As I noted earlier, I have added a PowerBook to my computer lineup. I enjoy using Mac OS X (10.4), and find it to rarely be frustrating, unless we’re talking about keyboard shortcuts, and usually pleasant. In fact, pleasant is an excellent word to describe the experience; it’s neither thrilling nor bad.

But this post is about my decision to leave Microsoft Outlook and turn to Apple’s PIM suite, which includes iCal, Address Book, and Mail. Reasons for this switch include:

• Increased use of my laptop and decreased use of my desktop, which makes having PIM data on laptop desireable
• (Alleged) Ease of synchronizing my Motorola RAZR v3 with Mac OS X, iCal, and AddressBook
• The use of open standards by the Apple PIM suite versus proprietary formats of Microsoft Outlook.

The Plan
Because I had heard switching out of Outlook could be difficult and because I did not know well Apple’s software worked, I decided a good plan was to do a series of test switches. I would move small amounts of information from Outlook’s Mail, Calendar, and Contacts sections to Apple’s Mail, iCal, and Address Book. I would also test syncing with my phone and PDA, a Handspring Visor Deluxe. If the transfers worked smoothly and if I liked the software, then I would make the switch. Otherwise, I would continue using Outlook and/or look for alternative solutions, including Microsoft’s Entourage.

In thinking, talking, and doing research about this process, I realized that the resources for such a switch are inadequate. Although I did not do an enormous amount of research, only enough to pull off the switch, I found that there was no central resource to guide a user through the process and the resources that were geared for each specific part of Outlook were poorly written, usually providing little background or explanation. I decided, therefore, that outlining my experience might be helpful to others, as well as demonstrate the difficulty of leaving Outlook.

Mail
From the beginning, I knew switching e-mail clients would be the easiest part. That is because transferring e-mail is essentially a process of e-mailing your old e-mails to yourself and then downloading and archiving them in the new client. The harder part of the switch would be to recreate the archiving system I use and establishing multiple accounts in Mail.

Because the e-mail process would be easy, I decided to not worry about it during the testing phase. Instead, I focused on the archiving system and multiple accounts. The first step was to create a single account. Mail makes this ridiculously easy, as it does for creating multiple accounts. In fact, Mail handles multiple accounts better than Outlook in a couple ways. One is that in each e-mail you create, there are drop down boxes that display and let you choose which account and signature to use. I believe that the signatures can be tied to the accounts, something I was once able to do with Outlook but currently do not. Second, when you create a new e-mail or reply to an existing one, Mail is smart about which e-mail account to use. More specifically, if you create a new e-mail, Mail sets the account to the one that you were last viewing (the Inbox of). If you are replying to an e-mail, it uses the account the e-mail was sent to. Very basic, obvious, and simple.

After setting up two of the several accounts I use, I was satisifed and moved on to establishing the archiving system I use via rules. The rules options are more limited than Outlook, but extensive enough to cover the basic tasks, especially if you are clever in how to create rules. I have some minor glitches to figure out, but I was able to crudely establish rules that saved every e-mail sent and received to specific folders. Particularly difficult, and something I plan on revisiting, is archiving the sent mail, as it appears the rules are only applied for e-mail that is received. For now, I have all e-mail sent BCCed to me, so that a sent mail rule is applied. Despite these problems, I was satisfied enough to deem the test a success and move on to the next part.

Calendar, Handspring Visor Deluxe, And RAZR
Outlook does not permit you to export its data in open standard format, such as vCards. There are export options, but my experience trying to sync my RAZR via CSV and TSV demonstrated that Outlook is deficient in its ability to properly place commas and tabs. In doing research for how to transfer my calendar events to my Mac, I found that many people used fairly complicated multi-program solutions. For example, they might use one program to import from Outlook, then export to another format, and then import that format to iCal. These roundabout solutions were not attractive and came with their own problems (think mapping issues).

