Writing Prompts for Navigating ‘The Messy Middle’
Today’s post includes prompts for uncertainty, setbacks, unfinished work, and finding a way forward, because the creative life we truly want and need rarely unfolds in a straight line.
August Theme: The Creative Life
Big Question: How do we build a creative life that works for us?
Week 3: The Messy Middle
Welcome to Week Three of our August Series, The Creative Life
Last week, we focused on fine-tuning the Creative Habits that work for us as unique and authentic creators. And the week before that, we focused on Making Space for our creative lives and explored the ways in which we intentionally make space for the creative lives we’re building, day in and day out.
So, if you’ve spent time writing from those prompts and exploring their related Dialogues and Books posts, you’ve already reflected on some of the best ways you can make space (both literally and otherwise) for the creative life you truly want, as well as identified the creative habits that will help you sustain it.
This week, we’re taking one of the most important steps in this series by focusing our attention on working through The Messy Middle, where uncertainty and setbacks may start to occur, as we continue to ask ourselves: How do we build a creative life that works for us?
At the beginning of a creative project, possibility is everywhere. We have ideas, energy, plans, and feel like we might finally know where we’re going with our project, even our creative lives overall.
Endings of projects can offer their own kind of clarity and satisfaction, too. We can look back at what we created, decide what worked and didn’t, close the notebook and note files we were keeping, send that final manuscript, publish that polished piece, or simply say, “I’m finished.”
But then there is everything in between, also known as ‘the messy middle,’ where ideas can get confused, energy starts to wane, and well intentioned and well thought out plans begin to disintegrate before our very eyes.
We all know this frustrating place in the middle of a project, where our first drafts no longer work, our exciting ideas become harder to execute than expected, and we begin to wonder whether the project we’re working on is worth finishing at all. That place and time during our project when we realize we might have changed our minds, lost our creative momentum, discovered a different direction we need to go in, or are simply unsure of what should come next.
And that’s exactly the place we’re going to visit and explore this week, ‘the messy middle.’ Mainly because it’s important to remember that while beginnings are exciting and endings are satisfying, the messy middle is where most of our creative work happens and the reality of our creative projects, and creative lives, really begin to take on shapes and forms of their own.
The prompts below invite you to explore uncertainty, persistence, setbacks, unfinished work, changing direction, and the surprising possibilities that can emerge when things don’t go according to plan. Please choose the prompts that meet you where you are.
Don’t worry if you missed last week’s posts, you can still jump into our conversation about The Creative Life today!
While all posts on Daily Drafts & Dialogues are connected to their monthly themes with weekly focuses (which start each Saturday with a post of prompts like the one you’re reading now) they can still be enjoyed individually as well and are always available in the Archive.
Remember, you’ll see my response to one of the creative prompts below in tomorrow’s post, my response to one of the reflective prompts on Wednesday, and posts with dialogues about books and the creative life over the course of the upcoming week too. This way, you’ll really be able to dive into how to deal with the messy middles that show up in your creative life.
I hope to see what you come up with for one of these prompts in the Drafters Workshop chat soon too, so we can discuss further what it means to build and enjoy the creative life that works for us.
General Tips for Every Prompt
You don’t have to complete every prompt, and you don’t have to produce something polished or publishable.
Start writing where there is energy and work on the prompts that allow your writing to flow.
If a prompt takes you somewhere unexpected, follow wherever it takes you and try not to overthink it.
Set a timer for 10–20 minutes and write without stopping and follow the details that surprise you.
If a prompt makes you uncomfortable, notice what kind of discomfort it creates and ask yourself whether that is something worth pursuing. If you feel nothing, however, skip the prompt and try another.
For reflective prompts, specificity will usually take you further than a perfect answer you think others would want to hear. Be sure to write about the actual project, actual setback, actual unfinished idea, or actual decision that comes up in your writing whenever you can.
For creative prompts, remember that you are not trying to prove anything about your own creative life. You’re simply giving yourself a place to explore it.
Invitation for the Week: Choose a prompt that really speaks to you, that really makes you think about how the messy middle shows up for you time and time again. Then really spend some time with it and bring whatever you discover to our ongoing conversation.
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 Prompts for Navigating ‘The Messy Middle’
1. Halfway There
Write a scene where a character realizes they are halfway through a journey but no longer knows where they are going.
Focus On:
how the character has already invested enough in the journey to make turning back difficult.
the ways the physical surroundings reflect or complicate the character’s uncertainty.
allowing the character to decide what matters when their original destination no longer makes sense.
something unexpected happening, which changes how the character understands their journey.
Skills to Practice:
Writing internal conflict through action rather than explanation
Using the setting to create emotional tension
Building a turning point in a story around a character’s realization
Tip: Don’t rush your character toward an answer or destination. Instead, let their uncertainty create the action and emotional setting of the scene.
