Around 2003, 2004 I had a bit of a mild obsession with organizing my life into digital form, creating as many mappings as I could from my everyday existence into some kind of digital form. This of course included ideas and thoughts, writings and paintings, music and movies, friends and bits of information about those friends etc. This amass of data have gone from one disjointed medium to another (.txt files in folders, emails, blog posts, napkins) without ever really achieving any chohesiveness or real improvement in my ability to actually synthesize or act on all that information.
At that time the closest tool I found that could come close to mapping ideas and thoughts in a way that made sense to me was "TheBrain" a piece of software intended for visualizing information, and as importantly, the links between that information. As a user, you add "thoughts" to your brain which become nodes in a large graph of ideas, thoughts, attributes, urls etc. You can then very quickly build child, parent and sibling links between those nodes to add more context and information. Those links can then be categorized to add even more context to the relationship between ideas which is often very important information. Unlike a lot of "mind mapping" tools I've used though, the brain does not force you into a tree structure. Your thoughts can have multiple parents and siblings or "jumps" to thoughts anywhere else in your brain, whether they are directly related or not. Hyperlinks, imagine that! I think for the actual exercise of brainstorming and free flow thought this is critical. It also mimicks how I visualize my own thoughts working. I've since tried personal wiki's which give you a lot of the same flexibility but lack the very fast keyboard entry for connections and nodes and force you to think at the level "inside" the node, by editing the page. Whereas the brain allows you to think and work at the level of the topology, which is really effective.
I stopped using the software basically because of the overhead of attempting to keep the futile mapping exercise up to date. Imagine if every idea and thought you had needed to be compulsively cataloged manually into a program in order to keep the overall picture intact. It just doesn't work, at least not for me, and not for long and detracts from my overall goals. I found that every time I opened my brain there was just too much catchup work to do in order to get things synced up and in order.
The other thing that changed for me since 2004 has been search. Between Google and Spotlight on my mac I basically stopped categorizing information in the same ways I used to have to. It becomes less and less necessary to build nested categories of programs or emails or documents etc. Search has exposed the entire hierarchy in a glance, in many cases keeping the context intact that would have derived the categories. Still there is value in the information of that structure, but in a far less visible way.
Well I've resurrected the brain and am using it in a new way that seems to be actually working for me. For starters I don't keep any notes or real content in the brain, this is one of the clumsiest facets of the tool and almost seems like an afterthought. It really is all about the topology, which for me is fine since the bulk of what I need is often in dedicated stores (subversion, sharepoint, team foundation server) I've found any attempt to use the clumsy palettes and data entry forms to just be too cumbersome to bother with.
Focusing on the nodes and connections, and learning all the keyboard shortcuts have enabled me to use the brain in a way that is a lot like I sometimes use notepad when I need to brainstorm. Except rather than dashes, asterisks and plus-signs I'm using jumps, parents and children of small snippets of text. It's really a cool feeling being able to navigate this very large graph of interrelated concerns and ideas with very little effort. Wiki's and other hypertextual forms have served me well too, but never with so little impediment.
For high level thinking and free form brainstorming this tool is the best I've used. And provided I keep it to just the free flowing jumping and navigating it's incredibly useful.