I was surprised to find that no one had thought of just syncing their PDA to Outlook then syncing it to iCal. I soon found out why no one recommended that. It turns out that Palm has let its Mac support languish in Mac OS X. On most installs, and nearly all installs for older PDAs, errors popped up with the syncing software. Although there is third-party syncing software, it is expensive and designed for newer models. After searching for some time, I realized that my Visor Deluxe and its Palm OS 3 were no longer welcome in the new technology world. It was either stick with Outlook and use my PDA or give it up and go with Apple.

I chose give up the PDA for two reasons. First, some of the benefits received from carrying the PDA around will be returned by my carrying of the laptop. For example, while traveling, I will have my PowerBook with me so it is not necessary to also have the PDA.

The remaining issue was day-to-day use, and for that, it was possible my RAZR could fill in. I decided to test the phone’s ability to sync with iCal and Address Book. I was pleased to find that the phone charges via the USB connection; I knew that could happen on a PC but had doubts about whether it would work on a Mac. During the test sync, I sent data from my phone to my Mac, as there was no data on the PowerBook. It worked great and so I felt confident that the phone could replace the PDA for basic use. With that, I decided to ditch the Visor and continue with the test phase.

Although the Visor failed and the phone passed, I still had not transferred Calendar data to iCal. The PDA transfer method did not work and a similar phone transfer method would not either because of the difficulty of syncing the phone to a PC. After some searching using various search terms, I came upon outlook2ical. It is a powerful macro that converts Outlook Calendar data into vCard format. The Web site offers directions that are clear enough for any user to follow. Exporting was a breeze. Importing was also simple. Because iCal uses different “Calendars” (really just different labels), I created a label called “Old” that I applied to all imported Calendar data. Then, as I go along, I can label events as “Personal” or “Work” or whatever else I want. This way, my mixed labeled Outlook-created events do not incorrectly mingle with newly created and properly labeled iCal events. Not only was the test phase a success, albeit long and arduous, but all data transferred so the final phase is also completed.

Contacts
I was most worried about the Contacts because, so far, I had not seen any solutions that worked, had seen solutions that did not worked, and had had past nightmares with mapping issues. However, I did quickly find the answer. Although Microsoft does not allow you to export your contacts as vCards, you can “Forward [them] as vCard” via the Actions menu. By selecting all of your contacts and forwarding them (via e-mail), you can have the vCard versions of the contacts on the Mac. Transferring them to Address Book is simple, either drag and drop them or use the import wizard.

For 90 percent of my contacts, this worked without problem. For 10 percent, however, some fields were added or the actual data was not imported/saved. Therefore, I recommend going through your Address Book list and comparing it to the Outlook list. Even though this takes time, it is much faster than manually entering the information or using a more expensive/less effective solution. As for the iCal switch, my in-depth test also served as the final phase full switch.

Returning To Test The RAZR
With all of my calendar and contact information on the Mac, I wanted to better test syncing the RAZR. As before, connecting and starting the sync was simple. This time, however, the results were not so spectacular. The syncing overwrote my phone book lists, placing all of my contacts in the same category (General). For the record, Motorola’s phone software is terrible, and so some blame should go there. Nonetheless, we have a problem. For the calendar transfer, however, the process worked incredibly well.

Despite the phone problems, I plan to move forward. I may just choose not to sync my phone list, and instead manually enter the list–I am not sure, though.

The Final (E-Mail) Phase
I am currently (20060210) finishing the final phase of the e-mail transfer. It is taking much longer than I expected to transfer my archived e-mail. Perhaps it should not, given that there is about 12,000 e-mails during the past 1.5 years (previous e-mails were lost in a total loss of data incident; thanks Linux!).

I have been using iCal and Address Book for a couple days and am happy with the switch. The keyboard shortcuts, as with all Apple-related software, are borderline absurd, and this is the worst part. I also do not like having three or four (e-mail, calendar, address book, notes) applications open at a time, but the quality of the software is worth it. Plus, I have just started playing with a virtual desktop program (thanks ZS) that could simplify things. Alternatively, once everything is switched over, I plan to add a second monitor to my laptop when I am at home (desktop currently has 19 inch CRT, 15 inch LCD, 27 inch flat screen tv, and there is a 15 inch CRT for the laptop that I do not use; plus a 17 inch CRT for my file server).