With the transition to business school, one of the things I struggle with is using Entourage for email and scheduling. For the last few years I used Gmail and Google Calendar at work. It was a relief to stop using Outlook — and at the time I vowed that I’d never go back. But apparently not every institution (Columbia) is comfortable with reducing their licensing fees and technology overhead costs.

Here are the pain points for me right now:
* Searching isn’t intuitive in Entourage. I have to use the search options to expand my search to include different folders and to search over the title/body/etc.
* Because search is a pain, I often resort to sorting my email (e.g. to find a message from a particular person or with an attachment), but that is even more time consuming. Then I have to unsort the mail when done.
* Organizing email is time consuming and restrictive. I used to just archive my email and not think about it. Now I’ve had to create folders for my email and file everything. In order to replicate the Archiving experience, I created a general folder called “archive” and just stick things there instead of deleting them (in case I need to reference them later).
* The outlook ‘Flag’ feature isn’t a substitute for staring messages.

And here are some of the benefits I’ve found from using Entourage and Exchange for my email/calendar:
* Nice integration with the iPhone, with push email, syncing and event notification. When will Gmail support push email?
* Entourage calendar syncs well with iCal, which I sometimes prefer to use.
* I like the ability to put the message preview pane on the right side of the screen instead of having it beneath the list of mail.