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Why I became a Gmail convert

Filters and labels helped move me from Yahoo Mail to Gmail; search and keyboard controls made me happy. Too bad about the rocky transition.

Here's why I'm a Gmail convert: for the first time since I started using e-mail nearly 20 years ago, I can keep my in-box tidy.

A month ago, I switched my personal e-mail from Yahoo Mail, with which I've been generally happy. What attracted me to Gmail was a number of specific Gmail features, but what I've come to appreciate is the big picture: a new way to look at the task of e-mail.

The old paradigm follows the metaphor of a paper-pushing office job with an in-box, trash can, and filing cabinet.

Gmail brings that paper pushing into the computer age. Most messages I care about are already organized with labels automatically as they arrive. I still must read and reply if necessary, but after that I just plop messages into a giant archive with no pesky manual filing. They can be retrieved easily via search or labels.

The result: my Gmail in-box has 14 messages in it, and I've had no trouble thus far keeping it in that neighborhood. I wouldn't say it's life-changing, but it's an improvement.

Here's one measure of its user interface success: several times a day, I miss Gmail features absent from my work e-mail, which uses Microsoft Outlook connected to an Exchange server. That Gmail accomplishment is notable given that its interface uses a relatively primitive Web-based foundation, while Outlook gets all the computing horsepower and interface richness of a Windows PC.

Google's filters automate the drudgery of organizing many e-mails, for example by applying specific labels to incoming e-mail.
Google's filters automate the drudgery of organizing many e-mails, for example by applying specific labels to incoming e-mail. (Click to enlarge.) Google

Google's philosophy with Gmail is to aim for the needs of power users. That might sound like foolishly overlooking the much larger mainstream market. But I think it's smart, because given the increasing importance of Internet communications, an ordinary user tomorrow will face the same challenges as a power user today.

Despite my overall satisfaction, though, the advantages I found in Gmail made its deficiencies all the more glaring. And the transition from Yahoo was extremely unpleasant. Here are some details for those of you thinking of taking the plunge.

The three Gmail features that wooed me
Three Gmail features got me to make the move, and all three proved just as desirable as I anticipated.

The first feature is labels. Yahoo Mail, like Outlook, Thunderbird, Eudora, and every other e-mail client I've used, requires me to sort keeper e-mail into folders. Many times, though, I've been bothered by folders' fundamental organizational limit: you can put a message in only one folder. So with a message from my old roommate about his new camera, do I put that into the folder for him or the one for photography? And a year later, when I want to retrieve it, where should I look?

With Gmail, you can have multiple labels on a particular e-mail--one for both "family" and "wife," for example, not to mention "money," "travel," "tech support," and various other categories I use often. By color-coding labels, various categories are easily found in my in-box, and clicking a label shows all mails that use it.

Yahoo Mail made major progress around this problem by finally fixing its previously ineffectual search ability, but I still like labels a lot better.

The second feature is filters, the automated tasks Gmail performs before I even touch my e-mail. Instead of having to manually move mail from my wife to a particular folder, I set Gmail to attach the appropriate label to any message from her. Any message I get that includes the words "itinerary" or "SFO" automatically gets a "travel" label, for example. Organizational drudgery is down and findability is up.

Filters can also forward, delete, and archive mail automatically. And when I set up my filters, it applies them to the existing archive, which helps ensure e-mail stays organized even years after I received it.

Third is IMAP (Internet Message Access Protocol). I've spent years using the earlier but decidedly inferior POP (Post Office Protocol), but IMAP handles remote access to e-mail much more gracefully. What surprised me was that I ended up liking Gmail's Web interface better than the e-mail client software running on my computer, so IMAP isn't as important as I initially envisioned.

Yahoo charges $25 a year just for POP access and at present doesn't grant IMAP access except to business partners.

The advantages I found later
I use search a lot. Gmail's search is fast and thorough. I particularly like how it can be controlled, for example by searching e-mail from a particular date range or searching for all messages labeled both "family" and "things to do."

I also expected to use Gmail keyboard controls extensively--I find it much faster than a mouse for the most part. Yahoo Mail has keyboard shortcuts, but they work erratically for me and don't cover as much ground as Gmail's. Less time pawing my mouse, combined with Gmail's generally snappy interface, means handling e-mail feels much breezier.

