How to sync 'On My Mac' calendar with multiple devices

Question

Hi
This is an ongoing problem for me and I have decided to become more pro-active in seeking a solution. I would be grateful for any help whatsoever.
In summary, I need to understand how I can sync calendars that are 'On My Mac' with iCloud, so that then I can see them on any of my devices. I don't mean export - I am looking for a solution that creates a constant, updating feed.
I cannot use iCal as my primary calendar location. I need to send a lot of calendar invitations to people who use MS Outlook for their calendars and MS Outlook does not accept invitations from iCal. Therefore I have migrated to Outlook for Mac 2011 as my principle calendar client. (A temporary work around was that I continued using iCal for a short while but send invitations using Gmail. This works, except that for my clients it became confusing and they started thinking that my main email address was a Gmail address and that is a problem for me.) So I am using Outlook for Mac 2011 which enables me to exchange calendar appointments with other MS Outlook users with no problem. At this stage these appointments don't show up anywhere except in Outlook for Mac 2011 on my iMac at home and I am hardly ever there. So I need them to reveal themselves on my Macbook Air, iPhone 4S and iPad as I drive around meeting everyone. The problem is made worse by the fact that I work for several companies, all of which expect me to use their own email accounts to set up these meetings. Outlook for Mac 2011 is good for that. So the next step for me is to go to Preferences in Outlook for Mac 2011 and select Sync Services. This helps because it sets up an instantaneous feed from Outlook for Mac 2011 to iCal on the same machine. Great, but not perfect as they are all stuck in the 'On My Mac' section of iCal - which does not sync with iCloud.
That is where I get stuck.
Can anyone help?
With best wishes,
Tom

Answer 1

Hi Snozdop,
Thank you for your quick and helpful reply. Yes it does seem astonishing that Microsoft is not helping with a problem that must be affecting many of their customers.
Actually pretty much all the appointments are already in iCloud as I exported them to Outlook for Mac as part of this recent burst of activity. So populating iCloud again will not be a problem, if I need to.
It is helpful that you have referred to Exchange. If I am hearing you correctly then you are saying that any appointments that I set up using email accounts that use Exchange can easily be set up to show on all of my devices. This means that if I set them up using Outlook for Mac, then I will not need to use Sync Services in Outlook for Mac to inform iCloud of my schedule.
But if I am also hearing you correctly, I will still need to use Outlook for Mac to set up the appointments because other people's Outlook systems will still not recognise calendar invitations sent from iCal, even if the email address used to set them up uses Exchange. Is that correct?
If so, then I suppose I can work with it - although it still seems somewhat elaborate. I would be using Outlook on my iMac and Macbook Air and iCal/iCloud on my iPhone and iPad - all connected via separate accounts using Exchange.