Chandler, an open-source, cross-platform scheduling app, was conceived back in 2002 as a potential Outlook-killer—a free organiser that would process all your email, calendar appointments and tasks into one smooth workflow, no matter what format or system they were on. Over its long and storied development, intriguingly chronicled in the book Dreaming in Code, Chandler morphed into a meekly-dubbed "Note-to-Self Organiser." There's a lot of neat ideas in Chandler, implemented in rough ways, and if you're a serious to-do hound, it just might find a place somewhere in your work flow. To find out, let's check out some screenshots of this long-awaited Personal Information Manager.
What CAN you do with Chandler?
The ideal user of Chandler is any computer user who sees all their work data—email, appointments, and individual checklists—as one big to-do bin. In other words, it's pitched at devoted acolytes of the Getting Things Done system. That user also doesn't mind spending some time setting up and learning their way around the particular way Chandler organises all that material, which, as we'll see, can be less than intuitive. You can read more about Chandler's abilities and features at their site, but for a three-minute summary of what Chandler can do, this video serves pretty well:
Once you've installed Chandler's desktop client in Windows, OS X, or Linux and launched it, you'll arrive at the "Dashboard," which, for first-time users, is a bit over-stuffed with example notes, events, and fake calendar items. Click on the "Dashboard" in the upper-left menu panel, and you'll see what I mean:
Note: Click on any large screenshot for a full-size view.
Tackling to-dos and events
Ignore all the buttons and over-loaded top-bar menus for a moment, and you'll see that Chandler is a kind of simplified, if slightly heretical, GTD-style manager. You create "Collections" of tasks and appointments, and can give them stars to indicate priority. There are no real tagging or context options, but you can implement them yourself by writing in notes and searching them. Everything gets a "Triage status" of Now, Later, or Done—though you can also tick a "Needs reply" checkbox for some items. You can view your notes/tasks in list or calendar views, or you can write up Notes that have no real time distinction (even if that goes against many productivity principles).
My major complaints here involve the input interface, along with the "Dashboard." You can quickly schedule events from the central quick-add bar—"5-8pm Friday Drinks at Captain Ron's"—but the event titles don't get reformatted to just "Drinks at Captain Ron's." Otherwise, it's hunting and pecking in dates and times through the sidebar column, which gets old real quick. As for the Dashboard, it's intended as the place where you can view all your events and notes at once. What's maddening is that the Dashboard holds onto items that you've deleted from your collections. In effect, this means you always have to head to the Dashboard to delete an item for good.
If that was all Chandler did, it would merely be a decent To-Do handler, with a few quirks. Instead, it asks you to find a home for it in your calendar, in your email client, and on the web. Here's a quick look at how it fares in those realms:
Chandler can't do two-way syncing with online calendars, unless they're run from a CalDAV server. You head to the "Share" menu, oddly enough, to choose "Subscribe," enter in the location of your .ics file, and then wait while Chandler does its thing. Google Calendar users, at least, should tell Chandler "No" when it asks to adjust your listings for your time zone—my GCal was already set to Eastern, Chandler didn't notice, and everything was shifted ahead four hours. Once everything's in, you'll get a new collection set up, one which you can't really modify, even if you're just trying to delete one of the possible hundreds of "Done" items that get thrown in. You also can't drag your read-only items into another collection to duplicate them—they're truly there just as reminders. The unspoken message is that you have to adapt to using Chandler as the Grand Central Terminal of all your data programming, or it's just not as useful.
Chandler doesn't try to filter and sort your mail itself, but it can grab events and to-dos from your inbox—kind of. The app lets you hook up most any POP or IMAP-enabled mail account, and then places three folders on that server: Chandler Mail, Chandler Events, and Chandler Starred. Any mail placed (or filtered) into those folders is grabbed by Chandler when you hit the big green "Sync" button, but not in the smartest way. The app doesn't seem to try to grab a relevant date from anywhere in the email, even the subject, so you end up scheduling important events yourself. A "Send" button appears once you open up an email, which could help with speedy replies or forwarding, but this hardly seems like the best interface to knock down email in. If you regularly get messages of the same type from the same source, this could be a useful capture tool, especially if you're good with a filter. Otherwise, it seems somewhat superfluous.
The one area where Chandler unquestionably shines is in its open-ended, share-friendly, web-savvy aspects. Sign yourself up for a free Chandler Hub account, put the credentials into File->Accounts, and all your original events, notes, and other tasks can be automatically backed up to your web account. You can import that data into a Chandler session on another desktop, or get at it from the Hub's web interface, which does a nice job of recreating the experience:
From both the desktop and the web Hub, you can share certain tasks/notes/events as read-only or invitations to edit, even to non-Chandler-types, and export your collections and items in a variety of friendly formats, like .ics, RSS, or CalDAV.
Finally, if you're an iGoogle user, Chandler's got a Quick Entry Gadget that can save you the trouble of firing up the desktop client, or logging into the web version, if you've got a quick task or note to jot off. Assuming you've got automatic syncing set up, any notes you punch in here end up in your desktop stack seconds after you open it.
Chandler's heart is in the right place, to be sure. It looks and operates almost exactly the same on Windows and Linux systems, and syncing my data between those two systems was seriously simple. It's completely free, uses open standards wherever possible, and has a GTD-centric approach to data filtering. So why won't I leave Remember the Milk and Google Calendar behind? To put it simply, interface and intuitiveness.
Chandler was born (and reborn endlessly) before clean interfaces and a less-is-more mindset came to dominate webapp and software design. Even the notoriously bloat-tacular Microsoft Office suite scaled back some with its 2007 edition's "ribbon" menus. Chandler, on the other hand, is easy to get lost in on your first visit. The "tools" menu alone is a dense thicket, and the interface doesn't point out any obvious actions or usefulness, until you poke and click around a bit. More generally, it seems like software that asks for an all-or-nothing conversion from its users, which, in a marketplace dominated by corporate-backed solutions, is a tricky proposition.
That's not to say Chandler isn't intriguing, or worth the time it might take to get comfortable inside of it. For one of the software world's most well-documented 1.0 releases, though, it still feels like a longer road lies ahead.