Okay, You’ve Declared E-Mail Bankruptcy. Now What?

There’s lots going on in Xconomy-land, so this week’s column will be shorter than usual. Which is probably fine with you, since everyone seems pressed for time these days.

Microsoft is notorious for its lame ad campaigns, but lately the software giant has been putting its finger on the overcommitment problem, through an amusing series of ads for Hotmail under the theme “The New Busy.” As Microsoft implies in its ads, everyone in a knowledge-worker role spends more time than they would like managing stuff like incoming e-mail. I can’t quite see how Hotmail solves that problem—but there’s no doubt it’s a real one.

So, on this subject of being too busy, I want to come back to a 2009 column I wrote about the “e-mail bankruptcy” method for getting over your inbox management blues. I’ve noticed more and more people turning to this technique. Just this week, for example, David Cancel, CEO of Amesbury, MA-based Web analytics startup Performable, tweeted that he was getting ready to do the deed.

Declaring e-mail bankruptcy is simple, and not nearly as painful as its financial namesake. All you have to do is admit to yourself that you’re never going to have time to deal with the huge backlog of unanswered e-mails clogging your inbox, and archive or delete them en masse. (It’s polite to let your frequent correspondents know that you’re doing this, so they can re-message you if they were waiting to hear back about some urgent inquiry.)

But clearing out your inbox is only the first half of the solution to chronic e-mail overload, and it’s the second half that I want to touch on today. The trick is to prevent another backlog from building up by completely emptying your inbox at least once every work day.

Emptying your inbox the first time is easy. But keeping it empty requires vigilance and dedication, as I learned after I deleted some 15,000 unanswered e-mails back in January 2009. I kept to my zero-inbox routine for a couple of months, but then I fell off the wagon, allowing one day’s accumulation of e-mail to build up to a week’s and then a month’s. Pretty soon my unread message count was back up to 3,000. That mountain of e-mail is pretty easy to build up in a hurry if you get 150 to 250 e-mails a day, as I do.

I knew I’d have to go through another bankruptcy eventually, but first I wanted to find some techniques that might help me adhere to the zero-inbox habit. My main challenge—and the big reason I’d given up on my routine—was that it was just taking too long. I’d put in a regular 8, 10, or 12-hour work day, and then I’d have to spend another hour or two getting through all of the stuff in my inbox. Faced with a choice between keeping my inbox empty and having a semblance of a life outside work, I had chosen life.

But after I was seated as a juror on a medical malpractice trial back in March and wound up spending three weeks away from the office, my e-mail log jam grew so tangled that I had to do something. In early April, after the trial, I cleared out my inbox once again. And around the same time I found some great suggestions online that have been helping me to stay at zero. Here they are:

1. Set up a system of working e-mail folders to temporarily store “difficult” e-mails. This suggestion comes from Matt Perman, a blogger in Minneapolis who wrote a long, extremely useful post in 2008 called “How to Get your E-Mail Inbox to Zero Every Day.” Perman is an adherent of David Allen’s “Getting Things Done” system, which recommends dealing with most incoming e-mails by either deleting them immediately if they require no action, or taking action on them immediately if the action will take less than two minutes.

The difficulty, of course, is that many e-mails require action that will take more than two minutes. “It is these longer-than-two-minute e-mails that ruin most people’s day,” Perman correctly noted. Perman recommended dealing with these e-mails primarily by creating three folders entitled “Answer,” “Read,” and “Hold.” The Answer folder is for all e-mails that require a response that will take longer than two minutes to write. The Read folder is for material you have to look at, but will require more than two minutes to digest. And the Hold folder is for messages that require your action, but only after you get some vital response or piece of information from someone else.

Once you have these folders set up, you can power through your whole inbox quickly—deleting notes that don’t require action, acting immediately on those that can be answered quickly, and filing away most of the rest (with an exception that I’ll detail in a moment). I’ve been doing this for a few weeks now, and I find that it’s a great way to keep my inbox empty. Which isn’t a wholly quixotic goal: I find that zeroing out my inbox is actually calming, because I know I’ve dealt with every incoming message or request, at least in a preliminary way. It also helps me avoid the trap of using my inbox as a kind of default to-do list. (This is a bad idea, I’ve found, because the list quickly grows so long that I lose track of the older items.)

What’s absolutely key to this system is that you make time every day to go back and deal with the messages that are now in your Answer, Read, and Hold folders. The stuff in Hold can stay there until you get the responses you need from other people. The stuff in Read can usually stay there until you have a 30- or 60-minute block of time to catch up on your reading.

Answering the messages in your Answer folder is the time-consuming part. There’s no way around this. But on the upside, I’ve found that I’m not putting as many e-mails into the Answer folder as I would have predicted, because I’m getting better at responding to most of my incoming messages in under two minutes. Also, I know that every time I put a message into the Answer folder, I’m just delaying the pain, which increases the incentive to deal with it immediately instead.

Finally, there is one more way to deal with e-mails that can save you from developing an overstuffed Answer folder. This is the exception that I mentioned a moment ago: it has to do with messages that don’t really require a written response, but do require some action—meaning they should be transformed into items on a separate to-do list. Which brings me to…

2. Pick a to-do list system that you like and use it. The to-do list is your repository for action items that can’t be crossed off just by sending an e-mail, but are part of the big ongoing projects in your work or home life. It’s an essential complement to your e-mail management system.

