Back in February I posted the article “How I’m Keeping My E-mail Inbox Empty” after applying many of the things I’ve learned in researching organization and self-motivation, particularly David Allen’s excellent book Getting Things Done. Since then I’ve had no trouble keeping my inbox empty, especially with tricks I learned since (see My Empty E-mail Inbox, 10 Weeks Later), except that, since I often read and answer e-mail on the go, I haven’t been able to use desktop e-mail applications I used to use like Outlook and Apple Mail. The problem with using these is that if I look at the same e-mail account with more than one system, I have repeat all my organization and inbox cleaning in every one of those–which means that it just won’t get done. Who wants to get home from a trip, for instance, and have to reorganize two hundred e-mails that were already organized on a laptop while away?

Failed (and not-so-failed) free e-mail options

I’d mentioned I was using a Web-based e-mail application provided by my ISP, but I’ve been disappointed to find that this application, although it has most of the features I want, is buggy and sometimes intolerably slow. So I’ve been searching for a replacement program I could use, something freely available on the Web that I could also recommend to my readers here.

[Added after the original post: If you're interested in using GMail with this approach, please see the comments, where D. Moonfire offers a potential solution to the problem I'm about to describe.]

You’d think I’d go with GMail, since it’s robust and efficient and feature-packed, but GMail is fundamentally unsuited to the task of keeping an empty inbox, because it doesn’t use folders: instead, it uses tags and categories. Rather than moving something off into a folder, you tag it with the folder name. This seems handy, and can be, and it also allows a single message to be categorized in more than one way, but since nothing can ever be moved out of the inbox, that means that there is no way to reap the organizational and psychological benefits of a clean inbox with GMail at all. Instead of facilitating a clean inbox, it assumes you’ll never be able to keep your inbox organized and doesn’t even provide the means to manage it. If it were a human being, we’d call it an Enabler, which in this case is not a good thing.

There may be ways around this in GMail; I’ll present them if I come across them.

One that works: Hotmail
The system I found that does work and that is free to all comers is Hotmail, a.k.a. Microsoft Live Mail. If you despise all things Microsoft, of course, this won’t appeal to you, but otherwise it does the job fairly well. You can set up Hotmail to receive e-mail from other accounts and can organize all your incoming e-mail into folders.  They even recently added a feature that gives you a little congratulatory message if you empty out your inbox (though I have a feeling this isn’t a message very many people see.) Hotmail is easy to use, has drag-and-drop functionality, and is very responsive.

There are a couple of drawbacks. One is that Hotmail doesn’t allow subfolders, so I can’t make categories out of my folders and collapse them when I don’t need them. It also doesn’t allow very long folder names. This is inconvenient, but I’ve worked around it by naming folders things like Read_offers instead of having an “offers” folder within my “read” (as in “already read”) folder. I also had to place underscore symbols at the beginning of the names of my utility folders so that they would be listed together at the talk, as Hotmail always shows folders alphabetically.

The other drawback is that it often seems to take about 10 minutes (very roughly) for an e-mail to arrive from an external e-mail account. Normally this doesn’t matter much, but it’s a big obstacle if you’re having a semi-real-time e-mail conversation with someone, if someone sends you something while talking with you on the phone, or if the correspondence is time-sensitive. This delay doesn’t occur with the free account you get from Hotmail itself, though.

So while I can’t recommend Hotmail wholeheartedly, I can say that for the month-and-a-half or so I’ve used it, administrating my e-mail has been easier than it ever has been before because Hotmail supports the “empty inbox” approach very well.

Any readers who have recommendations of other free or very affordable Web-based e-mail systems they would recommend for this purpose are very much encouraged to mention them in comments.

Ten weeks ago I posted the article “How I’m Keeping My Inbox Empty,” in which I described a new strategy I was taking to keep on top of all of my e-mail and keep my inbox completely clear. Some of the key points of my approach, which owed much to Dave Allen and his book Getting Things Done, were

• Make a set of special-purpose folders for e-mails that need follow-up, things to read, general information to keep, etc.
• Make tasks out of any e-mails that cause you to need to do tasks and put those tasks in a task management system
• If you can answer or deal with an e-mail within about two minutes, handle it immediately
• Look at everything that comes in as it comes in. Don’t put off any e-mails to consider later. If it’s going to take a while to respond, put the e-mails in your Reply/Act folder.
• Visit your Reply/Act folder often and deal with e-mails there, oldest first.

Of course there’s more to it (see the original post), but those are some highlights.

Ten weeks after I started, do I still have an empty inbox? Actually, yes! And this pertains to both a personal e-mail setup I have and a work-related one: the system has been working in both places equally well.

And have my inboxes been empty the whole time, or have I had to redo the cleanup? Amazingly, the system has worked consistently for me so far: I’ve never had to duplicate my initial effort (which wasn’t even so difficult: I outline how to pretty rapidly establish a clean inbox in the original post) and have had a clean inbox the whole time.

Have there been any unexpected snags? Yes, one: I sometimes get in the habit of watching my inbox like a hawk but neglecting my reply/act folder, which really needs to be addressed often. In online gamer slang (from my book Talk the Talk: The Slang of 65 American Subcultures), I’m “camping the spawn point,” looking for monsters where they appear instead of going after the ones that are already in place. But once I realized I was doing this, I began working harder at going back to that reply/act folder, and I’ve seen better results since. What’s wonderful is that even with that problem, I was being much, much more responsive to e-mails than I had ever been before.

Have you tried out this method of keeping a clean inbox? If so, I’d love to hear how it went for you in comments.

