How To Start And Maintain Your Digital To-Do List

On the desktop

EverNote

EverNote is far more than a to-do list manager; it's an all-in-one solution for taking and organizing notes in Windows. EverNote is so full-featured it has a cult following all its own. Currently on sale for $19.95 (with a free trial available), you can take all kind of notes with EverNote and use it to organize your entire digital life. And one of its many features is to-do list management, allowing you to create an unlimited number of to-do lists with unlimited items each. While EverNote is overkill if all you want to do is make a to-do list, it's worth checking out the free trial if you think you could make use of its other note-taking and productivity features.

ToDoList

At the other end of the spectrum is ToDoList, which does only to-do lists but does them very thoroughly. ToDoList is free to-do list manager that was clearly designed with power-users in mind. It lets you give to-do items priorities, due dates, and even sub-items, and you can make items repeat (e.g. weekly), attach files to them, track how much time you've spent on them, and, for team projects, even assign them to other people.

Rainlendar

If both EverNote and ToDoList are overkill for you in their own ways, give Rainlendar a try. At its core it's a calendar program, and it's a particularly fast and lightweight one with simple to-do list functionality built in. Rainlendar becomes part of your desktop, making your calendar, events, and to-do list accessible at a glance. Its appearance and configuration is highly customizable, and it does reminders and alarms as well. You can use Rainlendar for free, or buy the Pro version for 15 EUR (about US$22.20) which adds networked shared calendars and Outlook and Google Calendar integration.

Gadgets and widgets

If you have Windows Vista and just want the simplest solution possible, Windows Live Gallery has a number of free gadgets that provide to-do list functionality in a very small space. And if you use Google Sidebar there are a number of gadgets at your disposal as well like Tabbed Todo List and TODOinSYNC.

On the web

There are literally dozens of free and commercial services on the web that provide to-do lists to the connected masses, and rather than detail them all--which would take more than a few pages--I'll just tell you about two of my favorites.

Remember The Milk

Remember The Milk is a great general-purpose web-based to-do list manager. You can assign tasks priorities and due dates, and you can associate tags, URLs, locations, notes, and more with items. The interface, however, remains nice and simple--those features are smartly hidden away if you don't want to use them.

Remember The Milk's real strength, though, is its social features and integration with other services. You can collaborate on to-do lists or just lets others keep track of your progress--great for setting and sticking to goals. In addition, it can send you reminders via email, IM, or text message and you can create new to-do items by sending an email, and if you use Gmail you can add a Remember The Milk pane to Gmail's interface. It also sports iCalendar and Atom feeds. Finally, it supports Google Gears, the free framework from Google that lets you use the site when you're offline.

Remember The Milk is free, but there's also a Pro version that gives you access to an iPhone-formatted version of the service, a Windows Mobile client, and priority email support. Having said all that, I know there are more features in Remember The Milk that I've forgotten. If you're happy with using a web-based interface to manage and update your to-do list, Remember The Milk is ideal.

Todoist

Todoist lacks almost all of the features of Remember The Milk that I just described. And that's its greatest strength. Todoist is starkly minimal--essentially its only "extras" (save one, which I'll get to) are priority settings and due dates--but has a strong set of keyboard shortcuts that, once you've learned them, let you blaze through your lists. You can create multiple projects, of course, but what makes Todoist extra useful to me is the ability to put tasks in a many-leveled hierarchy. Using buttons or shortcut keys you can indent items, creating a nested tree that you can then expand and collapse. It might seem like this would add complexity, but for me it breaks up complex tasks into simpler and more manageable ones, which makes Todoist stand out from many in the crowd.

Other options

While I recommend all of the above solutions--you'll have to try them to find out what's best for your purposes--I'm barely skimming the surface of the market. If you prefer to manage your to-do list (and calendar) by sending and receiving email, give virtual assistant Sandy a try. If you're comfortable with the command line and prefer to work with text files instead of databases, try the super-geeky (but super handy) Todo.sh. And like I said, you can scarcely throw a rock without hitting a handful of web-based to-do managers. Here's a sampling: Ta-da Lists, voo2do, Bla-bla List, Tudu Lists, Toodledo, SproutLiner, Nutshell... the list goes on. And then there are the persistent rumors that Google itself will be adding to-do lists to Gmail any... day... now.