Calendar mayhem!

I have trouble remembering appointments, family events, birthdays, etc. so I rely heavily on a calendar to keep my life in order. This is true for both my personal and business life, so like to keep two separate calendars to keep things compartmentalized. The issue I’ve been struggling with is finding the most efficient way of dealing with these two calendars and keeping them synced with my computers and mobile devices.

So here’s what I have available:

  1. Personal calendar for my personal appointments and events
  2. Business calendar for my work appointments, travel dates, etc.
  3. An iMac at home running Snow Leopard Mac X OS
  4. A Dell laptop running Windows 7 for work
  5. An Apple iPhone 4 as my smartphone
  6. Microsoft Exchange Server for my work email, calendar, and contacts
  7. Apple MobileMe for Calendar, Email, and Contacts
  8. Google Calendar and Contacts
My goal, is to be able to view and edit my calendar appointments (personal and business) on my iMac desktop computer, Dell laptop, and iPhone device. I know there’s all kinds of 3rd-party freeware and commercial software for syncing calendar data between applications and the cloud, but I wanted to minimize that as much as possible to eliminate any chances of “foul ups”.
I ended up using this solution: Create two calendars with my MobileMe account that allows me to create,view, and edit appointments. If you’re unfamiliar with MobileMe, it is Apple’s cloud-based system which allows for centralized email, calendar, contacts, and offline disk storage. Using this method, I can always access my calendars via a web browser with an Internet connection. Because the majority of my devices are Apple-based, it made sense using this method for syncing purposes. So, I now use the Apple iCal application to access both MobileMe calendars on my iMac desktop computer, and the built-in Calendar app on my iPhone for doing the same. For my Dell laptop (running Windows 7), I use the Microsoft Outlook application along with a MobileMe syncing utility (provided by Apple) to sync my two MobileMe calendars with Outlook for local access. This method seems to work well so far, but I need to always make sure I’m viewing the two MobileMe calendars in all my apps and not the default local calendars (which should be empty).
Now, if I decide to move from an iPhone to an Android or WebOS phone in the near future, I’ll have to re-think this current setup. I don’t think there is an easy way to access the MobileMe Calendars on either the Android or WebOS devices (for viewing and editing), so that won’t suffice. Instead, I’ll probably need to substitute Google Calendar for MobileMe and try that method. The only bad thing with that plan, is that the free Calendar syncing utility provided by Google will only sync one calendar from a Google account to Microsoft Outlook, so I won’t be able to use two calendars effectively without possibly buying a 3rd party utility.
Or, I could just forget about using two calendars and stick with just one, which would probably be a Google Calendar since that is the most universal calendar on the Internet. If I did that then I certainly would not have the option of sharing that calendar since I want to keep my personal appointments private.
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