Many GTD-type software programs allow users to assign a priority to a to-do item. Gorsline argues (persuasively, in my opinion) that hard-assigning a priority to individual tasks doesn’t take into account the reality of how we engage with the things we do – or at least how GTD assumes we do.

Now, of course, we prioritize how we’re going to complete our tasks. But Gorsline writes that, at any given moment, our priorities will be determined by the context in which we find ourselves (am I at my computer? am I on the phone? am I at work?) – something that GTD asks you to determine as you create each task; the time available to you at any given moment; and your level of energy at the moment. Are you too tired to make the phone calls now? Better that they wait until you can give them the attention that they require.

Our priorities are constantly changing based on how this matrix interacts with our current situation. Assigning priorities to tasks means you’re likely to spend a lot of time shuffling the deck, changing your priority codes, when you could be getting real work done.

This article won’t end the debate over priority by any means, but it’s one of the best defenses for GTD’s more fluid approach to priority.

From my experience, this works better for me than hard-assigning a priority to each task. I find that after I’ve made it a “1″ or “2″ priority item, I tend to ignore priority… and, on-the-fly, I do the things I’m able to do at a given moment (context) or have the energy to do. The official priority that I’ve attached to an item becomes meaningless, essentially.

Now, what is still meaningful to me is when the task has to be completed. That’s something concrete. I realize that due dates are questionable in true GTD, but all bibles are open to some interpretation. The reality of my work environment is that some tasks can be completed soon, and some must be completed by a certain date.

Fake Due Dates

Interestingly, I’ve discovered over time that I have a strange habit of arbitrarily assigning due dates to some tasks, not because they must be completed by then, but because I think they might be or should be. This undermines the trust in my system and adds an unnecessary psychic burden, as tasks without a concrete due date begin to pile up in the “overdue” column. That aint good. The reason I haven’t completed those tasks is because I haven’t had the time or energy to do them. Making them artificially overdue is like being punished for something that’s not my fault.

That was an important insight for me, enough to make me open my task list and remove due dates from every task that doesn’t explicitly require one. I feel a lot better already.

Todd’s Six Workflow Requirements

Your list may differ.

• * Syncing to-do lists
• * Syncing calendars, contacts, mail
• * Document access
• * Notes
• * Voice recording
• * Cross-platform blogging workflow

To-do

I need easy, ubiquitous capture to make my to do list effective and trustworthy, but I also need immediate access to the full list. I use Remember the Milk to capture long-range thinking (the “Someday/Maybe” stuff in GTD parlance) and Omnifocus for managing day-to-day lists and projects.

RTM is web-based and I have all kinds of ways to get stuff on the list. I can email tasks to the list, send them via IM or Twitter, enter them directly on the phone, configure a browser bookmark to popup, etc. RTM has excellent functionality and it’s easy to use. Since it’s web-based, there’s no need for syncing; your modifications show up everywhere immediately. If you use RTM in Firefox, you can take advantage of Gears technology to get offline access to all your lists.

Omnifocus has been a favorite of mine since it was in alpha release. It’s a thoughtful implementation of GTD and it’s packed with capabilities. The software is somewhat opaque, however, and it loses a point or two on usability. There are fewer open doors into the device, but the ones that matter to me are available: I can email tasks into the system, and with the launch of iPhone’s 2.0 software, Omnifocus introduced an excellent app that syncs to the desktop using either MobileMe or WebDAV.

I feel more tightly connected to my to do list than ever, and fun perks like Omnifocus’s ability to use GPS to remind you of tasks that you can complete nearby, add to its indispensability.

Calendars, contacts, mail

Do I need to say much about this? Probably not. I have Gmail and MobileMe accounts; I can work with my mail on all web-connected devices, and both accounts play nicely with Apple Mail, thanks to IMAP. Contacts sync across devices with MobileMe, and my calendars are a web of syncing: basically, MobileMe and SpanningSync ensure that any change made to any calendar gets expressed everywhere, from iPhone to iCal to GCal.

Contacts and Calendar data also port to my Windows desktop at work, and here, your syncing method depends on your platform. GCal can sync with Outlook’s calendar with Google Calendar Sync; MobileMe has a Windows client that pushes contacts and calendar data to Outlook, too.

