Yesterday, Smashing Magazine featured an awesome little add-on for Outlook that synchronizes your Outlook calendar with your Google Calendar. The gSyncit add-on is quite light weight and it can automatically synchronize between your calendars.
I have a temporary page set up right now that displays my Outlook calendar. The idea is that people will be able to arrange appointments with me more easily without having to guess my schedule all the time. My schedule constantly changes and new appointments/meetings comes in all the time. Now that I have a public calendar that gets updated frequently, people can figure out what would be a good time to have those meetings before they even ask.
I primarily use Outlook because it syncs super well with my phone and doesn’t rely on an internet connection. Replicating the schedule to Google Calendar daily is just a huge time consumption (read: waste). Even though the evaluation version requires me to click on a button to synchronize, it is far more efficient than to create the appointments individually in Google Calendar.
Note: This plug-in is $9.99 USD… or $9.66 CAD at the current rate. 
My saviour! I have been looking for something like this recently.
I’ve found that the syncing is starting to get a bit bothersome… For example, I can’t minimize Outlook by clicking on the taskbar anymore. I have to use the top-right button. Also there seems to be far more conflicts than I like. And tagging and categories aren’t liking each other. Pity.