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OCTOBER 12, 2006

Byte of the Apple

By Arik Hesseldahl


The Apple Calendar Conundrum

There's no easy way to transfer addresses and other data from Mac to PC to handheld and back—but there should be


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These days when I use Microsoft Outlook on my office Windows PC I have a funny reaction: The song Why Can't We Be Friends? strangely echoes in my head.


Why in all creation would an e-mail application like Outlook trigger memories of lyrics sung by the funk band War in 1975? Because that's also my plea to the various entities that build the software intended to organize my life: Why can't you make your various islands of data work in total harmony?

Here's the nature of my problem: My daily calendar lives in Microsoft's (MSFT) Outlook as well as my Research In Motion (RIMM) BlackBerry. That much is straightforward. The BlackBerry is an Outlook user's best friend, and the compatibility between the two is legendary.

THE RUB.  It's when you bring the Apple (AAPL) Mac into the equation that things get tricky. I use a Mac at home. I'd like to use Apple's iCal to manage my calendar and its address book application to handle all my contacts. This I can do, using the BlackBerry as a go-between.

From there, I'd like to use Google's (GOOG) Calendar, aka GCal, to make a permanent, duplicate record of my appointment calendar so that I can refer to given dates whenever needed—from any browser, not just when I have access to Outlook. Theoretically, I should be able to publish my calendar from iCal directly to Apple's Mac.com service, and then subscribe to that calendar's feed using GCal.

Here's the rub. I don't want my calendar feed to be publicly available for just anyone to subscribe to—and that's the case with iCal. You can incorporate privacy features, but that just adds a layer of complexity to an already multistep process.

MEET THE MIDDLEMEN.  If this seems like a small and insignificant problem, I encourage you to do a Google search for "The Holy Grail of Synchronization." You'll quickly see there are legions of organization-obsessed geeks out there pondering the very same problem.

Take the exhaustive "how-to" by a Canadian blogger who wanted to get two PCs running Outlook to sync with a variety of other tools, including a GCal account, a Nokia (NOK) wireless phone, and his iPod—all at once. To what end? Only he really knows for sure. But getting it done involved installing an open source plug-in for Outlook called Funambol and using a free service called ScheduleWorld as a sort of middleman between Outlook, GCal, and everything else.

What amazes me is that getting various calendar tools to work together remains a vexing problem in a world where Web 2.0 applications are meant to "just work"—where data is data, and pretty much everything interesting on the Web these days has a smooth, snappy Ajax interface.

It seems to me that everything that by 2001 already needed to be compatible, from our PCs to Macs to wireless handheld gadgets, hasn't come anywhere close to that goal. And here we are near 2007.

A SOLUTION ON THE HORIZON?  A startup called Sharpcast is building a way to make complicated, geeky tales like mine and that the of the "Holy Grail" author a thing of the past. Sharpcast CEO Gibu Thomas demonstrated for me the company's photo-sharing service that takes all the guesswork out of keeping your photo collection in sync between computers.

Add a digital photo to your collection at one computer, and seconds later it's automatically made available on a second computer you designate. Right now, the service only works on Windows XP, and with a handful of mobile devices, including the Palm (PALM) Treo, the Motorola (MOT) Q, and a few others available from Verizon Wireless (a joint venture of Verizon Communications (VZ) and Vodafone (VOD)), Sprint (S), and Cingular (a joint venture of BellSouth (BLS) and AT&T (T)), but Thomas assures me that a Mac version of its software is coming soon.

The photo-sharing service was launched primarily to demonstrate what the underlying plumbing can do. Thomas hails from Palm and its sibling company Handspring, and was one of the people who worked on the Blazer Web browser for the Treo family of handhelds. Underneath that photo-sharing service is the infrastructure that I think promises to universally synchronize pretty much any kind of data you might tend to use on a daily basis.

THE ONUS IS ON YOU.  Take another data availability problem I run into from time to time. As a writer, I spend a lot of time in Microsoft Word, and store the documents I work on locally on my office PC. Often I want to access them at home, which means I e-mail them to my home address before heading home. But what if I forget to send that e-mail or neglect to attach the right document? Sharpcast's technology could make that Word document, or any Office file for that matter, available to me on my Mac at home just as readily as if I were at the office.

The same could easily be done with those irritating files of contacts. Many companies have tried to bridge the gaps between contact management software of varying types. The one I dislike the most is Plaxo. Users of Plaxo, which I have never tried, have this annoying habit of regularly e-mailing you, all but insisting that you update all the information about you shown on a little image embedded with an e-mail that looks a little like a business card. After getting a few dozen of these after switching jobs a year ago I started sending snide replies: "It's not my job to update your contact file." And "This is a Plaxo-Free Zone." Thankfully, their requests have declined.

It seems to me that contact data should be pretty universal. There are names, phone numbers, e-mail addresses, job titles, and a batch of other data fields that theoretically should be the most easily accessible bits of data we need, regardless of the type of computer or data device we use. And yet, they're not. Using a Mac only complicates the problem further. But with luck, all our data will be very friendly, and soon.

Hesseldahl is a reporter for BusinessWeek.com


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