August Theme: The Creative Life
Big Question: How do we build a creative life that works for us?
Week 3: The Messy Middle
The Question Behind the Question
This month, we’re exploring The Creative Life, and this week we’re exploring The Messy Middle, which prompted Monday’s question: Is doubt a normal part of the creative process or a sign something isn’t working?
Honestly, it was nothing but crickets after I posed that question, though I did receive some scattered responses. Yet those responses weren’t really speaking to whether doubt was ‘normal’ and instead alluded to general frustrations related to writer’s block and ‘the messy middle.’ So, I tried a different tack, as I genuinely did want to learn more about how our broader writing community perceived doubt and its place within (or outside of) the creative process, asking instead: What do you do when you are in ‘the messy middle’ of a draft? How do you overcome your doubts?
And the responses to those follow-up questions were pretty unanimous, with most respondents saying something to the effect of: You take a short break, then keep writing.
Whether you feel deluded when you keep writing or even like what you end up writing, respondents said that you should still keep writing. Whether you write something different than what you were working on before you got stuck or are only able to add one sentence to the piece stirring up doubts, they still said that you should keep writing. Which impressed me and made me feel less alone and more encouraged to keep going, no matter what, even when it feels like nothing is working and no one is paying attention to what I write. So, thank you for that!
In a roundabout way, then, it seems that most respondents did essentially agree that ‘Yes, every creator doubts,’ but that they should keep writing anyway despite their doubts. Which prompted an extended inquiry on my end, because then I wanted to know exactly HOW writers should actually deal with their doubts when they arise during the creative process so that they are intentionally mitigated instead of further instigated.
In theory I understand the sentiment of just bucking up and getting to work regardless of how you feel about it, especially when the work and writing needs doing. As the saying goes, “The story won’t write itself.”
But I also couldn’t let go of what doubts often indicate, especially in the midst of a creative project— that something isn’t working and needs adjusting, whether it be a mindset, a tactic, a tool, a voice or setting, etc. So, I ultimately felt unsatisfied that just ‘keeping on keeping on’ would work long-term for us writers and creators if the updated aim of this dialogue is to figure out how to deal with doubts that arise throughout the creative process. Hence, the remainder of today’s post.
The bulk of today’s post includes some diagnostic tactics and tangible step-by-step strategies for how to deal with doubt during your creative process, or whenever it appears during your creative life. A writer’s guide for surviving ‘the messy middle,’ if you will. Which I hope will help us expand and discuss this week’s original dialogue. Let me know what you would add to the writer’s guide that follows in the comments and Dialoguers chat so we can expand it if and where needed.
However, before we begin expanding this week’s dialogue, it seems essential that we first grant ourselves permission to accept doubt as part of the creative process— perhaps in direct relation to when it is and is not helping us build the creative lives we truly want.
✍️Permission to Doubt as a Creator and Writer
It’s helpful to accept doubt as a ‘normal’ part of the creative process when you know you’re not alone or failing when you experience it.
As the following excerpts attest, even well-known and revered writers have had to struggle with doubt or come to grips with what to do with it at some point, too.
“The greater the artist, the greater the doubt. Perfect confidence is granted to the less talented as a consolation prize.” (often attributed to Robert Hughes and other critics)
“The worst enemy to creativity is self-doubt.” (from The Unabridged Journals of Sylvia Plath)
“The scariest moment is always just before you start. After that, things can only get better.” — Stephen King
“Those who think they are not conceited are usually the most conceited. Those who are certain they are right are the ones we must fear.” (from Madeleine L’Engle’s Walking on Water: Reflections on Faith and Art)
“Have pity on those who are fearful of taking up a pen... because they are afraid that someone has already done so better than they could.” (from The Pilgrimage by Paulo Coelho)
“If I waited for perfection, I would never write a word.” (from Margaret Atwood’s lectures on the creative process)
“The problem with the world is that the intelligent people are full of doubts, while the stupid ones are full of confidence.” (from Charles Bukowski’s The Captain Is Out to Lunch and the Sailors Have Taken Over the Ship)
“Doubt is a sign of life in the creative process, not a signal to stop.” (from Dani Shapiro’s Still Writing: The Perils and Pleasures of a Creative Life)
“No extraordinary journey is linear. In reality, the middle is extraordinarily volatile — a continuous sequence of ups and downs, flush with uncertainty and struggle.” (from Scott Belsky’s The Messy Middle)
“The messy middle is a rite of passage for most writers. It’s where the complexities of your narrative are wrestled into coherence... The doubts you’re experiencing are not a signal of your inability.” (from April Dávila’s Embracing the Messy Middle)
📝How to Deal with Doubt During ‘The Messy Middle’ of Your Creative Process: A Writer’s Guide
Every writer knows and loves the initial spark that comes with a new project, when their characters are vibrant, their plot is seamless, and their creative journey and the blank page feel like a world of endless possibilities.
