I gave up on using folders for email management a while back for a number of reasons:

• No single hierarchy works well for me. I don’t think I’m unique in that respect. Humans generally have a hard time with cut and dry delineations, which is why uber-taxonomies have mostly failed but folksonomy usage is growing.
• Folders complicate search and discovery as they create sometimes artificial buckets of information. When you type in a search query, would you like Google to ask you which parts of the Internet you’d like the results to come from?
• Last but not least, putting things in folders requires constant action. For example, I receive in email about Allurent (one of my companies). Say, I’d have to put it in the Allurent folder. I reply. A response comes to my reply. I need to put that in the Allurent folder also. And so on.

The solution is to take a page out of Gmail’s book and use categories/labels/tags and the absolute minimum number of folders (for me it’s ultimately one as I’ve adopted Inbox Zero). There is no single hierarchy. Search/browsing works well. And I don’t need to always take an explicit action because categories propagate out with email messages. Well, at least they used to.

Enter Outlook 2007 where the good folks at Microsoft decided that showing the rest of the world what categories you apply to your emails is a bad idea. Not sure about you, but I tend you use fairly benign category names and wouldn’t mind sharing them with the world with my outgoing email, provided that I get them back with any responses and therefore don’t have take any extra effort to categorize (pun intended) incoming emails. For a discussion of how Outlook 2007 differs from Outlook 2003 in these respects, take a look here.

For those of you who, like me,  want categories to (a) go out with sent messages and (b) be accepted with received messages, you have to do the following:

• By default, Outlook 2007 installs and enables a rule to eliminate incoming categories.  If you don’t want Outlook to strip out incoming categories, rule “Clear categories on mail (recommended)” can be disabled via Tools > Rules and Alerts.  This will enable Outlook 2007 users to see the category assignments made by POP users on Outlook 2003 or earlier (and I assume other non-Outlook email clients as well). (quoted from the article linked above)
• You need to modify a couple of registry settings. In HKEY_CURRENT_USER\Software\Policies\Microsoft\Office\12.0\Outlook\Preferences, create (they probably won’t already exist) DWORD values SendPersonalCategories and AcceptCategories and set them to 1. I got this tip from Microsoft. You can download a registry file to make this fix from here.

There are two other annoyances with how Outlook 2007 handles categories. First, it doesn’t offer an option to set categories on outgoing emails (since they decided it was a bad idea in the first place). Second, the interface for picking categories is not designed for dealing with hundreds of categories. I developed a small module (technically, a form region–see pic below) that makes it easy to type categories during sending, reading and previewing of messages and tasks. It makes it really easy to work with folksonomies inside your mail system.

Here is how you can use it:

• Download form-regions.zip.
• Extract it to %userprofile%\Application Data\Microsoft\Outlook
• There are three files there. Double click categories.reg to load the appropriate registry settings.
• Restart Outlook.
• You can modify categories.xml file and set the showCompose, showRead and showPreview elements to 0 or 1 depending on where you want to see the categories form region.

Word of warning: this has only been tested on my system. However, there is absolutely no code–form regions are built using just configuration information.

Now I have to go back and deal with all the email that has accumulated while I built the form region and wrote this post. 😉