There's one good habit that, if adopted, can reduce the clutter dramatically. I'll go out on a limb and say that this one technique, if adopted religiously, can reduce the size of your currently unmanaged inbox by as much as 80%.

I'll call it "plowing through" but that doesn't do it justice because there's actually rationale and logic behind it. Others refer to it as "just do it"; a take-off on the old Nike slogan.

Over and over and over.

Oh, sure, every so often we act on one, but by and large that first scan is nothing more than an extended procrastination session. You don't want to deal with it now, so you'll deal with it later. And of course later never comes.

The result? An inbox overflowing with email you need to deal with "later".

That's a really bad habit. It's a daily process of digging a hole you'll never get out of.

So what's an alternative?

Well, we can't act on every message as they come in - "first in first out" may keep your inbox empty, but it doesn't account for any number of things that legitimately make some messages more difficult and time consuming to deal with.

So, we'll shoot for an 80/20 tradeoff. One new, good habit that if applied consistently is likely to be able to deal with 80% of the email you get every day.

The Two Minute Rule

Not long ago I read the book Getting Things Done by David Allen. One of the nuggets I walked away with was what he calls the "2 minute rule". It's the cornerstone of what I call "Plowing Through" your inbox.

It works like this: as you read your email, if it will take 2 minutes or less to act on it and thus be able to dispose of the message, then DO IT. Stop, right then, right there, before you move on to the next message and do whatever it is that the email is calling for you to do - whether or not you "feel like it". Use the 2 minute rule as motivation to get that message dealt with and gone.

Be brutal. If you know you're never going to do anything in response to the message, then delete it, or file it in a different folder, right then. Be honest with yourself. Deleting a message takes significantly less than 2 minutes.

Be responsive. If a message calls for a quick reply, then reply right then, before moving on to the next message. A short response need not take a lot of time.

Be efficient. Many messages actually don't require a response; certainly no response is both quicker and easier than even the shortest reply.

Be realistic. Don't get wrapped up in spam, delete it and just quickly and calmly move on.

And yes, of course if the message is going to take some time to deal with then leave it or file it in an appropriate folder for future action. Perhaps the message requires you to do some related work, take some time to respond to it, or is somehow something that will simply require an investment of over two minutes on your part. Fine. But I'm guessing the vast majority of what you receive every day can be dealt with in under 2 minutes each.

It really is that simple.

Two minutes?

The theory behind the two minute rule is simply this: for any message you don't immediately act on, you will spend on average at least a total of two minutes in the coming days, weeks or months simply re-encountering that message over and over again, and re-deciding each time "oh, I don't want to (or can't) deal with this now."

You can debate the specific number, though I tend to agree with it and strongly recommend that you use it at least as a place to start.

The key to the plowing through technique is consistency. Yes, "just do it". Don't let email accumulate only to suck more of your time later.

Use "plowing through" as a motivator to turn "I don't want to deal with this now" into "this'll be quick, let me get rid of it right now."

You'll achieve a sense of accomplishment, and what's left will be your most important messages that by definition you've already identified as being worthy of more of your time.

Yep, this is how we tame 80% of the beast that is email: one message at a time.

Quickly.

And over-used attachments? Those are evil.

How are they evil?

Let me count the ways.

Using unnecessary attachments reduces the probability that your message will be read.

I want to say that it significantly reduces the chances that your message will be read, but I just don't have the data to prove that.

But why take the chance unless you really need to?

Here's the classic case I see all too often. Someone types up a one page meeting agenda in Microsoft Word and then sends out that Word document as an attachment to the list of meeting attendees.

WHY?

Why not, instead, just copy/paste the agenda into the body of your email and not use an attachment at all?

Several good things happen when you do this:

• Your message is more likely to be read. Your recipients don't have to jump through any additional hoops to see it - it's just there right in the message. They may not even have needed to open the email message, viewing the message in a preview pane of some sort.

• Your message is more likely to be delivered. The presence of an attachment can be considered a mark against it as spam filters evaluate the "spamminess" of a message.

• Your message will be smaller and be delivered more quickly. This applies not only to the time your recipient needs to download the message, but also the time it takes to traverse the internet to get there.

And in case you're wondering (as I was) a one-page agenda that I recently received in Word is 20 times bigger than its content alone. That's 20 times longer to download, 20 times more disk space, and so on.

•

Using unnecessary attachments is being rude to your recipients.

Consider what you're doing with an attachment that isn't needed:

• You're forcing your recipients to download something that's much bigger than it needs to be.

• You're expecting your recipients to have the tools required to open your attachment if they want to be able to communicate with you.

• You're wasting your recipients bandwidth, disk space, and time to download, store and open/close your message.

If you look at it that way, it all seems pretty rude, doesn't it?

•

So what's a "necessary" attachments?

I'm not sure I'll ever consider an attachment "necessary", because as we'll see in a moment there are so many alternatives. However attachments can be an appropriate convenience in many situations.

I'll make two generalizations for when attachments can be appropriate:

• When the message isn't text.

• When the attachment isn't the message.

And to be clear, both of those are quickly invalidated if the attachment is too large. More on that in a second as well.

The message isn't text.

The clearest example might be voicemail or other audio recording: only sending an audio file as an attachment makes any kind of sense.

Sending a photo or short video to a friend or family member is also a fine example.

In both of these cases the "message" just isn't something that can be represented as text in the body of a message. (FYI: a photo that appears in the body of a message is still considered an attachment by both the mail system and for the purposes of this discussion.) Attaching the image, the audio or whatever else is simply the only way to get it across.

If it's small enough, that is.

The attachment isn't the message.

I'm playing a little with semantics here, but the idea is this: sometimes the "message" is something like "could you review this document", or "the third quarter financial's are attached for your review". The attachment isn't the message. It supplements the message, it's additional baggage that's referred to by the message, but it's not really the message.

However you choose to think about it, there are scenarios where Word documents and Excel spreadsheets and other types of documents must be transmitted whole. Typically they're scenarios where information in the attachment must live on after the message has been read and disposed of. Documents to be reviewed are perhaps the most obvious example.

The key is that what you have to say isn't buried in the attachment. That's in the email body that accompanies the attachment.

•

How big is too big?

One of the things I keep coming back to is the size implications of attaching files to your email, particularly when used in lieu of alternatives such as simply putting the message in the body and not using an attachment at all.

But it begs the question: if size matters, what are the rules?

Here's where you get annoyed with me.

It depends.

Or more completely, it depends on your recipients.

You know the old adage about writing: "Know your audience"? The same applies here: know your recipients. Know what you can expect of them, know what's reasonable to "force" them to do, know what may, or may not be an issue for them.

If you don't know, if you have to guess, then you probably want to assume the worst.

Let's say you want to include a Word document as an attachment. Let's also say that document is around 800,000 bytes.

First, realize that because of the encoding used to attach something to email, the attachment will actually be slightly larger than the original file size. In this example I'll say that the attached fill will be 1,000,000 bytes long.

Let's start with your recipient's download times:

• Basic DSL, or roughly 658k bits per second (which is what my 768k/128k DSL tested at some time ago) means the download will take about 15 seconds. Not too terribly unreasonable, I suppose.

• Dial UP, commonly around 28k bits per second: the download will take about 6 minutes. Suddenly things aren't looking so reasonable, are they?

Now, a lot of people argue that dial-up is dying, and that in most corporate settings people are connected via broadband speeds anyway. My response? That all may be true, but don't assume it. Know it, or assume the worst. If you assume that everyone can handle high speed you're quite likely to alienate the folks that you didn't realize were still on dial-up. (And even in professional settings, speed isn't all it's cracked up to be - just ask anyone who travels and uses various WiFi hotspots or hotel connections.)

Let's not forget disk space. You've just imposed a 1 megabyte disk space penalty on your recipient in order to receive your email. Is that reasonable? It might be. It might not be. If they archive their email, as many do, that's a permanent penalty. Is that reasonable? Is your message really worth that?

The fact is that the definition of "how much is too much" changes over time. 10 years ago one megabyte was huge, today it might not be. 10 years from now we might all be shooting around multi-gigabyte high definition videos laughing at "the old days" when a gigabyte downloads were measured in days, not minutes.

