I’m interested in what Dave Winer does. He’s been a part of innovations that are the foundation of the Internet. Sure, I don’t exactly agree with his view on comments, but I think he’s an amazing innovator and high on the list of people I’d love to sit down with in person. When he released a new tool, Little Outliner, I wanted to take my time to understand what it was, how easy I might learn to use it, what others might think of it and generally let the idea sink in. It’s important to let these things sink in when taking a look.

He’s clearly very fond of the idea of arranging text by way of some sort of structure. He’s already created a tool that does a similar sort of list-making called the OPML Editor. There many other examples of these kinds of tools, but on a larger level, the ideas of structured lists in various tools are not new at all. I recall using Lotus Notes to develop databases and the tool always forced you to represent items in a hierarchical list. Certainly, there are ways around that, but the structured list idea is all over the interface of Lotus Notes.

That structure is also similar to that of what you might see on a hard disk. It is top-level, and subordinate levels under that. The idea that you control everything from the text to the various levels makes this tool very powerful stuff like making lists.

After spending a few minutes with the tool, I was able to pick up the basics of how to create a top-level list, create sub-level items and then moved them around, edit them and delete. It all has a basic elegance to it and sort of forces you to stay organized. Enforcing those kinds of boundaries (For example Something either starts a list or is part of a list) keeps you thinking inside that structure. For someone who goes crazy for lists, this kind of tool is likely going to make them very happy.

The challenge, of course, is that most people aren’t natural list takers. At least I think that’s what I see in most people. I see countless people looking for ways to be organized for the sake of being organized. There are other cases where exposure to this tool will turn many people into list takers. Great. Many others will probably never grasp the idea of a directory structure; they endlessly hunt for that recently downloaded file in vain.

What is the best application on a computer for making lists or basic outlines? It is, definitely, notepad or any other text editor. It is the combination of zero barriers (installed on every device), zero learning curve (if you can write) and accelerated speed (notepad is probably the fastest process to load). That first one is important because often I want to grab some text or make a quick list and nothing is really as fast as a basic text file.

In fact, I make outlines every day. When I work, reports describe what was done on-site and these reports are done using the method of zero barriers. I generally write this out in text inside my calendar. In the past, I’ve written these reports on all sorts of devices and places (at one time I used Alfresco and a Blackberry).  Just the idea of using characters or indents to create bullet points is the simplest way to outline.

My reports look like this:

If I were to do the above in Little Outliner, I end up with this:

That’s pretty, isn’t it? Certainly, one of the major benefits of using Little Outliner is how nicely things are laid out. In addition, I can collapse the levels, if I just wish to only show each report’s date. For this kind of data, that may make sense, though, for other types of data, this organization makes no sense. I don’t see how, for example, creating a hierarchy of paragraphs that make a blog makes any real sense, but that’s my perspective.

The question I have is generally what is the “big picture” for a tool like this? Winer says that he’s not making blogging tools, but it’s clear that this tool can be used for blogging. I’m sure if this tool were to become a standard for writing blogs, that Dave Winer would take it. I can see this turning into a universal tool for connecting to various services in the cloud that lend themselves to using outlines.