Managing Mail Imperfectly

MailWe’ll never be able to defeat the onslaught of email. At least, that’s my impression. We’ve essentially signed on for a world in which we can be regularly assaulted by communiqués from anyone at any time, and in which those communiqués pile up more quickly than we can address them. As much as we can try to develop coping methods for better managing that continuous inflow, I just don’t seriously see a way for us to ever fully tame it.

In spite of the basic futility of the idea, people will feel compelled to try to tame email. Creative Good co-founder Mark Hurst, one of the smartest people I know, advocates aggressive management of one’s email store in his new book, “Bit Literacy: Productivity in the Age of Information and Email Overload.” His advice is to “empty the in-box at least once a day,” arguing that a full in-box “demoralizes users with feelings of overload.” The ideas that each email represents can be relocated to more appropriate contexts — to do lists, or folders in your email client — where they’re less obtrusive.

That’s great advice for many folks, I’m sure. In fact, about a year and a half ago, it was my practice to dutifully empty my in-box regularly, filing away emails in a complicated hierarchy of folders labeled with clients, projects, subject matters, or groupings of some sort. But, I soon came to realize that, for me anyway, it was more work than reward.

Today, I use Apple’s Mail program to manage my email, and I keep everything in my in-box, regardless of who sent it, what it’s about, or in what future context I might need it. And I’m much happier.

Folder Intelligence

There are a few tools that Mail provides that make this possible: its lightning fast search functionality allows me to quickly find messages by senders, recipients, subject line, body and other criteria. (And with the third-party Mail Tags, I can actually add keywords to messages for more specific search targeting, though I don’t do that too often. More on that below.)

More importantly, there’s Mail’s fantastic smart folders, which are essentially fixed, self-updating searches that can ‘see’ across your entire database of messages. I have smart folders that show me messages received today, messages sent today, unread messages received today, messages I’ve flagged for follow-up, and a few more that can reach back into the prior week in a multitude of ways. These are invaluable methods of looking into my in-box without being forced to confront the ‘demoralizing overload’ of all those older messages.

For me, the key thing about smart folders is that they let me avoid the tedium of manually filing messages into traditional folders and sub-folders inside my mail client. I used to be a big believer in that method, but I’ve since come to realize that the upkeep involved in such a hierarchy — knowing when to add or consolidate folders, remembering what folders are intended for which kinds of mail, all the while trying to avoid the duplication of similarly themed mailboxes — is simply more work than it’s worth. I just don’t believe that busy people have any desire to maintain what essentially amounts to a taxonomy of subject matter areas — especially as a method of organizing one’s corpus of email. It’s just more cognitive load than should be necessary.

Being Organized vs. Appearing Organized

When I think about it, I realize that the root of my earlier belief in hierarchical email filing systems wasn’t so much a desire to be organized as it was a fetish for the trappings of organization. Any random check of my email program (Microsoft Entourage at the time), would have revealed a spotless in-box and a carefully manicured tree-list of folders and sub-folders. It was very satisfying to simply preside over what appeared to be such a carefully maintained system.

At the same time I knew that I wasn’t always stashing my emails in the ‘right’ place. Sometimes they would simply be misfiled through simple clerical error on my part. For some emails, the truly logical thing would have been to file multiple copies in multiple folders, but of course that wasn’t easily. And often, I would look for previously filed emails in a location that seemed completely logical in the context of that very moment I was searching for them, when they had in fact been filed away at a time when they seemed to make more sense going somewhere else.

My point is that in the fervor to climb out from under deluges of information, there’s often a tendency to focus on creating superficially pleasing yet inefficient tools for organization. This was my experience attempting to use David Allen’s popular Getting Things Done method; after initially setting it up, I marveled for a few weeks at how organized I felt, before realizing that the whole system was too difficult to sustain.