If you care about your recipients, if you want to maximize the chance that your email is received and read, then simply do this: make your email as big as it needs to be, and no bigger.

And since you probably still want numbers, I'll throw out two:

• I'd think twice about sending any email larger than about 200k.

• There are ISPs and other mail systems that routinely block or discard emails larger than 4 megabytes, though sometimes that can be as small as 1 megabyte.

As I said, those numbers change over time, but as of today if you do nothing else, they're reasonable rules of thumb.

•

So what are the alternatives?

There are two:

• Put the content in the email body.

• Put what would have been an attachment somewhere else.

The first is fairly obvious: for example rather than sending a word document that contains your message, put the message in the body of your email and don't attach anything at all. Smaller, faster, more likely to get read. Everyone wins.

That's the preferred approach in general.

But sometimes, as we discussed earlier, text in the body isn't the answer. You actually need to share a file.

The second is only slightly more work, but will be very much appreciated by your recipients, because it give them control. The technique: upload your document or other attachment to a site that's accessible to your recipients, and then email a link to that document. Your email is short, to the point, and quickly transmitted, downloaded and read. Then your recipient gets to choose whether or not to download the document and when to do so.

The question that usually pops up is "ok, where do I upload that everyone can see?"

• If you're in a corporate environment, and all your recipients are in the same environment, I'll bet you have shared folders on your network that you can simply copy files to.

• If you or one or more of your recipients are just random internet users, then it's likely that your ISP allocated you some amount of space for a web site. You don't need to set up a web site, just upload your documents to that space, and email out a URL to the people that need to see it. (In a corporate environment you may already have web-visible locations for exactly this purpose. If not, lobby for it.)

• Use sharing or hosting services like Flickr or photobucket for images, and other similar services for other types of content. Even discussion groups such as Yahoo Groups include some amount of file sharing available to group members. This is actually a rapidly evolving market, mixing on-line backup with on-line content hosting, so the options here are growing and changing almost every day.

The other question I get about using any kind of accessible shared location is security. What if you don't want just anyone to see your document or files?

It's typically very easy to password-protect such a location, and then share the password with your recipients when you email the pointer to the document. If you can't password protect the document, then using a utility like WinZip (or the free alternative 7-zip), create a password protected ZIP file that your recipient can then download and unpack. The bonus is that zipping will also compress the file and make for a faster download.

And for the extremely security conscious - yes, passwords as I've described can be hacked by someone who's very motivated to do so. If your documents are that sensitive, though, then you shouldn't be sending them around as attachments anyway. Attachments are sent unencrypted, and anyone who can sniff your email (as that motivated person might want to do) then has access. You'll need a more secure solution that's beyond the scope of this article.

•

The whole point of sending out a message is to convey information; to get that message read. Among other things that means you want to do what you can to make it as easy on your recipient as possible. It's not just about being nice to them, it's about increasing the effectiveness of your email; increasing the chances that it'll actually be read and acted on.

It works both ways. Not only do you want to get control of everything that's arriving in your inbox, but effective communication means you're not feeding the beast that is email in someone else's inbox either.

Sometimes the beast turns around and bites back.

And yet we persist in treating as such.

Add to that the experience of getting an email on a topic you feel passionately about, and it's a recipe for a communications disaster.

I'm sure we've all been there. You're on a mailing list or in some kind of on-line discussion and someone says something that, to you, is outrageous - literally provoking outrage. You then experience an urge, a desire, a need, to respond, to respond before anyone else does, and to respond strongly to put that person in their place. Perhaps you want to point out the error of their ways and their thinking, and then perhaps move on to topics such as their parentage and personal hygiene.

And that's when all hell breaks loose.

What I am saying is this:

Email just sucks at properly conveying passion.

It's incredibly easy to do more harm than good with a less than fully thought out reply.

Unless you write for a living and treat each email as a manuscript to be crafted, rather than a quick-and-easy substitute for a face-to-face discussion, the chances are that everything you say in that quick and passionate response will be wasted. Right or wrong, justified or not, your message will likely not be heard over the emotion of the moment.

And in the words of the title of a good book I read recently, It's Not What You Say, It's What People Hear.

•

The fact is most of us are not good writers. Some are, but by and large, most are not. And in all honesty, that's usually ok for email. Email is not typically that demanding a medium. Messages are short and to the point; more of a discussion than an oratory.

Unfortunately when we get passionate about something our writing skills certainly don't improve. In fact, it's usually just the opposite; out the window they go. Just when we need it, our words fail us. In fact, the result of knee-jerk passionate responses is typically to do more harm than good.

I've seen it again and again; thoughtful and important opportunities for discussion and education get lost in heated words and accusations. Often relationships are damaged as the messages turn personal, and the entire point of the original discussion is lost.

I'm sure you've seen it too.

So what's the answer? What do you do when you feel that visceral "I must respond NOW!" reaction?

WAIT

•

I know, I know, you're thinking "but what if what I have to say is so important, so urgent, that it simply can't wait? I mean, the person I'm replying to is just so wrong, I can't let it go!"

WAIT anyway.

There's very little that can't stand to wait 24 hours. Really.

Email is not urgent.

Here's why that delay is so critically important.

Without getting in to a lot of psychological hoo-ha, that visceral "must respond NOW" reaction is your fight-or-flight reaction applied to a medium where it just doesn't make any sense. Your emotional response and reaction are governed by a different part of your brain.

And that part doesn't put words and thoughts together very well.

Waiting is all about letting your thoughts catch up to your emotions.

I guarantee you that if you wait 24 hours you'll write a better, more coherent and less offensive reply than if you give in and write it immediately. In fact, that's typically true for any response that requires a little more than average thought. Taking a little time to think it through almost always results in better email.

I'm not talking about your changing your mind or your opinions, though of course that can happen. All I'm talking about is changing your words, changing your tone and changing your approach. I'm talking about using words, tones and approaches that simply aren't accessible to you in the heat of the moment. I'm talking about choosing words, tones and approaches that focus on communicating your message, rather than blinding the recipient with your outrage.

And the absolutely wonderful, often-overlooked but critically important side effect?

Your recipient will be much more likely to actually hear what you have to say. Yes, you might actually get your point across.

Wouldn't that be cool?

Another side effect? You'll avoid causing the discussion to "blow up" and you'll avoid providing a venue for others to pile-on. You'll avoid filling your inbox and the inboxes of everyone watching with off-topic and often vitriolic messages.

Making the world a friendlier place is a nice side effect too, but I figure that reducing the amount of off-topic email you have to deal with might be more compelling if you're expecting tools and tips from a site called "Taming Email".

•

Sometimes "using email more effectively" is nothing more than "communicating more effectively". Sometimes you can make a huge difference in your approach to email, and the burden it places on your daily life not by focusing on the tools and the technicalities, but rather what it is your saying and how you're saying it.

I guess what I'm trying to say is that sometimes taming the beast that is email means taming the beast that is us.

I believe that 90% of your outgoing email should be in plain text format. Maybe more.

Why?

Aside from a collection of technical reasons I'll get to in a minute, it's simple really: you want people to focus on what you have to say, not how it looks. Lots of formatting, backgrounds, highlighting and using many different fonts and styles are all things that distract from your words. They're more about making your message "pretty" to look at, and rarely add value to your ideas.

I'm not saying never use HTML (or Rich Text) email, but I am saying default to using plain text and only use HTML email when you really need to, which is actually pretty rare.

The fact is, "pretty" is often at odds with "effective".

I frequently get email that's full of in-line pictures, borders, a busy background, highlighting, font changes, bouncing smiley faces and occasionally even music and animation. The problem is that somewhere in all that there's a message I'm supposed to be able to find and read. Quite often everything that went into making the email "pretty" or "fun" gets in the way of making the message "readable".

That's the usual objection to plain text email: It's plain. It's boring. It's not pretty.

And you know what? That's all absolutely true. And it's also all totally irrelevant.

All that has absolutely nothing to do with what you are attempting to do with email, and that is to get your email read and to get your message across.

Using plain text forces you and your reader to focus on the content of the message, not the look of the message.

