Reader Simon White has found himself sucked into the black hole that can be Outlook 2011. He writes:
I recently switched from PC to Mac but have issues getting mail, calendars, and contacts transferred. Initially I thought that continuing to use Outlook would be the way to go, so I installed Outlook 2011 for the Mac. But it doesn’t sync with my iPhone. So I decided to try using Mail/Address Book/iCal only to find that I cannot export my data from Outlook in any format other than .olm, which Apple programs cannot read. Is there a way to get my events out of Outlook’s calendar and into iCal?
It’s at times like these that I wish my response was accompanied by an animated GIF of me banging my head against the desk. Because that’s exactly the kind of reaction I have to Outlook’s terrible syncing support. But let’s both take a couple of deep breaths and proceed.
Unlike Entourage, Outlook doesn’t offer an option for syncing calendar events (you can sync contacts, however). This is a feature that’s been promised for a future Outlook update but Microsoft hasn’t said when we might expect that update. And, as you’ve discovered, iCal looks at .olm archives and shrugs its virtual shoulders. But there is a way—tedious and tiresome, granted, but still, a way.
That way is to select an event within Outlook’s calendar and drag it to the iCal icon in the Dock (or, if you like, drag it to the Desktop and then drag it into iCal). This dragging business converts the event into a .ics file, which is compatible with iCal.
Regrettably, you can do this with only one event at a time. You do not have the option to select all events in a monthly calendar or even Shift- or Command-click multiple events. It’s one at a time or nothing at all.
[Insert sound of further head banging here.]
Ideally, you haven’t been at this too long and you can return to your PC and export your calendars from there because, yes, it’s easier to do this from Outlook for Windows than Outlook for the Mac. To do that, just right-click on a calendar in Outlook for Windows and from the menu that appears choose Save As. The default option is to save the calendar in the iCalendar format. Choose this option and click Save. Repeat for other calendars you want to transfer.
Copy these calendars to your Mac and drag them on to the iCal icon in the Dock. You’ll be prompted for an iCal calendar to save them to. Choose the one you like—Work, for example—and click OK. All the events in the exported Outlook calendar will be added to your iCal calendar.