#GoneGoogle - Taking off into the Cloud

I originally micro-blogged about this on my twitter @MatthewMMorrow but here is a full write-up.

I don't know what initially caused it. It was like a disease. Us geeks get strange urges to do something geeky for no real reason. On the positive side, I am very happy where I've come. I have weaned myself off of my dependence on desktop based personal management software. I have left my comfortable Microsoft Outlook software and surrendered to Google.

How it was

I used to use Outlook for everything. I probably had a dozen email accounts so I could best filter my email and reduce spam. My Outlook PST files are now interred at a whopping 1.51GB. Performing a backup of my data would take a long time and couldn't be done with Outlook running so it rarely happened. Outlook was my email, calendar, tasks, contacts, and notes hub. The problem was that my laptop had to be running and I had to have access to it in order to check my email and go about my daily business.

How it changed

GMail
My first to step was to setup GMail and all my email accounts. Grabbed my desired username (which is used for all my Google services) and loaded up GMail. Luckily GMail will check external POP3 email accounts. (Guide from mydigitallife.info) Perfect! Now all future mail will be received by GMail. I turned on "leave mail on server" in each Outlook account so it didn't affect GMail's retrieval.

The next goal is to get all my old email into GMail.
There are notable differences in the features available to email messages:

• GMail uses "labels" instead of folders. Labels are quite different because you can have multiple labels per mail message. To maintain a heirarchical structure you can use the "/" character in your label. For example: Animals/Puppies will tell you that Puppies are grouped under Animals. In GMail labs I recommend the "Nested Labels" gadget will let you expand and collapse your label hierarchy like you would expect to happen to folders.
• Gmail uses "Star" instead of "Flagged". Again a GMail lab called "Superstars" will give you multiple "Star" actions.
• GMail groups your emails into converstaions. An email and all its replies will be displayed as one entry and expanded when opened. Keep that in mind while looking for old emails.
• GMail's Inbox is a type of tag. When you "archive" an email it will remove it from the inbox and it can be found in the "All Mail" screen or in the screen for the labels it was tagged with.
• GMail discourages deleting in favor of "archiving". I say just go ahead and delete something. Messages are held in trash for 10 days.

I used  this guide from labnol.org to help me move my emails. It was fairly straight forward but since I had an Outlook Archive PST I moved those folders to a special "Archived" label.  This is also a very good time to organize your emails. I would recommend organizing and double checking in GMail. You can do a simple item count to see if everything transfered but remember, converstaions count as 1 item while they can contain multple emails. Also, make sure you drag any "Sent Items" to the appropriate GMail IMAP folder.

I'll post later about how to trim down your unruly email cache.

Google Contacts
The next very important feature from Outlook was my contacts. Who would I email if I didn't have any contacts? Microsoft even tells you the easiest (but also less advanced) way to export your contacts. I'd review your contacts and make sure no important data is missing (e.g. birthday, anniversary, addresses). Export and Import wasn’t the approach I took…

Google Calendar (and Contacts again)
Since I can sync my phone to Outlook's calendar and contacts I also wanted to be able to sync Outlook and Google frequently and automatically. What is also important is that for the calendar I use multiple categories to color my items. There is another difference in Google.
    Google Calendar does not have categories. This is a huge oversight! GMail has labels but Calendar has nothing of the sort. The solution is to make multiple calendars. (Here's how: http://www.brighthub.com/internet/google/articles/2841.aspx). Unfortunately that means each event can be on one calendar (unless is just a copy) but its a simple solution for now.

So for my syncing I had to turn to some 3rd-party solutions. This section turns into more of a software review...

• Google Calendar Sync (http://www.google.com/support/calendar/bin/answer.py?hl=en&answer=89955) - This is made by Google. It doesn't do contacts and it only supports syncing with the main calendar so in my book it is pretty useless. It would be great if they expanded it!
• gContactSync (http://code.google.com/p/gcontactsynch/) - Contacts only. I for some reason it didn't correctly find my contacts so it didn't work.
• GO Contact Sync (http://lifehacker.com/5193636/go-contact-sync-keeps-google-and-outlook-contacts-matched) - This one worked OK. It was a little trick to get running the first time and it seems to get screwed up by adding contacts to both Outlook and Google. No category sync :-(. I was able to get my contacts into Google but then I stopped using this sync. Organized my contacts so now Google is my main repository.
• RemoteCalendars (http://remotecalendars.sourceforge.net/) - This doesn't actually sync your calendars it just displays them in Outlook. Works with any internet calendar.
• KiGoo (http://www.getkigoo.com/) - Again, no sync but is a very good Google Calendar integration. Shows up and is editable just like any Outlook calendar.
• SyncMyCal (http://www.syncmycal.com/home.htm) - This was ok but still not quite the feature set.
• OggSync (http://oggsync.com/) - Very good software. Didn't end up using it but it did give me the idea to setup filters to sync each different Outlook category to a different Google calendar.

The winner:

gSyncIt (http://www.daveswebsite.com/software/gsync/) - The software I ended up purchasing for $15. This will also sync notes (to Google Docs) and tasks (to Google Calendar) and has advanced filter options. Once its setup it works great.

NOTE: PLEASE BACKUP YOUR DATA BEFORE USING ANY SYNC SOFTWARE, ESPECIALLY IF YOU ENABLE "DELETES". I ACCIDENTALLY DELETED ALL MY CONTACTS THROUGH A BAD SYNC BUT GOT THEM FROM THE TRASH"

Google Tasks
Google Tasks is a joke. For a task you can only provide title, description and due date. My Outlook tasks were more complicated than that. I need at least repeatability and preferably repeat after completion. Remember the Milk doesn't provide the latter and does not currently offer any way to sync with Outlook.

My choice cloud-based task software is Toodledo (pronounced to-dull-due). They also recommend software that will sync between their service and Outlook software that will sync between their service and Outlook. Bonus: Toodledo also provides a "notebook" feature and the software will sync your Outlook notes with your Toodledo notebook! My favorite feature is syncing by importance (not priority). Importance = 2 + priority (3,2,1,0 or -1) + starred (1 if you marked it as starred) + due date (6 - overdue, 5 due today, 3 due tomorrow, 2 due this week, 1 due 2 weeks). This means that your lower priority tasks with a closer due date are more evenly matched with your higher priority far away tasks. Getting a pro membership will let you share task, create subtasks, show statistics, and give a recommended schedule of tasks to complete based on time. One downside is that completed tasks are deleted after a while (6 months) but I might not miss them.

Conclusion

Well that covers all the features of Outlook. I am very glad I moved my data to the cloud. About a month after my transition I spilled soda on my laptop and had to get it sent into the factory. All this time I don't have Outlook but it doesn't matter. I can check my email and tasks from any browser anywhere. Speaking of browsers, I'll write about how to make all my information more accessible using Chrome and also about the other Google services I've tried.

Of course there are other minds, like those at zenhabits.net which prefer to go Google-free. The main lesson I learned here is that cloud computing rocks and the more cohesive your services the more synergy you gain.