Document access

This is even easier – choose your preferred puffy cloud and go for it. I use a few: Google Docs for things I’m doing at work, particularly for stuff I want to share with others. MobileMe’s iDisk lets me put all of my personal documents in the cloud and keep a synced local copy on my MacBook Pro; they’re also accessible on my Windows desktop and my phone. I’m also a big fan of Zoho Writer, and I’ve used Writewith and Buzzword with good results. Zoho and Google Docs have good iPhone interfaces, which will help keep you sane if you want to review a document using your phone.

Notes

One of the most annoying things about the iPhone is the land-locked nature of notes on the device. Yes, you can email them to yourself, but that’s not a way to maintain notes that are synced across devices. Into this gap steps Evernote, which brings its strengths as a note-taker and capture tool to the iPhone.

Evernote’s first appearance on the phone was as a web-app, which allowed little more than access to notes that one had already stored in the system. (Evernote allows one to capture notes, sync them securely to Evernote’s servers, and make them available on other computers, or even make them public.) Since then, Evernote has evolved into a full-featured app for the iPhone. You can create new notes, edit them, sync them with the server, and access or edit them on your other computers, using either Evernote software, or Evernote’s web interface.

It’s free, but Evernote limits the amount of content you can upload each month. If you upload a large number of notes, you can buy additional space, too. I keep notes for work and home, all of my receipts, pictures of business cards I receive (Evernote’s software can recognize text in photos and make it searchable), and scraps of code… and I come nowhere near to maxing out my free account. (I you upload lots of photos into Evernote, you’ll want the paid account.)

Voice recording

Sometimes, it’s easier to record yourself a reminder than take the time to transcribe it. Jott is a service I use constantly to record small bits of information, which then get transcribed by a nice person somewhere and sent to me via email or sms. Jott also lets you set reminders. The Omnifocus iPhone app lets you attach voice recordings to tasks for those times when your task is a detailed plan for taking over the planet. There are also several iPhone apps devoted to recording memos or complete meetings and lectures. I use QuickVoice for recording items that aren’t task-related. Recorded to-do list items move through the Omnifocus system as attachments to tasks. If, six months ago, you’d told me I’d be using voice memos as a task input mechanism, I’d have said you’re crazy. But it works for me.

Cross-platform blogging workflow

I’m not going to pretend that I enjoy long-form blogging on my iPhone. I like the keyboard, but not that much. Chuck, on the other hand, uses the iPhone WordPress app to write short posts and edit his blog. It works for him. I don’t mind writing short posts in that format, but mainly my blogging workflow depends on MarsEdit, where I can publish posts to a number of blogs, work offline, edit existing posts, etc. I also edit draft posts on my phone.

As for microblogging, I use Hahlo and Twitterific on my iPhone.

Will I always use both Google and MobileMe apps? Probably. As long as they sync to each other easily, I don’t think there’s any reason not to. I like knowing there’s some redundancy, just as I like knowing that when I’m offline, I have local copies of everything. Thus far, I’ve been a very lucky MobileMe user, with about 6 hours total downtime that I’ve noticed since the first days of the launch of the service. Everything has worked almost without a hiccup. (Others haven’t been so lucky.) Should my luck run out, I have something to fall back on.

I think I may still write something about it – perhaps while flying on Wednesday – but probably as part of something that more broadly assesses GTD workflow, which shifts as often as the sands, don’t you know.

My own view of Chandler is a mix of most of the above – it’s interesting to me because it’s ambitious, but other times the ambition seems like overreach, and the longer I live in the Mac world, the higher my expectations are about concepts like beautiful software design, marriage of form and function, and flawless performance. (I use WIndows XP at work and that’s fine; I’m not a hater.)

And let’s just say it: in this day and age, fundamental activities like email, document creation, calendars, and contacts must work and sync seamlessly across every platform, whether multiple desktops and notebooks, or to your handheld device. In this reality, software like Chandler or 99% of all those to-do list programs in the iPhone apps store that don’t offer seamless transfer are dead in the water with web workers. I’ve got a killer flow going on, from iPhone to MacBookPro to, yes, Windows desktop at work, and I hesitate to introduce a deaf-mute application into this connected, multi-lingual world.

What was that about vacation?

Chuck and I are going to San Francisco on Wednesday, transporting a couple of 30 year old bottles of wine with which to toast our friends, Michael and Bob, who are getting married. I’m still so surprised that this is actually possible. I mean, I was born and raised in the US; I understand that the concept of equality is designed to be available to some in this country. I just never expected it to be available to Michael and Bob… or to us. Well, one step at a time.