There are many technical issues with rich text email, which I'll enumerate shortly, but this whole "substance over style" issue is something that many people seem to miss. Everything you add to an email that isn't about what you're trying to say detracts from what you're trying to say.

Many people spend so much time worrying about the look and style of the message that they forget (or run out of time) to work on the substance. Ultimately it's the words of your email, not the look, that gets your message across.

Think about the fun and pretty things you can add to HTML email; I mentioned some of them above: in-line pictures, backgrounds, highlighting, font changes and even music and animation. Does using any of these actually add value to your message? Do they somehow add something that your words won't convey? In my opinion, most of the time they do exactly the opposite: the distract your reader, and they detract from whatever it is you're attempting to say.

EMail is, fundamentally, about writing, not drawing.

•

Technical Reasons to Prefer Plain Text

There are several technical issues that make plain text email preferable to HTML:

• HTML email is more likely to be classified as spam. Put another way, your email is somewhat more likely to trigger a false-positive "this is spam" analysis if it's HTML than if it were plain text. The "why" is easy: most spam is HTML.

• HTML email is more likely to look different to different people. You can spend hours crafting the look and feel of your HTML email, and you know what? It'll still look like a mess to someone. There is almost no consistency of HTML support across email programs. In fact, the recent release of Outlook 2007 has apparently taken HTML email a giant step backwards, as support for many HTML constructs was removed. (Folks like myself who send email newsletters in HTML format were seriously impacted. More on that below.)

• Some people can't or won't read HTML email. Some email programs just don't support HTML email, and some recipients choose to turn HTML email off. What you so carefully crafted as "John: you must see this!" might well look like this: "<span style="font-weight:bold">John</span>: you <span style="font-style: italics">must</span> see this!" - or worse.

• Rich Text /HTML email is bigger and slower. An HTML formatted message can easily be twice as big as "just the message" it contains. Some email programs are notorious for generating horrible HTML email, and do even worse. Start adding fancy graphics and backgrounds, and it suddenly balloons to tens or hundreds of times as big. That size costs you in upload speed and disk space, of course, but you're also forcing that on your recipients, regardless of whether they even want or can view your HTML email. Particularly those folks still on dialup (something like 30% to 50%, depending on who you believe, and where in the world you're looking) can be extremely sensitive to the size of incoming email.

On the other hand, plain text email is universally accepted, it's as small as your message, and it's as fast as an email message can be.

•

HTML In Its Place

OK, so after all that, what about poor, beleaguered HTML email? I mean, I'm sure that some of you are already saying "Hey! You said you publish your newsletter in HTML! Are you a hypocrite, or what?"

I'll choose "what".

I'll absolutely concede that HTML has its place. It's just that your day-to-day email is not that place.

I chose HTML for my newsletter for two reasons:

• I asked my subscribers first. Not wanting to produce two newsletters, I simply asked my subscribers at the time I started which they would prefer: HTML or plain text, and the majority selected HTML.

• My newsletter is a formal, periodic, publication. It's not a person to person email. As such, there is a certain expectation that it'll look a little more polished. Yes, a little "pretty" even. In fact, it's that expectation that I believe drove a lot of the preference towards HTML when I asked.

The newsletter is also simultaneously published and archived on my website, in HTML.

And even with my newsletter, I take care to hand code the HTML, and use it fairly sparingly, so as to minimize the dependence on lots of different HTML "features", as well as to keep the size of the email from bloating.

Similarly, my expectation is that email from certain sources will be in HTML. This applies mostly to businesses, though. When I get my order confirmation from Amazon.com, for example, it makes sense that it look like the web page that I just left. (Though even then Amazon's email, like my newsletter, uses a technique called "multi-part mime" that provides a plain text message in addition to the HTML formatted message for those recipients who cannot view HTML.)

So when should you use HTML mail?

Rarely.

First focus on your message. Focus on your writing. Focus on what you're saying and how it all gets your ideas and thoughts across to your reader.

That's what's important. That's what truly effective email is all about.

•

Common Objections

But plain text is so boring! Email's only as boring as the message. Focus on writing email that's engaging no mater how it's presented.

Plain Text is harder to read. Actually I get the opposite just as often, if not more often: "HTML email is hard to read." The good news about plain text email is that it puts the control over look and feel into the hands of whomever is looking. With most email programs you, as the sender, can select how you want plain text to look on your machine without affecting others. Similarly, every recipient can choose how they want plain text email to look on their machine. Most email programs will let you choose what font and what font size should be used to display plain text email. If you don't like the default, change it.

Size doesn't matter. It sure does. Slower machines and slower connections are much more common than you think.

I only use a little HTML for emphasis. Then why use HTML at all? You're paying (and possibly forcing your recipients to pay) a high cost just to be able to bold a word or two. There are plenty of ways to achieve the same effect in plain text emails.

HTML is the default, so that must be the preferred format. Nope. Many email programs choose defaults that show off their features, which is not always the same as being effective. They may default to making email look pretty, but we know better - the message is more important. Change the default.

I want to include a picture. Attach it to your plain text email. It's rare that a picture must be in-line with the text for it to have value. On top of that many email programs disable in-line and remote images by default as a spam-fighting technique.

•

Write Email for Your Recipients, Not You

One of the challenges, responsibilities even, of taming the beast that is email is not to create a another beast for the people you send email to. You should be writing your email in ways that make it more effective for them. That often means ignoring your own preferences and thinking about theirs.

• Don't distract or annoy your reader with unneeded formatting.

• Use plain text to keep the message smaller, faster and less likely to be filtered.

• Focus on the message, not the style.

Understanding that can be very, very freeing.

We'll look at this from two perspectives: what email delays can mean to you as a sender, and how understand that email can be delayed can affect how you work with email as a recipient.

Email is never urgent? "But I can mark is as urgent" I hear you saying.

So what?

All that really does is place a little red exclamation mark next to the message in your recipient's mailbox. (Or some other indicator, depending on the mail program your recipient uses.) It certainly doesn't cause your email to arrive any quicker. It doesn't move it to the head of some line, or do anything other than maybe give your recipient a visual cue that you think what you're saying is important.

And it certainly doesn't avoid any email delays.

So again, I say: so what?

The fact is, if you need someone to get your message in minutes, then email's the wrong tool. If what you need to communicate is urgent and needs to be disseminated quickly, you can't count on email. You can use it, and "most of the time" it'll be fine ... but you can't count on it. I guarantee that at some point an urgent message will be delayed when you least expect it - and it won't be a mail system failure at all.

Email is what's called a "store and forward" system. When you send an email, it's received by a mail server, stored for some period of time, and then forwarded on to the next server in the path to get your email to your recipient. Finally it lands on the recipients mail server, where it's stored until the recipient downloads it (another kind of "forward" to their inbox), or reads it on-line.

Those "periods of time" that a server might hold on to your message before forwarding it are typically very short, but there's really no guarantee that they will be. There could easily be any of a number of legitimate different mail server delays along the path that your email will take to get to your recipient. That's not the system being broken, that's how the system works.

And of course on top of that, your recipient could simply be choosing to check email less frequently than you might need.

One of the huge benefits of email is that it puts the recipient in control of when they might want to read and/or deal with their incoming message. That's not something you as a sender can count on, or change. Instead, you need to deal with it.

If something is truly urgent, then pick a more appropriate tool. Perhaps instant messaging, perhaps a phone call, perhaps a walk down the hall. All of these are "real time" direct communication, with no multiple step storage delays involved.

•

Recipients

Actually, that whole section for the senders was really for you. Why? Because you, too, need to know that email should never be relied on to be a "real time" communications tool.

And that realization, my friends, is very, very freeing.

The reason I absolutely love email is very simple:

• When I send email, I get to write it when I feel like writing it, and my recipient gets to read it when they feel like reading it. I'm not intruding or interrupting what they might otherwise be doing.

• When someone sends me mail, I get to read it when I feel like reading it. I can choose to, or choose not to, depending on whatever else is going on in my life. And I get to choose when, how or even if to reply.

Email really puts both sender and recipient in positions of control, as long as they realize that the cost of that control is the potential delay between sending and reading.

Why do I call this so "freeing" for recipients?

Be cause you get to choose.

