9/2007 UPDATE: I’ve moved from OmniOutliner to flat text and will transition to TaskPaper as soon as it’s stable and a little more feature-complete. I beta tested the hell out of OmniFocus, but for me it was a very pretty, very interesting blind alley timesuck. I’m going to write an article about it, so keep in touch.

11/13 update: Links! Here’s Omnigroup’s official OmniOutliner page and MacDevCenter’s excellent article on extending OO. If you’re running Mac OS X 10.4, you might also want the OO Spotlight plug-in, which makes OO outlines available to Spotlight searches. And don’t forget to check out Kinkless, below!

10/6 update: I’ve just started using Kinkless, a package of AppleScripts and a template for using Getting Things Done with OmniOutliner Pro, and it’s really stepped up my game on the computer end of my system. I highly recommend trying it; the cautious can check out the demo movie [30mb] and Merlin’s review. Basically the advantage it gives you over a plain OO implementation of GTD is the way it keeps track of contexts, projects and next actions so that if you (for example) plug a new next action into a project and assign it a context, it will show up when you view things by context (at home, at work) and not just within your hierarchy for that project. It also generates a list of next actions for all your active projects and does a few other neat things. Now when I print my cards at night, I just go through the sidebar and print each individual pane as needed. Easy to intstall, easy to use, easy to customize and free - I love it! The only thing I can think of to improve at the moment is the condensation of the “sync” and “rebuild” buttons - I don’t quite understand the difference between them, and sometimes rebuilding is more through than syncing.

9/1 update: Whoa - Merlin linked to me and my traffic has been going crazy. Thanks to everyone who’s reading and leaving comments!

Getting Things Done
I’ve been using GTD for about a year. (Here’s Merlin Mann’s gentle introduction to GTD, if you haven’t heard of it.) I’m like 12% more efficient. But I’m 80% less worried about what I have to do, and that’s magic.

Tool Churn
I went through a lot of different tools in the first three months. Some I thought would be great, like my suspense file (a set of 43 folders you use to ‘mail things to your future,’ so to speak) didn’t work (although my mom lives by hers), and other things I thought would be marginal (like having an in-box) are fiery heat. Trying out lots of different cognitive toys is one of the pitfalls and pleasures of GTD, but the goal is to arrive at a place where your system is as unintrusive and close at hand as possible. I wore out

A Treo 600 (for keeping my lists; I still use it for other stuff, although I’m swapping it out for a Motorola Q as soon as possible)

VoodooPad (I love wikis, but not for notes)

DEVONThink (kind of amazing but I couldn’t make it work)

A pocket-size Moleskine

Backpack (Very promising but the fact is I’m just not plugged in all the time and I hate paying for shit monthly. I have a dream of a location-based web reminder service, but that’s a whole other post. Update: I wrote up my idea - take a look. Update update: such a thing exists! Check out Geominder. I’m going to try it out and write a post about it.)

Cardboard boxes

and finally settled on

A filing cabinet

An in-box

A large Moleskine (I don’t have a fetish for these things, but I’m okay with the price/quality ratio and the pocket is great.)

A cheap digital voice recorder. (A Sony ICD-B200, bog-simple, $60 at Amazon or Radio Shack.)

A cork board for tacking stuff up

and a Hipster PDA that syncs to OmniOutliner.

You’re so cheesy, Litwack
When I say ’syncing to paper’ I mean yes, printing lists on index cards. But seriously: I love outliners, and OmniOutliner in particular. And I got this Treo, and I decided to figure out a way to make it work with OO. And it’s obvious: export your lists to OPML, and then get an OPML-capable Palm outliner, like Natara Bonsai. The problem is, that took five minutes every time I wanted to do it, and I’m lazy, so I’d wind up with outdated lists on my Palm, which was my go-to device, and that was horrible. You have to be able to trust your system. So I switched to using Palm Desktop’s built-in To-Do List module, which at least would sync with a button-push. Then the issue was that Palm Desktop For Mac is basically still Now Up To Date 1.2 or whatever and the To-Do list module was ultra-limiting compared to OmniOutliner, so I wound up still keeping lists in OO and then making sure they matched up to my Palm To-Do list by hand. This was a huge waste of time, and it put six feet between me and my work.

