
Write the opening page of a story you have been afraid to begin.
Focus on:
Hooking the reader with an intriguing first sentence.
Establishing the setting through specific details.
Introducing a character with a clear desire or problem.
Creating questions that encourage the reader to continue.
Skills to Practice:
Strong openings
Showing rather than telling
Establishing tone
Character introduction
Tip: Don’t worry about where the story is going. Concentrate on making the first page compelling enough that someone wants to read the second.
2. The Doorway
Write a scene where a character stands at the entrance to something unfamiliar and must decide whether to enter.
Focus on:
Building tension before the decision.
Using sensory details to make the doorway and what lies beyond feel vivid.
Revealing the character’s thoughts, fears, and motivations.
Making the choice feel meaningful.
Skills to Practice:
Suspense
Internal conflict
Symbolism
Scene building
Tip: The doorway can be literal or symbolic (a new job, a relationship, a mystery, or even a difficult conversation).
3. The Unfinished Beginning
Write a story about someone who starts something important but has no idea how it will end.
Focus on:
The courage it takes to begin.
The uncertainty of the journey.
Small victories and setbacks.
Character growth through action.
Skills to Practice:
Character development
Plot progression
Writing uncertainty authentically
Theme
Tip: Resist the urge to force a neat ending. Sometimes the journey itself is the point.
4. The Letter from Future You
Write a letter from yourself five years in the future thanking you for beginning.
Focus on:
Writing with warmth and encouragement.
Reflecting on lessons learned.
Imagining realistic growth instead of perfection.
Including specific moments of gratitude.
Skills to Practice:
Reflective writing
Voice
Emotional authenticity
Positive visualization
Tip: Make the future feel believable by mentioning challenges that were overcome rather than pretending everything was easy.
5. The Unexpected Start
Write a story that begins with: “I never intended for this to become my story.”
Focus on:
Creating curiosity immediately.
Establishing a distinctive narrator’s voice.
Hinting at what changed everything.
Balancing mystery with enough information to keep readers invested.
Skills to Practice:
Narrative voice
Pacing
Foreshadowing
First-person storytelling
Tip: Ask yourself what happened that transformed an ordinary life into an extraordinary story.
Reflective Prompts
1. What creative project have you been waiting to feel ready for?
Focus on:
Being honest with yourself.
Identifying what’s exciting about the project.
Exploring what’s holding you back.
Skills to Practice:
Self-awareness
Goal clarification
Honest reflection
Tip: Try to distinguish between practical obstacles and emotional ones.
2. What does ‘beginning’ mean to you?
Focus on:
Personal experiences.
Memories of previous beginnings.
The emotions you associate with starting something new.
Skills to Practice:
Reflection
Personal storytelling
Finding meaning
Tip: Consider both literal beginnings (a new job, moving) and symbolic ones (changing habits or perspectives).
3. What fears appear when you think about starting something new?
Focus on:
Naming your fears specifically.
Examining where they come from.
Considering whether they’re based on evidence or assumptions.
Skills to Practice:
Emotional literacy
Critical thinking
Honest self-reflection
Tip: Sometimes writing fears down makes them feel more manageable because they become concrete rather than vague.
4. What would you begin if you knew you could not fail?
Focus on:
Dreaming without self-censorship.
Exploring your deepest interests.
Identifying what truly motivates you.
Skills to Practice:
Creative thinking
Vision setting
Values exploration
Tip: After you’ve imagined the ideal scenario, ask yourself which parts you can pursue even without a guarantee of success.
5. What is one small creative step you could take this week?
Focus on:
Choosing a realistic, specific action.
Breaking a larger goal into manageable pieces.
Creating momentum through consistency.
Skills to Practice:
Planning
Habit building
Accountability
Tip: Define your step clearly. Instead of “write more,” choose something measurable, such as “write for 20 minutes on Tuesday and Thursday” or “outline one chapter.”
General Tips for Every Prompt
Write first, edit later. Give yourself permission to produce a rough draft before making improvements.
Use specific details. Concrete images, sounds, and memories create stronger writing than broad descriptions.
Stay curious. Follow surprising ideas instead of forcing the writing in a predetermined direction.
Focus on authenticity. Honest writing is often more engaging than writing that tries to sound impressive.
Set a time limit. Writing for 15–30 uninterrupted minutes can help maintain momentum and reduce overthinking.
Reflect afterward. When you finish, ask yourself: What surprised me? What did I discover? What might I explore further?
These prompts are designed not only to help you write about and explore creative courage, but also to strengthen skills that inspire creative courage such as observation, emotional depth, character growth and development, authenticity, scene construction, and reflective thinking. Over time, revisiting them can reveal how your voice and perspective evolve, too.
Join the Conversation
I’d love to hear what these prompts inspired in you and your writing. If you’d like to share your responses, ask questions, or connect with other writers, join the conversation in the dedicated Drafters Workshop chat. We’ll be working on these prompts all weekend and throughout the week ahead, until the chat closes next weekend.
Whether you’ve written a single paragraph or filled pages, every beginning is worth celebrating. And we can’t wait to read what you create!
Please familiarize yourself with the Community Chat Guidelines.
Consider going more in depth with this month’s theme with July’s Creative Courage Writing Collection.
This 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.