You choose when, how, and what to send, you choose when to read, and you choose when, how and wether to reply. It's all in your control.

And yet, for something that you have so much control over, many people feel enslaved by their email, feeling that they having to read quickly and respond to everything. That's simply not true. You don't need to be constantly checking email (unless you want to), and you don't need to reply to everything (whether or not you want to).

You choose.

Let's put it this way: you wouldn't use email to call 911 for a life-threatening emergency, and neither should the people sending you email.

So why act like email is that time critical? Why choose to deal with email as if it were a real time communications tool, when by its very definition it cannot be?

Let it go.

Read your email. Reply to your email. Send your email. But do it on your terms and your schedule, not someone else's.

You choose.

So what if it the situation really is that important? What if it really is a 911-like situation where they need you now?

Email's not the right answer, regardless of how you use it.

They'll find another way to reach you.

They might even pick up the phone.

That essay closed with a simple little statement:

So if you need a selfish argument, it's that only replying appropriately will, as a side effect, also reduce the amount of email you need to deal with as well.

Here's the gem hidden in that statement: it's not just about replies.

Chances are it's quite a bit. Email's become quite the ubiquitous tool, and if you're interested in Taming Email, it's likely to be an important part of how you communicate.

Now consider that each and every one of those outgoing messages is request for a response.

I'll be more blunt: every time you send an email you are effectively asking the recipient to send you an email in response.

You may not be asking in the form of some text in the message that says "please reply", but as we've seen in Is a Response Really Required?, many people will respond anyway. And if your email is being sent to a mailing list? You've just asked for multiple responses to your one little email. You'll get more than you give, and in this case that might not be the best thing.

So the simple trick I mentioned?

Send less email to get less email.

Before you send your next email; before you even write it perhaps, but at least before you hit that Send button, ask yourself a few questions:

• Do the people who are about to get your message really need to see it? Yes, I'm asking you to actually question the value of the message you're about to send. The answer may well be "Yes", but it's always worth thinking about it first.

• Are you sending to the right people? Consider everyone who's about to see your message. Do they all need to see it, or would a subset of recipients be more appropriate. Remember, each recipient is an invitation for another response in your inbox.

• Do you want each recipient to respond? This works in two ways - it's another sanity check for making sure you're sending your email to the right person or people, and it's also an invitation to craft your message appropriately.

• Does your message imply a response is expected? Does it need to? Would it be appropriate to actually, specifically, say that no response is required?

• And lastly: is email the right tool for this job? I'll cover this in a future article, but while email is a very powerful and flexible hammer, not everything is a nail.

I don't mean to imply any absolutes in that list. Sometimes your email is quite appropriate and necessary, everyone does need to see your message, you do need to send it to a lot of people, and yes, perhaps all of them need to respond.

But by getting in the habit of asking yourself those questions before sending, you'll actually be reducing your own email load as a result.

And the email loads of others, which is also a nice side benefit.

Just recognize that sometimes that email you're about to send ... perhaps shouldn't be.

Or as the geekier folks often write it:

<AOL>
me too!
</AOL>

I really don't know what it is that causes it, but for some reason email seems to bring out the "me too" in many people. You know what I mean: you'll have a discussion, either one-on-one correspondence or more commonly an exchange on a mailing list, and at its close or at some other juncture, you'll get a completely content-free email or collection of emails from some of the participants.

Perhaps we feel the need to let people know we're listening. Perhaps it's the email equivalent of an head nod. The problem is, as I said, that it's otherwise completely content free. As a result, unlike an actual head nod, it's difficult to ignore. Someone must download it, read it, determine its value (if any), and then dispose of it.

It's quite alright to take the floor, if you have something to say. If not? Well, that's part of the point of this little essay.

If you have nothing to say, say nothing.

It seems simple enough. Before you dash off that next email reply - especially if it's going out to a mailing list - look at it carefully. Are you actually adding value to the conversation? Is it something that your recipients will value? Will they want to see it? Do they need to see it? If not, why are you cluttering up their inboxes and stealing their valuable time? For that matter, why are you taking your valuable time to do it?

My personal foible is my need to have the last word. All too often I find myself replying to an email and thinking "Why am I saying this? What's the point?" All too often the point is simply that I'm unconsciously attempting to establish some kind of position in the conversation by making sure I'm the last person with something to say. Unfortunately, the value of what I have to say decreases, since at this point I'm simply finding things to say, rather than saying something that needs to be said.

Another very common cause of replying a little to often is the need to correct, clarify or build on a point that someone else has made. All to often it's more about showing superiority than it is about clarification. If it's important, then fine - but be realistic about what's important. Quite often it's not as important as you first think.

Now, I'm definitely not saying never reply. Obviously it's quite possible that people are expecting you to join in the conversation, reply to a point or question, or an error does need correcting. What I am saying is think twice. Take a second to make sure that when you do reply, your reply has a purpose and that you're actually saying something. If not, perhaps you don't need to reply at all.

I think you'll find quite often that's perfectly acceptable.

So far it's also easy to consider this as purely altruistic - you're doing this to help others keep their inboxes clear, but it's not about your own, is it?

On the contrary. I've already mentioned the time saved when you don't reply to every random message you might be inclined to, but there's more. For everyone content-free email you send, chances are there's someone else on your mailing list who doesn't get the point we're making here, and will respond with a content-free email in response. And you know where that lands: in your inbox.

So if you need a selfish argument, it's that only replying appropriately will, as a side effect, also reduce the amount of email you need to deal with as well.

And that, too, is a good thing.

Yes, I see people asking for spam.

It's like they're putting a large sign on their virtual backside saying "Spam Me! Please!"

Oh, they don't realize that they're asking for spam, and if you asked them if that's what they want, they'd probably say "No, Definitely Not!" in the strongest of terms. And yet, I'll claim, strongly, that they're doing so. Perhaps not intentionally, but they're asking for it.

Are you?

Mistake #1

Posting your email address unadulterated in a public forum.

I've written about this out at Ask Leo! - Why shouldn't I post my email address in a public forum? - because I see it happen there several times every day. People place their unmodified email address into the body of a comment they post on the site.

The problem is that anything that puts your email address on to a publicly visible web page will cause you to start getting more spam. Lots more spam. Spammers visit all the web pages that they can, and collect anything that looks like an email address, and then they start spamming them.

Are you a member of a mailing list that has an publicly visible on-line archive? Spammers will get it. Does the site you're posting a comment on ask for your email address, and then re-post it in clear text? Spammers love that too.

Before you post anywhere be sure you know what's going to happen to your email address when you do.

There are three possible solutions:

• Don't specify or include your email address. That may not always make sense, since you may actually be attempting to provide your email address to the non-spammers that read wherever you're putting it. But it's hard to spam an email address you never supplied.

• Use a fake address. Many comment forms (including my own Ask Leo! comment forms) require an email address. Put in a fake one. It will prevent legitimate people (like me!) from contacting you, but it will also prevent spammers from doing the same.

• Obfuscate your email address. If you are attempting to supply a valid email address for "real" people (not scumbag spammers) to contact you, obfuscate it. As I said, spammers use tools that scan for things that "look like" an email address ... so make yours not look like one. Two approaches I use, for example are:

  askleo at gmail.com
  askleo@gmail.seeohem

  Both simply requires that you, as a human, read what's there, know that it should be an email address, and do the appropriate translation. You'd realize that the " at " needs to be replaced with "@", or you realize that the ".seeohem" really means ".com".

  The biggest drawback to these approaches is that the email links are not clickable. But anything you can click on to get an email address, the spammers can use to harvest it.

Mistake #2

Not opting out.

Installing software or signing up for a web service is getting to be quite the ordeal. I don't know about you, but I certainly have a tendency to say "yeah, yeah, whatever" as I skip reading the lengthy (and boring) license agreement, and zoom through the various options I'm offered - I just want the software, so install it already!

If I do that, I've probably just asked for more spam. OK, ok, technically it's not spam, as we'll see in a minute. But I did just say "Please send me more email - lots of email - please."

Many vendors are taking advantage of the length of the signup and install process, coupled with our impatience, to include options that, by default, cause us to get more email. If you're not paying attention you could well be signing up for a lot of email and not just form the vendor you're dealing with.

