Capture & Organize: Outlining a Book in Your Second Brain
Only start projects that are already 80% done. How to build a content database that makes book-writing feel like assembling LEGO bricks.
"The impediment to action advances action. What stands in the way becomes the way."
— Marcus Aurelius
"Be regular and orderly in your life, so that you may be violent and original in your work."
— Gustave Flaubert
The average author takes three years to write a book. In that time, Ryan Holiday didn't just write one; he wrote three. The last of these, The Obstacle Is the Way, not only claimed its place on the bestseller list but also captivated over 100,000 readers with the timeless philosophy of Stoicism.
How did he do it? It turns out that Holiday had a secret weapon: notecards.
Holiday carried 3 x 5 index cards everywhere, scribbling down ideas, quotes, and stories as he read and went about his daily life. This system was borrowed from his mentor, Robert Greene, the author behind mega-bestsellers like The 48 Laws of Power. Greene used notecards to capture source material from the vast array of books he consumed.
After amassing enough material for a full book, Holiday would sit down and rearrange the content at will—pulling from the treasure trove of material he had captured over time. This made the writing phase easy. With notecards in order, he could just fill in the gaps.
The 80% Rule
Note that Holiday didn't produce his books through laborious stints of unbroken "deep work" from an isolated cabin in the woods. Instead, he developed a system that allowed him to finish most of the work on his book before he ever started writing.
This aligns with a rule of thumb from Tiago Forte's Building a Second Brain:
"Only start projects that are already 80 percent done."
For our purposes: Only start writing a book that is already 80 percent written.
You don't need 80 percent of the content polished and arranged in its final form. You just need to have gathered most of the raw ideas and insights before committing to crafting your book's outline. You do so by capturing ideas over time so that the groundwork is laid well before the "official" beginning of the project.
Identifying Your Intermediate Packets
As with articles, writing a quality book with AI hinges on having source material. Audio transcripts are my favorite form to work with, but any of the following are fair game:
Pillar pieces: Podcasts, YouTube videos, and presentations
Micro-content: Twitter, Instagram, or LinkedIn posts
Newsletters/blogs: Both published and unpublished drafts
Voice memos: Notes on your phone
In Forte's framing, these all represent "intermediate packets"—smaller blocks of content that can be snapped together into larger structures like LEGO bricks.
Thinking in terms of intermediate packets reframes the process of writing a book from one that requires long uninterrupted blocks of forced effort to one where you can make consistent progress in short bursts.
Wherever you are starting, take stock. Write a list of everywhere your intermediate packets live.
Structuring Your Second Brain
Some people prefer the simplicity of an analog system like Ryan Holiday's box of notecards. Tiago Forte recommends creating a simple file directory on your hard drive.
My preferred "second brain" utilizes the versatility and convenience of a cloud-based workspace built within Notion. Notion allows me to create dashboards for each writing project, with customized content databases, dynamic outlines, and a host of AI features that save time when sifting through large volumes of information.
Whatever tool you choose, remember that building a second brain system is a personal endeavor. It's best to let your second brain emerge organically from sustained use, customizing a system to support your unique creative flow.
Organizing: The Two Levels of Book Outlining
With your content captured and assembled in a central database, you can get a better sense for the contours of your book. Now, your task is to organize your material into a broad-brushed outline.
The biggest difference between outlining an article and outlining a book arises from the volume of material involved. A database containing 50 to 100 podcast episodes can add up to over half a million words.
For books, unlike articles, there are two distinct phases of outlining:
Phase 1: The Macro-Outline (Table of Contents)
The overarching outline for the entire book—your broad chapter headers that support your book's central theme.
Phase 2: Chapter Outlines
Detailed outlines within each chapter, where the main point of each chapter shapes the flow of ideas.
At both levels, we're still applying the same progression:
Deconstruct source material into core ideas (Organize)
Identify the main idea ("The Point")
Reconstruct those ideas into a logical order (Distill)
Draft the text, one section at a time (Express)
Using AI to Suggest the Macro-Outline
When the overarching structure is unclear, you can use AI as a reasoning engine. Claude can handle an abundance of amorphous source material and propose a logical reorganization.
First, create AI summaries of every piece of content in your database. Then, copy and paste the titles along with summaries and keywords for all entries into Claude:
"I'm writing a book on [topic] for [audience]. Here are summaries and keywords from my source material. Please identify recurring themes and propose a logical chapter structure. Also suggest which content pieces fit best under each chapter."
This stage is an exercise in information architecture. We assemble raw material from our existing content to supply foundational blocks. Claude's capacities for pattern recognition help identify the weight-bearing walls to erect the overall structure.
As with writing articles, developing the macro-outline requires iterative feedback. Queries like "What's missing from this outline?" or "Does this re-ordering make sense?" can guide refinement.
The Goal
Whether you use Notion or notecards, you need a system to capture ideas that can later be organized into the foundations of a book. AI tools can accelerate the process compared to analog methods, but the important thing is that you have an easy, consistent way to jot down thoughts as they arise.
The goal is to make writing your book feel less like a marathon slog and more like snapping together the building blocks you've already created over time.
This post is adapted from "Commanding the Page" (2023).