Our weekend includes a long-anticipated dinner at The French Laundry, and three days in Napa at Calistoga Ranch, guests of our friends. I expect to twitter about it, Brightkite it, Loopt it, Friendfeed it.

Heck, kind of makes writing a big blog post about it seem downright old-fashioned.

I still have a shortlist of extensions that won’t work with FF3, but this was the big one; for a while now, I’ve been working with FF2 and FF3, reserving FF2 for travel so I could use the offline functionality of Gears. Now, I can “offline” using FF3.

I’ve written more about my LIKE for Gears here.

Thanks to Sally Church! Her tweet about Gears reminded me…

There aren’t many places in the urban sphere anymore where we can’t get a speedy, reliable connection to the Internet. There’s just one big exception: airplanes. We’ve seen a few baby steps toward in-flight Internet, but for most of us, the metal tube is an network-free zone.

Yes, there are benefits to this – no loud phone conversations, no new mail dribbling in while you’re pursuing Inbox Zero. But, many of us have shifted our email, task lists, and other key operations to web apps; five hours on a transcontinental flight without those apps is a long time to be deprived of your tools, and improvising with text files and sticky notes just means more work once you’re online again.

Google Gears has been around for awhile now, but I’m only writing about it now because it’s just now having a real impact on how I work when I’m not connected to the tubes.

Google Reader

When Google launched Gears, Reader was the first Google tool to sport the functionality. (That was the case till just a few days ago.) I track all my feeds in Reader, so the ability to download up to 2000 articles, read offline, share and star them, and sync up later, gave me reams of reading material and ended in-flight purgatory.

Remember the Milk

I love this task management system: it integrates with Gmail, Google Calendar, Quicksilver, Twitter, mobile, etc., etc., which means you have all kinds of ways to get stuff into the Trusted System and track it. RTM was also an early adopter of Gears, enabling full offline access and syncing.

Google Docs and Spreadsheets

As I write this, Google is progressively rolling out offline functionality to Docs users. The Docs implementation is somewhat more sophisticated: it syncs and then responds automatically, going local when you’re offline, reconnecting and syncing when you’ve acquired a connection again.

I’m highlighting these three services because there the ones that matter most to me. Other webapps also use Gears – a list is here.

Pre-Board Workflow

Now, when I’m about to pull the plug on the Internet, I open three tabs in Firefox, one each for Google Reader, Google Docs and Remember the Milk. Docs auto-syncs, and for the other two applications, I press the button to go offline. The switch to offline is nearly immediate, except for Reader, which downloads articles. This generally takes less than a minute.

When I open my laptop after take-off, I have access to these apps in an environment which mimics almost exactly the experience of being connected.

Almost. You can write and edit documents, create, tag, modify and delete tasks in RTM, and highlight blog posts to share on Google Reader. You can’t make changes to application settings, and in Docs, you can’t create a new document while offline. (This is also the case, at last check, with Zoho Writer’s offline functionality.)

In fact, this thing with creating a new document is the only thing that regularly annoys me about offline Docs. But I created a simple workaround: an empty document called “offline notes.” Any new document I want to create while offline goes on this empty page. Once I’m online, I copy it to another new document or rename the existing file and make a new “offline notes” file.

What if something goes wrong with sync and all your offline work disappears, never to be seen again? I take an extra precaution and copy the text into TextEdit, Word or Pages, so I have a local backup just in case.

Offline Wishlist

Every geek has their own version of this list. Mine includes Gmail, Google Calendar, Google Notebook, Google Wiki, Backpack, Buzzword and WordPress software. I don’t doubt for a second that developers of these webapps are working on it, whether they’re building it on Gears, or Adobe’s offline platform or whatever.

But web-to-local software integration also helps bridge the gap. Gmail POP3 and IMAP means I can write email in Mail.app or any other traditional email program and send it when I’m back online, and Spanning Sync (or similar programs) seamlessly keeps iCal and Gcal in lock-step, making iCal my offline Gcal.

There are a few keys to making this functionality successful – and the centerpiece is a seam-free blurring of boundaries between online and offline. Ubiquitous wifi is reducing the white space in between our internet connections; technology like Gears helps to make the white space somewhat irrelevant.

UPDATE 6/10/08: Gears now works with Firefox 3!