There are a number of changes afoot in my personal toolset. One of the big ones is that I am dropping MS Outlook for Google for my email, contacts, calendar, and tasks. And not only do I want it to be a smooth transition, but I also want all the connections to my current mobile, an iPhone.
I've been an Outlook user since about 1996, and my fingers have collected a strong muscle memory for where things should be. And my mind keeps thinking about things in the Outlook framework. This is why I've stayed with Outlook so long. And it is why I am surprised at how (relatively) easy this transition has been. For instance: in Outlook (and many computer-based applications) separate windows can open for each message or contact or calendarentry that I have open. In a browser, this changes either to separate tabs or the happy realization that Google remembers where you were.
The big question for me was how I was going to transfer my email, contacts and calendar entries from Outlook on my standalone computer to Google and "the cloud." Happily, there are a lot of people who have done this before and write about it in much more detail than I am going to do here.
For my email archive, I was not hopeful, but I found great success with the IMAP standard for sharing an email account at Google with a client like Outlook. Google Mail uses both POP and IMAP, and they seem to recommend IMAP. To use this, turn on IMAP in the GMail settings (Forwarding and POP/IMAP). Then add a new email account to Outlook (Tools -> Accounts -> add new). Follow the instructions that Google provides for making this connection. Once the connection is established, it's a matter of either moving (mouse drag) or copying (Ctrl-drag) the folders and email you want from Outlook into GMail. Depending on how much email you have, this may take a while. Note that a folder moved onto the top level GMail folder in Outlook becomes a "label" in GMail with all that mail residing there. If you drag a nested folder structure, it becomes labels that look like "top folder/sub folder." But in Outlook and other clients it retains a folder structure.
For contacts, there is basically one tried and true method: Export your contacts to a CSV (comma separated values) file via the File -> Import Export function in Outlook. From there, you go to your Contacts in GMail and click on the More Actions dropdown. From there pick "Import" and follow the prompts to upload your contacts. Google attempts to understand all of the fields from your CSV file -- and it keeps the data in the Notes for each contact, in case it got something wrong. Here's a feature I really like: If you happen to have multiple entries for the same person, there is a way to merge entries. Check the two entries that are the same, drop down that More Actions box and select "merge contacts." There is a bulk "find and merge duplicates" option that is good the first time through.
And then there are calendars. I have known about shared Google Calendars and the ICAL protocol, but I hadn't investigated very far. And Outlook does offer some mechanisms for reading and viewing "internet calendars," such as those shared from Google Calendar or my TripIt calendar. However, Outlook does a terrible job of integrating ALL the calendars into one view, so I have a number of workarounds, in particular the Remote Calendars plugin that reads those internet calendars into the main calendar in Outlook. I was dreading how this would look on Google. Again, happily, it is much, much easier. First off, I recommend removing any special calendars you have in Outlook, such as holidays, birthdays, etc. Then go through the same export routine as for the contacts: File -> Import Export and export the Calendar entries into a CSV file. In Google Calendar, go into Settings -> Calendars and find the Import option halfway down the page. Import into a calendar, and check that all worked correctly. I ended up doing a bit of cleanup with fixing time zones and re-setting repeated events (the export / import process doesn't remember repeat events that I could determine). One great thing about Google calendars is that you can have multiple calendars in one view - color coded to the different calendars. So, you can have the primary calendar, the shared family calendar (or several), and a calendar from your travel-planning service (TripIt in my case). Even better, you can add "Interesting" calendars to your list too: holidays in your favorite country / religion. Even birthdays and other dates from your contact list! This is why I removed my old birthday entries. This are available from the same Calendar Settings page, or from the left-side listing of "other calendars" - there is a dropdown that includes Interesting Calendars.
But then what about the iPhone. I actually checked this before deciding to do any of the above. Great news: all of the material I keep on my Google Mail, Contacts and Calendars can easily synchronize with my iPhone! And it's even better than I thought: it does it all over the air, rather than needing to do a daily sync through iTunes. Note that the standard IMAP setup doesn't do what you want it to do. Delete that mail account entry from your iPhone and go with the MS Exchange settings. Rather than tell you what to do, follow the guidance from Thomas E Cook on how to do it. The one nuance that he doesn't cover is that I had to visit the Google mobile sync page a couple times. The reason for using the MS Exchange option is that you can now have up to 25 calendars syncing with your phone! And in the iPhone calendar option, it is possible to turn on and off any/all of those calendars for viewing. A word of caution for people worried about bandwidth: I suspect this should be done when you are not roaming. (From what I have seen, there are similar capabilities with Android.)
One piece that is missing for me from the Google suite is personal notes from phone calls or other activities. Apparently, I am one of the few people who used the Outlook Journal feature to record notes from calls. While one could use Google Docs, it seems clumsy to do so for me. After asking around, I've decided to try Evernote once again: key reason is that I can use it on a computer (both Mac and Windows) as well as on the web and on my iPhone. I've occasionally missed not having these notes on the iPhone, as there was never a good way to sync them from Outlook.
I am sure I will learn many other things about this setup that will both annoy and surprise me. But after a couple days of this, I think I like it.
[Photo: "Traditional Personal Knowledge Management 2" by D'Arcy Norman]