The State of Personal E-mail:  Frakked

| Hidden Dimensions

“You can never solve a problem on the level on which it was created.

-- Albert Einstein

E-mail on any kind on any platform in any era has always been problematic. There are basic communication protocols and ports, like POP, IMAP and SSL. But when it comes to user specific implementations and business models, e-mail has been on a roller coaster ride. Now, Google is trying to re-invent e-mail with Wave by, possibly, asking the wrong question. What are the right questions?

The state of e-mail is not good. When e-mail was the killer app in the 1990s, there were many fine e-mail apps for the Mac. They cost real money and were supported. While fairly simple and limited, they got the job done in an era of dial-up connections.

Then, when Panther (Mac OS X 10.3) shipped, Apple included its own e-mail application that literally torpedoed the for-pay apps like Eudora and PowerMail. With their business model blown up by Apple, Qualcomm passed on Eudora 7, a Mac OS X native version, leaving it up to others to limp along *.

Enterprise E-mail

All along the way, business e-mail, on expensive broadband networks took its own path. Microsoft's Outlook, with extensive support for business needs, such as receipts proving the recipient read an e-mail, came to dominate the business world.

Emerging after that, but not yet solidified, is the Web 2.0 concept of Web-based e-mail for corporate users. The best example of that is Zimbra. Zimbra, developed by people who researched and well understood the problems with modern e-mail, is used widely in circles that are allergic to Microsoft. Zimbra provides the kind of collaboration and automation one would expect -- including scheduling of calendar items, shared files, contact lists. archiving. It's a complete solution, as is Outlook + Exchange, for businesses willing to sign on to the whole solution suite and pay for it.

What's Left for Me?

For the individual or small business, things aren't so great. Free e-mail apps are grudgingly used, but one gets what one pays for. For example, in the case of Apple's, instead of addressing the fundamental issues of e-mail handling, Apple has rather haphazardly "improved" the app by adding ToDo lists and RSS feeds. Then it turned around and gave an Apple Design Award to Things -- a tacit admission of its failure with the development philosophy.

As a result of this, the modern kinds of things that we'd like to do with e-mail remain out of reach. For sure, you can send a special invitation to another Mac user with the that will drop a calendar entry into iCal. But that depends on both users using Apple's

Fundamental Questions

In recognition of of the fragmentation of the e-mail user interfaces and technologies, and maybe a little bit of salt in the wounds of Microsoft, Google has asked themselves the question: "What would e-mail be like if it were invented today?" And came up with Google Wave. However, asking that question isn't the same as asking a much more complex series of questions:

  • How do individuals use e-mail in 2009? For example, some people only read their e-mail once a day, others every five minutes.
  • What are the fundamental issues that aren't being addressed by free apps?
  • Is e-mail really dying thanks to Twitter? Or is that a delusion because users are unhappy with the state-of-the-art in e-mail?
  • How can we bring the advantages of Zimbra to the personal desktop and remain competitive?
  • What kind of e-mail would be so compelling that people would actually pay for it? Or is there a modern business model that keeps the app free but pays on the back end?

Google's Wave approaches the issue in a social media way: "How can I engage with my friends in a persistent connection to exchange ideas and information?" That may be the way 25 year old Google engineers work, frenetically time-sharing, but it doesn't solve the fundamental issues of 21st century e-mail; it just brushes them under the rug. Google Wave is still too immature and has to small a market penetration to become the near-term answer for Jim and Mary, in their 30s, in Albuquerque who run a small gift shop.

One would hope that the company responsible for blowing up the paid personal e-mail app business, Apple, would pour the same level of creative thinking into its as Google is pouring into Wave. Regrettably, with each new version of Mac OS X, we get only minor and irrelevant refinements that are disappointing. That's because Apple has no motivation or industry expertise to envision what a remake of the e-mail experience could be. They're happy to limp along, as they did with iCal. Apple is asleep at the wheel on this.

The Next Generation E-mail App

When one looks at what BusyCal did for calendaring, essentially embarrassing Apple's iCal, one suspects that somewhere, someplace, someone can figure out how to make money with an insanely great concept for 21st century desktop e-mail. As it is, we're stuck with, Thunderbird, Mailsmith, MailForge and Opera.

The whole technology of e-mail is ingrained in our culture. It's private, even encrypted. It's read on our own schedule. It's not in your face, but allows us to move away as needed and be creative, in quiet time, with other tools. It can handle large amounts of text and attachments. Messages are ignorable and filterable.

I believe there is still time for developers to exploit these features of the e-mail experience and yet make dramatic improvements in handling, sorting, prioritizing, calendaring and the UI. An inbox with 2,000 messages leaves one with the same bad taste in the mouth as when we see an Macintosh novice who uses the desktop as his one and only filing cabinet.

Google Wave is the right answer to the wrong question. Maybe Apple itself is our only hope.


* Here's a full list of free mail apps for the Mac.

Popular TMO Stories



I am holding out hope for MailForge as it a “pay for” application. But, MailForge is not yet ready for prime time.


Twitter as an alternative to e-mail? You’re kidding, right? Twitter is an electronic soap opera at best.

Facebook and MySpace are like journals.

E-mail for Enterprise is so much more complex due to security, safety, and retention rules. E-Mail in government is even more complex because of open records laws, FERPA, Buckley, etc.

There need to be a whole lot more questions asked.

John Martellaro

Twitter as an alternative to e-mail? You?re kidding, right?

Indeed I was. And I was being sarcastic about those who see it that way.


