This afternoon, I sat down to work out the structure of a big document that a co-worker and I are supposed to produce for this internship we're doing. When I sat down to work on it, I was pretty confused about what we were trying to do. After two hours with OmniOutliner, I am no longer confused. I feel pretty on top of this thing.

OmniOutliner is one of the coolest little pieces of software I own. It's become completely indispensible to all my non-fiction writing projects. The funny thing is, it's difficult to explain why it's so cool. Basically, you can make hierarchical lists with it. It'll put checkboxes next to things so you can turn your outline into a to-do list. You can format the text any way you want, or color code pieces of your outline. You can add multiple columns: if you add a column for who's responsible for a given task and one for expected duration, you've got yourself a pretty nifty little project tracker.

Still, none of this really explains why OmniOutliner so quickly won a place in my working method. I'd never been much of an outliner before. The problem with most outlines, whether hand-written on paper, or typed in Microsoft Word, is that they're too static. The outline format tends to impose a structure on you, but the whole reason why you outline is to figure out the structure in the first place! But in OmniOutliner, it's easy to move elements up and down in the hierarchy or to a new spot within a given level of the hierarchy. Mostly, you just drag and drop. So, it's a piece of cake to move from an unstructured brainstormed list of ideas to a fully structured outline, and you never have to scrap what you've already done and start over.

My only complaint about OmniOutliner is that it is only available for Mac OS X. It would be a wonderful tool for collaborative projects, but all too often I find myself working with users of less enlightened operating systems. There is a bit of a work around: OmniOutliner will import and export plain text files with tab stops. I can open these text files in Microsoft Word, use Autoformat to turn them into Word outlines, and then use Word's Styles to make them look pretty again. And then I can share them with just about anyone. But then they don't get to take advantage of all of OmniOutliner's cool editing features.

I've even experimented with using OmniOutliner in my fiction writing. It hasn't been quite as indispensible there. I still don't really outline fiction, at least at the first draft stage. I do sometimes use OmniOutliner for tracking revisions.

Anyway, if any of my readers out there are Mac OS X users, I recommend checking out OmniOutliner. You can download a demo (see the link above) that will allow you to make outlines with fewer than 20 items. A full license is about $30, and if you qualify for an educational discount, it's $20. Best $20 I've spent on software in a long time.