Zen and the Art of Gmail, Part 1: Why I Switched
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. 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,” 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:
- I forced myself to let go of the need to file obsessively, via either filters or manual operations. I’m a professional, not the clerical help. I don’t even approve of the concept of clerical help — technology should eliminate the need for obsessive filing, and I’m letting Gmail do that for me now. This reduced a lot of stress, and after two years of usage, I haven’t yet missed my old filing system. Similarly, I’ve given up on managing an address book, which is possible because Gmail’s auto-fill of previously used addresses, both in the address fields and the search field, is wonderfully instant and accurate.
- Email is a constant stream, and while I want to be able to ignore it for a weekend, while I’m working, I want the option of seeing and responding to messages quickly and concisely. By eliminating the concept of checking mail, Gmail allowed me to escape the check/send cycle. Mail is either present in Gmail or it’s not; there’s no intermediate server where it could be. (In fact, because I still use Postini for server-side spam filtering for some tidbits.com addresses, this isn’t quite true.)
- While I don’t want to file messages, email should naturally collect into appropriate groups. Gmail does this brilliantly, automatically collecting messages with the same Subject lines into conversations, and making it trivial — far more so than in traditional programs — to collect messages associated with specific individuals or groups via a search.
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.
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 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,” 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 (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, 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”). Then, in “Zen and the Art of Gmail, Part 3: Gmail Labs,” 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,” I’ll look at the Mac program that makes using Gmail far more palatable than just having it in a Web browser tab.
Great set of articles. I've been living in Gmail for a couple of years now, and the only real complaint I have is that it doesn't seem possible to delete an attachment from a message without deleting the message itself. As I approach the 7.5 GB limit of the free version, that's an issue for me.
It did help to remind me that it's only $5/year to buy up to 20 GB of space.
Yes, I found that out recently too, because I ran across the Find Big Gmail service, which identifies your largest messages. But you do have to delete the entire message, not just the attachment, as far as I can see (hmmm, wonder if an IMAP client would be able to detach the two?)
But for $5 for 20 GB for a year, it's not worth hardly any time to investigate.
I have found that the total inability to get huge amounts of old mail reliably into GMail is a huge problem for me. Additionally contacts totally suck in Gmail, especially if you want to keep them in sync with your Mac and/or iPhone (the database fields are just too primitive and limited). I really like to use ONE database for my contacts, including street addresses, phone numbers, birthdays, company names... and Google has really nothing to offer here.
In fact Gmail just teems with good ideas and brilliant features but also has all the functionality gaps, bugs and shortcomings I've come to expect from Google.
I have heard many complaints about importing large quantities of email into Gmail, which is why I didn't do it, and as I noted in the article, I haven't missed it at all (and I have mail going back to 1992 in Eudora, and earlier in other programs).
As far as the contacts go, I have just the opposite desire - I don't want my email contacts cluttering up Address Book on my Mac or iPhone, since they're _email_ contacts and I interact with them only in Gmail.
That said, Mailplane lets you work around this, providing access to your Address Book. Plus, you can sync your Address Book with Google Contacts (see below). Google Contacts has fewer fields, yes, but my guess is that if you add data to other fields in Address Book, it won't be deleted (thought I haven't tested that).
I have just one problem with this article — your terminology. Gmail is not a program; it's an pop/imap e-mail service along with a web front end offered by google which also has the capability of retrieving from and sending email through third party mail servers.
Otherwise thanks for your review.
I think Gmail would best be described as a "Web application" (since they often combine a service with an interface) - I'll have to go back through the articles to see if I'm being inconsistent in a way that would cause confusion.
Thanks for the reply. I admit that googles Gmail has a really great scripted interface for it's email service, but a lot of providers offer e-mail with a web front end. Although Gmail was first introduce through its web-front, with access for third party clients (at first POP which was then followed by IMAP) coming later, it's still a service which is served through a server. I do not want to sound like an ass, but I am tired of new terms beings used to represent tried and true methods that have existed for a long time. Case in point is the term 'Cloud".
