Having used Outlook myself for amny years I would advise against it. I ran into far too many issues with it, if you really want I could list a few of them.

I'll put in a plug for Thunderbird. Pros:

• Should be easier to migrate mailboxes from Eudora to Thunderbird (one set of warnings and helpful tools here)
• GTD starter tips here -- these are the ones I use myself.
• Least-sucky IMAP implementation commonly available? Only relevant if you want IMAP, though.
• Thumb-drive friendly, if not speedy with Portable Thunderbird. Of course, you could install this to any writable space (iPod, external drive, network share, etc.) with a corresponding boost in speed.

• IT may not support it.

As far as searches go, I'm pretty happy with it. Using a nearby IMAP server, I searched through my Archive folder (1553 messages, 535 MB) with the following results:

• Subject search: around 1.0 seconds
• Full-text search, including message bodies: under 7 seconds, depending.

I'd expect searching a local store of email would be faster, but this is fast enough for me. As often as I've seen others' search methods devolve to "sort by sender name, page through results, squint at screen", I'm way ahead.

I used Outlook for many years prior to finding GTD. I found Outlook to be a great program, and I liked how everything - calendar, email, tasks, notes, and contacts were in the same place. It really allowed me to see the "big picture" of how people, events, and tasks were interrelated.

Then I found GTD. I expanded my system for use at work and home. I realized that Outlook, despite its many great features, wasn't doing it for me. My planning/tasks process is all-analog now, super portable, and without the software bulk. Because I needed a portable system, I switched to using Essential PIM on my thumb drive for my calendar and contacts. Not only is Essential PIM free, but it looks and feel very much like Outlook minus email. (I'm not affiliated in any way with the company). I'm very happy with it.

I'd recommend trying Outlook if its available, especially if your IT will support it. Sure, it's limited to the desktop, but I know many people who use it with success. If you don't like it, you can always find a replacement.

On a side note, whatever program you decide to use, be sure to archive your email messages. My company uses Novell Groupwise. I opened my archive folder the other day to discover that emails dated prior to 3/23/07 had been deleted from the server. :eek: Luckily, I had the important ones saved in Evernote.

Most IT places which delete mail after a certain time do it for good reason and archiving your mail may be forbidden as well, better check first.
OK, Outlook Issues, I've worked with it since OL97 in both a support and user role:
#1, everything isn't in the same place. You have t look in the calendar for appointments, the tasks for todo's then in the journal for other things, then if you want reminded of a simple birthday you have look in the contacts or set a reminder manually as there isn't much integration between the parts of it. You can get kind of a big picture of part of your data on the outlook today but not all of it.
#2, is the use of the PST for data store for most of it (if your not on an exchange server), though in new versions you can use ical. The PST is a huge database file which likes to get corrupt easily and you can't make backups without closing outlook first because its locked for writing all the time. Run scanpst often and make backups often. Then if your on an older version you have to archive to keep the pst from hitting the 2G limit and with newer versions you still want to keep it smaller than 2G anyway. then comes the problem of opening those archives, sometimes one gets stuck open and other times mail sorting rules send your mail to the wrong .pst file even if you don't have it open.
#3, you will need serveral third party plugins to get some of the basic functions that are found in decent mail programs then your Av program will have to understand outlook macro virus as well.
#4, too high of cost, if OL could be bought for under $50 it might be worth it but a real license is around $100 or pay hundreds for the whole office suite with more buggy programs.

yes OL looks nice and has a lot of nice feastures, but once you get to power user status you start to find a lot of issues, bugs that have been there through many versions which never got fixed, badly thought out workflow issues, etc.

Another option might be Penelope, an interesting hybrid of Thunderbird and Eudora that's being developed:

http://wiki.mozilla.org/Penelope

I tried it for a few days. Then I switched back. At least I was smart enough to leave my mail on the server during this experiment, so it was remarkably painless to switch back. I'm not ruling out changing software tools eventually, but I figured out that now is NOT the time to do so. I'm still getting my GTD system up & running, so what makes sense is to stick with the tools that I already know well.

In other words, concentrate on the "meat" of personal productivity, collecting & processing, accomplishing tasks, reducing my stress level while increasing my throughput. Not learn a new software tool.

-Mark