Pay careful attention to the next signup or install you do. Look for phrases like "Notify me ..." or "Share my email address with partners..." or anything that sounds like an invitation for the vendor or their partners to contact you in the future. In many cases it's checked, or on, by default. If you don't pay attention, and just accept all the default answers, you are explicitly giving the vendor, and possibly anyone they care to share with, permission to send you email.

I'll say that again: you are giving them permission to send you more email.

Spam is defined as "unsolicited commercial email". By giving them permission, you removed the word "unsolicited" from that definition. Anything they send you is technically not spam. Why?

Because you asked for it.

So don't.

Pay careful attention to what you're signing up for. Check all the options in the signup process, and look for those checkboxes that given the vendor permission. Look Carefully! Many are "check this so we can send you more email", while others are exactly the opposite "check this to stop us from sending you mail". And many are hidden, sometimes off the bottom of a scrolling list and not even visible by default.

Mistake #3

Using your email address unadulterated on Usenet.

My wife gets way more spam than I do.

And it's all my fault.

Way back when, before I knew better, I used her email address to post on behalf of her business on a Usenet newsgroup. In fact, proving that things never disappear on the internet, you can see that post from nearly 10 years ago, here. While Google has (properly) obfuscated the email addresses in the header and in the post today, but the address was out there on the Usenet for all the world to see in its bare nakedness.

Yes, I asked for spam, on behalf of my wife. (Sorry, dear.)

The problem is that unless you're using something like Google groups, you need to configure your newsgroup reader (Outlook Express, Thunderbird and many others) to access newsgroups. And what do each of those configurations ask for?

An email address, of course.

Don't do it. Or at least, don't use you bare naked email address. Obfuscate it somehow. (This is actually where I started using the ".seeohem" method I mentioned above, since an email address cannot have spaces.)

When you make a post on Usenet, or other Usenet-like newsgroup facilities, your email address is posted in the header of the Usenet posting, much like in email, as who the post is "From:". Spammers once again scan Usenet for From: lines that look like email addresses.

Usenet use is, in all likelihood, on the decline in favor of web based discussion groups and email mailing lists. But even so, as my wife will attest to, a single error can have long lasting ramifications. If you do use a newsreader or newsreading function of a program such as Outlook Express or Thunderbird, take care how you configure it.

Is it Too Late?

So you've been using your email address for some time. Perhaps your spouse mistakenly used your unadulterated email address in a Usenet post. In any case, you're getting spam.

Is it too late?

Yes and no.

First off, it's never to late to keep the problem from getting worse. If you keep making the mistakes above, you will only increase your spam problem.

Avoid those mistakes, if for no other reason than that.

Also, as I've outlined that previous article you should have more than one email address. By avoiding these mistakes from the start on any new email address you create, you can avoid or at least reduce the amount of spam those accounts will receive.

But whatever you, don't ask for more spam.

I just shake my head.

My advice?

Chill out, relax, get over it, and use the most under-used key on your keyboard.

But spam filters are easy to find these days, and in fact most people have one in place already. Most of the people I'm hearing from are stressing out about the spam that still gets through.

The fact is that spammers are crafty, and no spam solution is perfect. Some spam still will always get through.

In my opinion, it's just not worth the angst. It's not worth getting upset about. Spam is here, and unless some major changes happen to the fundamental infrastructure of email, it will be here for a very, very long time. Just like junk mail in your postal mailbox, there will always be spam.

And what do you do with that junk mail from your postal mail box? You throw it away.

So do the same with the spam that makes it through to your inbox.

That under-utilized key on your keyboard? Delete. Apply liberally.

When you see spam - delete it.

One of the common complaints is that all that "stuff" gets in people's way. It interferes with their "real" work, and dealing with their "important" email. It adds stress.

It doesn't take long to recognize spam and hit the delete key. I do it hundreds of times a day. And if you've already set up some basic rules, you can even reduce the effort, or prioritize the important stuff ahead of dealing with spam.

But the basic rule is very simple.

If it's spam, delete it and move on.

Don't stress out about it; it's just not worth it. Life's too short.

I don't know about you, but I actually look at the Subject field first. Often before I even look at who the email is from.

Now, I can almost hear many of you already saying "Yeah, subject line, big deal. Whatever. It's not that important."

You are so wrong.

My guess is that even you look at the subject of the message (before or after seeing who it's from) before you do anything. I'll bet you immediately look at anything that sounds important, on-topic or relevant to your situation, and skip the rest - either for later, or for "when I get around to it", which is really just another way of saying "never".

Now imagine you're trying to get your email read by someone who's incredibly busy, and suffering form email overload because they haven't been reading Taming Email. What are they going to pay attention to first? The email whose subject line tells them clearly what the message is about.

It only makes sense.

Or worse yet - no subject at all! (Something I see surprisingly often.)

Describe the Email

A good subject is like the title of a report, or the title of a chapter in a book; it describes what follows. It describes the contents of the message in such a way that the recipient can quickly and easily determine what the email is about. Without opening the email.

The subject is a decision tool for the recipient. By describing what this email is about, you're doing your recipient - who's probably just as busy as you are - a huge favor. With one look, one glance, he or she can see what your message is about, and act accordingly.

I mean, really, which would you open first? "Subject: News" or "Subject: New Year-End Bonus Structure"?

Be Concise

A good subject is short, yet information packed. Notice that while "Subject: New Year-End Bonus Structure" is short - just 5 words - it carries quite a message! People getting that message will know exactly what to expect inside after having only glanced at the subject line in their inboxes.

On some occasions the subject can be the entire message. There's nothing at all wrong with that, if appropriate, and again - if short. "Subject: Meet for lunch at McDonalds 12:30 PM Tuesday [eom]" is a great subject, and a great message. It's almost the equivalent of a text message on your phone or pager. It's informative and complete. The "[eom]" at the end? That's a shorthand that makes the subject even more informative. It stands for "End Of Message", and lets the recipient know that they don't even have to open the email - everything they need to know is in the subject line.

Stay on Topic

A good subject reflects the contents of its email message. That means that if the topic of discussion changes, so should the subject. This particularly true of email discussion lists where conversations often start on one topic, and then branch off on to other things. There's nothing worse than opening an email that you think is about "New Year-End Bonus Structure", only to find that the discussion has moved on to News Year's eve party planning or other topics completely unrelated to what's stated in the subject.

One approach that I really like is the use of the word "was" in the subject line. For example, let's say that a discussion list was, in fact, talking about the "New Year-End Bonus Structure", and as part of that discussion, someone decided it would be a fine time to ask everyone what their year-end plans were. A great way to "branch" the discussion would be a subject like this:

Subject: New Years Party Plans (was: New Year-End Bonus Structure)

This allows everyone reading the discussion to know two things: this email resulted from the discussion about the bonus structure that they were participating in, or not, but it's now about something else. The subject of the discussion has been changed, hence the subject of the email has been changed to reflect that.

Spammers Prove My Point

If you've been getting any spam at all lately (and who hasn't), you'll notice that spammers have learned what I've been talking about here. A lot of spam has some very engaging, though misleading, subject lines. Why? They know that a good subject line means more people will open the mail.

So naturally, a subject line isn't the only thing we look at before acting on email. That's why I look at who the mail was from, as well. (And also, in part, why I make extensive use of Message Rules to pre-organize my incoming mail.)

Why Do So Many Subjects Suck?

My theory is that most people focus first on their message - that's where they pour their energy, heart and soul. The subject is simply an after-thought that's even sometimes forgotten completely.

In reality, they have their priorities reversed. The most perfectly written email message is totally wasted if the recipient doesn't read it. Or reads it too late.

I mentioned that the subject line is a decision tool for the recipient, and that it is. But it's also a tool for the sender - a tool of influence. A tool that, if used properly can help get your message read, read more quickly, and can generally help you communicate more effectively in email.

Factoring in the "New Mail" sound of many email programs, it becomes Pavlovian - we hear the sound and like a well trained puppy we go check our email, interrupting whatever we were doing.

Who's controlling who? Or rather, what's controlling you?

At a conference a couple of years ago, a good friend made a simple suggestion had improved his productivity dramatically. You almost could feel the productivity of the room increase as others implemented his oh-so-simple suggestion.