Terrific series and overall, the best discussion on why gmail is a good email solution (most reasoning seems to circle back to "it's free" and "it's Google", with no focus on the true differentiators).
My biggest concern, though, is Google's lack of support. If there's ever any problem, the end user has almost no recourse and no way to directly contact a human to get their issue resolved.
Perhaps not an issue for self supporting users like us, but as a tech consultant, I have trouble recommending gmail to my customers.
You've got a good point, Max, and I agree that Google support is essentially non-existent. I have had fairly good luck with posting in Google's forums for other Google services, though, since there are so many users of Google's services that there are often experts willing to help out.
Also, if you're a consultant, I could see Gmail as an opportunity, since you could provide the training and setup (like proper backups) that Google doesn't. :-)
You can filter on more than Google has exposed through the interface. I have a number of filters based on the list ID, which is defined as (e.g.) 'list:tidbits-talk.tidbits.com' in the ‘Has the words’ search field. There's a full list at http://mail.google.com/support/bin/answer.py?answer=7190
Yes, that's true, but it's still not any arbitrary header line, which is a little too bad.
Adam, like you I lived with Eudora since forever, it seems, and was loath to give it up, yet I, too switched to Gmail. But I was not happy with the interface—and everything being on their servers.
Then I discovered Eudora OSE (Open Source Edition) and I find myself with the best of both worlds—without having to forget old or learn new habits.
I haven't tested Eudora OSE seriously yet, since it came out relatively recently, whereas I've been using Gmail for several years now and have become utterly addicted to things like conversation view (Eudora actually had a "content concentrator" that working along the same lines as Gmail's conversation view, though it wasn't quite so successfully implemented) and Priority Inbox.
One thing I should make clear is that as much as I liked Eudora, I still wanted it to evolve. I was under no illusion that Eudora 6.2.4 was the pinnacle of email client behavior, and in fact, some of the things I suggested to the Eudora team back in the day were along the lines of what I found in Gmail.
Been using Eudora since early 90's. I've been using gmail for about 3 years also. I access my gmail via Eudora POP, which leaves a copy on gmail. I use the Eudora search function to great advantage- better than spotlight and comparable to HoodahSpot for other files.
I've tried thunderbird - but find it wanting. I've never had a storage problem crash and very few Eudora crashes in over a decade. For my primary use, they will have to pry Eudora from my cold dead keyboard. I'm using Eudora on Snow lepord with a SSD main disc with no problems. Gmail is my second choice, and IMHO yahoo and aol are and have been non starters
Thank you for affirming Eudora as a product worthy of holding dear for so many years. I'm in your same boat, having branched out to Gmail. I wish there was a way to import Eudora's Address Book in to Gmail's Contacts. Wishing, wondering, yet assuming it'll be a couple of afternoons spent copying them person-by-person, street addresses, birthdays, kids' names, and misc info into Gmail's far less "pretty looking" Contacts. I love(d) Eudora's address book - it was my one and only, so classy, enjoyable to use. Thanks to author Eudora Welty for lending her name to such a great product.
This came up in another comment somewhere, but here's what I'd do. First, you really don't need things like birthdays in email - it's just different data. So I'd import your Eudora address book into Mac OS X's Address Book. Then you have two options. You can sync Address Book to Google Contacts, or you can just leave them separate, and have Gmail build up its own list of correspondents over time (you'll have to copy a few people in, but it remembers people you've mailed in the past).
To convert your address book, I'd look at Eudora Mailbox Cleaner.
Importing historic email to GMail is indeed a slow process but it worked pretty well for me. I've loaded about 6GB of old mail over a few months using Emailchemy and the Google Updater. An advantage of some merit is that the Google mail store will only hold one copy of any message and since I had a lot of duplicate messages from various places, this removed almost all the redundant messages. I've been sending a copy of every message I've received since GMail started into the Google store -- that plus my archived mail (some back to 1996, so far) makes for an amazingly useful resource. "Why do you keep everything?" you ask ... because it's much easier than any alternative and Google storage is dirt cheap.
