Rewrite Planning

I’ve been doing a lot of “planning” ever since I decided to rewrite my book from scratch. This planning falls into these broad development categories:

  • Characters
  • Themes
  • Plots

I also have a large number of “notes” that I take throughout the day, either audio voice notes, written notes, emails, or bits I tell Siri or Alexa to remind me about. All of this data can be quite overwhelming so I’ve been working on ways to bring order to chaos.


I use Ulysses for all of my writing. I use it for many reasons:

  • It’s well-written
  • It works on Mac and iOS and seamlessly synchronizes via iCloud
  • I like the easy and future-proof open format used for writing, Markdown
  • It allows me to organize all of my projects in a hierarchical manner
  • The “sheet” mechanism and the way collections of sheets can be grouped in the hierarchy and “glued” together offers me a lot of organizational flexibility

So, all of my ideas eventually funnel down into Ulysses. The voice notes I take are reviewed and typed out and sometimes hilarious especially when I am drunk or high or both. The e-mails I send myself from work with some game-changing idea are pasted into my notes sheet periodically. But then it comes time to tease it all into a structure. When I wait too long, the number of ideas can accumulate and be daunting to reason through.

To begin, I start to organize these ideas into broad themes and categories. When I ‘m done, I have a list of themes/categories and the associated notes organized beneath each.

The number of notes can still be a lot so I like to go through a reduction phase where I remove redundancy and draw out the more important ideas and simplify or outright remove the less important ideas. This is easier once the notes are organized into themes.

Mac OS Mechanics

I use MacOS for all of my work so I do my best to take advantage of any organizational features it offers. Here are some of my favorites:

Command-` (backtick) allows you to switch between different windows in the same application. I use this when I have two “windows” open in Ulysses. To switch between two different applications, you’d use Command-tab.

You can also tile the windows, which is useful when I’m transferring notes directly into my outline. For this I use a cheap and well-written utility called Magnet since it expands on some of the basic window layout commands built into the Mac. On Windows, you can dock a window using Windows+arrow keys, but the Mac doesn’t have that exact behavior built-in.

Lots more keyboard shortcuts here.

I am back-posting this post since I wrote it a while ago and have already started writing!