Twenty-two years ago, I started writing a business novel called Rolling Rocks Downhill.
Eleven years ago, I finally published it.
It’s done well—still sells, still gets recommended. But at 73,000 words, in a world with so many easy forms of entertainment, it’s a time commitment that lots of folk don’t want to make.
But … I’ve often wondered if I could create a shorter version that captured the essence without the sprawl. The kind of thing someone could read in an evening and still walk away with the core ideas.
(I’ve written 5 books like that - I call them BabyCrocs because they’re short and snappy - and they’re so much easier to write (and finish!) and so much easier to read. Still hard work, but my readers love them.)
I never had the time or energy to attempt a rewrite. Until two days ago.
I’ve now spent less than 10 hours working with Claude (Opus 4.5, via Claude Desktop’s new Cowork mode) to produce a complete condensed edition. It’s around 14,000 words. It stands alone as a story. And honestly? The quality is better than I expected I could achieve on my own, even with unlimited time. I still need to do some editing work, but it’s about 2 or 3 rewrites away from being publishable.
Here’s how the workflow has evolved.
The Setup: Obsidian + Claude Cowork
For this project, I keep all my writing in Obsidian, because Claude Cowork can read obsidian easily. I pointed Cowork at it, then uploaded the original novel .docx and it converted it into .md files, and then I spent about 4 hours summarising the book, so that Claude and I could both get our heads around it. (It’s surprising the bits I remember, and the bits I’ve forgotten!)
In case it’s not clear: I pointed Claude Cowork at my Obsidian vault. That’s it. No copying and pasting, no uploading files to a web interface. Claude can read and write directly to my vault.
(Side note: Obsidian itself seems to have got nicer recently. Maybe it’s just me, but the experience feels smoother. Or maybe I’m just enjoying using it more because Claude makes the whole writing process less of a slog.)
The Process: Conversation, Not Commands
The work has been genuinely collaborative. I’d explain what I wanted—“condense Act 1, keep the voice, preserve these specific moments that readers love”—and Claude would produce a draft. Then we’d refine it together.
Too and Fro. Too and Fro.
Sometimes I’m driving and it’s navigating. Sometimes we swap seats.
Some examples of what that looked like:
- Structural decisions: The original book has 61 chapters. We condensed it into five parts. Claude helped me identify what was essential versus what was scaffolding I’d needed to write the full version but didn’t need in the condensed one.
- Preserving voice: I have certain phrases readers mention to me years later. “Nibbled to death by ducklings.” “Don’t think about small batches”. “I love the smell of jet lag in the morning”. Claude understood which bits mattered and kept them intact while trimming around them. I did have to instruct it to make sure it kept almost all of the special bits that people like about my writing, and not turn it into a dry text book. It did that better than I could, I suspect.
- Gap analysis: After drafting each section, I’d ask Claude to check for “dangling references”—characters or concepts mentioned without proper introduction. It caught several and fixed them. Claude makes these sorts of mistakes while writing, just like I would. The difference is it can also systematically find and fix them, in moments.
- External review: I fed the draft to ChatGPT, Gemini, and a separate Claude instance to get fresh perspectives. Then Claude helped me work through their feedback systematically—adding timeline breadcrumbs, a mid-book scene to keep a character visible, clarifying a plot twist the reviewers had missed. Very helpful all those fresh eyes.
Version Control: Local Git
Here’s a Mac Power Users detail: Claude set up a local git repo inside my Obsidian vault. It told me what it was doing—just a few terminal commands in its Linux environment—and now I have proper version history with commit messages like “Extended small batches scene” and “Added Hal mid-book check-in.”
The git repo lives in the vault folder, which syncs via iCloud. Belt and suspenders. No GitHub account required—it’s entirely local unless I decide to push it somewhere later.
I hope that’s the best thing to do - we chatted for a while, and it said it was. I haven’t properly used version control this century, so …
What Surprised Me
The quality. I expected Claude to be useful for grunt work—finding inconsistencies, suggesting cuts. I didn’t expect it to understand the story well enough to suggest that a character who disappears mid-book should have a callback at the end. This is Claude Opus, and I’m paying for the medium-sized max plan, btw - it’s incredible, and far better than anything else out there for writing (at least of this month!)
The speed. Ten hours across two days, including all the back-and-forth, the external reviews, the refinements. I’ve spent longer than that agonising over single pargraphs in the past.
The collaboration. It genuinely feels like working with a skilled editor who has infinite patience, has read my book carefully, and is available at 11pm when I have an idea.
The Result
I now have a 14,000-word condensed edition that:
- Stands alone as a complete story
- Preserves the voice and humour of the original
- Teaches the same core ideas without lecturing
- Ends on exactly the right emotional note
Is it ready to publish? Not quite—I need to park it for a few days and then read it with fresh eyes. But it’s close.
Closer than I thought I’d get in two days.
If you’ve got a long-form writing project you’ve been putting off because it felt too big, this workflow might be worth trying. Obsidian for organisation, Claude Cowork for the heavy lifting, git for peace of mind.
I’m genuinely impressed. No - that doesn’t do it justice. I’m gobsmacked, amazed, blown away. And delighted that I can share my book that took me 11 years to write, with a whole new audience.
