As web workers, we are often asked to help friends and relatives fix computer problems. For me, the majority of these problems seem to be related to email. It’s ironic, as email is now less popular than social networks.

So why is email such a hassle?

• It’s more than 30 years old. Email has come a long way, but its underlying protocols haven’t changed much since the 1970s.
• It’s really three different systems. Sending (SMTP) and receiving (POP or IMAP) are totally separate functions, and are often handled on different servers. That’s why I often hear comments like “I can receive, but I can’t send” from clients.
• It’s being used for a lot of things it was never designed to do, like send images and attachments, highly formatted messages, signatures and calendar entries.
• It’s been overrun by spam, and even well-designed spam filters aren’t perfect, and cause unwanted side effects, like messages that get misidentified as spam, or just go away.
• Email software is too complex. These programs that were originally built for offline use; that is, they were set up so that users could read and write messages without being connected to the internet. Sending and receiving would happen in batches. That made sense when internet connections were slow, expensive and charged by the minute. Now that most people have always-on connections like cable or DSL, that process is less necessary. Desktop email client software is a pain to set up and use; as someone who helps many people with email, Outlook is the bane of my existence.
• Many of us connect to the Internet in more than one place — at work, at home, and on cell phones. It can be very frustrating to realize that we’ve left the message we needed to reply to at the office.
• Many of us have more than one email address. I try to keep my work and personal email separate, plus I have a series of email addresses that I use when registering on websites that might try to send spam. And I have several email addresses that were given to me, such as the ones that are automatically created when signing up for instant-messaging services like Yahoo, AIM and Windows Live/MSN.

What can be done to overcome these problems? Here are some tips that might help you and your clients and friends be more productive.

• Get your email on the web. Dump your desktop email software, and switch to Gmail/Google Apps or another online provider like Yahoo. If your Internet connection is unreliable, Google Gears lets you work offline.
• Create a master inbox. If you have multiple email accounts, you can set up forwarding to receive and send email from one place.
• Use IMAP. If you need mobile access to your email, set up your phone software to use IMAP, not POP. By using IMAP, your messages will sync automatically in all of the places you check your mail.
• Use social networks. It seems like all of my friends under 30 don’t do email anymore, but they’re on Facebook a lot.
• Use instant messaging. For short, simple conversations, IM can be very efficient. In a few seconds, you can schedule a meeting or a lunch date. It’s much faster than email or phone conversations.
• Use file-sharing services for sending large documents. There are lots of such services, and new ones are popping up all the time, including Fluxiom and FileShareHQ. And Dropbox and the new Opera Unite service allow you to share files directly from your computer.
• Organize your electronic communications. Celine wrote about this recently, and I’ve talked about it, too.

Oh, and one more:

• Remember your passwords. This is obvious to you and me, but I’ve heard “I didn’t know I had a password” way too often. Online services like LastPass, or programs like 1Password, SplashID, or the free KeePass (Windows and phones; also available for Mac and Linux) can be lifesavers.

How do you keep email simple?

Image by stock.xchng user chris27.

As Google deepened its support for offline access via IMAP this week, Zoho, its closest competitor in the web office space, was publicly unveiling its own support for offline and access, ironically using Google’s own Gears platform.

Curiously Zoho decided that to bring users’ mailboxes offline, Gears was a better technological platform for offline access than the IMAP protocol; though we’re assured IMAP is coming.

Regardless, the offline features seem pretty comprehensive despite currently being restricted to Gears for Firefox and Internet Explorer and with most online features being available offline – messages, images & attachments are optionally available and a clever connectivity detection feature automatically determines whether a network is visible, flipping between offline and online modes as appropriate, with offline messages queued for later deliver when connectivity becomes available.

A Gears configuration dialog allows users to select the number of messages to download initially, how many Sent Items should be stored for offline access.

Finally, though Zoho is pitching mobile access alongside offline support, in reality Zoho Mail is currently only optimised for the iPhone.

