Among my favorite types of computing applications has always been the organizer/checklist/outline kind of app. Back in my PDA days, the Palm apps Bonsai and ShadowPlan competed for my heart with each new update. When I got a Mac it came with a version of OmniOutliner which I loved a lot, but alas because it was one of those “came-with-the-Mac” things, as soon as I tried to install a new update it broke my fragile registered version, and I was pissed about it and refused to pay for it, so it was gone (I’m currently having that relationship with ComicLife).

The other problem I have with tasks in general is that the default Apple apps have a really stupid way of handling them, or at least stupid to me, growing up with Palm’s big four apps: Datebook, Contacts, To-Dos and Memo. Apple seems to hate to-dos and memos, so much so that after what seems like centuries in technological time, we may soon finally be seeing them sync between iCal, Mail and the iPhone. What, I ask, was the damn point of using them at all until now? First I stopped using tasks, because I could never get them to sync properly between iCal and my Treo. So I just wrote everything as a note. Now as an iPhone user my notes don’t sync with anything (???!!!!WTF??!!), and yet I still write everything as a note. Occasionally I will email that note to myself if I really need it in another format.

So of course I looked to the App Store to see what the third party developers had come up with that might serve as a basic tasks app. I honestly wanted a basic tasks app — a list and a bunch of giant checkboxes. I tried, I really did. But at the time the basic apps were either ugly, overpriced, or reported buggy and lacking basic features. Who knows, since there are no free trials. But the one that sounded the best to me was the most complicated of all — OmniFocus. At $20, it’s one of the more expensive apps in the App Store, but that was back in the day when an average game was $10, so it didn’t seem as expensive to me then as it might now when everything else is 99 cents.

Using OmniFocus brought some kind of order to my life. I use it sometimes for shopping lists, generally more of the long-term stuff, not like “what I need to get from Duane Reade in 3 hours,” which is usually a straight list. I write down things I want to work on with my computer, like reinstalling Parallels, which I forgot to do the last time I was home; and things I need to pack for the next leg of the tour, or what I hope to accomplish during my down time on the next load-in day. I also have a special project for fight call, which is really not what OmniFocus is designed to do, but I tried it anyway. With both Henry V and The Spy, we have a rather extensive fight call, running through distinct sections of fight choreography with different actors. There is a standard order which we have developed for that, and especially because we perform The Spy so infrequently, Nick and I needed a way to keep track of that order and make sure we’ve hit all the proper scenes. So I have a project for Fight Call and a sub-project for each show, and inside each are the actions representing each individual fight and the actors needed. I’m not sure exactly what app Nick uses for his list, but he has it on his Blackberry. This allows both of us to open our phones at the top of fight call and Nick runs the current fight while I can let the actors know who is up next and which scene it is, and make sure they have their weapons ready when it’s their turn. This is sort of a recurring checklist rather than a regular list of tasks, and the blending of the two types of lists is kind of weird to me, but I think OmniFocus can be made useful for things like this, or prop checklists, with a little work.

Anyway, I was very happy with my purchase. Of course it’s designed to sync with the desktop version of the app. That is, if you’re willing to pay $80(!!??!!WTF??!!) for it. It’s kind of all or nothing. There’s not a way to say “Gee I’d like to be able to see and edit my OmniFocus file on a desktop machine” without fully committing to using the software to run your life. I’m not sure exactly what happened to me, I think it was a conversation over drinks with a few of my colleagues about organization and task lists that led me to question if the fact that my technology has failed me, and is driving me closer and closer to having to etch my tasks on tablets, might someday result in me screwing something up. I’ve done OK with this seat-of-the-pants way I’ve been running my life and career with the occasional iCal appointment (with or without an alarm) to remind me to do things, or with a plain-text list in my iPhone’s notepad. But really, how far I have fallen since the days when there was a checklist for home and shopping, and work stuff was laid out in fancy outlines with multi-part projects and due dates and things!

So I decided — by way of writing an action in OmniFocus on my iPhone — that when I got a chance I would download the 14-day trial of OmniFocus desktop. I have been using it for about two days, and so far I am hooked. It’s got an even steeper learning curve than the iPhone version, but the larger screen in some ways makes the relationship between the different views and types of data clearer. I’ve also been watching some of the introductory videos on the website. After that, I discovered a great set of video podcasts called ScreenCastsOnline, which do in-depth screencasts of popular Mac apps. I’ve only watched a couple, but they have tons available that I want to see. They also offer podcast subscriptions in HD or iPhone-compatible sizes. I sense this will be a new favorite podcast of mine. You can get the links to either of these feeds on their website.

In all, I’ve been having fun trying to think of every little thing I need to accomplish and entering it into OmniFocus and categorizing it. I think I’ll be much more efficient using the desktop app since the majority of what I need to accomplish either requires me to be at my computer, or in an environment where my computer is out. This way, the iPhone app, which is a little more cumbersome to use due to the fact that it can’t run in the background, is only really needed when I’m out and about. More thoughts to come as this experiment goes on…

UPDATE: there is now an entire page of the site dedicated to OmniFocus tips!