The Perils of Org

The problem I keep running into with org is that I really don't prefer to work in org-mode. [1] Org is great and very flexible, but I don't like that it means that all text-based work is dependent on emacs. My brain is already wired for Markdown and reStructured Text from years of blogging and work projects respectively.

And then there's this organization problem. There are two ways you can organize content in org-mode. The first is to just dump every thing in one org-mode file and use the hierarchical outlining to impose organization to organize everything. The second is to have every project inside of it's own file and use outlining incidentally as the project needs it. Content aggregation happens in the agenda.

The problem with the "large files" approach is that you end up with a small handful of files with thousands of lines and imposing useful organization is difficult (too many levels and things get buried; not enough and inevitably your headings aren't descriptive enough and you get confused. Furthermore, I end up living in clone-indirect-buffer-other-window'd and org-narrow-to-subtree'd buffers, which is operationally the same as having multiple files it just takes longer to set up.

The problem with the other approach, having lots of different files, is that I have a hard time remembering what is in each file, or in logically splitting big projects into multiple files. The agenda does help with this, but the truth is that the kinds of org-headings for organization and tasks are not always the same kinds of headings that make sense for the project itself. I often need more tasks than organizational divides in a project. I tried this approach a couple of times, and ended up with useless mush in my files.

Typically, I can never make the "lots of file approach" really work, and the big files problem lead me to general avoidance of everything. Not good. The key to success here is good aggregation tools.

Hodgepodge

In response, I've made a couple of tweaks to how I'm doing... pretty much everything. That is:

• I've moved most of my open projects into a locally ruining and compiling ikiwiki instance. Both laptops have this setup, and there's a central remote to keep both (all?) machines in sync.
• I'm using ikiwiki tasklist to basically replicate the functions of org-agenda. Basically this crawls the entire wiki looking for lines that begin with certain keywords and generates a "todo" page based on these notes. Really simple, incredibly useful and it solves much of my aggregation needs.
• I still have some stuff in org-mode: notes for the nearly-finished novel, lots of random old (legacy) data, 12 various open tasks, and org-capture. I'm thinking of pointing various org-capture templates at files in the wiki but haven't gotten there yet.
• I've basically taken the "lots of little files," approach to my writing and work. I've not over-leaded the system yet. Each major project gets a page in the root level of the wiki for overview and planing, and then sub-pages for all related project files (if/as needed)
• It turns out that the markdown-mode for emacs has gotten a few improvements since the last time I downloaded the file, including better support for wiki-links that are mostly compatible with ikiwiki. Also from the same developer deft which implements a pretty nifty incremental search for text files in a given directory. So between these tools, ikiwiki, and the ikiwiki-tasklist there's support for the most important things.
• In terms of publishing, beyond ikiwiki for tychoish.com and the personal organization instance, I have a couple of other smaller wikis (also ikiwiki powered,) and I've been playing with Sphinx as publishing for more structured documents and resources (i.e. documentation, novels, and collections,) particularly those that need multiple formats and presentations.

I'm sure there will be more shifts in the future, I'm sure. I think this is a good start. Thoughts?