Pretty hard, I guess.

Recently I wanted to sync up my calendar and contact info between my home and work instances of Outlook.  In fact, I was slightly more ambitious.  I thought this could be a good stepping stone towards moving off Outlook altogether if I could get everything sync’d to appropriate Internet cloud applications.  Little did I know!

I started with Google Calendar Sync, because, “Hey, it’s Google!”  I did this leg at work and it appeared to be perfect that first time.  I got home installed it on the home PC, and low and behold about 60% of the appointments didn’t go through.  Doh!  I could see them get created and then almost immediately deleted.  It seemed like the more complex an appointment was (e.g. recurring, with a long note attached, with attendees, or whatever), the more likely it wouldn’t come through. 

I tried all the troubleshooting suggestions and then went into Google Groups to see if their community had anything going.  What a mess!  Lots of people just blasting out their problem.  Most of them didn’t seem to be getting any response.  Very little rhyme or reason.  I must’ve found 5 or 6 recent posts with the same problem as me.  None of them had any answers.  Clearly it was a common problem.  Does everything at Google get done in people’s 20% time?  I can’t imagine shipping a bug like this and just leaving it.

To make matters worse, Google syncs the calendar, but not the contacts, even though Gmail has contacts.  You’ll need another solution for that.  I reluctantly exported the Outlook and was resigning myself to exclusively using GMail for contacts.  At least iTunes synced the contacts from Google perfectly.  This is a blessing because there are a very limited number of places the iPhone could sync to with iTunes on my PC.  Guess I shoulda bought a Mac, eh?

When I got back in to work and found even my work Google Calendar Sync could no longer do the right thing, I uninstalled and went looking for the next thing.  I also resolved that if I couldn’t use Google Calendar, I didn’t particularly want to leave my Contacts in GMail either.  I prefer one-stop shopping for these simple chores.

I got the bright idea that since I was syncing two Outlooks perhaps I should look at Microsoft Live.  If anyone could sync two Outlooks, it ought to be Microsoft, right?  Wrong!  

Microsoft delivered this steaming mug of Fail:

Excellent!  The only thing worse than unreliable desktop software is unreliable cloud software.  I tried both in the morning and this evening as I write this.  No joy!

Onward, there are many more syncing options to try.  I downloaded two other programs from small startups.  One didn’t work at all.  One sort of worked.  I only synced for 3 days (nice to have the option not to do it all) and it appeared to duplicate appointments the first time.  I tried again and there were no more duplicates.  This was kind of okay, but I worried about the dupes and they were going to charge me about $30. 

There was a sojourn through Yahoo Mail and Zimbra, because a co-worker used Yahoo and pointed out iPhone could sync to it and because I’ve always admired the Zimbra apps.  But somehow, it just didn’t seem easy, so I didn’t even finish trying out Yahoo.  Plus, you never know where that crazy company will wind up these days.

“Let’s try one more,” sez I.  So I tried Plaxo because I read somewhere that it works pretty well for this.  Low and behold, it worked perfectly, both at home and at work.  My Outlook calendars and contacts are perfectly synced now.  I can view them online in Plaxo if need be.  I’m a little uneasy that this isn’t really what Plaxo is meant for (I see it more as a LinkedIn competitor), but what the heck, it works!

Now why couldn’t all these others get their stuff to work?  This shouldn’t be that hard.  My very first stop, Google, should have worked, worked well, and handled contacts.  I should never have even needed to try all the rest. 

And what does this say if I do want to abandon Outlook altogether?  Some would say it makes it easier just not to worry about sync, but I need to take my data with me when I drop of Outlook at the wrecking yard so that won’t work.  Oh well, onward.  Today’s primary problem, syncing, is taken care of.  Tomorrow I’ll worry about web apps.  It’s no wonder Microsoft still sells a ton of Office!