That solution?

Turn off automatic new mail checking.

"However will I get my new mail?" you might ask. Simple. Manually. When, and only when, you decide you want to check.

The problem with automated checking is that it's an interruption. Often it's a frequent interruption that breaks concentration and dramatically impacts productivity.

If you've ever worked on something so intently that you've lost track of time, you know what I'm talking about. That was probably very productive time for you. The technical term "flow", and it's very cool when it happens, because it typically does indicate a high level of concentration and focus on the task at hand. In other words, productivity.

Now, imagine if you're interrupted every 10 minutes with a "bing bong" announcing new mail. The temptation is too great ... you'll probably interrupt what you're doing, and go check. You might even take "just a second" to respond to a message or two.

But the "flow" is broken, the moment is gone. You've lost your focus.

And let's face it, why should email be anything other than on your terms? We all feel like computers are running our lives at times, this is one simple way you can take back some control.

Phones and Rubber Bands

This really isn't new. In fact, it's an old idea applied to new technology.

In the past, it was the telephone.

Frequently, even today, when a phone rings, people will interrupt what they were doing - even a conversation with someone right in front of them - to answer the phone.

Some years ago I read a time management book that describe an office that made two changes:

• Older phones had actually bells in them - loud, obnoxious bells that demanded attention. They opened up their phones and wrapped a rubber band around the bell. Now, instead of a loud obnoxious RING, it made a soft purr. Much less insistent, and much easier to let go.

• They defined it as "ok" to not answer the phone. Messages could be left, and would be answered at a time more convenient to the recipient.

Productivity increased.

It's the same principal as checking email on your schedule, not someone else's.

But I Want It Now!

So if you're in a situation where you need to be quickly accessible?

To begin with email was never the right solution. There are legitimate reasons that email might be delayed, sometimes for hours. You should never rely on email being near real time, even though it often is.

Instead, consider the other ways in which you make yourself available: phone, instant messaging, pagers and more. Let email be what it was designed to be: a store-and-forward approach to message delivery without a specific time requirement. Use more immediate technologies for more immediate needs.

Naturally those technologies have many of the same risks. If checking your email every 10 minutes is replaced by an IM interruption every 10 minutes, we haven't solved anything. Make sure that immediate needs are truly immediate. If not ... turn off your IM client or ignore your phone and use voicemail (put a rubber band around the bell, if need be :-).

One Reason Not

There is at least one reason you might leave automated email downloading enabled. If you typically get a lot of email or large emails, the time it takes to download might be significant. It's nice to turn to your computer and have it already be there.

The solution is simple.

Turn off the notification.

Let email client download all it wants to, whenever it wants to, as long as it doesn't interrupt you. If you don't notice then it's nearly equivalent to it not happening at all.

If you find yourself distracted by the download, then it's not working. Better to switch to a download on your terms, than run the risk of periodic distraction.

Just Make Sure It's Your Choice

The bottom line is simply that you should make sure that you are choosing how, and when you're willing to be interrupted, and by what.

Then use that control to ensure you get the time you want to focus on whatever it is you're doing.

Without a "bing bong" every 10 minutes.

So today I'm going to look at creating just one rule, the one rule I consider to be the most important rule you can have. So important that I'll call it The Golden Rule.

The popular Golden Rule goes something like this: "Do unto others as you would have them do unto you." Our golden rule isn't really all that different, at least in intent. It's more along the lines of "Prioritize the people you know."

If I could have only one message rule, this would be it.

Email that I recognize, or rather that my rules recognize, is moved into other folders. My "Golden Rule" is simply this: if the "From:" address is in my contacts or address book, then move the message to my "From Contacts" folder. I then look at that folder before dealing with any other email - people that I know should get priority over people that I don't know, and certainly they deserve my attention before the spammers. It's that simple.

Defining The Golden Rule

Here's the definition of my actual rule in Outlook 2003:

"PST Contacts" is the name I've given to the Contacts that are stored in my primary PST, or Outlook Personal STore file. "09 Address Book" is the folder into which I place email from my contacts. As I described in an earlier essay, Rules to Live By, I actually have many rules, and many "sub" inboxes ... senders in my Address Book are actually 9th in my priority list behind additional rules that identify some higher priority senders - like my wife.

The neat thing about using your address book as an email filter is that it's so easy to add people to it. If you discover that someone's not on your list, most email clients provide a shortcut to quickly add them. In Outlook 2003, just right click on the sender's email address and you'll get a pop up menu with "Add to Contacts":

Once you've done so, their mail gets prioritized and moved properly.

In Thunderbird you can set up a similar rule (called a "Filter" in Thunderbird):

Exactly the same idea: if the sender is in your personal address book, then move the mail to a folder specifically for those senders.

Sadly Outlook Express does not have the ability to create a rule based on your address book. I do, now, recommend Thunderbird over Outlook Express for many reasons, this being just one of them.

Other email programs may, or may not, support this type of message rule, though most do.

Living by The Golden Rule

Remember, though, that using this rule effectively also requires some behavior modification on your part. Sometimes the hardest thing in the world is to not look at your inbox first. With a rule such as this in place, to properly acknowledge the higher priority of your contacts, you need to act on the folder that they were placed in before you deal with the contents of your other lower priority email. That, in fact, is exactly the point - this rule enables you to give your contacts higher priority by separating their email out automatically.

(I'm going to assume, for the moment, that your spam is taken care of elsewhere. Obviously in most cases, deleting spam is probably a goodly portion of what you're doing too. Dealing with spam, however, is a topic for another day.)

Wouldn't it be nice if you had someone to sort your email for you? Show you the email that's most important to you first? Perhaps even collect all those email newsletters for you to read and peruse later, when you had the time? Perhaps even completely filter out the email that you simply don't want to see?

Well, you already have such an assistant.

Inbox Rules.

Creating Inbox Rules is perhaps the single, most important thing you can do to Tame your Email.

Inbox Rules are simple. All they are is a condition, and an action.

If an incoming message meets some criteria

then

do something to it.

Really. That's all there is to it.

The "criteria" can be as simple as "if it's from Leo", to "if it's from Leo, Kathy or Matthew, and is set to high priority, and has the word 'outlaw' in the message body". In fact, depending on your email program, you can define some fairly complex criteria. But the good news is that 99% of the power of Inbox Rules are in the simplest of conditions - if it's "From" someone specific or if it's "To" someone specific. Those two criteria alone can clear up 80% of an inbox.

The "do something to it" can also be as simple as moving it to a folder, or as complex as replying with an email, raising an alert, playing a sound and changing the message to be bold in the list. Once again the good news is that the simplest of actions will give you 99% of the power: move or copy a message to a folder.

A tremendous amount of taming to be had with just these two simple ideas:

• To or From someone

• Move or Copy to a folder

As I type this, my inbox is empty. Zero messages. And it's all because of Inbox Rules.

Let me explain how that is.

The Rules to My Empty Inbox

First, let me give you two caveats:

• This is how I manage my email. I think it works, and works well - for me. After learning about rules, and matching your own work process to your email flow, you'll probably want to do something different. Learn from my examples, and then "do your own thing".

• My inbox is empty, but that doesn't mean that there isn't email waiting for me to act on it. My "assistant" - Inbox Rules - has sorted, filed, and most importantly prioritized the mail that has arrived into an array of folders. Key in on that word "prioritize" - if you take only one word away from this essay, that would be the word.

I have 36 separate rules in Microsoft Outlook that route incoming email into something like 30 different folders. (Remember, I said your situation will be different, so don't let the numbers scare you. It's likely you'll not need that many.)

I have what I consider to be 14 "sub" inboxes. Mail that I need to act on is routed by Inbox Rules into those folders as it arrives. And the folders are organized by priority. In the morning, when I start reading my email, I start with the most important, not the most recent, email, and work my way down. I may not get down the entire list, but that's OK, because I'm dealing with the most important stuff first anyway. Throughout the day I pay attention to those "important" folders more frequently than the less important ones.

So what are the rules and priorities? Once again, it's not really that complex in concept, but I do have several:

• Folder #1? Email from family. Yes, my wife and other family members come first. The rule: if it's an email message From one of them, move it to the #1 folder.

