With this so-called “cloud computing” stuff, the theory is, if you want to do something, you “do it in the cloud.” The prospect of having your data, applications, life, beaming magically “up there somewhere” to be fetched from anywhere is kind of liberating. It’s a realization of a promise from the early nineties, when the interconnectedness of all the computers on earth offered up a world of possibilities and captured our imagination.

I’ve found there are some facets of our digital life that work well “in the cloud.” Without realising it, services like Picasa are cloud services which were around before that term was trendy. For newer stuff, I’ve become an instant convert to online file backup services like DropBox: they seamlessly bring the cloud into our computers and we take comfort that a copy of our data is “up there” and kept in sync with the “real version” on our laptop.

But what about calendaring, contacts, etc.? The advent of smarter PDAs has meant that in theory, at least, you can keep your life organised and in your pocket. Microsoft Exchange and all your traditional Mail servers have been a kind of cloud service for email and calendaring for ages. With the advent of PDAs came the complex nut of keeping things in sync. It was easy when there was a wire, but then you really only had 2 copies: one on the PDA, and one on your laptop or the exchange server. If you kept them both in your bag, and your bag went missing!

I’ve been trying to achieve the dream of separating my work calendaring from my non-work; do calendar sharing with my work colleagues (for the work one) and with my wife (for the non-work one); have the calendar, contacts and task data synced between my iPhone and laptop; and keep a backup of each of these in at least one other place – in the cloud.

If you have an iPhone (and like me, a Mac), your world is simple and you don’t mind paying, you can just use MobileMe. It even has its own version of file storage in the cloud which can extend to your iPhone with a free app: iDisk. But I use an Exchange server: actually it’s Zimbra -, Google Calendars (because they’re the easiest to share and they’re free, for personal use), an iPhone and a Mac.

As I searched for ways to make this all work, I found the choices are almost infinite. Where should the data “reside?” Which device or service should be the “authority?” The epiphany came when I realised you have to think of your iPhone and the Mac as viewers of data out in the cloud. The cloud copy is the authority, and your apps (iCal on the iPhone and Mac, for example) modify the data in the cloud when you interact with them. The piece that’s missing is what happens if the copy in the cloud gets corrupted or goes offline? At the moment I don’t have an answer, but I’m working on it.

So on the Mac, I setup Google Calendars using Caldav and also set up Zimbra using the same. On the iPhone, Zimbra works natively as an Exchange server, so that part’s easy, and from 3.0 onwards you can setup Google using Caldav, too: which means you get to modify events and do everything natively from your iPhone. The final trick was to enable the subscribed calendars from Google to show up on the iPhone as well, using this less well-known info. It all looks easy now, but it took ages of Googling, trial-and-error, losing appointments, duplicating all my contacts, and other fun to make it fly.

My next challenge is to find a web interface I can use in the unlikely event that I don’t have a Mac or an iPhone handy that lets me see all calendars together – and despite my best efforts, I haven’t found one yet. Google’s apparent ability to view a read-only version of the Zimbra calendar works in theory, but it doesn’t show up: so go figure. It’s not a major problem but if anyone else has solved it, comment away.

Ok, so here comes the point of all this rambling: if I had to go through all this jiggery-pokery to get the cloud to work for something simple like calendars, what hope does your average busy enterprise worker have of using all the great apps the cloud has to offer without losing data, keeping it all in sync, and not going mad? As all the apps move from the desktop to “somewhere out there” will they communicate? Get backed up? Meet the business requirements that were solved with the shrink-wrapped stuff? Does anyone else smell chaos ensuing?