Over the last few weeks, I’ve been looking for an online service to help me stay organized. My system at the moment is a patchwork of paper, desktop apps, and willpower that has worked well enough in the past but has begun to come apart at the seams as I take on a growing number of responsibilities. Since I work at several different locations, I need to be able to access a single source where I can access tasks, files, and reference information — from wherever I happen to be.

I’ve yet to find the system that works best for me, although there are plenty of slick apps that look promising until I actually get down to working with them. After a few days of excitement, I find myself coming up against barriers to productivity — some of them because of poor design, some because of differences in philosophy between myself and the programmers, most because I’m simply not the target client — and find myself spending time looking for workarounds to make the system work rather than actually getting stuff done.

Looking at and evaluating all these applications has forced me to consider what exactly it is that I’m looking for in an ideal GTD app. Here are a few of the features I think are important:

• Supporting materials should be bound to projects: Most of my projects involve the creation of documents, and many of them have associated reference materials as well. I would like to be able to look at a project, or a task under a project, and with a click create or open an associated document. For instance, I’m working on a long academic article for a book; I’d like to have all of my notes, PDFs of research materials, drafts, and other materials available whenever I open that project. Foldera does this in a way, but I’ve found it difficult to work with, and it is geared more towards business collaboration than towards individual task management.
• Document editing: I want to be able to create and edit documents from within the same interface that I use to look at my projects and tasks. Whether this uses an internal document editor or a link to a third-party service like Google Docs or Zoho doesn’t matter, as long as the document is saved back to the project it belongs to. So using the above example, if I am working on a draft of my article, I want to be able to open the document, write, and save the document back into the project it belongs to.
• Bulk upload: Why on earth do so many online apps allow you to upload documents only one at a time? What I’d really like to see is a desktop app that would allow me to synchronize files, perhaps by flagging them on the desktop in some way, and then upload them in the background — but I’d settle for a file manager that either allowed me to drag and drop multiple files or ctrl-select them to upload all at once.
• Integration with desktop tools like Outlook: I’d like to be able to work in Outlook or other desktop apps and have the work appear in my online space — and vice versa. So when I check a todo list item “done” online, it’s also marked “done” in Outlook. Several online apps do one-way imports from Outlook, and a few do manual syncs — I don’t see why this couldn’t be automated.
• Integration with mobile tools: For me, like many others, a PC isn’t the only tool I work with. I use a Treo, and others use iPhones, Blackberries, and even Windows Mobile devices (it’s true!) when a PC isn’t handy. Yet few online apps try very hard to integrate with them. Even if access can’t be “live”, it would be nice to have work show up at least when the device is synchronized. What I’d really like, though, is integration with my smartphone’s apps, or third-party apps like Google’s — Google has shown that it’s possible to make sophisticated online apps that work on a variety of mobile devices.
• Automatic promotion of future tasks: When I develop a project outline, I generally write down a list of tasks that need to be done to complete the project. But when I look at my todo list, I just want to know what to do now. Most of the apps I’ve seen dump all the todos from all my projects into one master list, which is useless to me — how can I revise the first draft of an article when I haven’t even been to the library to check out the books I need to research it yet? I want my GTD app to promote the very next action to my todo list whenever I mark the item right before it as finished.
• Links to other services: I’d really like to see a way to pass data back and forth between online services, but barring that I’d like at least to add links into the interface to other online services. It’s surprising to me how many GTD apps don’t have anywhere to put links.
• No-nag tasks: I like to schedule time or set reminders for things that I only need to be reminded about once. For example, driving time — I schedule my regular commute in my calendar, and sometimes I do need a reminder (”hey, you gotta get going, buddy!”) but if I miss the reminder, that’s because I’m probably already driving. I’d like to be able to create a category of reminders that go off once and if I’m not there to respond to them, they just disappear.
• An exit strategy How I get my data out of an online app is at least as important as how I get it in. My needs are bound to change in the future, or the programmers may decide to change something in a way that no longer meets my unchanged needs — or the company that hosts the service may go out of business or cancel the service. If my data is trapped in their system, I’m screwed. I need a way to bulk download everything in their original formats (for documents, files, etc.) or in documented web standards (xml, RSS) that can be ported to a new system, or at least opened on my desktop so I can transfer information over manually.

What about you? What features are you looking for in a GTD app? What services do you use, and what would you change to make them suit your needs better? Is there a great out-of-the-box service out there that I’m missing? If you could design your own perfect online service, what would it do?

Let us know your thoughts in the comments.

Dustin M. Wax is a contributing editor and project manager at lifehack.org. He is also an anthropology and women's studies professor in Las Vegas, NV where he lives with his partner and three children. His personal site can be found at dwax.org.

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