If you have Gmail keyboard shortcuts enabled, typing ? will pop up this abbreviated view of keyboard commands. (Click to enlarge.)
If you have Gmail keyboard shortcuts enabled, typing ? will pop up this summary of keyboard commands. (Click to enlarge.) Google

The archive feature is nice. I worry that my e-mail usage will encroach on Gmail's storage limits, but so far it looks like my needs won't outpace the gradually rising limit. Mostly I like it because I'm a pack rat; though I certainly delete dozens a day, too, I've often found it handy to refer later to seemingly nonhistoric messages such as flight confirmations. Gmail's archive-and-search philosophy is a refreshing change from the keep-your-in-box-small-or-we'll-revoke-your-privileges attitude that still prevails in many parts of the world (not at Yahoo Mail, though, which offers me unlimited storage.)

Gmail also seems to be under more active development. I've seen essentially one change in Yahoo Mail since 1998, the arrival of the "all-new" interface. Though Yahoo is working on more changes now, some of them potentially dramatic, I like Gmail's lab projects, a few of which I use.

The final pleasant surprise was conversation view, which assembles the back and forth of e-mail exchanges into a compact thread. Once I got used to typing P and N to navigate to a list's previous and next messages and O to expand a message from a title to its full content, I was sold. I also like the fact that an archived conversation pops back into my in-box when a new reply in the thread emerges.

What I don't like
My biggest complaint about Gmail is its contacts system, though I say this advisedly because I have yet to run into an address book I like and it's still a step ahead of the primitivist Yahoo Mail address book. Google made Gmail contact list improvements last week that help distinguish people I care about from anyone I've ever e-mailed, but managing contacts still involves a lot of tedious pointing and clicking and scrolling, especially when it comes to dealing with hundreds of contacts.

It took me some time to master the selection of messages I wanted to do something with. Both a small pointer and a check box to the left of each message can be used to select them; the pointer is used to open messages or add stars, but the check boxes are used to delete, archive, or label them. This particular complication isn't a big deal if you're a point-and-click mouse user.

The 'labs' tab in Gmail settings has experimental options for users.
The 'labs' tab in Gmail settings has experimental options for users. Google

It falls short for people with multiple e-mail addresses; I couldn't find any way except deleting and re-adding e-mail addresses to make sure a contact's particular e-mail address is the top and therefore primary one that will be used in a mailing list, for example, unless you want multiple entries for a single individual.

Another gripe is with conversations. It's fine for one-on-one chats, but group mailings can blossom into a confusing, hard-to-navigate morass.

I'd love to see offline access for Gmail, which is in the works. So far I don't care much if I'm only able to check personal e-mail while online, and I could always use client software if I really wanted to work offline, but for companies thinking of Gmail, some of the cost advantages of cloud computing are eroded if the IT department still must set up Outlook on every employee's computer.

I initially missed the Yahoo Mail feature that let me write multiple e-mails simultaneously. It's possible with Gmail--typing Shift+C will pop up an empty message in a new browser window--but Yahoo Mail's tabbed interface made me feel like the mail operation is in one place.

Transition woes
Some of my biggest troubles with Gmail were related to my transition from Yahoo Mail.

First off, when I set Gmail to slurp in my Yahoo Mail archive, I neglected to check the button that would have left the originals alone and Gmail gutted my archive. Be careful if you're making the move. Google sets the default to delete the remote messages because people often have capacity limits on the other accounts, but for me, it effectively meant no going back to Yahoo Mail.

Keystrokes are often a matter of programming one's muscle memory, and shifting to a new set of motions made me clumsy. Gmail takes its cue from vi, the venerable Unix text editor that, for example, uses the forward slash key to initiate a search and J and K to scroll up and down. Yahoo Mail uses Outlook-like conventions, though, with the up and down arrow for moving through the in-box and the delete button for deleting messages. I'm most of the way there with the new shortcuts, but I still mess up and type A rather than E to archive.

The biggest single pain of moving was getting my address book out of Yahoo and into Gmail, and frankly, I'm still only partway there. Some of the blame here goes to Yahoo, whose interface on more than one occasion deterred me from trying to clean up my contacts.

I ended up exporting my contacts and manually scrubbing them in Excel before importing them into Gmail. Even then, a large amount of structured data, while preserved, lost its meaning. Many instant messenger nicknames, birthdays, and mailing lists were converted into boring text, so it's up to me to go through my list to fix it. Yahoo had labeled this data, so I put the blame here on Google's inadequate parsing tools. Perhaps with Yahoo's newly open address book interface this pain will become a thing of the past.

But now that I'm up and running, Gmail works well for me. And until Google dramatically departs from its don't-be-evil philosophy or something even better comes along, I'm willing to entrust the company with an important part of my electronic life.