So you're using a Google Apps account, Gavin? Or does Emailchemy also work with standard Gmail accounts?
Emailchemy can do it via a workaround. Emailchemy has an embedded IMAP server, and, IIRC, gmail should be able to fetch email from that.
In any case, if your email is already in the mbox format, the Emailchemy folks offer the simpler (and cheaper) "ImportServer," which is a POP3 server, and Gmail will definitely work with that. http://www.weirdkid.com/products/importserver/index.html
Note: most corporate firewalls tightly control outgoing POP/IMAP servers, so it is unlikely that Gmail will be able to connect to either Emailchemy or ImportServer through a corporate firewall.
Adam, thanks for finally launching your series on Gmail. You successfully convinced me to make the leap 18 months ago, and I'm supremely happy I did. I can't imagine going back.
That said, I suspect even cloud-based email is going to give way to more sophisticated forms of messaging in the next few years. Twitter and Facebook Messages are a hint of where it may be going (but only a hint).
I guess the best news is: it's only going to get better.
Indeed - things are changing and there are definitely lessons to be learned from the success of Twitter and Facebook. But I don't see email going away, and I wrote about this a while back in:
Thank-you for the info about gmail.
What's the best way of archiving email.
Periodically (eg each year) or at the end of a project I want to archive old email (and attachments).
Do you recommend any file format or method?
Well, it's an interesting question, and I think I'd turn it around and ask what the benefit of archiving the old mail is.
In Gmail, there's no need to archive mail, since you want to have searchable access to those old messages in the future (or else you'd just delete them instead).
So what I'd do to simulate a project archive in Gmail is go into the Settings > Labels screen, and hide the label associated with the project's label. It doesn't go away, but you don't see it.
You could also download the messages to your Mac using an IMAP client, and then save the mailbox they're in separately, but to my mind, that's just extra work that results in a less-functional collection of mail.
I work out of several locations and as many computers, and love gmail.
But the recent gmail outage scared me, even though I wasn't affected: I have a bunch of messages in one folder that I really would like to archive to one of my computers.
I haven't figured out any way to archive those without sending them individually to an account. Anyone have a good archiving method?
The solution isn't an "archive" so much as a "backup." (Generally, an archive implies that the messages are no longer accessible in their original location.)
So all you do is configure your email client of choice (Apple Mail is free and easy) to connect to your Gmail account and download all your mail. Then you just make sure to launch it however often you want a backup and let it retrieve messages. Then they're on your computer should something happen to Gmail, and you can back them up locally with Time Machine or any other backup program.
Be sure to read Joe Kissell's excellent article on integrating Apple Mail and Gmail for tips on things like turning off IMAP access to the All Mail label, which prevents downloading duplicates of everything.
In addition to the lack of support from Google, there's also a lack of control. If they decide to revamp the service/application in a way that makes it less useful, you generally won't have the option to use the previous version. If Google decides to turn off Gmail tomorrow (admittedly unlikely), there would be no recourse. Unless you have local backups, your e-mail history would be gone along with the service.
Eudora has been working solidly on my brand new MacBook Pro so far, but I'm always looking at the options and I appreciate the article.
Oh, absolutely, but the same is true of any IMAP provider, and is precisely why I suggest using Apple Mail or some other IMAP client as a backup. You'd back up your email if you were using Eudora and POP to protect against hard drive crashes or fire or theft; there's no reason to act differently with Gmail, even if the reasons for the data loss would be different.
I'm not generally a scold, but I wanted to point out that "Google's free email service" is free because of the advertisements. So touting Gmail while teaching people how to turn off the ads seems counterproductive at best.
I've looked into this in the past, and I really don't think it's concern, largely because Google made Gmail entirely accessible to traditional email clients via POP and IMAP, thus hiding their own ads from their users.