• #2 is purchase orders for my wife's doll shop. These are emails sent to a specific email alias, so the rule is: if it's email sent To that alias, move it to the #2 folder.

• #3 and #4 on my list of priorities are administrative discussions and approvals, respectively, for an email list I help moderate.

• #5 through #8 are all about email relating to another very active discussion group I belong to. Email sent to that group, email sent by group members directly to me, and email sent to a couple of sub groups, are all routed into their own, prioritized, folders.

• #9 is powerful: email from everyone that's in my address book lands here, if it hadn't already been processed by previous inbox rules. The bottom line is that if I know you, you should probably have more priority than if I don't. Seems only fair, right?

• #10 is for automated server management emails. Again, email that's sent To a specific alias I have.

• #11 through #13 are all about Ask Leo! emails. Questions submitted, comments made on the site, and email sent to the email address I publicize to my newsletter subscribers all get routed into these three folders.

• #14 is where all my newsletter and other mailing list subscriptions go. More on how they get here later, because this, too, is an important approach to managing email flow, especially when traveling.

A number of additional rules automatically file other email into other non-inbox folders for archival purposes that I actually don't need to look at at all on a daily basis. And yes, there's even a rule that automatically deletes one class of spam.

When all those rules are done I'm left with two types of email in my inbox:

• Email from individuals I haven't heard from before.

• Spam

Even after downloading a couple of hundred emails, I have had mornings where I've looked at what was left in my inbox, and been able to delete all of it. All of it.

And you know what that leaves.

An empty inbox.

The Rules to Your Empty Inbox

As I said, it's unlikely that you're going to need 34 rules and 14 sub-inboxes. But take two, maybe three of those rules, and a couple of folders dedicated to automatically sort and prioritizing your email, and you'll have made a huge step towards taming your email.

Inbox Rules are powerful. In future essays I'll walk you through exactly which ones I think are the most important, and include the explicit steps to create them in email clients like Outlook and Thunderbird.

Until then, I strongly urge you to investigate the Inbox Rules abilities of your own email client. It's not only an important part of choosing an email program, but understanding how your email program handles Inbox Rules is a key part of Taming Email.

Apparently a lot of my life revolves around email.

Unless you're a geek like me (and heaven help you if you are), you don't need a long list of email programs. You probably just need one. The right one, of course.

So which one do you need? And how do you choose from the tens or perhaps hundreds of other choices?

How do you choose what email program to use?

Tools for Taming

An email client must, in my opinion, have certain functionality to enable you to properly handle a large volume of mail. These are the features and functionality required to manage your email, and on which I rely heavily, and simply assume are available in my essays here.

As far as I'm concerned, these features are not negotiable, though they may be implemented in different ways using different terms in different email programs:

• Folders: You're going to need to be able to put mail you send and receive into separate buckets. Most email clients support this as "folders" into which you can place, or direct email. It's a key building block to managing your email.

• Rules: Rules, sometimes called Message Rules, Filters or other terms, are, after folders, the single most important tool to getting your email under control. Rules applied to incoming mail will allow you to automatically categorize, prioritize, alert and perhaps even discard if appropriate, incoming email so that you can not only spend less time managing your email, but you can be assured you're spending your time managing the right email. I'll spend a lot of time discussing rules here in Taming Email.

• Search: The ability to search, both within a folder of email, and across multiple folders of email is one of the ways we take some of the worry out of how we organize our email. Let's face it, we never get the folders right - did that email get put in the client's folder or the project folder? It matters not, as long as you have a powerful search that can search not only the mail headers, such as "To:", "From:" and "Subject:", but the body of the email as well.

• Multiple Accounts and Multiple Addresses: Part of our strategy to tame the flow of incoming email includes using different email addresses that all deliver to the same email account, and using more than one email account. Your email client must be able to handle both scenarios well.

• Archival: It must be easy to archive email, and recover email that has been archived. You shouldn't expect, or even want, all your email to be active within your email program at all times. As a result it's important that you be able to save mail away in a form that can be easily re-loaded into your email program later.

Tools for your Personal Habits

Now things start to get a little fuzzier. This is where we start to look at personal preference, and how you go about dealing with email, and with the rest of your on-line world.

These items are not necessarily requirements, but they are items to consider as you evaluate different email programs.

• Look and Feel: probably the fuzziest of all, but this is important. Do you feel comfortable using the mail program? You'll be spending a lot of time using it - does it make sense, when compared to others. Can you find the features you need an care about?

• Calendaring and PIM: do you need an integrated calendar? Or do you need a full-blown integrated PIM (Personal Information Manager) with calendar, address book, notepad, task list, and other features that aren't strictly email, but work well when integrated?

• Hand-held Synchronization: do you need to synchronize your email, or your address book with your handheld device or cell phone? Not all email programs are supported for this.

• Encryption/Security: need to regularly encrypt or "sign" email? Then you'll need to choose an email client that supports this and makes it easy, as well as making sure it supports the encryption scheme's used by the people with whom you'll be exchanging email.

• Spam control: do you need additional spam control, or will that be handled on the server? If you need it, make sure your email program can support it.

Tools for the Boss

We all like to believe we're the masters of our own domain, but in reality, we don't always have all the choices available that we might want.

Our boss, our company, our organization ... any or all of these might, in fact dictate our choice of email client. Working with an Exchange Server for email? Then you have very few choices. Is a particular plug-in or add-on required? Then you're limited to those email clients that support it.

The message here is to pay attention to what might be imposed on you, and not waste any time making choices you don't really have.

Recommendations

So naturally people will read all that and say "Yeah, yeah, whatever. I don't want to have to understand all that. Just tell me what you recommend."

Well. Ok. I have two recommendations.

Thunderbird

Remember those fill in the blank questions in high school? "A is to B as ___ is to 2" - well here's another:

Firefox is to Internet Explorer
like
__________ is to Outlook Express

The answer, of course, is Thunderbird. Just like Firefox is a capable replacement for Internet Explorer, Thunderbird is a fine replacement for Outlook Express. In fact, I consider it an improvement in many ways.

Like OE, Thunderbird is free. Unlike OE, Thunderbird is in active development. Also unlike OE, Thunderbird has an extension model, which means that features and functionality can be added to it. Many of the items I list for consideration above are, in fact, supplied by extensions to Thunderbird, and not by the basic program itself.

Besides having most all of the basic features and functionality that OE has, Thunderbird made at least one design decision that I find very comforting after fielding so many questions from OE users in trouble: Thunderbird stores your email in flat, plain, text files, one per folder. Yes, there's a companion index file, but when that index is corrupt or missing, it's simply regenerated. Folks who've lost or had trouble migrating email from OE's ".dbx" files will appreciate that. A lot.

For folks with basic to moderate email needs, Thunderbird is the right solution. And where I used to recommend Outlook Express, I now consider Thunderbird a superior choice.

Outlook

Even though I just recommended Thunderbird, I live in Outlook.

Outlook's biggest strength is that it's a kitchen sink application. It's more than a mail client, it's a personal information management application. Email and contacts, of course, but embedded junk mail / spam filtering, full and extensive calendaring, notes, tasks, exceptional integration with Microsoft Exchange server, a full macro language and Microsoft Office-complimentary object model make Outlook a one-stop location for all things email and more.

Outlook's biggest weakness is that it's a kitchen sink application. It's big, and 80% of its functionality is not used by 80% of those who use it, I'm sure.

To carry forward the theme, Outlook's approach to storing mail differs from both OE and from Thunderbird. Outlook uses a single data file, a ".pst" or Personal STore to store all email, calendar, contacts and other information. Given that it's a single file, it's a snap to backup and/or copy to other locations as needed. The downside, of course, is that PST's are a proprietary format, and only Outlook can read them.

Quite often the choosing Outlook is driven by your place of work - it's often a workplace standard, especially for corporations that have implemented Microsoft Exchange Server as their email solution. Even if that's not your situation, Microsoft Office includes Outlook, and if you consider yourself a heavy email user, Outlook's worth a look.

