Best way to manage across Outlook at work and other system at home?

I have been using GTD to some degree or another for 6+ years. The more I use it, the better it is, but a challenge I have is running one system seamlessly across Work and Home. I use Outlook at work, which is nice because I can drag and drop e-mails to the calendar and tasks, etc. Unfortunately Work doesn't make it easy to connect with a portable device such as an iPhone. I have an iPhone with a task app--works OK for things like a shopping list and keeping track of borrowed/lent, but I don't use the calendar on my phone. Any suggestions? The options I see, none of which seem great, are:
  • Use Outlook at work, and iPhone at home--not seamless, 2 calendars doesn't work
  • Use Outlook at work for all home and work tasks, print hard copy for home--don't have remote access to to-do list and calendar
  • Use work-provided blackberry which has calendar and tasks--device is awful

Any suggestions?
 
My approach...

I am in more or less the same position and know exactly where you are coming from. As a freelancer, I have to manage my own personal and professional activities and also be flexible enough to tie into a variety of clients' systems.

I have found Outlook excellent for desktop based GTD because of the drag and drop of emails etc and the categorisation of tasks.

My best compromise so far is to use a hosted Exchange 2010 service which integrates seamlessly with Outlook on my laptop for personal/professional use and I use Outlook Web Access 2010 (useful new task management features in v2010) for access to that information across the Internet from client systems. I also use Windows Mobile to sync the Exchange information to my HTC phone so I can see and update the Exchange information there too.

It's definitely not perfect and has a few frustrations but it's workable. I have been working with this tool for a couple of months accepting having effectively two versions of Outlook open on the desktop while on a client site.

I am experimenting to see if I can sync calendars etc. between client systems and my own but it all takes time and can easily get unwieldy.

I'd be interested in tips on how to improve and 'future proof' this approach.
 
What I Use ...

N8ster;81238 said:
Use Outlook at work, and iPhone at home--not seamless, 2 calendars doesn't work

This method is what I use and it can work!

My technology options at work create a segmentation to my GTD system that I think of in two parts - Main GTD and Work-specific. I don't think this way but that is how technology lines up.

For "Main" calendar I use iCal synced to my iMac, iPhone & iPad (via Mobile Me). On most days I go to my office so I don't worry about putting any work-related stuff in iCal. On some days there is a "cross-over" where I put vacation days, travel, etc. onto iCal because it's out of the norm. My Work calendar is Outlook synced to a Blackberry. On some days I might put a doctor's appointment on Outlook to block it for meeting purposes.

To me it's a seamless process even if it's not literally one calendar.

It's kind of like having two physical in boxes. I need two but I don't need three!

Mark
 
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