Though the offline support appears to work well enough – as do other Gears-enabled services such as Google Reader – mainstream offline access seems a little too fragmented for comfort.

Where standards such as IMAP are pretty much guaranteed to work across multiple platforms, clients and services, supporting entire classes of application, such as email. AIR, Gears, Prism and Silverlight all seem to be mechanisms for locking users into a vendor platform, forcing developers to have to divide their efforts in supporting them.

As an industry, we should be thinking more responsibly about data portability through standards…a complex endeavor, but in the longer term much more viable and stable than the collection off offline platforms and browser combinations we see today.

Read more about Zoho’s offline and iPhone support here…

(Incidentally, I’ll be meeting Zoho’s evangelist, Raju Vegesna, later this month at O’Reilly’s Web 2.0 Expo Europe. If you have questions for Raju, please drop me a message!)

Gmail, a staple of our work environment, becomes a little more like “big-boy” IMAP courtesy of Google Labs. Hit the Labs button in your Gmail account and you’ll see a new “Advanced IMAP Controls” function. Enable it and you can begin to take advantage of the following new features:

• Auto-Expunge: it sounds like a dirty word, but expunging is a good thing for data that’s no longer needed. Up to now, Gmail would simply mark items for deletion in clients and not immediately delete them. Enabling the Auto-Expunge feature kicks those deleted messages to the curb and gets them out of your e-mail system.
• Delete Forever: one the benefits of Gmail is that like an elephant, it never forgets. All of your mail is archived in the Gmail / All Mail label or folder unless you manually clean it out. This often results in wasted space, messages in multiple locations and more bandwidth required for mail synching. You can now expunge mail forever by setting Gmail to simply move it to Trash upon deletion.
• Selective Syncing: you can now pick and choose which labels or folders you want synchronized between Gmail and your web or desktop client. This comes in handy for archived folders that don’t change much. For example, I still want my “CES 2008″ folder data, but I don’t need to see it every waking minute of the day. I’ve disabled that one for now because I’ve got an active “CES 2009″ folder for planning purposes.

Each of these features can be useful, but for me the ability to say good-bye to the All Mail label usage is key. I often work remotely over wireless broadband connections where there’s a 5GB monthly data cap and 1.5-hours of work already uses near 45MB. Why should I be synching the near 53,000 e-mails in my All Mail folder when I’m already managing the ones I need with custom labels?

With Microsoft’s announcement this week that Outlook and Outlook Express will no longer support desktop access to Hotmail accounts raises some interesting questions on data portability.

After 30th June, Microsoft’s Windows Live Mail application will be the only means by which desktop and offline access to Hotmail accounts will be supported. This effectively means that a Hotmail user’s messages continue to be imprisoned within a closed ecosphere of services and applications. OK, smart people won’t be using Outlook, Outlook Express or Hotmail, but millions do and many have years of messages archived that they may wish to continue accessing outside a web-based interface.

However, there are some unofficial mechanisms that can not only continue to provide offline and desktop access, but also standards-based access into most email clients

• IzyMail has close to a decade of experience in delivering webmail gateway services. A one-off payment of $17.95 buys a one-year subscription that equips any Hotmail, Yahoo, AOL and Gmail account with a POP and IMAP ‘wrapper’, so users can send, receive and synchronise messages using most desktop clients, such as Thunderbird, Apple Mail and Outlook

• Thunderbird’s WebMail extension plays a similar role to IzyMail, though is of course limited only to Thunderbird and doesn’t necessarily support the various permutations of a service like Hotmail (Live Hotmail, Hotmail Classic etc.) but does support a wider range of services

• Apple Mail fans can use a similar plugin – HTTP Mail – to retrieve Hotmail messages and folder.

Of these solutions, I’d recommend IzyMail’s standards-based approach, freeing the user to employ any both leading mail protocols with the widest range of clients. Indeed, IzyMail saw a huge spike in subscriptions with the launch of the iPhone last Summer as users utilised POP and IMAP webmail gateways to synchronise their email with their phones.