What keeps me in Outlook versus Thunderbird personally? The list is getting smaller, and it's quite possible that I'll be changing at some point in the near future. But right now the list of features that I rely on in Outlook includes:

• Calendaring (there is very promising calendaring add-on to Thunderbird in the works)
• Treo Synchronization (again, I believe that there are solutions to this for Thunderbird, and I need to investigate both their level of support and stability)
• My years of archives in Outlook. I could convert (though I believe it's a painful process), but pragmatically, even if I do switch clients, I'll probably always have a copy of Outlook around to pull items from my archives.

Now remember: those are my recommendations without knowing anything about you. I strongly recommend you actually do your own research and make your own selection. If you're spending as much effort in email as I'm thinking you are (why else would you be reading this site?), then the time investest in selecting the right email program for you is well, well worth it.

DIS-Recommendations

I can't, in all good conscience, let this essay go without taking a strong stand on one potential solution that I recommend avoiding at all costs.

Don't rely on free email providers.

This really belongs in a discussion on choosing an ISP, and I'm sure I'll say it there as well, but free web services also bridge the gap - they're both service and email program. Needing nothing more than a web browser and an account, you have email, anywhere.

There's actually nothing wrong with that as long as you don't rely on it as your sole repository for information.

Let's say you have a Hotmail account. Let me put it to you this way: if that Hotmail account went away tomorrow, and you lost all of the email and contacts within it, would that be a disaster or an inconvenience?

Remember, free email accounts come with zero customer support. So there's no real way to get your information back.

If it's a disaster, then run, don't walk, and get yourself a "real" email account with a service provider that will support you when you run into problems. Use a "real" email program, like I've been discussing here, to download your email to your machine where you can control it, back it up, make copies of it, whatever. If you need a web interface, check with that service provider and make sure they provide one in addition to your being able to download your email.

Web accounts are great for many reasons. My advice here is simply don't rely on them. Make sure that if they go away it's an inconvenience, not a disaster.

The reason I feel so strongly about this is that they do go away, for various reasons, some of which seem totally random. I regularly hear truly heartbreaking stories of individuals and businesses that lose all of their email and contacts because a free email account was compromised or lost. It certainly doesn't happen to everyone - my Hotmail account dates back to the days when Microsoft first acquired HotMail, and I've never had a problem. But based on the questions I get and the stories I hear, the risk is both real and significant.

In order to tame your email, it needs to be under your control. Free mail services simply don't give you the control, the safety and the support that you need.

In short, I asked the senders to stop.

The Sin of Omission

One of the very common techniques businesses use to attempt to establish an email relationship with you is a silly little checkbox that often looks something like this:

Yes, keep me informed of product updates!

Sometimes it's "helpfully" checked for you even. What they're really asking is "may we send you mail". Technically it's not spam because you asked for it by leaving that checkbox checked - you "opted in".

You'll find that little checkbox, or checkboxes very much like it, quite often when you're checking out of an on-line store, or perhaps when you install software on your machine. In the most egregious cases, it can be quite well hidden. You might find it only after you scroll down in some list of other options, for example, or in small print "below the fold" (off the bottom of the first screen full) of some web page.

A reputable company will use it to trigger a double-opt-in confirmation to join their mailing list. That means you'll still need to respond to a confirmation email before you'll actually start receiving their mailings. However, especially when it can be claimed to be part of a "business relationship" (and online purchases or software installs count), that confirmation isn't technically required, and is often omitted.

The lesson here: Any time you're filling in forms that require your email address, or any time you make an online transaction, and any time you install software, actively look for and unselect any requests to be placed on mailing lists, to send you updates, or to keep you informed by email.

Unless, of course, you really do want the email. Sometimes we really do want to be kept up to date, or whatever. Just make it a conscious choice.

Just Say No

Say you're like me and in your younger days you were lazy. You didn't know better, and you have companies or other concerns with which you occasionally do business sending you email. Maybe it's the latest sales flyer from an online store, or the latest upgrade announcement for the whiz-bang software you use once or twice a year.

What to do? Can you get them to stop?

The answer is a qualified yes.

The qualifications are this: you need to be able to tell what is and is not actually spam, and this really only applies to reputable companies.

Let's take an example. Let's say I purchased a shirt online at Joe's Shirt Shop on the internet. A couple of weeks later I start getting promotional material from Joe's Shirt Shop. Whoops! I forgot to uncheck the "keep me informed" button. Very technically I gave Joe's Shirt Shop permission to send me email.

Now, I know Joe's Shirt Shop. They're national, they have a good reputation, and I trust them. I just don't need their weekly email.

So, at the bottom of each email from Joe's Shirt Shop is an unsubscribe link.

This is not spam, I trust Joe and his Shirt Shop, so I hit the unsubscribe link. Joe, or his IT department, does the right thing - they remove me from their mailing lists, as requested.

I recently went through a round of this myself. I've been receiving email from various and sundry firms that I've done business with in the past. As a new marketing mail came in, I judged whether or not this was really from who it claimed to be, and if it was, I unsubscribed. As simple as that. And yes, it worked.

So obviously, avoid implicitly agreeing to receive email in the first place, but don't be afraid to unsubscribe from mailing lists you know to be legitimate. It does work. Really.

Just Say Maybe

So all that does beg the question: what if you're not sure? How do you tell whether something is "legitimate"?

Here are a few tests:

• If you've never hear of the company or sender, or know that you've never done business with them, go ahead and assume it's spam. (Note I did emphasize know that you've never done business with them - it only takes once, and it could have been some time ago. If you think you might have, continue on with the next tests.)

• If the unsubscribe instructions involve clicking on a link, will it actually go to where it says it will? For example, hover over this link to eBay: http://www.ebay.com. You should see that it doesn't go to eBay at all! That's a sign ... often a strong sign ... that what you're looking at is an attempt to deceive. On the other hand, if the link matches, like this one: Ask Leo!, where the text "Ask Leo!" makes sense as a match to the destination URL "http://ask-leo.com", then that's a good sign, and speaks to the link probably being legitimate.

• If the destination of that link doesn't make sense, or perhaps is in a foreign country, than you might be looking at another attempt to deceive. A reputable company will either route things through its own servers and domain names, or that of a reputable email service provider. For example the unsubscribe link for Joe's Shirt Shop mail should either be a link to a page on Joe's Shirt Shop's internet domain, or that of a mailing list provider such as aweber.com, lyris.com or others. Most importantly, if it goes off to a domain in a foreign country (say a domain ending in ".ru", for Russia, where sadly a lot of phishing attempts originate, or any of a host of others), then you probably want to think twice before clicking on it.

• If the instructions are to click on a link to send mail ... don't. Instead, copy the email address using copy/paste, or by hand even. The techniques I mention above about deception in URLs apply equally well to links for email addresses. In fact, all of the comments regarding the domain apply as well: it should somehow relate to the company involved, or a mailing list service.

If it passes those tests, then chances are you're dealing with a legitimate email, and my approach would be to follow the unsubscribe instructions.

If the email fails some of those tests, then I would treat it like any other piece of spam, and avoid the unsubscribe instructions completely.

Just Say Yes

Remember, this isn't about stopping all email. This is about making a choice. Getting the email you want, and not getting the email you don't.

In many cases email from a business relationship is, in fact, critical. Consider your bank, for example. If your bank has something to say to you, you're likely to want to hear about it. That's one of the reasons that phishing scams so often target banks - not only is the bank "where the money is", but recipients of those scams are likely to care about whatever their bank might be trying to tell them. Fortunately phishing scams typically fail one or more of the tests I've outlined above.

So you probably don't want to "opt out" of your bank's mailing list. In fact, you might even elect to give it a higher priority.

This is one of those situations where, if you've followed my recommendation to have multiple email addresses, you might elect to use your private, closely held email address. That way you know that any email coming in on other email addresses claiming to be from your bank are either forgeries, or at least unimportant. By registering your private email address with the institutions you trust and place high importance on, you know that anything truly important will be sent to that address.

It's All About Choice

For this class of email that we're cleaning up, it's all about choice. Choosing not to get email in the first place. Choosing to stop email from legitimate senders that we don't need. And even choosing to accept, and prioritize, the email that we do want.

Ultimately it's about consciously making choices to get less mail.

The power of choice is yours. Use it wisely.