Gmail had a great idea: replacing the limitations of hierarchical folders with the flexibility of labels. Now they are promoting the notion that they've "improved" Gmail by making labels work more like folders. How is that an improvement?

The common wisdom is that marking things with tags or labels (so you can later search for them by tag) is better than organizing them hierarchically into folders.

For one thing, having a strict folder hierarchy means that the thing you are saving for later search and retrieval lives in one named place, and is thus forced to fit into one defined category. Applying this notion to an email message, you can put it in your FAMILY folder, or in your FRIENDS folder, or in your WORK folder. But if the message involves friends, family, and workmates, where do you put it?

Tagging your email—or to use Gmail's vocabulary, "applying labels" to your email—alleviates this problem. That email message could be tagged with all three labels: FRIENDS, FAMILY, and WORK. This doesn't mean that Gmail would keep three separate copies of the message in separate folders. One message would simply have all three labels associated with it. And when you searched for any one of those labels, that message would appear in the search results. (Moreover, if you did a more restrictive search for all three labels together, that message would similarly appear in the results.) The idea that a message can have multiple labels associated with it really does add flexibility to the process of organizing your saved emails.

Even though Google recently added IMAP support to Gmail, that didn't mean mail was being physically organized into folders within their filesystem. We have to assume Gmail is still keeping one copy of a message on disk, and that a request for the messages in the "FAMILY/DAD" folder simply presents all the messages that have that label. The "hierarchy" is virtual. Anything less would be ungoogly...

Google's mantra is "search, don't sort". For Gmail, this mantra might be phrased as "search by labels, don't organize into limiting hierarchical folders." Google is (or should be) justifiably proud of this break from traditional hierarchical thinking about storing email.

The problem is that people don't seem to "get" labels or grasp what the inherent advantage is in not organizing things into folders. They WANT folders. They ask "when will Gmail support folders?" (A lot.)

Folders, after all, mimic the structure of a computer's filesystem. When you save a file, you try to put it in a place where you can find it later: in a directory or folder under your "Documents" (or "My Documents") folder, within a "Pictures" folder, maybe within a folder labelled "Family Photos". You know which folder it's in. Granted, programs like Apple's iPhoto deliberately obscure the underlying filesystem hierarchy—you're not supposed to care anymore which folder a file is in, or even what its name is, you just need to know how it's tagged to find it and look at it again in the future. Knowing that you saved a photo as "C:\Users\me\Photos\ArizonaTrip\GrandCanyon\DSC97854.JPG"? How 20th century! That's for geeks and control freaks!

The idea that "you don't have to organize your files yourself—your computer will do it for you" anticipates in many ways the technodystopian nightmare world in which computers gain more and more control over our lives, where we serve the computers rather than them serving us. (Of course that could never happen...) But it also "validates" the slobbish approach to computer usage. "I was right to just drop all my files in a single folder called STUFF and let my operating system's search engine find things for me. So screw you, anal-retentive folder-based organized people!" Yeah, right.

So what happens to the John Connors among us who fight back, who WANT to organize their mail into folders? Who demand that Google provide support for folders in Gmail?

Apparently, for better or worse, they get their way: coinciding for all intents and purposes with its "coming out of beta", Gmail is now promoting the fact that "labels are more like folders now." In a big way.

The push seems to come from statistics that show only 29% of Gmail users are making use of labels. ONLY 29%? Think about how many features Gmail has. What percentage of users use themes? Keyboard shortcuts? Filters? Fetching email from other accounts? 29% seems like good penetration for a Gmail feature.

But apparently it's not enough for Google. They see Gmail actually losing ground to other services like Yahoo Mail, and they see lack of folder support as a primary reason for this.

Frankly, in my own admittedly unscientific limited survey of people I know who use Yahoo Mail instead of Gmail, their primary reasons revolve around Gmail's performance and their dislike of "conversation view" (which is not an option like many other Gmail features and cannot be turned off). The drag-and-drop folder capabilities weren't a critical part of their decision.

The recent addition of a "Move to..." button foreshadowed Gmail's new attitude towards label functionality. A message could be now "moved" into a "folder" in one step, even though under the hood the message was being archived (removing it from the inbox) and a label was being applied to it. Instead of getting people to understand the advantages of labels over fixed hierarchical folders, Google elected to retreat into framing labels as "just like folders". Instead of being a leading-edge email interface, Gmail becomes an also-ran, touting not advanced original functionality but the ability to do what the other email interfaces can do. (They probably would have gotten a lot more mileage and gained a lot more traction providing the capability to disable conversation view.)

But Gmail's new attitude towards labels has another negative side effects. For one, the capability to have your labels displayed on the right-hand side is now gone. This angered a large number of Gmail users, who have grown to depend on this feature. Others complained that the changes broke Folders4Gmail, a GreaseMonkey script included in the popular Firefox extension Better Gmail, which displays multi-level labels (e.g., "FAMILY/DAD") as a nested hierarchy. How ironic that making labels behave more like folders would make them behave less like folders. On the positive side, labels are moved up to a position of prominence in the left margin, but even that was confusing—only your "most-used" labels appear there by default. (After deeper investigation, I found out you can pick and choose which labels appear in that position of prominence... but in alphabetical order, not a priority order of your choosing).

The drag-and-drop capability seems to have been lifted right out of Yahoo Mail. You can now drag a message from a displayed list onto a label in the left-hand margin, the Gmail equivalent of dropping a message into a folder. You can even do the reverse: dragging a label from the left-hand margin onto a message. All well and good: but if you can drag a message into a folder, shouldn't also be able to drag it out? Label removal by dragging a label off of a message seems a reasonable capability, but no sign that anything like it has been implemented.

These changes to Gmail seem motivated more by a desire for greater market share rather than by a drive towards technological advancement. Labels are much more flexible for organization and searching. It's a pity Google felt they needed to take a step backwards by saying "yeah, OK, these can be like folders, too, whatever." This is a failure resulting not from the feature's original design but from Google's inability to promote it and educate users about it.