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Ebook Outliner

Most expertise books fail at the outline stage, not the writing stage. The creator brain-dumps everything they know in no particular order, gets stuck at Chapter 4, abandons the project. The Ebook Outliner architects the book so thoroughly that writing becomes execution, not invention.

What this skill does

Books fail in the outline, not on the page. The brain dumps and the course transcripts both die for the same reason — no chapter momentum. Each chapter sits next to the others instead of building on them, so the reader gets information but not progression, and the writer stalls because there's no internal logic pulling the next chapter into existence. A detailed outline solves both problems. You always know what's next, and the reader feels the book accumulating toward something.

The skill starts with three structural tests before it writes a single chapter title. The One-Sentence Test: can you state what this book argues in one sentence? If the sentence is vague, the book is vague. The Shelf Test: which two or three books sit next to this one in the bookstore? A book that doesn't fit anywhere is usually a focusing problem, not a positioning innovation. The Competitor Gap: what do the existing books get wrong or miss for this specific audience? If there's no gap, there's no reason to write. The skill won't proceed past these tests if the answers are mush.

Structural model selection isn't decorative. Framework Book (proprietary model, each chapter teaches one component), Journey Book (sequential transformation, each chapter is a stage), Principles Book (one insight per chapter, semi-independent, unified thesis), Problem-Solution Book (each chapter solves one named problem). The skill recommends the right model for the user's expertise and explains why. A pricing methodology is a Framework Book; a memoir-led leadership book is a Journey Book; "10 laws of marketing" is a Principles Book. Pick the wrong structure and the writing fights you every chapter.

Each chapter gets a full template — thesis sentence, opening hook, 3-5 key concepts, stories and examples needed (specified even if the author has to find them later), exercises or application prompts, the chapter outcome (what the reader can think or do differently by the end), the bridge to the next chapter, and a target word count. The narrative arc gets mapped across the whole book: orientation in chapters 1-2, core building blocks in 3-6, the hard part in 7-8 where serious readers separate from browsers, integration in the final chapter. Non-fiction needs an arc too — readers feel its absence even if they can't name it.

Output includes a writing sequence recommendation that almost always starts somewhere other than Chapter 1 (the intro should be written last, because you don't know what the book really is until you've written the middle), a realistic timeline based on 500-1,000 polished words per focused writing session, an editing pathway that names which stage catches which kind of issue, a content reuse map if the author has existing blog posts or course materials, three title options (one straightforward, one intriguing, one benefit-driven), and a one-paragraph cover design brief for whichever publishing route fits the book's purpose. It won't outline a book that fails the one-sentence test — sharpening the premise comes first, every time.

When this triggers

  • ·You've started a book three times and stalled — usually around the same chapter
  • ·You want a book that builds authority and feeds the email list, not a vanity project
  • ·You have blog posts, course content and talks lying around and need them mapped to chapters
  • ·You need a chapter outline detailed enough that you always know what comes next
  • ·You want the book positioned against actual competitors, not pitched into a void

Example

Trigger

User: 'Book on pricing for freelance designers. Target reader: 1-3 years freelance, undercharging chronically. My angle: hourly rate is a junior mindset, not a pricing model. Want ~30K words.'

Output

Premise (one-sentence test, passed): "This book shows freelance designers in their first three years how to price for client outcomes instead of their own hours — by treating the hourly rate as the entry-level pricing model it actually is." Structural model: Framework Book (you have a proprietary pricing matrix — each chapter teaches one component). Comparable books on the shelf: Pricing Design (Dan Mall), Pricing Creativity (Blair Enns) — sit between them, more practical than Enns, more opinionated than Mall. Chapter outline (8 chapters, ~3,750 words each): 1. Why hourly is junior — the trap, not the floor 2. The Outcome Audit — what clients actually buy 3. The Anchor Conversation 4. The Pricing Matrix (your proprietary framework) 5. Reading the Brief 6. Talking About Money 7. When the Number Lands Wrong 8. The First 90 Days at the New Rate Each chapter: thesis + opening hook + 3 key concepts + stories needed + exercises + chapter outcome + bridge to next + word count. + narrative arc map, front/back matter plan, content-reuse map (which of your existing posts go where), writing sequence (start at Ch.4 not Ch.1), editing pathway.

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What you get

  • 156-line SKILL.md, ready to drop into ~/.claude/skills/
  • Tested through 3 Karpathy-loop iterations (versions v1.0.0 → v1.3.0)
  • Triggers automatically when relevant — no command to remember
  • Lifetime updates as the skill is refined further

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