How I solved my Outlook-Google Calendar issues

Working on a number of different PCs and connected devices introduces all sorts of complexity. A constant issue is how to keep all of the information I need access to at hand, regardless of the device I happen to be using. E-mail is pretty easy - between Gmail and IMAP I can access all of my e-mail from any device I use. Calendar info, contacts, task lists, and files all present tougher issues and, as I'm now in  full-time platform switching mode using both the Tablet PC and the MacBook as well as the Treo 700P and the Nokia N93, the complexity has increased in a big way. I'm well on my way to having it all figured out though and thought I'd share some of what I've learned over the past couple of months as I've worked my way through all of this.

Like most GTD practitioners, I rely heavily on my calendar and my task list and reference both many times during the day as I'm working through my projects. Because so much of what is actionable in my life arrives via e-mail, I have developed techniques that make it fast and easy to transfer what is actionable from an incoming e-mail message onto my calendar or task list as it arrives. This is the essence of my ability to keep my Inbox empty (I'm averaging a zero Inbox state at least 4 days a week).

Doing this in Outlook is easy enough. I've written extensively about the "magic act" transformations that Outlook makes drag-and-drop simple and how they allow me to process much of my incoming e-mail in seconds. In essence, I drag a message to either my calendar or to my task list, depending on whether there's a hard date associated with the action required (calendar) or not (task list) and then file the e-mail away which I use the SpeedFiler utility from Claritude Software (shown at right) to make fast and easy from the keyboard or with the stylus. From the keyboard, I use the standard Move to Folder shortcut (Ctrl+Shift+V) and type the first few letters of the folder name I want the message filed in and SpeedFiler word wheels the list down as I type. With the stylus, I can select from a list of the folders I've most recently accessed or tap on the folder hierarchy to locate the right destination. Either of these is easier and more precise than dragging a message with the stylus across the screen. There's a lot more to Inbox triage than that but this simple explanation suffices for the current discussion.

In Mail on the Mac, I use Scott Morrison's MailTags to accomplish the same thing. In addition to tagging my email messages (assigning context in GTD terms) and associating them to a current project or activity, MailTags allows me to add either a calendar item or task to iCal while I'm viewing the message itself.  MailActOn allows me to file messages in appropriate folders with a keystroke by enhancing Mail's built-in Rules engine. Both are essential add-ons for the Mac's e-mail application.

To get the calendars on my two PCs in sync I rely on two utilities and Google Calendar as the "glue" to make all of this stick together. To sync the iCal calendar to Google, I use Spanning Sync which was officially released today after an intensive seven-month beta test. This utility matches calendars in iCal with corresponding calendars I've set up in Google Calendar and performs a very fast bidirectional synchronization on either a timed or manual basis. It's easy to set up, fast to sync, and has been trouble-free since the day I began using it. With the official release, Spanning Sync has announced their pricing model - $25 gets you a one-year subscription to the service and $65 gets you a permanent license. I like the options and consider either to be well worth the investment for the trouble-free way the utility helps me keep everything organized.

Charlie Wood first announced Spanning Sync during a panel on APIs and Feeds I moderated at the Office 2.0 Conference last Fall and I've been following the development ever since on his blog. I began using the utility when I picked up my MacBook at the beginning of this year and it has become one of the most heavily recommended utilities in my toolkit - especially for web-facing folks. There are two big advantages to keeping the iCal and Google calendars synchronized for me. The first is that my calendars are now accessible from either of my mobile devices as both the Treo 700P and the Nokia N93 can access the Google Calendar in their browsers with no problems. I also sync iCal with the Treo and Nokia built-in calendar applications using iSync as I tend to use my mobile devices for creating appointments more than just about anything else when I'm out and about with the possible exception of adding actions to my tasks list. I'll discuss how I've brought all of my tasks into a single accessible environment in an upcoming post.

The second advantage to having all of my calendar events synced into Google Calendar is that, as I mentioned above, it acts as the "glue" between iCal and Outlook. To achieve the same bidirectional sync with Outlook's calendar, I've been using SyncMyCal. This Outlook add-in works in much the same way as Spanning Sync and allows me to associate one of the calendars in Google Calendar with a calendar in my Outlook PST file. In my case, I associate all of the calendars I'm actively using with the main calendar file in Outlook. SynMyCal can perfor either a one-way (Download Only) or bidirectional synch on demand or on a scheduled basis.

SyncMyCal is available in two versions. The free version lacks only the ability to perform automatic synchronization and to specify a date range to sync. It will sync only a seven-day range. To add these two features, the full version is a reasonable $25. PDA synchronization is promised for a future release which will add additional value to an already useful tool.

So there you have it. Using these tools I've created a pretty much foolproof system that guarantees that regardless of which of my devices I happen to be using, I'm able to access an up to date calendar and feel confident that any changes I make will be updated on all of other devices in a matter of minutes or on-demand, depending on the current context in which I'm working.

This is part of a larger effort I have underway to assemble a "unified field theory of productivity" to address my increasingly mobile work and inability to use just one device. In future posts, I'll address how I'm solving the same issues as they relate to my tasks lists and files. I welcome any suggestions about web services or Windows and Mac utilities you've found to be helpful in keeping your information in sync between your your devices. Feel free to chime in in TalkBack.