One of my main issues with Mail (and Outlook) is the restriction on filing. As someone who works on a number of projects where other members of the team also require access to e-mail correspondence, I have been trying to establish if there is an automated way for all emails relating to a project to be stored as a file in the project folder (a project folder in the Finder rather than a folder in the Mail app). To date, everyone tells me this is not possible. If emails are manually dragged from outlook into a project folder, the useful information such as date, recipients, etc are lost from the title. I think that with a little thought and a few hours of programming, an elegant way could be found - but Apple and Microsoft just don’t appear to recognise the importance of this type of functionality.



I feel like this would be possible with and it’s Rules preference pane. You could make an applescript that automatically copies the email to a file when you add it to a certain folder or something similar. I am not an expert, but this seems like something that is doable unless I am misunderstanding your situation.


Great article, John. Being a (former) follower of BSG, I have to especially appreciate the headline. smile

Maybe I’m not terribly imaginative or my needs are pretty darn basic… I really don’t see the need for any sort of massive overhaul for the way we do emails. With IMAP, smart phones, sophisticated search capability like Spotlight or Smart Folders, I think email clients - in general - are as pervasive and flexible as what probably 98% of everyone needs it to be.

I do have to agree that Apple doesn’t really push its organizer software to its potential. I mean seriously… the latest and greatest with iCal was Exchange support?

I had never heard of Things, and their stuff seems pretty nice - but extraordinarily overpriced, for what it is. My company uses a web service called Basecamp ( that does pretty much the same thing - except that it’s geared more towards work groups - for a much more competitive price.

Bosco (Brad Hutchings)

John, search iTunes for Chris Anderson’s “Free” and spend the 7 hours or so listening to it. It’s free, by the way. You can lament the collapse of paid desktop software in categories like email and web all you like, but that’s just the way things are. If a developer wants to do something great, they’ve got to find something up the value chain because people do not expect to pay for mail software, and you need widespread adoption to change the product category. You get widespread adoption by not having hurdles (i.e. toll booths).


John:  You’ve discovered what I’ll call the “Conventionality Trap.”  That is when someone provides for free a good or service that is sufficient to satisfy conventional needs, so that most people won’t pay for innovation with the result that innovation ceases.  We have seen this a lot in the tech industry.  It occurred frequently with Microsoft’s Windows, where, because Microsoft earned its income from Window’s royalties, it added many free features to Windows that destroyed entire businesses.  Those free services enhanced the value of Windows and the royalties from Windows but obliterated the businesses of companies that had been selling those services.  An example, was the web browser and the destruction of Netscape, until Mozilla and others matched the free Internet Explorer with their own free browsers.  Free email clients are just another example of the problem.  Free kills innovation, leaving us with the conventional; thus, the Conventionality Trap occurs wherever you have a person or entity who offers something for free because it somehow benefits his/its main revenue generating business.

The solution to the Conventionality Trap is difficult but not impossible.  One way is to develop a proprietary innovation that is so superior and necessary that the conventional is no longer good enough, and, thus, people will pay for it.  The other way is what we’ve seen with Mozilla’s Firefox.  That is someone subsidizes offering innovation for free, because it benefits their other revenue generating business.  Google subsidized Firefox, because it needed to wrest control of the browser from Microsoft.  IBM and other major companies subsidized the development of Linux, because they needed to outflank Microsoft in the market for enterprise servers.  Apple has supported and subsidized several open-source projects (Apache, BSD, et al.), because it served its strategic interest to do so.

Alas, poor email, it awaits either that break-through and proprietary innovation or that sugar Daddy who will subsidize providing innovative email for free for its own strategic reasons.


I’m curious why Gmail doesn’t get a mention here? John, can you comment on Gmail and your thoughts on how it fails, too? Just thought that since you mentioned Wave, you ought to at least share your thoughts on Gmail.


Bosco (Brad Hutchings)

Following up on JonGI’s question… There is a great EconTalk episode with Paul Buccheit, original developer of gmail.

One point that he makes about email and a founding principle of gmail is that many of us really just throw all of our email in one box and want to be able to search it rather than having to organize it. Nemo talks about “The Conventionality Trap”. It goes deeper than a race to free/adequate with email and much of personal storage in general. We’re really caught in a “Hierarchical Filing Trap”.


As Bosco noted, organization into the one large inbox might be the current email limitation, but also the best place to improve.

I used to delete any old emails, judged ‘not important’, simply because I wanted a clean inbox. This yahoo/hotmail issue was improved by gmail archiving, and yet, it was only a small improvement as old emails were simply stored into a second, bigger ‘archive’ folder, thus cleaning the bedroom by sticking everything in the closet.

Commercial product improvement often tends towards speed, convenience and automation.  Most users would appreciate a webmail application that ?cleans their room? for them, much like the Christmas-hyped robotic vaccum, ?the Roomba?. 

People want more time and they want it easier.  Our current click and drag email filing (if a user is motivated to organize) is paramount to labeling every new song you download, and any itunes user would go crazy if they had to personally organize their music, and yet that’s the industry standard for email. 

For the past month I’ve been using a webmail that solves this all-in-one box problem.  Booztermail, a free web application designed in France, automatically classifies emails through a learning system. 

Each email is marked with
WHO (which contact),
WHAT (sent, received, pdf, photo etc),
WHERE (to do, travel, family/friends, work, technology etc) and WHEN.

This makes searching for former emails a calculated reach into a predesignated drawer, not diving into the closet to retrieve that one sock among the hundreds ?archived?, thus saving time and mental energy.

This has simplified and organized my email experience and I see the future of webmail heading in this automated, intelligent direction.


Anyone have thoughts on Postbox?


I think that with a little thought and a few hours of programming,an elegant way could be found,but Apple and Microsoft just do not appear to recognize the importance of this type of functionality.Facebook Layouts

Log in to comment (TMO, Twitter or Facebook) or Register for a TMO account