But inevitably they hit the ‘messy middle’—that sprawling, chaotic territory around chapter fifteen where their initial excitement has evaporated, the ending feels miles away, and their inner critic starts screaming that everything they’ve written is absolute garbage and might never be fixable.
Yet this feeling of stagnation and dread doesn’t occur only inside a manuscript. It can also mirror ‘the messy middle’ of a creative life. And this daunting ‘messy middle’ phase of life can arrive after your first few creative projects launch, where their initial novelty wears off, burnout creeps in, and your ultimate long-term creative career goals start to feel impossibly far out of reach.
Creative doubt during these ‘messy middle’ phases isn’t a sign that you are a bad writer, however. In fact, it’s proof that you’re doing the difficult work of making art and living a creative life.
Still, when your narrative starts tangling itself into knots and your creative confidence begins to dip, the secret isn’t to wait for inspiration to return to you and your project. Instead, you need a strategy to identify the specific type of doubt holding you and your work hostage and a concrete, step-by-step process to write your way forward because, as we’ve already established, the best way to overcome doubts in the writing and creative process is to keep writing your way through them.
What follows is a guide in three parts for how to diagnose your creative doubts so that you can conquer ‘the messy middle’ whenever and wherever it appears during your creative process and life.
🫤Part 1: 5 Types of Creative Doubt (And How to Handle Them)
Not all creative doubts are the same, and each one can require a different type of intervention.
Before you can fix your creative mindset or the trajectory of your creative work, in other words, you have to first diagnose exactly what kind of doubt is plaguing you and why. Then you will have a better idea of what you can and should do next, and the approach you’ll want to take to mitigate it.
1. The Imposter Doubt (“I am a fraud.”)
The Symptom: You feel like you lack the talent, credentials, or right to tell the story you want to tell or live the creative lifestyle you want to live.
The Fix: Shift your focus from your identity to your output. Your job or writing goal should not be centered around being a perfect ‘creative genius’ author in every facet of your life but driven by your desire to tell the specific stories you want to tell as honestly as you can.
The Micro Exercise (The Third-Person Resume): Open a blank sticky note. Write down three things your current manuscript does well but write them in the third person as if you are a literary critic reviewing someone else’s work (e.g., “The author creates a deeply claustrophobic atmosphere in Chapter 4.”). Then read it aloud to step outside your own subjective ego.
2. The Structural Doubt (“This plot is a disaster.”)
The Symptom: You look at the middle chapters or sections of your manuscript and see gaping plot holes, incomplete thoughts, pacing issues, and flat characters.
The Fix: Realize that a messy middle is not only functionally normal, but an acceptable and crucial part of the entire writing process. Just like you cannot evaluate the architecture of a house while its framing is still exposed, you can’t evaluate your entire manuscript when all you’re looking at is the bare bones of the story you’re telling. Keep writing and building your story and be prepared to fix any issues with your draft’s structural alignment during revisions.
The Micro Exercise (The 5-Sentence Summary): Step away from looking at the hundreds of pages in your first drafts at once by writing out the entire rest of your book’s plot in exactly five sentences. This will force your brain to zoom out from the messy micro details you’re in the middle of and instantly remind you of the macro destination you are writing toward.
3. The Comparison Doubt (“Everyone else is better.”)
The Symptom: You read a brilliant book by another author you admire and want to delete your entire hard drive.
The Fix: Remind yourself that you are comparing your messy, unpolished first draft (or creative career) with another writer’s heavily edited, published final product that required an entire team of professionals to create and distribute. You never witnessed the complete creative process they went through. You didn’t see their work during their messy middles, where their drafts were undergoing serious revisions and they underwent serious doubts regarding their abilities and the promise of the project they were working on.
The Micro Exercise (The First-Draft Forensic): Pick up your favorite book. Flip to a random page in the middle of it. Then rewrite that single page as a terrible, clunky, basic, no-adjective, no literary color or language ‘bad first draft.’ Visually seeing and reverse-engineering how a masterpiece likely started as a flat skeleton with more potential than praise will break the illusion of overnight perfection.