Feeling Stuck?
Consider: What if the character finds a sign, object, person, or place that makes them question why they started the journey in the first place? Consider what or who prompts the character to realize they are lost or uncertain first, then go from there.
2. “I Thought I Knew What I Was Doing.”
Write a story that begins with the sentence: “I thought I knew what I was doing.”
Focus On:
making the opening sentence create intrigue about what went wrong.
how the narrator will gradually reveal what they believed would happen versus the reality they’re experiencing.
a small detail or decision that exposes the gap between intention and reality.
creating an ending that gives the narrator a new understanding of their situation.
Skills to Practice:
Creating narrative tension from the very first sentence
Intentionally controlling when information is revealed
Developing a narrator whose understanding changes over the course of the story
Tip: Let the reader discover the problem alongside the narrator instead of explaining everything at the beginning.
Feeling Stuck?
Finish the opening sentence for yourself with your own private answer first. Write, “I thought I knew what I was doing, but…” then follow the ‘but’ and see what happens and what characters begin to take shape.
3. Almost Giving Up
Create a character who almost gives up on something important.
Focus On:
a specific reason the character has for wanting to give up.
how their struggle reveals what their goal means to them.
the character reaching a genuine point of exhaustion, doubt, or frustration.
whether they decide to continue or walk away, and how that decision changes them.
Skills to Practice:
Writing believable motivations for characters
Escalating emotional stakes while developing characters
Allowing a character to make a consequential choice
Tip: Make giving up a real possibility rather than making the character’s situation seem temporary or like they’re only confronting an inconsequential obstacle.
Feeling Stuck?
Ask what your character has already sacrificed, then imagine what would make them decide that the sacrifice is no longer worth it. And or ask what else your character needs to sacrifice in order to continue on their current path.
4. A Moment of Uncertainty
Write a poem about a moment of uncertainty.
Focus On:
capturing one particular moment via senses rather than explaining uncertainty in general.
including concrete images that carry some, if not all, of the emotional weight of the poem.
highlighting contradictions, ambiguities, or unanswered questions in the poem.
leaving the reader feeling uneasy or uncertain rather than comfortable or enlightened.
Skills to Practice:
Turning an abstract emotion into sensory imagery
Using precise language to describe something imprecise
Resisting the urge to resolve every question that arises
Tip: Start with what the speaker of the poem can see, hear, touch, smell, or notice (sense) rather than naming or explaining the emotions they’re experiencing outright.
Feeling Stuck?
Write five things the speaker of the poem can see during the exact moment the poem is trying to capture, then choose one of those images and let it become the center of the poem. Or use something they can hear, touch, or smell after making lists for one of those senses.
5. The Unexpected Opportunity
Write a scene where a failure or setback leads a character to an unexpected opportunity.
Focus On:
how the character’s setback initially feels like a genuine loss.
the ways the character reacts to the failure before recognizing the opportunity it brings.
why and how the opportunity arrives in an unexpected way.
the character’s decision whether to take advantage of the unexpected opportunity or not, and why.
Skills to Practice:
Transforming conflict into opportunity without making a failure seem artificially positive
Creating believable cause-and-effect relationships and events
Writing about opportunities that emerge naturally from complications, or what are initially perceived as complications
Tip: Don’t make the character’s failure or setback secretly good or desirable from the beginning. Instead, let its consequences feel real before the character recognizes the opportunity it brings.
Feeling Stuck?
Take something your character desperately wanted or was trying to achieve, then remove it from their circumstances. Next, ask what new person, place, skill, or other possibility is able to arise because of that loss or disappointment.
Reflective Journaling Prompts for Navigating ‘The Messy Middle’
6. The Hardest Part
What part of the creative process feels hardest for you, and why?
Focus On:
identifying the specific stage, task, or moment that creates the most resistance.
describing what happens internally when you reach that point, especially if it is physical.
discovering whether the difficulty comes from the work itself or from what you expect of yourself and the work.
exploring what might make that part of the process more manageable.
Skills to Practice:
Naming your creative resistance(s) precisely and honestly
Distinguishing between difficulty and failure
Turning self-awareness into useful information
Tip: Replace ‘the creative process’ with one concrete creative activity such as brainstorming, drafting, revising, sharing, finishing, etc. instead.
Feeling Stuck?
Complete this sentence several times: “The part of the creative process I avoid most is…”
7. When the Work Isn’t Going Well
How do you respond when your work isn’t going well, especially when you’re in the middle of a project?
Focus On:
describing what you actually do when your momentum disappears or doubt sets in.
noticing the difference between your first emotional reaction and your eventual response.
identifying which habits help and which ones make the situation harder.
envisioning what you would like your future self to remember during a difficult stretch.
