I’ve been thinking about a better email strategy. About 8 years or so ago, when I was still using my university’s email account, I signed up for a forwarding address from Bigfoot (which at the time was still free and without any limitations). This allowed me to keep using the same email address until now, even though the actual mailbox that it was pointing to changed numerous times when I switched ISPs, domains, etc. Bigfoot introduced their own webmail service later, which provided a decent way for me to check my personal email at work, for example.

However, there are several problems with this approach:

  1. The way Bigfoot works, all incoming emails are forwarded both to my Bigfoot webmail as well as to my ISP's mailbox. This means that I essentially have to go through all my email twice, once on webmail (usually while I'm on work), and once again at home, when I download my email from my ISP's mailbox using POP3 and my email client, at which point I also file it in folders, etc.
  2. I have had this email address for around 8 years now, and particularly in the early years, when (believe it or not) spam wasn't a big problem yet, I used it pretty liberally when posting in Usenet newsgroups or on public forums, when signing up for various accounts, ordering things online, etc. Because of this, I receive a tremendous amount of spam (on the order of 100 emails a day). Granted, much of this is caught by Bigfoot's anti-spam solution and never even forwarded to my POP3 mailbox, but unfortunately there are quite a lot of false positives, and about half of the actual spam emails are not caught... Suffice to say, I finally need to get rid of this email address.

There are obviously many different solutions. In fact, there are so many completely different solutions that it makes it hard to decide which one to employ. Here are my criteria:

  1. I would like to have constant and consistent access to my email (both new and archived, and sent as well as received) from wherever I am (home laptop, home desktop, work, traveling, etc.)
  2. I only want to manage (file, delete, etc.) my email once, not twice as I currently have to (Bigfoot webmail plus POP3 mailbox).
  3. I want to be able to change my email service any time, without having to notify all my contacts of a new email address.
  4. I want to minimize spam, while avoiding false positives. Ideally, I'd like to be able to use several email aliases that all forward to the same mailbox, which would allow me to for example use one or more aliases when signing up for any services that might attract spam (such as when placing orders online or posting to mailing lists with publicly accessible archives), while using a more stable alias for my personal email. If I end up getting too much spam from one of the extra aliases, I can simply turn it off without fear of losing any actually important email.
  5. I want to be able to back up all my email.

At this point, I am mainly considering two solutions:

  1. IMAP My current hosting provider (as well as most providers these days, I assume) supports IMAP as well as POP3. In addition, I finally have more than enough space on the filesystem for my domain, which would allow me to easily store a few hundred MB of email on the server. This way, I could access my new as well as my archived emails from home or from work using whichever email client I prefer (I currently use Outlook at home on my Windows laptop, and Evolution at work on my Linux workstation, although I am considering switching to Mozilla Thunderbird for both environments). When travelling, I would still be able to acces my mail using my provider's webmail service (they use SquirrelMail, which, while not necessarily fancy, fulfills its purpose well). Backups could presumably handled using the IMAP client software, although I could probably just back up the entire mailbox from the server using FTP. I would be able to set up as many aliases as I need and have all of them point to the same physical mailbox.
  2. Google Gmail I received an invite to Gmail about 5 months ago, but I haven't really used it so far, mostly, because I wasn't sure how to fit it into my email strategy, as I already had a Yahoo webmail account in addition to my POP3 mailboxes and my Bigfoot forwarding address. Yet another email service seemed like the last thing I needed... However, at this point I think that Gmail would be an excellent solution. It is fast, intuitive, has many great features (such the excellent search functionality, which I can only assume is a lot better and faster than what Microsoft has built into Outlook), comes with ample storage (1GB), has a clean and lean UI (in typical Google style), an excellent anti-spam solution, and much more. As of recently, Gmail also supports email forwarding as well as POP3 access, both of which make a big difference in convincing me to give it a try (forwarding means that I could decide to no longer use Gmail and simply forward all emails that might still be using this address to my new email service, while POP3 would allow me to download all emails to an email client should I be so inclined). Google also has some features that are beyond the capabilities of most mail clients, such as displaying a threaded view of email conversations. Another interesting feature is Gmail's use of labels instead of the typical email folders. They might take some getting used to, but I have a feeling that they, combined with Google's strong search functionality, would work very well. About the only downside I can see at this point is the fact that backups would be a lot harder to accomplish. Sure, I could just download all emails using POP3, but that way I would lose all label classifications, which means that I'd end up with a big folder containing thousands of emails that I'd have to manually file into folders... I'll have to do some research to find out if anybody has built a tool that downloads emails from Gmail and maintains their labels, possibly even filing them into corresponding folders. Given that people have gone so far as to build Linux filesystems on top of Gmail, I would not be surprised if such a tool already exists. Of course, I could still combine this with the same alias approach as above and have several digitalhobbit.com email addresses that all forward to my Gmail account. Gmail does not allow changing the From address, but at least I can change the Reply-To address to point to my digitalhobbit.com forwarding address.

It’s a tough call. I know that the first approach would work fine and provide the ultimate level of control, but somehow the second approach seems sexier. :)

I think I’ll give Gmail a try for a couple of months. I’ll let you know how it goes…