This article originally appeared in TidBITS on 2011-03-16 at 1:32 p.m.
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Zen and the Art of Gmail, Part 1: Why I Switched

by Adam C. Engst

For the record, it has now been some time since I used Eudora 6.2.4 as my everyday email program, and I have instead switched to Google’s Gmail [1]. I realize that may come as a surprise, considering that I wrote the “Eudora Visual QuickStart Guide” back in 1997 and was long a vocal supporter of the program. But Eudora had started crashing more frequently and corrupting mailboxes in the process. I could fix the damaged mailboxes (see “How to Fix Corrupt Eudora Mailboxes [2],” 4 April 2008), but doing so had become an annoying interruption when I just wanted to move forward with the day’s work.

I held onto Eudora as long as I could because I liked the way the program worked. I liked the fact that it was tweaky and customizable, that it reported clearly what it was doing, and that it was entirely straightforward. I’ve used and written about most other Mac email programs over the years, and if I was forced to generalize, I’d say that they all feel to me as though they’re starting from the same conceptual base as Eudora, but with a different set of priorities. Since I had become utterly familiar with Eudora’s mindset, all these other programs simply felt like awkward take-offs.

That’s why, when it came time to choose a new email program a while back, I picked Google’s Gmail. Alone among my choices at the time, Gmail’s engineers decided to rethink the entire concept of email, throwing out many basic assumptions and designing from scratch. I felt that if I were going to make a major leap (and since email is my primary communication medium, it truly is a huge leap for me), I wanted to develop a new and better way of working, not merely adjust my old habits to a new program that lacked the parts of Eudora I liked.

The classic email program, Eudora included, takes its architectural cues from the stereotypical 1950s office environment, where incoming mail arrives in a single location, is routed according to various rules, and ends up in a single destination where, after being read and potentially replied to, it will be filed away in a hierarchical filing system or deleted. This approach is functional, but many of the advances in email programs over the last few years have been aimed at making it easier to deal with a large influx of mail, easier to file messages, and easier to find them after they’ve been filed. In other words, these changes are simply trying to build robots into the 1950s office environment so everything moves faster. Meanwhile, the world has moved on from those days of secretaries taking dictation from snazzily suited executives.

Gmail’s engineers instead focused their efforts on search, a far more modern concept. After all, Google’s skyrocketing fortunes gave some indication that search was a winning idea. With search at its core and Google’s unimaginably massive server farms backing it up, Gmail could do some seemingly simple things that standalone email programs have been either unable or unwilling to do, most notably trading the old “folder” concept for a modern “label” approach and generating every collection of messages via a search.

As an aside, I’m quite depressed that only Google has been able to do this successfully. I see no reason that a modern Mac couldn’t offer the same level of functionality, and the fact that Gmail can be made to work offline via Google Gears shows that it should be possible. That said, I don’t use Gears; it was flaky last I tested it, and if I don’t have Internet access, there’s not much I can do anyway, since most of my work requires more than just the capability to read and write email.

The other reason I chose Gmail was that, although I wanted to use its Web-based interface, since that’s where all the innovation is, I also appreciate the fact that it provides access to my email via IMAP, for a local backup and in case I want to switch to some other email program in the future. (For some people, the capability to access Gmail from any computer with a Web browser is a big deal. Since I seldom use any computers but my own, this isn’t a significant advantage for me.)

Giving even more weight to my decision was the fact that, although I have my own mail server, I’d rather forward mail to Gmail and let Google’s engineers deal with keeping things running. Acting as my own email admin hasn’t been fun for years, between dealing with spam and the stress of being responsible for the email accounts of a number of local users.

So here’s my new philosophy of email, which has proven significantly less stressful than the last few years of using Eudora:

Gmail Limitations -- Though I’m currently a big fan of Gmail, I think it’s important to acknowledge Gmail’s limitations up front. None of these are more than a minor irritation for me, but not everyone will agree.

First, some common concerns: privacy, security, and advertising. Although Google has a privacy policy [3] that claims it won’t share information in unreasonable ways, the fact remains that Google stores all your email (as does any IMAP email provider). Since I’ve long subscribed to my mother’s advice not to say anything in email that I wouldn’t want on the front page of the New York Times, I’m not particularly concerned about Google having theoretical access to my email. Nor am I worried about Google somehow selling access to my mail; if such a thing ever happened and became known (and it would, given the scrutiny Google is under), it would cause irreparable damage to Google.

Also, with all your email online, all that protects it is your password (so pick a good one!). If that’s not sufficient for you, Gmail recently added two-step verification that requires a level of security beyond your password when your account is accessed from a new device. Lifehacker [4] has a good explanation and tutorial, but beware that two-step verification can be a pain to use if you use other desktop or Web applications that access Gmail or other Google services and aren’t yet updated for two-step verification.

And the ads? Gmail analyzes every email message and displays contextual ads at the right edge of the message, ranging from the ridiculous to the occasionally creepy. Honestly, I seldom even noticed them, and now that I’ve installed the Rapportive plug-in, they don’t appear at all (see “Rapportive Plug-in Replaces Gmail Ads with Sender Info [5],” 27 March 2010). Similarly, Gmail’s distracting Web Clips, which display news items in a little box at the top of the Inbox, can contain ads; I just turn them off in the Web Clips screen of Gmail’s Settings (to access them, click the gear icon at the top of Gmail’s Web interface page and click Mail Settings in the menu that appears).