Many people just keep their to-do lists on paper, which works perfectly well. For a while, I was a devotee of the “Hipster PDA” method, which involves carrying a stack of index cards held together with a binder clip and using a separate index card for each action item. But I’m too much of a gadget freak to resist the call of the multitudinous software-assisted to-do list options. (There are at least 500 to-do list apps just for the iPhone and iPad.)

Lately I’ve been using Bento, a program from Apple’s Santa Clara, CA-based subsidiary FileMaker. If you just want to keep a to-do list, Bento is definitely overkill; it’s a powerful consumer-oriented system for building customized databases that can help you keep track of everything from your favorite recipes to your contacts and calendar events to your home inventory. But I like it for several reasons.

First, the customizability means that you can fuss to your heart’s content with the template for your personal to-do list. If you want a field for the status of your items (In progress? Completed?), the due date, or what overarching project they belong to, you can easily create them. Then, once you have a bunch of to-do items stacked up, you can sort them according to the various fields. If you need to see what’s due tomorrow, for example, you can sort the items by date, or if you need to see them separated into project categories like Work, Home, or Shopping, you can do that too.

Also, I’m a fan of Apple products, and Bento makes interoperable versions of its software for the Mac, the iPhone, and the iPad. This means you can review or update your to-do list on your laptop, your phone, or your tablet and wirelessly sync the changes with the other devices. (Thankfully, this synchronization occurs over your local Wi-Fi network and does not depend on Apple’s MobileMe service, which doesn’t work worth a damn, in my experience.)

Of course, whatever to-do list system you use, you’ll find it much easier to add items to your lists than to cross them off as completed. I can’t help you there, and neither can Matt Perman or David Allen or any of the other productivity gurus. But if you can use tricks like folders and lists to get control of your e-mail inbox, you’ll have a little more mental space free for tackling the big stuff.

Wow—I said at the beginning that this column would be shorter than usual, and here I am at 1,600 words. I’d better head off to deal with my inbox, which has doubtless swelled quite a bit since I started writing this. I plan to make short work of it.

For a full list of my columns, check out the World Wide Wade Archive. You can also subscribe to the column via RSS or e-mail, and you can download Pixel Nation, an e-book version of the first 80 columns, as a free PDF file or a $4.99 Kindle edition.

Wade Roush is the producer and host of the podcast Soonish and a contributing editor at Xconomy. Follow @soonishpodcast

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  • I moved to keeping an empty email box about a year ago, but I did it gradually. My first move was to make sure it was empty just once a week, on Fridays. You can imagine the wonderful (not) Friday evenings I spend adhering to that goal. I shifted to a daily goal and pretty much keep to it, using a version of the process you described. My own rule is to have no more than a viewing pane of emails in the inbox, most of which would fall in the “read/hold” category you mentioned. The biggest key to doing this is indeed handling the quick ones on the spot, as you prescribe.

    I still haven’t totally gotten over the “email inbox as to-do list” issue. It is still a “to-do” to keep on top of it the way I do. One big giant, soul-sucking, boring, and annoying “to-do.” It’s an understatement to say that I have no love lost for email.

  • Wade, I wish you’d been at MassInno on Wednesday, because our presentation for Boomerang was pretty much a carbon copy of paragraphs from this article in terms of laying out the problem, plus a few humorous images.

    We gave a demo of how Boomerang makes it easy to manage those emails that Matt described, helping people to handle email without feeling like robots.

    It sounds like you’re on a Mac, but if you’ve got a copy of Outlook kicking around, let me know! Otherwise, we’ll have a version for Gmail coming out in the next couple weeks.

  • @Jules: I feel your pain. And I admit that I do leave some e-mail in my inbox as reminders of things I’ve got to take care of. I think the danger is that if you let them stay in there longer than one day, there’s much less chance that you’ll actually get around to doing them.

    @Alex: Thanks for your comment. I’m aware of Boomerang and similar tools like Followup (which Erin profiled here recently). Thankfully I escaped from Outlook a few years ago and would never consider going back. But I’d love to try out your Gmail version when it’s ready. Generally though, I’m skeptical about the idea of dealing with the difficult e-mails simply by forwarding them to yourself in the future. This seems like just another way of delaying the pain. Of course there are people who argue, in all seriousness, that putting off as much stuff as you can is a good time management technique!

  • Michael Hawes

    Wade, thanks for another excellent article. I find all your articles informative, well-researched and well-written. Keep it up!

  • Alex Moore

    Aye, at some point you have to pay the fiddler’s bill.

    To be honest, I was skeptical too, until I started using the thing every day. Knowing that there are 3 difficult emails left, and nothing else, is psychologically very different than looking at an Inbox with 20 messages in it, only 3 of which are actionable right now. Looking forward to seeing if the Gmail version has the same effect on you!

  • Bill Baker

    A small additional tip for Outlook users, but likely applies to all or most other email clients: Your answer, read and hold folders will be spread out in your folder hierarchy, because the folder list is usually alphabetical. Read might not even show in the first N folder names. I named mine ‘0 – Answer’, ‘1 – Read’ and ‘2 – Hold’. They are always at the top of the folder list and top-of-mind.

  • @Bill Baker—that’s a really good point. I actually did the same thing in Gmail, which has folders but calls them labels. I created three labels called “1 Answer”, “2 Read”, and “3 Hold”, and now they’re at the top of my label list, which makes it easy to drag-and-drop emails right into those bins.