Diving head first into GTD with OmniFocus

I think it’s safe to say that Things and OmniFocus are the top two GTD task manager dawgs in the field right now. And yeah, I know – Things is the shizzle right now and the application looks pretty darn fine. I spent a lot of time over the past week looking at both applications, giving them a little initial test run, etc. before finally settling on OmniFocus.

Two reasons finally swayed me to OmniFocus:

1. Right now, out of the box, it syncs between multiple Macs and the iPhone. (Things doesn’t – although that’s coming in the future)
2. I know some of the Omni guys and I think they do some darn nice stuff – I feel good about supporting folks who’s office is just within a couple of miles of my house.

Diving in headfirst, I got both the desktop and iphone versions of the app. Getting started with OmniFocus is, well, heady. There’s a lot in there, and a fair bit to learn. I was jones’n for the simpler “just tag the thing” structure of things for a bit, but I’m coming into sync with the OmniFocus way and getting some goodness from it. Since it caused me some gnashing of teeth to start, I thought I’d share what I’ve learned.

The two primary ways of looking at your work in OmniFocus is by project and by context. They’re orthogonal – so a given task can have a context and a project, and those don’t need to be related. The context setup flipped my trigger a couple of times, trying to get the sense of what they hell it was for. I’m not even sure that I’ve nailed it – but in my world, “context” in the OmniFocus set up is a description of the limiter to where you need to be or who you need to be working with to get something done. I’ve stripped out the default contexts and drained it down to “Office”, “Home”, “Online”, and a list of my team members.

The “Office” vs “Home” is really the differentiator for me. I’m online damn near all the time – but I kept that in the pile to keep it separate from contexts where I might be out somewhere and needing to get something done (like picking up groceries, in the classic setup of the app).

The “people as context” is my stab at dealing with follow-ups and tasks associated with the awesome team that I’m managing. The whole reason I decided to dive into GTD in a serious way was so that I had a handle on the sheer information volume load that was flowing through and around me – an order of magnitude greater than when I was just knocking stuff down by myself and mostly on my own recognizance. I’ve just started with the people as context setup – but so far it looks to be working OK. The question that I haven’t answered, and lies before me is do I want to track tasks that I’ve delegated to folks within my team in my OmniFocus task list. I may try it – but I fear that’s a slippery slope. I’m thinking that I’ll only really want to aim that towards when I need a follow-up or information back to do something else.

Projects are the other big deal in OmniFocus. I’ve got a ton of projects. I’ve also got them cascading down with folders (took a while to sync into that setup) and I’m using default contexts with those folders. So for something related to, oh, say one of those “Enterprise Software” systems I was tirading about yesterday – I make sure I have a pre-set context to “Office”. Any tasks I create under that project from there automatically get the “Office” context, which saves my fingers a few typings.

I also work between Mac and (sob) Windows. Nothin’ doin – it’s just the state of the world that I need to interact with both worlds constantly. I’ve also migrated my half-assed attempt at GTD with Outlook’s task manager (couldn’t keep a damn thing organized with that setup) fully into OmniFocus. So the trick is dealing with emails that come in from Outlook, asking for me to do something. I’ve taken advantage of the nifty Mail.app rules integration to enable me to forward email to a different inbox and that gets ingested into the world of OmniFocus. Works really well too – I just leave Mail running on the laptop and stuff gets crammed into my OmniFocus inbox for me to categorize and deal with at my next round of that (currently I’m doing that at the end of the day, cleaning up as it were).

I haven’t yet jumped in to reviewing my tasks and projects, but I’ve set up a repeating “to do” item (tickler, in GTD parlance) with OmniFocus to remind me to do just that. I also haven’t looked at the Calendar sync – at some point I may dive into that, but I haven’t so far.

Finally, Perspectives are the key to making OmniFocus really sing. You can set up one (or several) views into your world based on due dates, contexts, projects, etc. You can save a window’s view as a “Perspective” – and I’m making aggressive use of that setup. My only gripe there is that perspectives aren’t shared with the OmniFocus database – I had to set them up on each machine I was working with.

Finally – the iPhone app:

So far, it’s mostly a way for me to ingest tasks while I’m in a meeting. I can tap the task in there, and I feel a lot more confident that I won’t loose track of it. I generally just shove things into my Inbox from there, and at the end of the day I review all the stuff I need to get done, tasking it out further if needed and categorizing it from there. I tried to set up the location based context mappings, which seemed kinda nifty, but I ran into something unhappy there, and I’m working with Omni’s tech support to get that nailed down and straightened out. Not sure why – but it’s not ever returning a location to the application.

The sync, my key value and reason for choosing OmniFocus, is working great though. The end result is paying a bit more for the setup (desktop & iphone application), and I wish it would sync a bit faster than it does, but it DOES the sync and everything is being kept up to date.

As a final note to anyone reading this far – if you’re going to invest in the software to do GTD and you choose to do it with OmniFocus, take the time to watch the videos that they provide and spend a weekend getting used to the software. Also – like writing software – don’t be afraid to trash what you’ve done and rejigger the thing based on what you’ve learned to make it better for yourself.