For a lot of my career, I was only really given the “what” of my work. This needs doing, someone has to do it, and that person could be you.

The “when” of work can be really contentious. I had a music professor who said that amazing things happen around deadlines. I wish it weren’t so, but this is true. A lot of my projects that never got finished (or never got finished getting started) simply didn’t have deadlines, so I continue to this day to delay them. (On the other hand, I trust in my ability to work without deadlines, even with evidence to the contrary piling up.)

A better motivator for me is “why”. Help me understand why this action is necessary. Knowing your place in a larger process is hugely motivating: you’re not just working to get the job done, you’re supporting a system of people and plans that (maybe indirectly, but maybe directly) rely on you.

GTD tries to wean you off of “when”. You do it when you can, when you have energy, when you’re where you need to be, and whenever you get a chance. But one thing GTD reinforces is “who”: mostly, it’s you, but if you’re not the best person to handle it, you have to delegate. (Sometimes “who” comes down to “not me”: just saying “no” is kind of delegating, and it’s super important.)

Working from home on two days a week has brought a sharp focus on the “where” of work. I feel very limited by the things I can’t do on Tuesday and Wednesday afternoons, but I suppose we all have to deal with people who don’t share our schedules or our office spaces. The “where” of work changes more than all these others every day.

The reason I’m writing all this, though, is the “how” of work. I have new responsibilities, and I am feeling terribly under-supported. I have questions that only experts in my field could probably answer, and my team doesn’t reach out to help me. I am trying to get up to speed with books, forums, and training, but I still am not sure how to do a lot of the things that I know the “what”, “where”, and “why” of.

Beyond that, there are things that I really do know how to do, and work comes to me with a “when” and “how” attached. There is no quicker way to make a smart person feel micromanaged than to tell them exactly how to get their work done. I wish I could find a balance across my domains right now: some days I am completely lost on the road, and other days I’m insulted by the map I’m handed.

Wow, the internet is lousy with halfway-there GTD apps. It’s disappointing, because as much as you can do this whole thing with paper and pencil, it lends itself supremely to the digital world.

First things first: chop off the parts of GTD that won’t work better in the computer world. Ubiquitous capture just can’t happen online, in a desktop app, because you aren’t always there. (If you are close to always there, then you are close to ubiquitous capture, which isn’t ubiquitous at all.) So throw that out. Higher-level reviews are really about life planning and not losing what you considered life-focusing or important at any day or time, so I guess some sort of master list of that stuff could go in there, but you’d really want it journaled, wouldn’t you?

It leaves a to-do list. Really, really amazing to-do lists are trying to pass themselves off as “GTD solutions”, and I’m not buying it. The key to the GTD to-do list is that it has to be multi-dimensional.

Basically, all the tasks have to have a matrix of optional attributes, including:

• project
• context
• topic (high-level project)
• time estimated
• deadline
• urgency
• importance

Some of these dimensions are actually multi-dimensional themselves, like a project tied to two life-goals or a task that can be completed in any of a few contexts. The kids today love organizing that by “tags”, because it’s a freeform way to describe your stuff, but the open-ended tagging systems I’ve used (in stikkit, rememberthemilk, and others) are simply too open-ended. It’s great to be able to describe your tasks in these ways, but you can’t stop there. I haven’t seen in any system a way to pull the tasks that are lacking a context, for example, or the ones that don’t have time estimates, or ones for which the deadline is in the next 7 days, or whatever.

If you think about it, this is the exact same kind of filtering that iTunes does. I think the optimal solution is something along those lines: enter a ton of tasks, projects and ideas (as simply as possible), and then slice and dice through those based on what attributes they need defined (to finish up the data entry) or already have. iTunes playlists can tell you what jazz tracks, four stars or higher, haven’t been listened to in the past four weeks. Address Book can tell you which contacts you have in Ohio with no home phone number defined. A GTD to-do list should offer just as simple filtering.

The best thing about this approach is that it’s not too difficult to set up (if the data entry is simple enough), maintain, or tweak. iTunes newcomers don’t have their custom playlists tweaked out into infinity, but those who do can share their playlist definitions with others. It’s simple and extensible.

The important part of this is getting out of the way of data entry, because “task definition, assign context, tie to project, set importance, enter deadline, estimate time” doesn’t work for everyone and/or every task.

Honestly, I think the problem is pretty simple, and is just being danced around / poorly understood by the people who are doing this work. I like ThinkingRock best so far, because it actually meets you halfway between “anything goes” data entry (because this kind of work really is creative) and a supportive structure. It doesn’t go tag-crazy (and it could, and it will, I’m sure), it doesn’t accommodate time estimates (which I find useful, just because I pick off 15 minute things more often than I plan half-day things), but it reflects what I understand about GTD better than any other solution (downloaded or home-brewed).

