Jon Udell: Instant Outlining, Instant Gratification

April 1, 2002

Jon Udell

UserLand Software has sent up a volley of fireworks this year. January brought Radio UserLand 8.0, the subject of last month's column. Late February was the target date for Radio Community Server (RCS), an add-on that transforms an instance of Radio into the same kind of community server as Radio.Weblogs.Com.

That means an RCS can broker the files upstreamed by Radio bloggers, and serve as a hub for recent updates, rankings, and referral logs. It's designed for private use, typically behind a firewall, and aims to support intranet or extranet collaboration. RCS slipped into early March, but when it did arrive nobody complained. The price, which had been rumored to be up to $1000, turned out to be $0.

Then in late March, while Radioheads were still busily absorbing the implications of the RCS release, UserLand's Dave Winer dropped the other shoe: instant outlining. There will be much debate in coming weeks about what this technology is, and what it means. Here I'll simply offer first impressions, based on a few days' worth of experimentation with what is still, as I write this column, a rough but functional beta release.

The roots of instant outlining go way back to the 1980s. The history of Winer's outlining software -- including ThinkTank, the first outliner I ran on my original IBM PC, and MORE -- can be relived at

Today, most of us probably don't consider ourselves to be users of outliners. In fact we are, in the sense that the ubiquitous tree control is the major tool we use to organize folders and files in our operating-system shells, and in most applications. That metaphor sometimes percolates down into the documents we write and edit -- some people, for example, make use of Microsoft Word's outliner -- but I think it's fair to say that structured editing is the exception rather than the rule. Certainly that's true for the application through which the vast majority of our keystrokes flow, namely email.

Given Winer's roots, it's no surprise that outlining is deeply wired into the scripting engine and Web-publishing system at the heart of Radio UserLand. In that environment, developers have always used an outliner to manage the object database, to write code, and to produce content. Last fall at UserLand, the core development team began to use the outliner in another way: to communicate and collaborate. This instant outlining technique, now becoming available to Radio users, blends instant messaging, outlining, and blogging to create a new synthesis that Winer claims (and I hope) is a way out of the email hole we've dug ourselves into.

In my book and elsewhere, I've cited a litany of email woes, which I would sum up in a single phrase: email is not a context-preserving medium. Life is just too short to waste time looking for missing attachments, or trying to remember who was cc'd on which part of a discussion, or organizing inboxes by project, role, and priority.

Instant outlining is not a solution to these problems. No technology, in and of itself, is a magic wand we can use to wave them away. But instant outlining is, perhaps, an environment within which we can finally begin to make some headway.

A First Look at Instant Outlining

In this picture, you can see my buddies list displayed in Radio's outliner.

Buddies List
An outliner-based IM buddies list

These are people who maintain outlines, in the form of Outline Processor Markup Language (OPML) files (1, 2, 3, 4), to which I am subscribing. Some of them also subscribe to my outline, but not necessarily all of them, and this is one of the really interesting twists on email. Communication in this environment is by invitation only, and two-way communication requires mutual invitation. Sayonara to spam. If someone annoys you, just drop his or her feed. Conversely, if you annoy other people they can drop you. This social model is closely related to last month's notion of blogging as a conversation by mutual consent, subtly but crucially different from a discussion group or mailing list where it's much harder to filter out noise.

All the key elements of instant outlining are visible in this picture. When a buddy's name is bold, it means his or her outline has been updated and contains new information. Double-clicking the name opens the outline -- which is to say, fetches the OPML file from its canonical location, and renders it in the outliner.

Outlines are hierarchies of nodes containing text. Your own outline is editable; others are viewable and navigable. As an outline writer, you can assign two kinds of links to a node: normal Web hyperlinks and OPML links. The picture shows an example of each. The link labeled (1) is a hyperlink which, when clicked, opens in a browser.

The link labeled (2), which refers to an OPML file, does something new and exciting. It opens in situ, expanding within the current context of the outline. Transcluding content in this way is a long-overdue feature of the Web. What's especially stunning, though, is that the feature is here woven into an authoring tool that aims to replace email as the primary mode of communication in closely-knit collaborative teams.

Instant Outlining Netiquette

Winer and his team don't email one another any more, and they claim radical productivity gains as a result of the switch to instant outlining:

We've been using this tool since November, internally at UserLand. We shipped Radio 8 with it. When we switched over our workgroup productivity soared. All of a sudden people could narrate their work. Watch Jake as he reports his progress on the next project he does. We've gotten very formal about how we use it. I can't imagine an engineering project without this tool.

If you read their outlines, which you can do because this experiment is being done in full daylight (if you're not a Radio user, you might try these renderings rather than the raw OPML files), you'll get a sense of the conventions that are evolving in this new space. Here are some of them:

  • Blog-like journaling is the basic style.

  • The top level of each item is date-stamped, and preferably includes a short description.

  • Older entries are archived (an easy manual operation in the outliner).

There are subtler conventions that relate specifically to outlining as a way of organizing and communicating information. Outlines are context-preserving. When you save an outline in a certain state, that's the way it opens for your teammate. So it's good form to leave your outline in a state that establishes context not only for yourself, when you return to it, but also for the team with which you are sharing the outline.

This kind of subtlety both fascinates and worries me. It fascinates me because I spent years discovering and evangelizing these kinds of techniques for group attention management in another medium -- the email/NNTP hybrid that was the subject of my book.

In Radio's instant outlining I see even more powerful tools for doing the same things. There are also many things missing from this software, notably the unread-message-tracking and WYSIWYG-hypertext-authoring features that made Netscape Collabra so useful to me. But these omissions are all easily correctable if this kind of communication tool, unlike Collabra, becomes a hit. And that's what worries me.

When I turned in the first draft of my book, my editor, Tim O'Reilly, said: "This is great, but you ask too much from people." And he was right. I was advocating not just a communication tool, but a way of using it to optimize collaboration. That meant asking people to narrate their work, but also to think carefully about the attention demands they placed on their coworkers, and to label, structure, and layer their communications accordingly. Most people didn't want to do these things, and most people still don't.

What does all this portend for instant outlining? There's reason to hope. It's been clear to me for a long while that the only thing that might displace email would be some kind of persistent IM. That's exactly what instant outlining is. If it catches on, and it's buzz-worthy enough to do that, we'll have a framework within which to innovate in ways that email never allowed.

The key ingredients of that framework are structured storage (for content and metadata) and structured messaging (for data transmission, and publish/subscribe/presence notification). It's all XML, and really simple XML at that. The protocols and formats are open; they can and hopefully will be cloned. At first, it will seem that nothing has changed. A few highly-motivated people will find they can improve their collaboration in new and powerful ways; most will still tend toward ill-considered and unstructured communication. But perhaps in this medium we can finally bootstrap software that encourages and supports best practices. I'm keeping my fingers crossed.