What Happens When a Windows Mobile/Mac OS X Gal Gets Her First Blackberry

Since starting a fulltime webworking job in August 2005, I’ve found that 90% of my non-talk time on my smartphone is spent in email, and too much of that time is spent struggling with the email application. I’ve been a Windows Mobile user on my phones/PDAs since 2004, and have gotten quite comfortable getting around the operation system. Being able to check email on my handheld affords me flexibility in my day that I wouldn’t have otherwise. I’d be chained to my desk for longer stretches of time, since the primary way I interact with co-workers and colleagues is through email.

I recently became eligible for a Cingular/AT&T phone upgrade, and used that opportunity to replace my Cingular 8125 (running Windows Mobile 5.0 Phone Edition) with a Blackberry 8800 for better messaging. Of course all the cubicle slaves carry a Blackberry, but what about the independent web worker who doesn’t need to sync to a corporate Exchange account?

To complicate matters further, my current computer is an Apple MacBook Pro which runs Windows XP through Parallels, and my primary email application is Outlook 2003. I thought syncing my new Blackberry to my desktop would be as simple as installing the desktop software into Windows XP in Parallels. Guess again.

First of all, the ease of setting up and using email on a Blackberry compared to the same on Windows Mobile cannot be overstated. I have two email accounts, one for work (not an Exchange server) and one for personal email, through two different shared hosting providers. It couldn’t be easier to create a Blackberry Internet Service account and configure the two addresses so my POP3 email could be pushed to my Blackberry. It’s not quite true push email, since the Blackberry service checks the email at set intervals and pushes it to my device in batches. But it works far more reliably than the email client that comes with Windows Mobile. Even better, Cingular/AT&T’s Blackberry unlimited data plans are priced better than their data plans for non-Blackberry devices at $29 per month with voice plan, instead of $39 per month.

While Windows Mobile functions very much like a desktop operation system, the Blackberry operating system does take some getting used to when making the switch. I keep reminding myself not to tap the screen to navigate, for starters. I appreciate the little magnet in the included case that puts the phone in stand-by mode automatically when you slide the device in.

But how do you sync calendar and contact data to a Blackberry if your primary desktop isn’t running Windows XP/Vista or your primary organizer isn’t Microsoft Outlook, Lotus Notes or one of the other PIMs the desktop software supports? It can be done! It just takes a little hoop jumping. Sometimes, you just have to take the winding path when you can’t get from A to B in a straight line.

I tried the Blackberry Desktop software. Did not work in Parallels. I am not the only one. Luckily, the good folks at Mark/Space have a solution in their Missing Sync Blackberry software for Mac OS X. It was just released and costs $40. It syncs the later model Blackberry devices to iCal for calendar events, Address Book for contacts and their own Notebook application for notes. It also does iTunes for music, iPhoto for photos and iCal for tasks. But since I use Outlook as my organizer, due to required syncing with colleagues and our organization’s CRM, I have to take the extra step of getting my data in and out of Outlook first. I am unable to use a different desktop email client.

I didn’t want to import/export calendars and contacts, since they are updated often. I wanted a solution that worked in the background as items changed. Here’s how I did it:

1. Sync Outlook calendar to Google Calendar using SyncMyCal ($25 for unattended syncing)

2. Sync Google Calendar to iCal using Spanning Sync ($25 per year or one-time purchase of $65)

3. Sync Outlook contacts to Plaxo, which syncs to Mac OS X Address Book (Premium Edition is $50 per year to manage more than 1,000 contacts)

Now everything is where it needs to be so MissingSync can do its thing. It works quite nicely for my $100 in software fees, giving me all the benefits of Google Calendar while still having the compatibility of Outlook for working with my colleagues. Eventually, I need to figure out how to sync tasks and transfer applications, but for now I am enjoying hassle-free mobile messaging.

Any other tips & tricks to get the most out of a Blackberry in a non-Windows/non-Outlook environment? What hoops do you have to jump through to get your technology to work in ways it wasn’t originally intended?


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