So at just about that chronological moment, computer nerds started carrying around paper index cards and writing on them by hand and talking shit about how they were bolting their old PDAs to their Linux boxes and using them as external CPU performance monitors because fuck it, they didn’t need them anymore. And if the serious nerds can do it, I thought I’d give it a try. And lo, it worked and was excelente, as David Martell used to say on television.

It looks like this
I print my next actions on a white card, my active projects on a white card, put a blank white card behind that for notes, print my book list on a blue (cool == incubate) card, my media list (music, movies, comics, video games) on a blue card, and a boxy calendar for the month I’m in on a blue card. The last card is a GTD quick reference from A Million Monkeys Typing’s excellent HPDA package, which I look at when I do my weekly review. And I clip these cards together with a 1″ binder clip. I love this system. Every night I print virgin cards (not all the cards, usually just the next actions one) and rip up the old ones. So satisfying.

They look like this. Yes, the type is really tiny.

Technical bits

Make a custom 3×5″ index card size in Page Setup… with margins you like.

This is janky, but I copy the stuff I want to print out into a new OmniOutline. OO Pro supports page breaks, which would be a better way to do it.

Select Print, then pull down Paper Handling… and choose your custom index card size.

Feed your printer an index card. I couldn’t do the small type without my HP LaserJet 1200, though.

That’s it. There’s an excellent article on the 43folders wiki about implementing GTD workflow with OmniOutliner, but that method for whatever reason is antithetical to the way I work. NOT A CRITICISM! Different strokes for different etc.

You’re one of those nerds. You’re embarassing me.
Yeah.

Things about GTD I try to keep in front of me
When you read David Allen’s book, and you totally should, there’s a lot of information in there, and some of it is more important than others. Like, some things should be in 90 point bold type that wraps and what kind of pen to use or whatever is beside the point. This is why the book needs to be revised, and I’m sure it will be. Anyway, my bold-90 things are as follows.

The power of Greyskull is the power of the next action. The next physical action. Writing “sit down at computer, open Pages, and read the first paragraph of Moon College” is a million times less natural than writing “Edit Moon College” but when I read it I’m much less likely to immediately shove it toward the back of my brain and read I Love Everything for an hour instead. This is because I’m retarded, but you have to work with what you have.

Have more than one next action for a given project, if possible. For months I was a one project, one next action guy, but that’s crazy. Do things in parallel, not serial.

Contextual lists work. Mine are @home, @moleskine, @internet, @phone, @email, and @outdoors. So if I’m waiting at Napa Auto Express for my oil change, I don’t have to think about cleaning my toilet, which is on my @home list (or should be) and can make phone calls instead.

Don’t think about what you have to do, that’s what the system is for. Look at the system and decide what to do. This goes back to my 80% less worried thing - I don’t think about anything anymore, I just do what I can when I can.

Don’t think the same thing twice unless you enjoy that thought. I’m pretty sure David Allen wrote that one, and it’s true.

Capture everything. In order to keep thoughts that occur to me, I use OmniOutliner at the computer, my index cards when I’m out, my Moleskine when feeling contemplative, and the voice recorder by my bed when I’m half dead and something occurs to me, as it always does. Build a little redundancy into your system.

The weekly review makes for good next weeks.

Review your completed next actions. I never used to look back, but I do now for two reasons: it makes me feel good to briefly remind myself of what’s been accomplished, and I always think of new stuff that goes in the system.

The two best insights working GTD has provided me with this year
are: I don’t enjoy 80% of the things I do. That’s average, I think. But by reflecting on what I do at the end of the week, I’m able to get a better handle on what to do in the future. I don’t like to grocery shop, so I’ve gotten it down to an exact science over time - not because I’m a listmaking control freak, but because it’s easier the way I do it now. Conversely, I’ve better able to recognize the things that give me joy and I’m trying to amplify them without breaking the spell. I think GTD increases awareness of what you’re doing with your time.

The other thing I always tell myself is: iterate. For most things, throwing yourself at the wall over and over is a better way to improve than thinking hard about the wall and taking pictures of it. I’m sensitive to criticism and failure, so this has been quite a lesson to learn, but I think I’ve got it now.