The ONE Shift That Will Help You Actually Finish Your First Draft

How to keep writing through the messy middle when you want to give up

When I began my first novel draft at the end of 2020, I noticed I ran out of steam around the 50-60 page mark. The messy middle, as I soon would learn it was called. And that was exactly how it felt — clumsy, boring, and discouraging. A real pile of garbage.

I’ve since learned that this is where a lot of writers stop entirely. The desire to write a novel has called to them, and they have the momentum and stamina to get fifty or so pages in. But the task suddenly feels impossible when faced with the challenge at this early, tender stage of the process. You may know where you want your characters to end up at the climax of the book, but now you have all these pages to get them there. How do you fill them, especially in a wild and messy first draft?

I’ll be honest, at this point in my journey, I very much wanted to quit. I was genuinely convinced I might not be able to write a novel after all.

If you don’t even know what is going to happen, how can you write the whole book? — a mean phrase I uttered to myself far too many times.

But I learned along the way that it took just one shift in my perspective that allowed me to continue. Be playful. Be curious. Approach the page like a child excited to find out what happens next.

Once I internalized this shift and began to act on it, I noticed a lightness and, dare I even say, joy around the work that wasn’t there before. Not that all of a sudden the writing became easy, and I knew how to progress my plot along. Not even close. But the work felt less like work in the traditional sense. The insane amount of pressure I was putting on myself before had begun to dissipate and I was able to actually find more momentum and stamina without that ugly weight holding me down.

Once I stopped trying to control my draft and started to explore it, something opened up.

Being playful reminded me that writing, despite all its challenges, is something I love to do. And so in this less stressful state, I was able to approach the messy middle with openness. It was there that I found my way through. The writing didn’t magically become easy, and my plot certainly didn’t untangle itself overnight—but the work felt lighter. The joy returned.

I talk often about the phrase hold the work loosely, borrowed from Alan Watt’s The 90-Day Novel. It's about releasing the grip of perfectionism, of outcome obsession. It's about giving yourself permission to second-guess yourself and focus on the process rather than the result. That’s how I made it through the messy middle and the draft as a whole. Not with elegance or mastery—my first draft was pretty terrible, to be honest—but by holding the work loosely. Letting it be bad. Letting it be mine.

This is where we will meet in my Wild Draft novel writing cohort— in that tender, messy, and wild first draft. This perspective shift of being playful and curious on the page will guide us as our cozy, small-group container embraces creative experimentation, writerly joy, and the three-act structure to write a first draft (in whatever state that looks like!) in 6 months. As I guide you in building forward momentum, we’ll also deepen your trust in your voice and develop a framework for finishing your novel—through play, curiosity, and creative inquiry.

Drafting is where the real magic begins. Only once the words exist—messy, raw, and alive—do you have something to revise, reshape, and refine. But you can’t edit a blank page. You have to write it first.

Ready to turn that curiosity into a full draft? That’s exactly what we’ll do inside The Wild Draft.

This is a high-touch experience designed to help you finish a draft of your novel—and believe in it.

We meet biweekly from June through November, building your draft through craft lessons, supportive feedback, structured accountability, and creative momentum. This is a space to experiment, grow, and write the story that’s been waiting to emerge.

It’s for writers with an idea, a voice, or a spark—who crave structure, community, and the guidance of an experienced coach who gets the highs and lows of the process.

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🦋 Practicalities at a Glance

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• Duration: June–November 2025

• Live Calls: Biweekly on Wednesdays, 7–9 PM EST (starting June 4)

• Group Size: 6–8 writers

• Format: Zoom-based cohort with 1:1 support + community check-ins

• What You’ll Write: A full novel draft—your first, fiercest, or most unfinished

• Includes:

  • 13 biweekly live sessions

  • 1:1 coaching call with Kailey

  • Feedback on your first 50 pages + editorial letter

  • Personalized revision roadmap

• Cost: $1,800 (Pay in full or in 4 monthly installments at checkout)

• Enrollment Deadline: May 28, or when full

• Commitment: 4–6 hours per week for writing & reflection

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