4. The Fatigue-Driven Doubt (“I hate this story.”)
The Symptom: The plot or manuscript you’re working on feels incredibly boring, predictable, and tiresome to write.
The Fix: Recognize that boredom while writing is often just exhaustion in disguise. Because you have lived with the idea you’re working on for months, maybe even years, it feels old to you. However, it will still be entirely fresh to a reader experiencing it for the first time, once it’s complete.
The Micro Exercise (The 180-Degree Shock): Take the current scene or section you’re working on. Write down a single sentence detailing the absolute worst, most ridiculous, or opposite thing that could happen or come next (e.g., if two characters are having a quiet dinner, write: “The waiter accidentally drops a live grenade on the table.”). You don’t have to keep what you write in your polished piece, of course, but writing something absurd for a few minutes might shock your brain out of its boredom and fatigued state.
5. The Creative Career Doubt (“I am stuck in ‘the messy middle’ of a creative life.”)
The Symptom: The initial thrill of being a new artist and creator has faded, as your early creative milestones are behind you. So, you’re starting to feel stuck in an endless, unrecognizable grind of work and expectations, with your ultimate creative career goals still far away and seemingly out of reach.
The Fix: Redefine and restructure your creative identity and career around the daily practice of your craft rather than external milestones or accolades that are never guaranteed since they are out of your direct control.
The Micro Exercise (The ‘Just for Me’ Sandbox): Spend 10 minutes writing something completely unsellable, unpublishable, and unrelated to your main project. Write a ridiculous fan-fiction scene, a terrible poem, or a rambling journal entry. Creating something with zero commercial pressure tied to it will remind your brain that you make art for the joy of it, not just for the accolades and external rewards it could potentially offer.
💪Part 2: 10 Tips for Surviving ‘The Messy Middle’
When you are deep in the trenches of ‘the messy middle,’ use these practical strategies to keep your pen moving forward.
Write a ‘Zero Draft’: Give yourself explicit, written permission to write badly. Call it a placeholder draft if it helps lower the stakes. Keep writing to keep your creative momentum without any other agenda.
Lower Your Daily Word Count: If a target of 1,000 words per day feels paralyzing, drop it to 500 words or 300 words, then see how much you end up writing at the end of the week or month. Progress is still progress when all is said and done, regardless of your daily quota or output, and will help keep your creative momentum alive.
Skip to a Fun Scene: If you are stuck in a transition chapter, leap forward to a dramatic confrontation or a climax scene you are excited about writing.
Turn Off the Editor: Turn off your spellcheck, change your font to Comic Sans (which can trick the brain into taking the work less seriously), or write with white text and a dark background. Do whatever works to get your brain into a creative flow rather than an editing flow. Turn on your creative mind and turn off your inner critic by adjusting your writing tools and apps to make this happen.
Interview Your Characters: When the plot stalls, step outside your draft. Write a journal entry from your protagonist’s perspective, asking what they want right now or how they’re feeling. Or pretend you’re interviewing them for a magazine. I’ve even written obituaries for my characters in the past, which helped my creative flow immensely.
Track Momentum, Not Quality: Keep a calendar where you simply mark an “X” for every day you sit down and write. Focus on protecting your daily momentum rather than the quantity of what you produce each day. Sometimes writing only one sentence and getting your rear end in the chair is more than enough to keep your creative momentum going. Read Striking the Right Balance with Quantifiable Creative Habits for more on this.
Introduce a Wrench: If the middle of your story is sagging, throw an unexpected problem at your characters. Raymond Chandler famously advised: “When in doubt, have a man come through a door with a gun in his hand.”
Revisit Your Original Spark: Go back to your initial brainstorming notes or the playlist that inspired the book to remind yourself why you loved this idea. I wrote about how and why I do this in What I Do When I’m in ‘The Messy Middle’.
Separate Writing from Editing: Never try to polish a sentence while you are still trying to figure out what happens next. Writing and editing use completely different parts of the brain, so keep your writing time separate from your editing and revising time, always.
Build a ‘Fix-It’ List: When you realize you need to change something in Chapter 3 when you’re writing Chapter 5, don’t go backward. Instead, write down what you need to change on a separate notepad (“Note: Change Sarah’s job to a detective”), but keep writing forward. You can revisit this list when you’re revising later.
