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Source: https://writers.stackexchange.com/a/5140
License name: CC BY-SA 3.0
License URL: https://creativecommons.org/licenses/by-sa/3.0/

I tend to write outlines using emacs and org-mode, because I do technical research that involves a lot of programming, and as a result, I live in emacs. [Aquamacs](http://aquamacs.org/) is an emacs port for OS X that's free and has a nice Mac interface you can use instead of many of the Unix-based keyboard shortcuts. Aquamacs comes with [org-mode](http://orgmode.org/), which is a nice text-based format for outlining and text-folding (so you can hide various parts of your outline). What I like about text-based formats is that it's easy to determine exactly what changes have been made between revisions (hell, if you want to track versions, use a version control system like Mercurial, Git, Subversion, etc.).

The advantages are that it's free, and highly customizable (up to a point). The outlines are exportable to a number of different formats.

The disadvantages are that the workflow tends to be designed for people who are programmers, and work in emacs. There's not much of a GUI to speak of, beyond the toolbar at the top of the screen (and each window). Emacs is written to be a highly flexible text editor, and org-mode is a plug-in; it's not designed to be something like Scrivener, which, as far as I can tell, bundles together all of the tools that they think writers need (and in a cool-looking way). If you want something to keep track of your sources or research, you'd need another program (like Mendeley, for instance, which does a pretty good job of acting as a database for PDFs and media). If you want version control, you need another tool for that. I don't know of anything that corresponds to the "corkboard" functionality. So if you want extra functionality, you need other programs to fill in the gaps.

Original score: 1