Imperfection Matters

The beauty of Mail, I think, is that it allows highly imperfect yet still efficient management of your messages. In fact it embraces that imperfection. If you look at my in-box, it’s really a mess; there are messages in there that I should just delete because I will never, ever have use for them in the future. And yet, Mail makes no demands on me to separate good information from bad information; those superfluous email messages don’t stand in the way of my finding valuable email messages at all.

This is something that systems — and the designers who create systems — often underestimate: the importance of allowing for imperfection. It’s incredibly difficult to create a perfect system, even if that system has only one user (you) and it administers a relatively knowable body of information (like your email). I find it’s better to just embrace imperfection, to avoid fighting it with laborious hierarchies, and to give in to the fact that we’re never going to win in the fight against email.

Can’t Get Enough Email?

Speaking of email, New York Times Deputy Editorial Page Editor David Shipley and Will Schwalbe have a great book just out about the subject, called “Send: The Essential Guide to Email for Office and Home.” It’s sort of a cultural look at the way email is used, abused and misunderstood, and it’s quite fun. They had a great and lively panel on this book in March at South by Southwest Interactive, too.

  1. I also use Mail and keep everything in my Inbox. The only ‘maintenance’ that I perform is once a year I move ALL of my messages from the previous year — including many messages that I will no doubt never read again — into a seperate archive folder labeled ‘2006’, ‘2005’, etc. This speeds up Mail’s ability to sort and search the current items in my Inbox, and still enables me to find old messages easily.

  2. Khoi, how do you create a smart folder for messages sent today? There’s no criteria in the create dialog box that allows for choosing “sent.”

  3. Excellent article. However, this assumes that you have the choice with your email client @work… which choice some of us do not have. I’ve got to use Outlook, and the folders structure is pretty mandatory.

  4. Outlook has search folders, which from what I understand, allow for the same basic ‘smart folder’ functionality.

    Whether you can search within a search folder, I don’t know.

  5. I agree to a point with your idea of imperfect efficiency. But I’ve always been looking for a more radical solution — an email client that would keep the past five messages from every sender, regardless of date, and chuck (or archive) the rest. I rarely need more than the last few bits of correspondence to continue the conversation. So there you go — I’d like an inefficient AND DESTRUCTIVE email client.

  6. Your approach, Khoi, probably only works (or at least: works best) when you store your messages locally. I use IMAP to keep my mail account synchronised across machines and, especially, to make sure I see the same in Mail and my Webmailer (Squirrel). With hundreds and thousands of emails stored in your IMAP inbox, the server connection becomes a troublesome bottleneck.

    Oh I love Gary’s idea… There might be a possibility to do it – by tweaking Mailboxer for example. How neat would that be?!

  7. Great article. And so refreshing to hear someone else take a mild shot at the ridiculous obsession with GTD and email organization perfection that seems to be so popular these days. I’m with you entirely. In fact, that’s why, although I’m a faithful Mail user (w/ MailTags, which are awesome BTW), I’m starting to use the Gmail web interface for my Gmail account. I just like the “Archive” button on Gmail. It’s essentially the same process as what you describe–keeping it all and not worrying about it–but with the added visual delight of having an “empty” inbox. All in all, I think your approach is very sensible.

  8. Andreas: I actually use IMAP myself. One thing I left out of this post was details of how I archive my messages. At the beginning of each month, I will move all the messages from two months ago from the IMAP store and to my local hard drive. I find that I only rarely need access to that older mail, and then never urgently.

  9. The use of smart folders and powerful search as a foundation of email use is pure gold. The key, of course, is that the mail client must have decent implementations of smart folders and search.

    Thus, my gmail account is all stored in the inbox. Gmail does email search so well that I only deal with a small handful of tags/filters. (Which is no surprise given they’re Google).

    But with my work email, currently being handled with Thunderbird, I’m still forced to manually sort/move/archive. TB’s search and smart folders just aren’t quite good enough to rely on. (Side-notes: The search box in the toolbar should search all my mail, just the current folder; or at least give me the option to. The search account interface is clunky at best; and a new window no less. And I have to manually add each and every folder to a particular smart folder, especially when adding new folders.)

