I switched to a Mac last year and I couldn’t be happier … except for one thing. Apple Mail and iCal just aren’t powerful enough for me.
As the Director of Carson Systems, most of my day comprises of emailing, coordinating things and checking to-dos. Ever since I’ve moved to a Mac, I’ve been frustated with the disconnected nature of Mail, Address Book and iCal.
Here’s what frustrates me about Mail/Address Book/iCal:
- There’s only one flag in Mail. Life is complex and email doesn’t often fit into one category. I hate having to move mail into seperate folders as it’s a waste of time. I’d rather keep everything in my Inbox and categorize and flag it as necessary.
- To-dos in iCal are a complete joke. The lack of categorization and easy reminders makes life hellish.
- Address Book is pretty good, in general. But it doesn’t need to be a separate program.
- Mail often freezes up on me as it’s not built for the huge amount of email I send and receive.
I’ve tried really hard to make Mail/iCal/Address Book work. But it’s just not good enough. I know that a lot of folks preach about how simple software is better. But you know what? If you’re a power-user, early adopter, it often isn’t.
Why I’m switching
Here are the features in Outlook 2007 that I’m switching for:
- Categorization of emails, todos and calendar items is simple yet powerful. Instead of moving emails into folders, just categorize them appropriately (You can create custom categories and assign them colours).

- You can choose from a set of flags (Today, Tomorrow, This Week, Next Week).

The beauty of this is that as soon as you flag it, it automatically creates a to-do for you and sets a reminder. Bam!
- The calendar in Outlook 2007 now supports the ical format, so you can subscribe to Google Calendar. We do this at Carson Systems to share the company calendar (annoyingly, however, you can’t update from Outlook - you have to go to Google Calendar).
- You can assign to-dos to people. This is brilliant for delegating (which is how Directors spend most of their day!)
Latest version of Parallels makes it even easier
I just upgraded to the latest version of Parallels and it makes it even easier to use Outlook 2007. Here’s why:

The above image is a screengrab of my OSX Dock. Parallels actually seperates out each Windows program! Now I can go straight to Outlook, Excel, IE, etc with one click, like native OSX programs.
And running Parallels in ‘Coherence Mode’ means you don’t have to look at the rest of the (ugly) Windows XP/Vista OS.

Getting things done?
As probably most of you know, I’m a GTD freak and I love being efficient. I thought I had it nailed with my Omni Outliner to-do method, but I found it was starting to slow me down. The fact that Omni Outliner doesn’t support due-dates and reminders is a real problem. I found myself having to go into iCal and set reminders for the really important date sensetive stuff.
I’ll report back to you with how it’s working for me.
The annoying parts
Before you all go off and buy Parallels and Outlook 2007, let me tell you about what isn’t so great about it:
- Key-mapping is a bit of a pain. For instance, you have to hit fn-backspace to delete things (MacBooks don’t have a Delete key).
- You need to have a seperate backup solution for Outlook. We use Super Duper for OSX and it rocks. But now that all my super important data is in Outlook, I’ve got to figure out a seperate solution for it as well (any suggestions welcome!)
- It’s expensive (XP + Outlook 2007)
- You have to spend a day moving your data across, which is major pain-in-the-neck
- If you’re in an airport and you buy a wifi pass (while in OSX), it won’t let you use it in Parallels, as it thinks it’s another computer. Argh!
However, even given those negative points, I’m very excited about the productivity gains I (and the company) are going to reap for switching.
Tips for migrating
If you’re going to follow my lead (which I recommend you think long and hard about first, here are some useful tips for moving over to Outlook 2007.
- Use this tip for moving mail from Apple Mail to Outlook 2007. It’s a bit crazy, but it works. Some of the characters in email get screwed up, but overall it works fine.
- Use this vCard converter tool to import your contacts into Outlook 2007. It’s well worth the $25. Outlook supports vCards (hooray!) but has problems importing more than one at a time (boo!). This tool helps you get over this problem.
- Get your to-dos into CSV format and then import them into Outlook.
Please comment and let us know how you get on with this, if you decide to migrate.