For a single mom with three kids, two of them teens, keeping a schedule is complicated enough. Add someone like me to the mix and things get out of hand pretty quick. Because that’s the situation my soon-to-be-wife Laura and I have created, I’ve been asked/directed to figure out a good, friendly, reliable and especially non-geek-usable way to do shared calendars where everything just works. I think the term Wife Acceptance Factor is about to have very real, personal meaning in my life.

At any rate if you have any bright ideas let me know. Here is what I have come up with and am thinking about so far:

• Google Calendars on a new Google Apps domain — I have already acquired and set up a custom domain (ourfamily.cc) so we can have individual and shared calendars, docs, email, chat, etc. in that environment. We want to share calendar details with each other, not the whole world.
• My other calendars at greghughes.net — I have this hodge-podge of Hosted Exchange and Google Apps Calendars on this domain. I will need to find a good way to sync and share the info without sharing it to everyone.
• Work calendar(s) — Typically on Exchange and accessed via Outlook, and I need to share only the free/busy data, and only for certain item categories to be appropriately security-conscious.
• TripIt calendar(s) — for travel arrangements, keeps things automagical and simple. Want to incorporate those.
• Access via Mac (iCal or Entourage), PC (Outlook), mobile phone (Android and iPhone) and via the web (Google Apps), with all the info always synced and up-to-date.

Tall order? Might be, but it seems to me this is they way it should be, so it’s what I expect: Any device, anywhere, any calendar, always in sync, full authorization control over sharing and updating, no worries, no hassle, and easy for non-IT folks.

I’ve read over my friend Scott Hanselman’s notes about how he has set up his system for similar needs, but that post is about a year old and he refers to some unnamed, secret-sounding plugins so I will need to touch base with him and see what he knows and thinks. In the podcast he and Carl Franklin recorded on the subject back in 2007, Scott noted “the fact that it’s no trivial task and I struggled with it speaks to the state of Internet calendars in general.” Surely things must have improved since then.

And then there’s this blog post. Wow, uber-geekness.

I’ve used Google Calendar Sync before, but the laptop it ran on has since taken a long dive off a cliff and is no longer with us. I think I probably need to check out SyncMyCal, as it would allow me to be more granular than with Google’s app. A comparison with Google Calendar Sync is here.

Someone really should write a tool that does all this or all of us, cross-platform, and make it all Automagical ™. Anyone want to partner on a project?

What’s worked for you? Anything? Let me know!

To read more about this sort of thing, converting HD DVDs to Blu-ray, exchanging water-damaged iPhones, network security, setting off fireworks on the 4th of July, or whatever else Greg Hughes feels like talking about, you should drop by his blog. He may not update daily, but the wait’s always worth it!

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