Other factors in favor of not worrying about the ads include:
* Apart from search (and YouTube), few other Google services even have ads. Google's stated goal with free services is to increase use of the Internet in general, because they know they'll do better as more people rely ever more heavily on the Internet (and thus search).
* Unlike search, email is a situation where you're interacting with your data, rather than acting in an exploratory mode. So the clickthrough rate on ads in email is far, far lower than in search.
* Finally, they could prevent the ads from being blocked, and they don't.
My suspicion is that Google put the ads into Gmail very early on because they could, and to see what happened, and it earns enough to warrant not taking it out.
I don't get why Gmail gets so much credit for search in email. To me, do a solidly marginal job. For instance, try searching for "devon." You won't find your tidbits email, because it referenced DEVON(think
note) -- there is no submatch (but at least the capitalization doesn't matter!). If you did seem to remember to search for the entire 'DEVONthink,' wouldn't it be nice to then filter the results by sender, date, has_attachment, from a contact, etc. If you know the magic keywords, you can type in some of these refinements into the search bar, but, other webmail apps have followed iTunes refinements to make it much easier (and apparent on what to refine).
Your criticism of Gmail's lack of partial-word searches is accurate, more or less (when I search for "devon" in Gmail, I do get the TidBITS issues, probably because of the hyphen in www.devon-technologies.com), but as I noted, it's not something that has hit me in years of real-world usage.
I believe that's because it's just like searching Google. Do a search on "devon" in Google, and you won't find DEVONthink either. Since Google search is dominant by far, I'd guess that most people use it successfully and can thus translate those search skills to Gmail.
Now, as to your comment that adding a visual interface for refining a search might be useful; that's potentially a good idea for people who have trouble formulating search queries. Google did add that to the main search engine, so perhaps they're thinking about it for Gmail too.
I'm curious to know if you looked into MailForge. This is an effort by InfinityData to re-create Eudora. Unfortunately when we tried it early last year, the software was less-than beta quality. But it might have improved since then.
I haven't tried it recently, no. When push comes to shove, I'm no longer seriously interested in an email client that isn't at least as capable as Gmail, which means things like conversation view, Priority Inbox, and a speedy search-based architecture throughout.
I often want to read email when there is no Internet connection so I need more than a web interface. I've used Eudora for many years but it has problems, e.g. giving a error when I try to move a message to another folder until I quit the application and restart it. I recently joined a company that uses Gmail. Since I didn't want to be lmited to web access, I chose to use IMAP to Apple Mail. I agree with the value of labels, particularly the ability to assign multiple tags to one message. I've been using MailTags to provide that function in Apple Mail. It works well but I wish those tags would transfer to Gmail so that the same tags would be usable on the web interface.
I use several GMail accts, gladly, and funnel them to my Eudora which has never given me any problems since I started with it in '99. Tried Thunderbird and have it as a second option on a MacBook but sure would like it to be more like Eudora. Working offline is the biggest plus; the net goes wonky my mail is right here on the desktop, nice. Blessings to Eudora Welty.
Combining Gmail's web interface and access via a traditional IMAP mail client is very powerful. Gmail's conversation view has its annoyances, but is very handy for following an email thread. In contrast, using a traditional client with Gmail allows you to blast through reading individual emails much more quickly than the web interface. I use both approaches, depending on the task at hand, and IMAP keeps web and client in sync.
From a web interface perspective, you can enable/disable many interface elements, and that can really impact performance. It's definitely worth poking around the settings tabs. You can also use the "Basic HTML view," which sacrifices certain features for performance and compatibility with old/unusual browsers. It's like going back to 1999 in some ways, but it is very fast. Just click on the "basic HTML" link on the bottom of a standard Gmail page.
Finally, I'm a fan of the Google Labs options on the Settings tab. "Undo Send" has saved my bacon more than once.
regarding searching on gmail and whatever. I have yet to find a search function as easy and complete and useful as that of Eudora. The closest is HoodahSpot for all other files. Spotlight sucks IMHO.