✅Part 3: The Step-by-Step Process for Navigating ‘The Messy Middle’
When doubt begins to completely paralyze you and you are ready to abandon your manuscript, or your creative life altogether, walk through this exact four-step process first.
Step 1: Acknowledge and Pause
Stop trying to push through your doubts when it’s only making you more miserable and despondent. Close your eyes, take a deep breath, and state whatever you’re feeling clearly: “I am doubting _________. And I feel _______. But what I’m experiencing is normal and just part of ‘the messy middle’ stage of creating something.” Labeling the doubt you’re feeling and why strips away its power to convince you that your creative project, or your desire to live a creative life, is uniquely broken, when it’s highly unlikely that’s the case.
Step 2: Dump the Mess onto the Page
Open a blank document completely separate from your manuscript or creative project. Write out a chaotic, bulleted list of everything you think is wrong with what you’re writing or working on, or your creative life, right now. Getting the tangled plot lines and insecurities out of your head and onto the page makes them manageable problems you can identify then pragmatically address rather than an overwhelming cloud of anxiety swimming around your head and body.
Step 3: Freewrite for Exactly 15 Minutes
Set a timer on your phone for fifteen minutes. Commit to freewriting whatever comes next in the story you’re writing, or the story of your creative life, without stopping, editing, or deleting a single word until the timer goes off. Tell yourself that you can quit the moment the alarm goes off before you begin, but while you’re writing don’t worry about what comes out and onto the page. More often than not, breaking your creative paralysis for just fifteen minutes can reset your focus and get the words flowing again, even if those words never make it into any final drafts.
Step 4: Celebrate the Messy Page
After the timer goes off and you’re done freewriting, look at the words you produced. They might be clunky and awkward and revisable, but they exist and a blank page no longer does. Which should drive home the reminder that it’s impossible to fix a blank page, but always possible to move past a messy middle that has some words, any words, to work with.
💬Dialogue Wrap-Up and Reflection
Bottom line, I believe that perceiving and accepting doubt as a critical and ‘normal’ part of the creative process is necessary. However, it’s just as critical that we have pragmatic ways to mitigate our doubts when they rear their ugly heads, lest we succumb to their powers and influence.
The ‘messy middle,’ whether it happens while writing a book or during a creative career, is the exact place where the invention and intention of art happens and thrives.
Sometimes navigating ‘the messy middle’ can feel like navigating an existential crisis but is actually a rite of passage for creatives in a lot of ways and often indicates that things are going well.
Every brilliant novel on your bookshelf or awe-inducing piece of artwork hanging on your wall survived a ‘messy middle’ of some sort, or their creators did anyway. So, it’s okay and reasonable for you to believe that you’ll get past all your messy middles too. Especially if you’re armed with a pragmatic approach or guide for dealing with them whenever and however they arise throughout your creative projects and life.
If you’re feeling lost in the fog of your creative project or creative life, it doesn’t mean your original idea or path is lost too. It just means you are deep in the middle of where the real transformation of your work and creative life takes place.
All you need to do now is trust that your creative horizon is still there, even if you can only see a few feet ahead right now. Just keep your fingers on the keys and keep writing.
Follow the guide outlined above whenever you need it and let the work you do be messy if it needs to be. Also remember, as many of you have already intuited, that the only way out of ‘the messy middle’ is to write your way through it. One word. One sentence. One page. One draft. One day at a time.
An Invitation to Reflect and Discuss Navigating Our Doubts and ‘The Messy Middle’
I invite you to join this month’s Dialoguers chat to share how you’re navigating ‘the messy middle’ whenever and however it appears in your creative life. Your insights could inspire or encourage someone at the exact moment they need it. And vice versa!
Whether you join to share your responses, ask more thought-provoking questions, or connect with other writers and support their work, we look forward to your contributions and insight and can’t wait to engage in further dialogue with you.
Continue Exploring August’s Theme, The Creative Life
This Week: The Messy Middle
Writing Prompts for Navigating ‘The Messy Middle’
Is doubt a normal part of the creative process or a sign something isn’t working?
Reading Notes: The Cemetery of Untold Stories
What I Do When I’m in ‘The Messy Middle’
Popular Posts from Week 2: Creative Habits
Immersive Storytelling Mode and the ArXiv
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
Popular Posts from Week 1: Making Space
A Day Alive in the Lakeside Library
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
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