Skills to Practice:
Observing your creative patterns without judging them too harshly
Identifying strategies that support persistence when things get uncertain or difficult
Turning difficult experiences into practical knowledge you can use
Tip: Write about a specific project or moment instead of answering in generalities.
Feeling Stuck?
Think about the last time you wanted to abandon a project, then write down what happened immediately before, during, and after that moment.
8. The Unfinished Project
What unfinished project still occupies your thoughts, and why?
Focus On:
naming the project and remembering what originally drew you to it.
considering why it stopped rather than simply labeling it ‘unfinished.’
exploring what still feels alive, unresolved, or important about the idea.
deciding whether you want to complete or transform the project, or leave it behind.
Skills to Practice:
Looking at unfinished work with curiosity rather than guilt or anxiety
Separating your attachment to the project from your sense of obligation
Recognizing when an old idea still has creative potential, and when it doesn’t
Tip: An unfinished project does not automatically need to be finished. Sometimes it has something to teach you that can be wrapped up in your understanding of when and how to let it go.
Feeling Stuck?
Describe the project as though you were introducing it to someone who has never heard of it and notice which details you still care about and which ones you don’t.
9. What Difficult Times Taught You
What have difficult creative times in your life taught you about the creative life you truly want?
Focus On:
pinpointing one difficult period that changed how you approach creativity.
naming something you now understand that you did not understand before.
deciphering what the experience revealed about your needs, boundaries, values, or ambitions.
using this lesson to describe one element you want to incorporate into your creative life now.
Skills to Practice:
Finding meaning without romanticizing previous difficulties and challenges
Connecting past experiences to present choices and desires
Defining your creative life through lived experience
Tip: You don’t have to turn a difficult experience into a major success story. Sometimes the lesson you learn can simply include something you know now that you didn’t know before.
Feeling Stuck?
Finish the sentence: “I used to believe that a creative life required ____, but now I believe it requires ____.”
10. Persist or Change Direction?
How do you know when to persist and when to change direction, especially when you’re in the middle of a project?
Focus On:
identifying the signs and signals that tell you a project still matters to you.
noticing the signs and signals that suggest a current approach is no longer working.
exploring the difference between temporary frustration and a genuine need to change course.
defining what a thoughtful change of direction might look like for you.
Skills to Practice:
Making thoughtful decisions without demanding absolute certainty
Distinguishing helpful persistence from unhelpful stubbornness
Recognizing revision and redirection as integral parts of creative work.
Tip: Instead of asking “Should I quit?” try asking “What needs to change, and why?”
Feeling Stuck?
Imagine you are advising a friend who is facing the exact decision you are facing right now. What would you tell them to pay attention to, and what to let go of?
Join the Conversation
The messy middle is often easier to navigate when we stop treating it as something we have to figure out alone, especially because we don’t!
Join us in the Drafters Workshop chat this week to share your responses to one of these prompts, an excerpt of your other writing, a thoughtful question, or a note about where you are with your creative work.
You can also get a conversation going by answering this week’s question: What helps you keep going when you don’t know where your creative work is taking you?
Whether what you share is a single sentence, a completed prompt, or a longer reflection, your perspective may encourage someone else as they try to navigate through the messy middle. And vice versa!
Thank you for spending part of your week exploring The Messy Middle with us. I hope this week’s prompts and posts encourage you to notice the routines, rituals, and everyday practices that can intentionally shape your creative life for the better over time. We can’t wait to see what you contribute!
Please don’t forget to like and share this post if you enjoyed it so others can enjoy it and draft with us too. Thank you, and happy writing!
Continue Exploring August’s Theme, The Creative Life
ICYM Week 2: Creative Habits
Writing Prompts for Building the Creative Habits You Want
Immersive Storytelling Mode and the ArXiv
Should writers have quantifiable creative habits?
Reading Notes: The Unabridged Journals of Sylvia Plath
The Habits That Help Me and My Creative Life Most
Striking the Right Balance with Quantifiable Creative Habits
ICYM Week 1: Making Space
Writing Prompts for Making Space in Your Creative Life
A Day Alive in the Lakeside Library
Do writers need to protect creative time like an appointment?
Reading Notes: Tomorrow, and Tomorrow, and Tomorrow
My Ideal Yet Practical Creative Life Scenario
How to Make Space and Time for Your Creative Life
The Creative Life as Play and Work
Consider going more in depth with this month’s theme with The Creative Life Writing Collection
Every prompt, draft, and dialogue begins a conversation, but some of those conversations deserve more of our time and attention.
If today’s post sparked an idea or practice you want to explore further, The Creative Life Writing Collection offers a guided month of prompts, craft exploration and techniques, reflection, and customized reading recommendations for writers who want to go deeper.
And if you want to explore past themes, paid subscribers also have access to the full archive, including previous writing prompts, discussions, and reading lists, as well as full access to the community chat and Daily Drafters Exclusives writing collections.