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Rethinking Email

by Kerry Dawson

There’s a growing movement to rethink email as it currently works for us. This movement to look at email in a different fashion is actually being driven by IOS developers as there are chinks in the armour of traditional email. There actually has been for a long time. Lauded at its inception and through time as one of the biggest productivity enhancers in many ways it has been and continues to be a huge drain on productive output for a variety of reasons.

Email as the Glue that Binds

Email has been around for longer than people think. It first really got its start in corporations as a way of more rapidly communicating with others and transferring information electronically within an organization. Prior to email, fax was probably the first thing that arrived on the scene to speed up the transmission of information and fax is still with us. Fraught though with numerous problems as it is paper in and paper out it is very physical. Email was really the introduction of the virtual or digital transmission of information and with that came far fewer problems from the mechanics of its operation.

I started using email in 1984 and was part of the deployment team at my company to introduce email. Greeted at first with delight, it quickly began turning sour as people started cc’g everyone under the sun with emails that were irrelevant to many. Inboxes started filling with crap and what was important was sometimes getting lost in the maze of pointless email. People’s delete keys started working in overtime.

It became quickly apparent that rules had to be established for the proper use of email and one of the prime rules was to only send email to those that absolutely needed the information. As people adjusted, things started running smoothly again and email did become an enabler of enhanced work efficiency on many fronts.

The physical metaphor for mail though quickly took shape in that you cleaned out your inbox as fast as possible and dealt with the issues when appropriate all the while filing your email in the proper folder for easy retrieval should that information need to be logically recalled. This too actually worked quite well for people once they got onto the translation of the physical into the virtual metaphor.

Email, via the internet, then rolled out on mass to the general population. Once again it was greeted as this amazing thing which in reality it is. Email has survived many things that disappeared and even with the newer technologies, such as chats and social media, email still remains probably the prime form of virtual communication of information. Certainly, much has been added to support the efficient transmission of email such as dedicated servers to transfer large files that email systems aren’t intended for but even those notify the user a file is ready for download via email. The most current of social media technologies such as Twitter and Facebook still utilize email to advise users that something important awaits them and a large part of the reason is email is not only ubiquitous it has become pretty well universal. In many ways, our email ID is like our social insurance number.

If it ain’t Broke, Don’t Fix It

Before I venture on, it’s important to note that if your email system, the way you currently are using it is working for you and works well for you, then don’t play around with it. Email is too critical for experiments. I can only emphasize the old adage at this point that ”if it ain’t broke, don’t fix it” as you’ll likely regret it. If it’s serving you well and your adept at it and it’s use leave well enough alone.

However, this is definitely not everyone’s situation. The situation that I described earlier wherein people were being flooded with email can and is happening again to the point people are becoming slaves to their email inbox. On top of that, email flooding your system that can’t be put off till a later time or dealt with in some different method so that it doesn’t distract you will only get in the way of accomplishing anything positive. There’s no way we can’t live without our email systems today but there is every reason to rethink how we’re handling it if things are just not working the way we’d like.

Two difinitive but sometimes Opposing Approaches to Rethinking Email

For many of us though it is time to rethink just how we’re handling email. For many of us, email is dominating our lives too much and slowing us down. It’s also not making as much sense in terms of locating what’s important or to be acted on using the old paridigm.

IOS Developers are taking more of A Radical Approach to Email Rethink

As I mentioned earlier, IOS developers are pushing a definitive rethink in the way we deal with mail from that of just an enhanced interface approach that handles aspects of traditional mail in a more effective fashion. Althought the interfaces might be somewhat different, like in the case of Mailbox, a highly popular IOS email application, they can also be quite radical in a complete overhaul in the manner in the way mail is handled. Mail Pilot would be an example of the very radical, turning email into really task items that are incomplete, to be acted on, deferred to another time and to be managed without the traditional mailbox or folder approach to mail.

These are but two examples of a multitude of email clients that are being generated in IOS. They can be both aesthetically pleasing with the promise of a unique approach to rapidly dealing with email effectively.

It is my view though, at this time, that these approaches so far that have been generated are not architecturally sound. They live in IOS and don’t consider OSX which is our real production environment for most of our work. IOS is most definitely becoming a production environment but much of what we do with mail has been integrated tightly with other applications. Sitting in isolation, these IOS apps fail to deal with this effectively and in some ways impose a framework on mail that is fine in IOS but is not transportable nicely to OSX. Really, only Apple’s mail currently resides in both environments in a relatively similar fashion but even here there are breakages. That which might be integrated at the IOS level isn’t integrated at the OSX level and that which is integrated in OSX isn’t available to these foreign email clients.

For the IOS approach to be effective, the email clients need to run identically in both OSX and IOS. Further, a lot of the IOS applications are very new and buggy. Mail Pilot is a good case in point. Fascinating in design and approach it fails at delivery. It isn’t ready for prime time and just really doesn’t work that well. However, the developers of this app are planning on delivering an OSX counterpart and that’s the only way something that is this different could in anyway be functional as a real mail replacement.

OSX Mail isn’t Resting on its Laurels

There really isn’t much that is available for OSX as an alternative to mail as a client. Outlook traditionally was the client one turned to for a more advanced approach to mail than that of Apple’s mail however, it is definitely old school and no longer works very well at all. In fact, only Outlook’s mail really works. All the other modules simply don’t work in Apple’s new ecosystem based on iCloud. It’s impossible to sync contacts, events and tasks in Outlook with the Apple equivalents. Without that, it’s an expensive client that no longer delivers what Apple’s Mail can deliver via third party pluggins.

