I shot a question off on Twitter last week simply asking for a decent Outlook replacement on the Mac. I received a few recommendations, mainly Entourage & Thunderbird. I thought it best to detail my needs in a blog post to solicit more detailed responses.

I have email correspondence dating back to 1988, when my messages were either on electronic bulletin boards, Prodigy, or Compuserve. My message archive has been copied into Word documents, converted to Compuserve mailboxes, and ultimately into Outlook PST files. It is my hope that at some point I can transcribe some of those messages into a memoir of some kind.

Given the GINORMOUS archive of messages, I have been slow to move away from Outlook, currently the only PC application I still use. I know I can run virtual Windows on my Mac, but I really don’t want to fire up Fusion just to check email. I also have pushed the limits of the program by including Notes & Categories in all my Contacts, while tagging messages & calendar information. Currently, I sync my Outlook calendar to my Google calendar which makes it easy to get my schedule to people who need to know. And there’s the little used Journal feature which helps me track billable time on projects (also tagged with Categories & associated to Contacts). Outlook also syncs with my phone so I have a 90 day snapshot of everything I need on the road. Chances are you could ask me what I have done on any given date in the past 20 years, and I could find it somewhere in Outlook.

Which leads us to my original question – what application (or group of apps) would best suit my information management needs?

I use Gmail which excels in terms of message searches. I do not have any folders setup for my Gmail account. I simply search for the thread I need, and it’s so much quicker than Outlook.

Thunderbird looks like a possible option, and it appears to have a calendar plugin, but what about contacts? I would want to use the Notes (& Categories if possible) from my existing Outlook contacts.

Entourage seems like a poor man’s Outlook. I’m not sure I want to exchange one single-file message system for another single-file message system. Also, I remember reading something about Spotlight searches were incapable of reading the Entourage data file. I would lose my Google calendar sync option with Entourage.

I might have to change my approach to this problem. I was hoping to move some of the current Outlook information into the new system I choose, but I may have to do a “clean slate” cutover. This would entail still using Outlook for message/calendar history, but that may be the front-runner solution.