While Gmail’s Web interface is extremely good overall, there are certain areas where it falls down. Most notably, Gmail is occasionally slow to send a message or load a new one, showing a small progress message while I sit and stew. Most of the time it’s not an issue, which makes it all the more annoying on those occasions when it takes five to ten seconds to send a message or open a new one. Those are the only times I wish for a desktop application.

That’s not quite true. Gmail’s Web interface is designed for a single window, which is generally fine, since most email either doesn’t require reference to other messages or requires only checking back in the same conversation. But on those occasions when I need to refer back to a message in a separate conversation, it’s clumsy to pop an in-progress message into its own window so I can get back to the main Gmail window, perform a quick search, and refer to the older message while writing the new one. Gmail does offer both on-screen controls and keyboard shortcuts for generating separate windows, but it’s clearly of secondary importance and harder than it would be in a desktop application.

And of course, while you can download a local copy of your email via Apple Mail or any other IMAP client, you do have to do that if you want a backup of your mail. There’s no reason to believe Google would lose your mail permanently, but it’s always best to have a backup you control as well.

Most of the rest of Gmail’s problems are part and parcel with its innovations. For instance, as fabulous as conversations are the vast majority of the time, they sometimes get in the way. As an example, when we send out email about a new Take Control book, Tonya receives a number of email messages that all need individual attention. But because people often reply to incoming mail as a way of generating a new message, she’s often faced with a multi-message conversation where each message is actually an independent unit that’s harder to work with in the conversation than it would be on its own. (You can turn off conversation view entirely in Gmail’s Settings screen, but that’s overkill.)

Similarly, threads in mailing lists sort into conversations too, which is almost always a help. But if there’s private mail with participants of the thread, it can occasionally be confusing to have the private messages mixed in with the public ones. It would be nice if Gmail enabled us to explode any given conversation into its component messages.

There are a few areas where Gmail doesn’t compete with traditional email programs. For instance, when building spam-catching filters, it’s nice to have access to grep capabilities so you can match patterns of text. Gmail can’t do that, and in fact, all searches are word-based, so you can’t even do partial-word searches. Also frustrating is that you can’t search on arbitrary header lines, which can be useful for eliminating foreign language spam, for instance. Gmail does support searching on From, To, Cc, Bcc, Subject, and Delivered-To, along with dates and attachments, and realistically, I haven’t felt hampered by Gmail’s search limitations.

If you receive a ton of email, with lots of large attachments, it’s possible that the 7.5 GB of free space you get with a Gmail account might not be enough. However, at $5 per year for 20 GB [6] (up to 16 TB), it’s hard to be too concerned about this.

Lastly, it’s not particularly easy to import old local email messages into Gmail. There is a Google Email Uploader for Mac [7], but it works only with Gmail within Google Apps, not with standalone Gmail accounts. The alternative is to connect your old email client to Gmail via IMAP (or import your old mail into Apple Mail or Thunderbird, which talk fairly well to Gmail via IMAP) and then copy messages manually, mailbox by mailbox. When I tried this with Eudora, I lost original dates on the imported messages, rendering it useless, and I’ve heard that it’s difficult to import significant quantities of mail at once, with the actions timing out and messages failing to transfer.

After considering the situation, I decided there was no significant win in importing my old Eudora mail. Eudora still launches and runs fine on my Mac Pro under Mac OS X 10.6.6 Snow Leopard, so when I need to find a really old message, it’s all still there. If Rosetta really does disappear in Mac OS X Lion, I may have to import all those messages into another program. Starting from scratch required some visits to my Eudora archive for the first month or two, and it took Gmail a short while to learn the email addresses of my most frequent correspondents. But the switch was otherwise entirely painless.

If nothing else, Gmail is free, offers excellent spam filtering, can accept mail forwarded from another account, and provides access to all your mail via POP and IMAP, so it’s easy to test.

In the next article in this series, I’ll explain in some detail how Gmail’s search-centric approach to email enables an entirely different technique of reading email (see “Zen and the Art of Gmail, Part 2: Labels & Filters [8]”). Then, in “Zen and the Art of Gmail, Part 3: Gmail Labs [9],” I’ll delve into the many ways to extend and improve Gmail via Gmail Labs, and in “Zen and the Art of Gmail, Part 4: Mailplane [10],” I’ll look at the Mac program that makes using Gmail far more palatable than just having it in a Web browser tab.

[1]: http://mail.google.com/
[2]: http://db.tidbits.com/article/9545
[3]: http://mail.google.com/mail/help/privacy.html
[4]: http://lifehacker.com/5756977
[5]: http://db.tidbits.com/article/11117
[6]: https://www.google.com/accounts/PurchaseStorage
[7]: http://code.google.com/p/google-email-uploader-mac/
[8]: http://db.tidbits.com/article/12037
[9]: http://db.tidbits.com/article/12038
[10]: http://db.tidbits.com/article/12039