Apple’s Mail is actually a very viable option for enhancing one’s use of email and making it more efficient. It runs almost identically in OSX and IOS and for that matter through it’s web interface if you use iCloud. Although based on the original paridigm around email wherein folders rule the day, through rules and plugins mail on OSX can be dramatically enhanced. That just leaves IOS out in the dark. There is this chasm between the two environments that needs bridging but that bridge is taking time.

Architecturally though, this is a better approach to mail. Running almost identically in IOS and OSX from an interface perspective friction in terms of operation is drastically reduced than if you were to go for a completely different client in IOS yet rely on OSX to do a lot if not probably the bulk of your email.

Enhancing Mail through Plugins

Rather than re-engineering mail from the ground up to be a completely different client and somewhat foreign, companies have provided very capable plugins that improve the efficiency of mail and help get that email moving once again. It is more than possible to get to inbox zero everyday utilizing these plugins.

I’m going to briefly outline two plugins that synergistically work extremely well together to improve your email experience substantially. Not that you need both as you might find one works for you just fine. I find though that both prove to be quite effective and don’t collide with each other.

Indev’s Mail Plugins

Indev makes three mail plugins which are now mature, robust and tried and true. Not that you need all three but I’d recommend all three as they work nicely together and there is a cost savings by buying all three products.

The three plugins are:

  • MailTags for tagging your mail, setting a reminder, assigning a project to the email item and some notes around the item
  • Mail Act-On a quick acting plugin that will act on your mail as you’ve assigned to from tagging mail to moving it or copying it to the appropriate folder while working with a rules based engine similar to Apple’s mail rules. In fact, when you install Mail Act-On Apple’s mail rules can now take on Act-On characteristics while Act-On has it own set of rules that are far more extensive than Apple’s mail rules. Regardless though, Mail Act-On, once you have it setup right, can manipulate your mail extremely fast.
  • Perspectives a simpler add on that just allows you perspect your mail in a simpler and faster fashion.

For the enhanced control the give your over mail they are well worth the cost. Further, you’re still working with the Mail app you know and love except you’ve more or less supercharged Mail.


MailHub is yet another plugin that works with your traditional folder structure but analyzes the way in which you file or handle mail. As such, it provides an add on to the toolbar that will learn how you file mail and make suggestions as to where your email should be filed. It will also file your sent mail in the corresponding folder increasing the logic of which mail resides with which. As it learns, you can trust it more and more that its recommendations are correct and just quickly hit the file or delete button. Rather than having to think about where does this mail item logically fit, it’s done that work for you.

There is a slight overlap with Indev’s plugins but not really. As I said, as you get to know these products they work synergistically. With say Mail-Tags you might find yourself getting carried away with tagging mail that doesn’t need to be tagged. In this case, rather than spending the time tagging it, let MailHub just file it for you. Should though you feel it needs a more enhanced treatment, use Mail Act-On to tag your email and file it for either future action or reference. With a bit of time you’ll quickly get to know which product is the right one to employ. You’ll soon have your out of control email inbox coralled and under control.

Unfortunately though for IOS, should you be doing your mail there you’ll have to do it in the standard fashion. Regardless, because this is architecturally, sound mail will undoubtedly end up in the right place no matter whether you’re working with IOS or OSX.

Don’t throw the Baby out with the Bath Water

It’s definitely important to rethink the way you’re handling mail especially if it’s no longer working for you in an efficient fashion. If mail feels like it’s out of control and running your life, it’s time to sit back and take stock of what you’re doing and how you might do it differently to regain control and in a worst case scenario sanity. However, I would highly encourage you not to throw out the baby with the bath water but rather enhance upon the tried and true.

Radical departures are sometimes necessary when they’ve become antiquated and in these radical departures it’s essential to be able to adapt and learn new skill sets. This goes for anything. However, in the case of email I don’t think it’s necessary to go down the road of a radical departure. A lot of third party software is integrated with Apple’s mail and you could end up loosing that. As an example, DEVONthink Pro Office allows you through it’s own plugin to directly import a mail item into DEVONthink. This is valuable, as this might be where you’re handling the most critical of mail. If you were to decide to go with say Mail Pilot, even if they do a port to OSX and they get the kinks worked out of their IOS products ask yourself carefully are you loosing something that’s important.

Looking at this from IOS solely, Drafts is a popular capture utility for thought and ideas. It’s integrated to a number of environments wherein you can send you’re draft or fully crafted text to another environment to be actioned. That text can be sent to IOS mail. From IOS mail you can action it right then or there. You can. However, this mail that you’ve now actioned will be sitting in OSX should you want to action it in any other way.

Take Stock

Carefully take stock of how mail is working for you or not. If it is working for you just fine do nothing and allow yourself to continue to efficiently work with your email as you do. If it’s not and you’ll know it’s not as it’ll probably be starting drive you crazy, definitely look at the options for enhancing how you handle mail. That is, rethink your email process. My recommendation would be rather than to take a radical approach to changing the way you do mail unless it’s totally called for and fits your new needs, you’re better to enhance what you have with the plethora of enhancement tools available to you as I’ve outlined above.

You might even decide to put mail completely aside for parts of the day so that you can concentrate on your work and only deal with mail if something urgent should appear. Using a third party product such as AwayFind, you could set parameters to allow AwayFind to alert you on your iPhone that an important email has arrived that needs your attention. Otherwise, concentrate on your work and then deal with mail so that it doesn’t distract your focus and thus productivity.

Rethinking email is not a bad thing at all. Whether the rethink produces the result everything is well and good or no, something needs to change, a revisit regardless is beneficial. That way, you’re in charge. Not the other way around and that’s the way it should be.

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