Photo by mek22

This morning I got out of bed with the realization that I often have to sort out the same set of e-mails twice: once on my desktop and once on my laptop. Realizing that this was getting in the way of me keeping on top of e-mail as it comes in, I found myself a good Web-based interface for my e-mail, where I started by working on just my last ten days of e-mail. I went through every single non-spam message I had received in that time, sorting them into appropriate folders, responding to or following up on the ones that could be done within a minute or two, and putting about half a dozen that will require more time into a special “REPLY/ACT” folder where I’ll be able to easily tackle them in order. Then I went over the past month and a half and any marked e-mails in my own inbox and added anything that stood out to the REPLY/ACT folder.

And now my inbox is empty. This doesn’t mean that I have no e-mails to respond to, but that I’ve cleared away everything except the e-mails that will need detailed responses and have those easily accessible in priority order. As new e-mails come in, I’ll deal with them in a similar way, since I have a system in place and am going to the same spot to handle e-mail whether at home or on the road. Instead of always opening my e-mail box to a long list of mostly-unimportant e-mails, I’ll open it to a few things that I’ll review, fire off quick replies where those are needed, and have a single place where the bigger tasks will go. Everything else will get filed away. This takes very little time, now that my system is set up. And since I had been gradually developing my ideas of how to sort e-mail in past attempts at this process, it all came together quickly, in just over an hour!

Update, March 30th: I’ve continued emptying my inbox this way virtually every day since I started the process, and it has continued to be much easier than my old process. My REPLY/ACT folder sometimes gets more full and sometimes less, but “full” in this case is at most 16 items. The system seems to be working, and I’m definitely much more responsive than I have been in the past, in large part because I get the short responses out of the way immediately regardless of how important they are and have the e-mails that need longer responses somewhere they’re easy to find and pick off.

What Stress Has to Do With Organization
We can mostly only do one thing at a time, so ideally we’d always know exactly what that one thing should be at any time. Let’s say you’re at home, no phones are ringing, and nothing’s on fire. What do you choose to do with your time? Relax and watch a movie? Wash the plate and glass on the counter? Go over your kid’s homework? Fix that squeaky door? Catch up on some reading for work? Call your old friend from college you’ve been wanting to get back in touch with? Organize papers for tax season? Every responsibility–like housekeeping, friendships, bills, work, concerns about world hunger–and every way we communicate–like mail, notes sent home from school with kids, email, voice mail, conversations with family members–provides another potential source of things that might need to be done. And it’s exactly the same in a work or school environment, often with a completely separate set of systems in each location.

The problem is that all of these inputs can be stress-producing, if not overwhelming. Without some serious organization, it’s next to impossible to keep track of all of them at once, which means that anything that isn’t getting taken care of can potentially be a distraction and a worry. You find yourself regularly pushed around by thoughts like “Do I really have everything set up for the trip next week?” or “I keep thinking I need to pick something up at the hardware store” or “I’ve got to remember to get back to that prospect with a quote.”

Fortunately it is possible to channel some of this chaos and cut back on stress. Here are a few quick tips to that end, inspired in part by my continued reading of Dave Allen’s excellent organizational book, Getting Things Done, along with other sources.

Recognize your inputs. Anything that’s not in the place where you want it to be, may need to be acted on, needs to be reviewed to decide whether you need to act on it, is in the way of you knowing or doing something you need to know or do, etc. is an input, a potential “to do.” That doesn’t mean that you need to waste attention to all of those things every time you notice them, only that they’ll tend to dilute your focus unless you’ve got some kind of reliable system in place to handle them.

Don’t let the noisy things distract you from the important things. An e-mail about a new version of some software you use may be interesting and may pop up right in front of your face while an important financial matter that doesn’t have a specific deadline could be lingering in the background. It can help to have places to put lower-priority things  as they come in, for instance an “Interesting/check out” folder in your e-mail program for that e-mail to go until after the financial matter is settled.

Minimize the number of task systems you use. Almost everyone needs more than one task list: for instance, you might have an e-mail program with messages that need to be read, responded to, or acted on; plus a traditional “to do” list, a place to stack incoming mail, etc. But it’s easy to let task systems proliferate–a few notes written on paper here, an occasionally-updated PDA task list there, a stack of unreviewed papers on your desk to go through, etc.–making it difficult or impossible to determine what the one thing you want to do at any given time is, because there are too many places to look to figure that out.

Ditch unimportant tasks. Still have last week’s newspaper because you didn’t get around to reading it but might still? Consider how often you’ve gotten around to ever reading a week-old newspaper before, and if it’s close to 0% of the time, the newspaper can go. I’ve found sometimes in the past that I’ve been hanging onto an unimportant tasks for years–something that really would be good to do, but has never been important enough to trump all the other things that are going on in my life on a daily basis. It can be freeing (and a good way to cut down on an unrealistically long task list) to be able to look at some items like this and say “I’m just going to decide to not do that one.”

Part of how you’ll be happiest dealing with all of these inputs will depend on whether you want to organize your life or just keep the noise level down a bit. You may find you want the productivity and peace of mind you can get from a real organizational system. Allen’s book is a good resource for tackling this if you decide to.

On the other hand, maybe your life isn’t all that hectic, but a little additional clarity and order will help–in which case the suggestions above might be enough to give you the lift you’re looking for.

If you’re not sure whether it’s worth committing to a big organizational effort, ask yourself: Am I sometimes not taking care of things I need to get done, with bad consequences? Do I feel overwhelmed or anxious about the things I need to do? If either of these is a yes, time spent organizing effectively can provide relief while making more efficient use of your time. A successful organizing effort pays for the time it takes to do it in short order, and doesn’t have to necessarily be done all at once to be effective.

Photo by andres.thor