    So to all the readers here, can anyone suggest a good Windows mail client that combines the search power of gmail and the smart folders of (I’m even considering pine/mutt/et. al.)

  10. I can do you one better. I use as well, and I keep the majority of my emails in the Inbox. But I do have regular clients with whom I exchange messages on a daily basis, so I find it easier to just sort those into folders. But I don’t do it manually.

    I use’s built-in “Rules” to sort them for me. I have one Rule for each regular client, so any email that I receive that comes from goes in the Client 1 folder and anything from goes in the Client 2 folder, etc.

    I also use the Rules to highlight emails coming from my coworkers in one color and my family and friends in another color so I can spot them at a glance. I automatically delete known spammers’ messages with prejudice so I never actually see them, not even in the Junk folder.

    It’s a system that takes just a few minutes to set up and keeps me unfetteringly organized because there’s almost no chance that I can personally screw it up.

  11. Khoi: fair enough.

    What you have done with Mail is also happening on a larger scale, of course – the progress from categorisation (physical folders, each message has to be saved in exactly one folder and can only be seen right there) to classification (associations based on each individual’s personal imagination are connected with messages, which are stored wherever and can be displayed in any combination).

    See here, for example: Ontology is overrated.

  12. Thank you for this post.

    I agree that smart folders in Mail in combination with such an efficient search, make the organisation and maintenance of my inbox very easy, particularly if you are receiving emails for more than one email address locally.

    Rules, as Sean Flanagan said, are also very useful but in theory you could do the same job with a client/contact/domain-specific smart folder I believe.

    It’s important to also mention Apple’s Spotlight when discussing mail retrieval and search. I didn’t use to search for mail with Spotlight because I was worried I’d get overwhelmed with results. But you should give it a try next time you need to find an email fast and don’t have Mail open. There’s a dedicated category for Mail Messages in the results.

    Oh, and good advice for what to do with IMAP.

  13. Khoi,

    Appreciate your kind words and the link to the book. (You may know that you’re quoted in the book, too 🙂

    As for your system of keeping everything in the inbox… a question – how do you keep up a todo list? In particular, how do you separate what’s important to do *today* from what’s only important in the future?


  14. Mark: There are two ways I manage my to-do items. First, I keep a simple to-do list using OmniOutliner. If an email arrives that sparks a to-do item, I’ll type it into the Outliner document and consider that email ‘cleared.’ Another thing that I do is if an email requires action — usually a reply — I’ll flag it using Mail’s built-in flagging system. One of my smart folders scans for flagged items, so it works as a kind of to-do list of its own.

  15. That’s a great system for todos that have no inactive phase… i.e. those that need attention NOW.

    But what for the (majority of) todos that get created well before when they need action? The issue of follow-up is a big one here… for example, when you ask someone a question, how do you get reminded in a few days, or weeks, to make sure they answered the question?

    I’d say it’s essential to have a way to send todos to your future self, and not be bothered with them in the meantime (i.e. what a bit-literate todo list like does)… most todo and flagging systems have no capacity for this.

  16. I don’t actually look at my Inbox. I have used (for over a decade now) rules that puts mail that matters into a virtual inbox. The first rule is by date. Anything that wasn’t received today doesn’t appear in this inbox. Second, I white list. People related to projects I’m currently working on or keywords on those projects also end up in that folder.

    Anything else fades out. This lets me focus on important matters and ignore the things that don’t matter until I have spare time to look into it. Not all mail received is worthwhile to look at.

  17. As far as I know, Mail keeps a cache of all your IMAP accounts in your local file system. When searching, it shouldn’t be much slower than POP, if at all.

    And here’s a tip for you IMAP users. If you want to keep your drafts or your sent messages synchronized as well, you will need to enter “INBOX” in the IMAP Path Prefix field, under Preferences > Advanced.

    Took me forever to figure this one out!

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