Did you ever know a person in school that was into the same kind of stuff you were into, but because that person was such an insufferable know-it-all, the stuff you had in common actually drove you apart? It’s like that with me and lifehacker.com. I should be a huge fan of the content (which is about cool useful tech stuff, as long as it’s about getting something else done, not just tech for tech’s sake), but there’s something about the tone over there that just drives me insane.

And so it goes for their year-end apps list. I would link to it, but so much of it is so good (the selections, I mean, not necessarily the writing), that I have to note some of it here.

1. Parallels. LH writes “THIS is the reason any on-the-fence switchers with cash for spendy Apple hardware and an affinity for that one Windows app will make the jump to a shiny new Mac.” She misspelled “available consumer credit”, but other than that, she’s got me pegged. I wouldn’t have even considered a Mac until Parallels came out. I don’t even use it that much (I run it on my XP box, actually, so that a very badly behaving networking app only takes down its virtual machine, instead of my whole system), but the fact that it’s there lets me explore Apple’s offerings with a safety net.
2. Google Reader. LH writes “My longtime love affair with Bloglines ended this year with a switch to Google’s new feed reader, and I’ve never looked back.” I look back kind of a lot, but I did ditch Bloglines for Google Reader. I don’t think you’d go wrong with either app: Bloglines offers single-use email addresses, has more “per-feed” options, but Google Reader seems to be up more often and has some more tools for tagging, sharing, etc.
3. Windows Vista. Ho boy. See what I’m saying?
4. Google Calendar. I am not a power calendar user. While I’m capturing more good stuff in my GTD system, and making better decisions about it all, I’m not honestly that busy. I find ways to fill the time, but very little has to be done at a certain time in my life. (At work, it’s a little different.) The point is that I can’t get myself involved in the calendar vs. calendar wars on the internet right now. Comments say that 30boxes integrates better with Flickr. Seriously? It’s a poorer calendar app if it doesn’t share photos? If you say so.
5. Hamachi. A free VPN solution that apparently works very nicely. I have been obsessing about VPN / SSH / tunneling for about a month now (I’m using WiFi at Caribou, and learning more about how you can leak plain text during a GMail / surfing session), so I’ll have to look into this. (But SSHing into a home server is working just fine for now.)
6. Campfire. If someone can sit down and explain Backpack, Basecamp, Tadalist, and Campfire to me, I’ll make them some brownies. The appeal of this stuff eludes me like owning a ferret. I am hoping there’s nothing very cool I’m missing out on, because “group chat in a browser with your coworkers” sounds like as much fun as catching your finger in a car door.
7. OpenDNS. I use this, but I am no longer sure why. It, uh, goes faster? It catches phishers (reactively, not proactively), but seriously. Maybe I was having nameserver problems with my ISP. Either way, it’s not a bad layer to throw between you and the real-deal internet.
8. Foxmarks. I can’t say either way. Bookmark syncing is a pretty hairy programming problem, but I think you’re better off throwing links into del.icio.us and hoping for the best. I just don’t sync anymore.

So yeah, overall - good list of apps that came out this year, and a couple I have to give a chance to.

The whole point of GTD, for me, is that each project might have a bunch of actions, but only one is Next. My todo list should only have the things that don’t have prerequisites: the prerequisites should be on the list instead of the dependent action.

I don’t care very much for contexts… I have to make pretty agile decisions about what I’m working on, and sometimes that’s calling for an oil change from work, or doing a report from home. The overhead of having to ignore things I can’t get done from my physical location is minor compared to the overhead of maintaining contexts and thinking about how they all apply all the time.

I also have two PCs I use a lot, and the system (which is in the computer, of course,) should be reflected from one to the other.

The combination of pyGTD and FolderShare is actually meeting my needs quite nicely.  The idea is that you fill a “projects” folder with Fitness.txt, WeddingAnniversary.txt, Housework.txt, and each one is full of tasks:

* Clean the gutters.
1. Borrow a ladder.
2. Start scrapin’.

And a Python script (really!) churns through them, parsing everything out and giving you a reasonable to-do list.

Awesome story: I found this app through some dumb list on Listible, and having found a few bugs (and a note on the author’s website from a year ago, saying he’d update the documentation), I wrote him an email.  He real quickly said that he hadn’t used his script in a while, since it didn’t work on multiple PCs, but that my FolderShare solution sounded interesting.  So he might update it, and I might have helped him!

Either way, I have been doing my daily and weekly reviews, getting back in charge of the actual urgent things and the dumb someday-maybe stuff, and pretty happy about it.  This week was so busy, good lists were about my only salvation.

(Since the author doesn’t explain how he handles contexts, I’ll tell you in a little bit how I handle them.  It’s not hard, it’s just a little hacky.)