Choosing an Email Program

I'm going to break down requirements into a couple of categories: Tools for Taming, Tools for your Personal Habits, and Tools for the Boss. I'll explain each as I go along.

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• Archival: It must be easy to archive email, and recover email that has been archived.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.