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.

Now, there’s a more direct way to sync your calendar. Google Calendar has added CalDAV support – which is the web protocol that iCal uses for calendar data. The current flavor of CalDAV works only with iCal, although other calendar programs support the protocol and will presumably be able to sync at some point.

Google’s instructions for setting up CalDAV on iCal.

I set up the syncing for my principle calendar earlier today, and in a couple minutes (it can take up to 15 minutes) my Google calendar appeared as a separate calendar in iCal. It’s easy, this is a two-way sync, and it updates about eveyr 15 minutes.

It’s not as full-featured as Spanning Sync, however. With SS, you can sync multiple calendars, and designate existing iCal calendars to sync to GCal – the CalDAV creates a new calendar. You can sync multiple calendars with CalDAV but it’s not as straightfoward; that said, it ain’t rocket science.

So, if you use Calgoo or SS or another syncing program, you might want to investigate CalDAV – you don’t have to abandon your chosen program to do so. Or if you’d rather not… carry on!

I experienced some calendar downtime for a couple hours on Monday, but otherwise, I’ve not had trouble. Syncing remains almost immediate between the iPhone and the cloud… around every 15 minutes as far as the computer is concerned.

I’m going to have to pay attention to this over the next couple weeks, and I have no intention of shutting down GCal, but I’m surprised how quickly I’ve taken to the calendar function on MobileMe.

So, to answer the question in the title of the post, not yet, but this bears watching.

Given that outpouring of response, I thought I’d give you an update. But first, a recap: in September, I determined that my vital archive of around 65,000 emails – maintained for so many years on laptop after laptop, then carefully uploaded using IMAP to GMail where it could live in the cloud, safe from catastrophic loss, then backed up on a second GMail account because one can never be too careful – was really just a useless waste of space – even when it’s Google’s space.

I began the rampant deletion of email; in total, I round-filed about 50,000 emails; my current trove, once again living on my hard drive, numbers about 15,000 emails.

For 4 weeks, the trashed emails lived on in Gmail purgatory; this week, they reached their 30 day limit and disappeared forever. What’s the impact? Well, in the first 2 weeks after trashing them, I made somewhere between three and five visits to the Gmail trashbin to search for something I needed. That’s not exactly an overwhelming endorsement for the Vital Email party, is it?

I’m not going to pretend that getting rid of the email has helped me feel whole again or achieve defined, meaty abs… but the point is getting rid of clutter. I have come to believe that clutter impedes energy, and without getting all Deepak Chopra on you, I think that having less clutter frees the mind.

Want to know my cheat? The backup Gmail account? It still exists, with all 65,000+ emails. It’s going to be my safety net and in 6 months, I’m going to delete those copies, too.

It’s worth delving into this concept of “safety net” for a minute. Why did I keep all that email? A variety of reasons; for instance, I would probably save lint if one could easily mount it in a scrapbook. But my biggest reason was that those email messages contained information that I was afraid of forgetting or losing or not having. Yes, most emails we get or send consist of the response “OK, see you soon!” but a fair number contain information vital to our work or life.

For a long time, keeping the emails has been my haphazard way of holding on to that information. I say haphazard because, although it’s “all in there,” you have to dig through the haystack to get to it. I’m slowly but surely trading in the “keep it all” approach for a new method: process the inbox every day, harvest all the important actionable or reference information out of the email, and get into a trusted system where I can see it, synthesize it, create tasks around it, delegate it or defer it.

I don’t throw away all the email. For work, there’s some stuff I have to keep. There’s also some stuff I just want to keep. That’s fine, but the reason I’m now keeping it is because the email itself is a document that has value. All the usable information locked away in it, however, has been lifted out and transported to another system that I use daily to track my tasks and projects.

I won’t pretend that it’s working perfectly; I won’t win Miss GTD. In fact, I’ve discovered an early warning sign of stressful periods – I start putting every email I get in the archive box and neglecting the data mining. But the system seems a lot smarter and when it’s working, it leaves me feeling more relaxed.

The first purge (we call it The August Putsch) helped us find new homes, or a final resting place, for a couple hundred books, some furniture, and a pile of old clothes. The second purge (The Glorious Revolution) allowed us to rid ourselves of most everything else, it seems. About 500 books went to Planned Parenthood for their annual book sale; a half-dozen sacks of clothes went to Goodwill; and we took advantage of living in a neighborhood to unload all but 6 pieces of furniture on the front lawn, all of which disappeared within seven minutes.

The result? Our new loft high above downtown Des Moines has only the books we want to own, only the clothes we wear, only the files we’re keeping for a reason, and only the cool furniture we purchased for it.

Pristine.

If only my digital abode were in such a state.

I listened to Peter Walsh’s book “It’s All Too Much” and felt all smug because I’ve overcome my need to accumulate stuff. (Walsh’s book, by the way, is excellent. Whether you’ve had to buy a second home to contain all your things, or you have a few piles of crap here and there, you’ll find lots of helpful advice inside.) It’s only been in the past week that I’ve realized I have an obsessive-compulsive habit of digital accumulation.

We all know the scientific rule-of-thumb of digital storage: it gets cheaper every time you turn around. I take more pictures, download more audio and video, generate more documents and emails, with no concern about filling up the available space. It’s all very well organized, filed, managed, tagged. Gigabytes of invaluable information, available at my fingertips.

Yet, how is this different from having a closet full of clothes I haven’t worn in five years? Or a thousand books I’ve either read or will never read? Just because it’s digital and fits on a 2.5″ hard drive, does that mean it’s not useless clutter?

Certainly, there are some things I need to save – financial documents, tax forms. A lot of my email is important for one reason or another. I don’t want to lose my photo collection or my iTunes library. But there’s another class of saved material that’s more about my psychological satisfaction with the idea of completeness; and when I look at my Finder from this perspective, it starts to get a little embarrassing.

I have all 118 episodes of the CBC Radio 3 podcast. I like the music, so I could argue that the nearly 120 hours of content is still valuable to me. However, I have only the latest 3 episodes in iTunes. The other 115 episodes are archived on a backup disk, which I never access for listening, only for backup. Now, if a meteor destroys the Canadian Broadcasting Centre in Toronto, I’m ready to step forward with my priceless archive. But if I had 118 shirts that I never wore in a closet somewhere, I’d reach for a big plastic bag.

Improving search and tagging capabilities mean I have more control over my archive of 65,000+ emails. But what am I saving? A pivotal communication from a friend on June 22, 2002 reads: “OK.” To what question was that friend responding? Why, I have that email, too.

Space is cheap; online, it’s often free. So don’t throw anything away. Archive it.

What I’ve discovered as I’ve started “throwing out” gigabytes of stuff is that the result is the same as ridding one’s home of physical accumulation: a growing sense of well-being, a psychic burden lifted.

Some things, whether physical or digital, are meant to be used, enjoyed, admired for a time. Then the physical stuff can find a new home where it will be appreciated. When the digital stuff is no longer contributing to my life, the place for it is the trash bin.