Software is never really finished. It gets released, like the guy who broke into your house last year, helped himself to a couple of cameras and the good silver, and then was caught in the spiteful act of shaving all of your housepets when that time could obviously have been better spent making good his escape. You know what I mean? In software development as in the justice system, there’s a point where you acknowledge that you can’t keep this sorry example locked up forever and that at some point, you need to send it out into the population, for good or for evil.

It’s an ongoing process and the upshot is that every time a piece of software is upgraded, it’s a brand-new opportunity for the app to either make up for all of the slights, indignities, and injustices that it inflicted upon you with the previous edition. Or it can be such a grotesque parody of its former greatness that it obliterates every last feeling you had about the product and its publisher. And possibly Humanity in general.

A month or two ago, I downloaded a huge new upgrade to what was already one of my favourite pieces of software and as always, I launched it with a sense of excitement and trepidation. But ever since I first fired up the ideas-manager OmniOutliner Pro 3.0 from OmniGroup (, I’ve been doing the Happy Dance right in my seat.

Why, pray tell, aren’t outliner apps a much, much more prominent product category? Why does every Mac ship with a browser, a mail client, a contact manager, a movie editor, a Chess game… but no outliner? Why aren’t developers of outliners treated like deities, held subject to no law of God or Man? Are there any babies born since 1984 named “Outliner”? If you’re female, resemble either a slightly-more-intense Kate Winslet or a slightly-less-so Uma Thurman, would you be interested in meeting up with me the next time I visit London and remedying this sad situation? You may write me at [email protected]

Outliners are Nature’s most Perfect Food, and the Third Great Construct of digital documents. Computers made a great start with the Endlessly Scrolling Document. When you’re focused on the words, things like the beginnings and ends of pages are an artificial limitation. Next came the Spreadsheet, in which a document is gridded into an infinite landscape of cells, each with its own formatting and agenda, capable of becoming something as simple as a table of data or as complex as a way to calculate to a thousandth of a penny how much it’ll cost to settle lawsuits filed by an indeterminate number of people who’ve had both their thumbs pulled off, and whether it makes sense to just redesign that balky toaster and go ahead and announce a product recall.

An electronic outline is perfection. By its very nature, it makes sense out of information. Whether you’re plotting a novel or a scheme to invade Canada and somehow pin the blame on Greenland, an outliner allows you to simply let the ideas, facts, and concepts flow from your brain through your fingers and into a document, and then to slide them all around into hierarchies until their logical flow and order presents itself.

The best way to explain the benefit of Universal Outliner Suffrage is to describe the OmniOutliner documents that are currently open here on my PowerBook:
Notes I took during an hour-long phone briefing about a major new operating-system upgrade I obviously didn’t know what this guy was going to tell me until he said it, and the outline format allowed me to keep my notes in some sort of order so I could spot inconsistencies and ask coherent questions.

A list of topics for future newspaper columns Putting an idea into this outline is like putting a seed into the soil. I glance through it and I get another idea and I make it a subhead. Or I come across a Web site with exactly the information I need. I drag the proxy icon from Safari’s window and I drop it into a spot in the outline...blammo, it lands in there as a live link, headed by the Web page’s title.

Let’s stretch out legs a bit, and really give the app a workout. At the moment, I’m nearly done writing my big new book about Tiger (Mac OS X 10.4). The book started as a simple outline of chapters and sub-chapters. OmniOutliner also lets you define columns of added data. So as the project progressed, I added a column so that I could set the status of each chapter through a popup menu (To-Do, First Draft, Edited Draft, and so on). Then I added checkboxes so I could tick off which chapters were complete. Problematic chapters were flagged red.

When my editor emailed me yesterday to complain that I seemed to be missing a section from Chapter 17, I clicked into the outline, clicked a triangle to expand Chapter 17 into full view, and then I double-clicked on a file icon to open the chapter. By attaching the project files to the relevant bits of the outline, the book practically organizes and keeps track of itself.

The point is that the app is like Silly Putty. It becomes more or less whatever you want it to become. Part of this power is due to the fact that OmniOutliner 3 is a terrific outliner. But to be fair, most of it is a testament to just how flexible and powerful the basic concept of an electronic outline actually is. There are many, many reasons why Apple’s Newton MessagePad PDA, though gone from this earthly plane for lo these four years, remains one of the most brilliant PDAs ever shipped: it had a built-in outliner. The outliner gave the MessagePad purpose beyond mere function, and the absence of a similarly slick app for either Palm or PocketPC means that my PDA of choice these days is a pocket-sized notepad.

Needless to say, I love OmniOutliner and I think it’s worth every penny of its $70 price. But I dearly hope that that Apple does the same thing to OmniGroup that it did to the makers of the Watson internet search utility and the Confabulator JavaScript/CSS widget architecture: namely, put ‘em completely out of business by coldly incorporating something damned-near identical into the Mac OS.

After all, good ideas are worth stealing. But great ideas are worth stealing and then giving away to all of your users. MW