Outlook detox

Been a little quiet around these parts. Two reasons. I’ve been battling a mutant sinus virus that caused a skull-crushing headache and a high-pitched ringing in my ears that still hasn’t completely gone away. (Sonically isolating myself in a float tank probably didn’t help, I admit in hindsight.) But really the blog went quiet because I was in the middle of a project that knocked my world completely off-kilter: changing personal information management software.

I’m no fan of Microsoft, but I have been saying for years that they actually got it right with Outlook. I’ve used Outlook on my primary machine (a PC) as a standalone PIM and e-mail client since 1998 and have loved it. But I’ve known for probably a year that I had to wean myself. Here’s why:

– Non-standard data formats. Moving your information from Outlook to anything else requires third-party software and a masochistic tolerance for inaccurate field mappings and system freezes. I can’t stand having such critical data in a proprietary format, especially one controlled by MS.
– There’s no easy way to view data on multiple platforms. And no easy way to view data, replicate it, or back it up online (since I don’t use Exchange).
– I’m completely enamored with Mozilla Firefox and the extensions to it from the open source development community. Thunderbird and Sunbird were calling me.

Moving off of Outlook was pure hell.

I decided I was going to tackle Thunderbird first. I had to extract several year’s worth of e-mail with attachments using a variety of filters and applications (Outlook2vCal and Outlook2Mac) to create mbox files. This was the least painful part of the transition and it took me days. Thunderbird isn’t quite as elegant as Outlook, but it is damn close and the extensions for it are superb. I route through Gmail now using POP forwarding so, in essence, I have online replication too. Thunderbird also integrates with Plaxo, the online contacts management service, so I have online replication there too. E-mail transition happiness: 99%.

Next up, calendar. Suffice to say that getting meaningful appointment data out of Outlook is tragicomedy. As in, one must laugh in order not to cry. I imported the data in Sunbird only semi-successfully. Sunbird left me wanting, though. It is not as mature or stable as Firefox or Thunderbird. So I took a completely different tactic, moving all my calendar and task data to Yahoo! This was an interesting experiment that ultimately failed. I like Yahoo! Calendar a lot, but after using it exclusively for a few days I knew I need a desktop calendar app too. The web just isn’t the best medium for sustained calendar manipulation. (Though an AJAX-powered calendar would probably be usable. Listening, Google?) Also, Yahoo! Calendar only replicates with Outlook. And I wanted to eradicate Outlook completely.

Back to Mozilla. I switched from Sunbird to Mozilla Calendar because it was slightly better integrated with Thunderbird. I got the data in relatively cleanly. I learned more about the iCal format that Moz uses and then stumbled upon PHP iCalendar, a truly amazing web calendar viewer that actually has a better interface than even Outlook. So, though there’s no synching per se, I could publish/backup from MozCalendar to the web. But the best part is the iCal standard. Once I found iCalShare and subscribed to all kinds of calendars, I was off and running. I also subscribed the iCal app on my Mac to the published calendar file. I should have known that, per usual, Apple’s calendar was by far the easiest and most elegant solution available. But since I have a PC laptop it couldn’t be the only one. Sounds complicated, but it really isn’t:

– Mozilla Calendar is used to create and edit all appointments and tasks. It publishes the data to a webserver.
– PHP iCalendar allows viewing (but not editing) of this data online. It also provides RSS feeds for day, week, and month views and clean printer-friendly page layouts.
– The Mac iCal app subscribes to the published file online and so allows “replication” across multiple platforms. This replication is one-way. I don’t push changes back up. (There’s a nifty little AppleScript, iCal Calling iTunes!, that lets you schedule playlists to begin and end at certain times. Great for falling asleep to continuous streams, like the Sleepbot Environmental Broadcast.)
– Various other calendars (US Holidays, NASA events, Chicago events, etc.) are overlaid on my personal calendar data in each of the views.

Mozilla Calendar is slow and clunky, but it has a lot of promise and the feature set points in the right direction. I figure I am making a down payment in diminished usability (compared to Outlook) for the potential for functional and usability payoffs later on. The Lightning integration project is cause for optimism. Calendar transition happiness: 85%.

What about synching to the phone? Ack! There really is no good Thunderbird-to-phone app available. Mobile Master makes a valiant effort, but it sacrifices elegance for comprehensiveness. My phone, a Sony Ericsson S710a, supports syncML — but not much else does. There’s Mobical.net — a service for synching an online calendar with a phone over the cell network. It is a very cool idea, but of course it cuts out the desktop app and that’s a deal-breaker for me. And how often would you really need remote synchronization? Mac to the rescue again. Since my calendar data is subscribed on the Mac and since Plaxo exports to the Mac Address Book I use iSync to send data to my phone and to my iPod. Again one-way. (No more need for the PC iPodSync, a good program but one that’s also tied to Outlook.) Mobile device support transition happiness: 75% (due to a lack of PC-to-phone synch).

The only thing really missing from my new set up is some way to manage the hundreds of Note scraps I collected in Outlook. I played around with Tada List and Backpack and while they are super-usable they also limit you to only a few entries in the free version and they don’t synch with any kind of desktop application. Yahoo! Notepad synchs, but only with Outlook. I’m sure something exists. Just haven’t looked hard enough.

I’ve settled into the new tools now. The tremors have subsided and I think I am Outlook-clean. ‘Course it didn’t help that this whole migration was a subset of a much larger transmogrification of my PC into a more Mac-like, open source software animal. In the past few months I have installed TopDesk (an Expose clone), ObjectDock (a Mac dock clone), Xpize (an XP DLL refresher), and the OpenOffice.org suite. The only Microsoft app I am currently using is the OS itself. A significant one to be sure, but the Linux migration of my laptop — if it ever happens — is the subject of a future blog post.