As a software engineer, I find that I apply basic software engineering principles to all aspects of my life, and a big one is the “don’t repeat yourself” philosophy, or DRY. Nowhere have I felt more pain on this lately than with trying to solve the problem of a unified email, calendar, and contact solution that is available to me wherever I am. Let me state the problem more clearly:

At Cantina, we make heavy use of all that Google Apps has to offer to provide a cost effective, yet extremely functional solution to email (both web-based and IMAP) and shared calendars. This, for the most part, suits our needs adequately and with minimal cost and maintenance. Now, throw into this scenario the fact that we are consultants, and as such end up making heavy use of our clients’ respective email and shared calendar solutions, most if not all of which are handled via Microsoft Exchange Server. There are a whole host of reasons why this is a good thing for our clients, however this presents a problem for someone like myself, who likes to keep everything in one place, depending on where I am:

1. If I’m at my desk, I want it on my Mac laptop and want all of my email managed via Apple’s Mail application, and all of my calendar managed through iCal
2. If I’m out and about, I want it all on my iPhone (you can see my brand allegiance here - not a fanboy just like low maintenance and high integration)
3. If I’m really in a pickle and don’t have my laptop or my iPhone (this is rare), but still have internet, it would be ideal to have a unified web interface to get to all of this stuff, perhaps via Google Apps. Again this is a rare case.

Now, there are a myriad of synchronization technologies and solutions out there that attempt to bridge the gaps between these various components, such as:

• IMAP: Apple Mail - Google Apps Mail & Gmail (works great apart from the lack of Label/Folder IMAP subscription)
• Apple Mail’s Exchange Support: Apple Mail - Exchange (still requires IMAP to be enabled, which isn’t always the case)
• Spanning Sync: Google Calendar/Contacts - iCal/Address Book
• Entourage with Sync Services: Exchange Calendar/Contacts - iCal/Address Book (issues with multiple exchange accounts)
• NuevaSync: Google Calendar - iPhone (over the air, doesn’t require cable, yet takes up your only Exchange account on the iPhone)
• Active Sync on the iPhone: Exchange - iPhone (over the air, but only supports one Exchange account at a time)
• And so on…

All of these little “bridges” spanning the gaps between various applications each have their own small set of problems and limitations which makes this whole sync ecosystem break down. What’s worse, is that sometimes, attempting to make this work can have unintended or potentially disastrous consequences (Imagine all your calendar events from one client syncing onto another client’s Exchange server).

So there’s the problem, but what is the solution? For many people, a single Exchange or Mobile Me account will do the trick, but for me (a consultant using multiple services), it does not. Sure, there are some glimmers of hope. Apple is bolstering their Exchange support in their applications following the introduction of Active Sync to the iPhone. Sure, there might be a day soon when the iPhone supports multiple Exchange accounts and can subscribe to CalDAV on Google.

These are all patches to a solution that lacks a holistic view of the problem. Where have we seen this before? How about a unified login? OpenID attempts to solve the real and very present problem of managing separate authentication credentials across the vast ocean of sites requiring registration on the web. Though it’s not quite a homerun yet, there’s progress being made. Any standard will run into this issue, even HTML.

The questions here are these: Can we extend this concept of online identity beyond logging into sites? Can we aggregate our various online presence (including email & calendars) to our one true e-self? I think the answer is yes, but in time, and I think Apple’s lowly Address Book application, the humble servant of contact management on the Mac may serve as an example. You see, in Address Book, there is a particular contact card that is designated as “Me”, the current user. In this contact card, I can add any number of phone numbers, fax numbers, etc., but more importantly I can add multiple email addresses and IM screen names, which all are identified as “Me”. This means that no matter what email address in Apple Mail I use to send or receive email, if it’s in my “Me” card, the system knows it’s “Me”. I think that this very basic approach can be extended to aggregate online identity at a much higher and more meaningful level, across the various services I might use as a result of my online existence. Now we just have to agree on what that will look like, and if history has taught us anything, it won’t happen fast.

Thoughts?