Thinking outside the inbox.

Email is a victim of its own success.

In the 1990s, email ruled the world of digital communication. It was really the first form of digital social media and changed the way we worked and played. Email was an important driver in the creation of a connected world and the formation of what Clay Shirky calls the cognitive surplus. Email was the primary mechanism for implementing the modern flat organization structure. It enabled companies to work with employees in other cities or at home. It liberated low-level employees to communicate directly with the boss.

In the first two decades of this century, email has fallen from its exalted role, replaced by other communications tools, including private messaging systems embedded in applications like Facebook. Email has always had potential far beyond what it achieved, but was mortally wounded by inevitable market forces.

By market forces, I mean Microsoft. And by inevitable, I mean completely evitable. In the 90s, Microsoft conquered the email marketplace with Outlook. Their email product was, like all of Microsoft’s products, just good enough to eclipse their current competition, while being marketed and sold much more aggressively and skillfully. Microsoft killed all of Outlook’s competitors and scared away the venture capital community. No VC wanted to compete with the 800-pound gorilla regardless of how promising a new email entry might look. With no chance of any competitors arising, the creative energy that gave birth to email went looking for greener pastures.

In 1945, mail was sorted on “Railway Post Offices” while on the move.

I call Microsoft’s strategy of targeting their competitors instead of their users “scorched Earth” after the ancient military technique of destroying anything that might be of value to the enemy. Microsoft wrecked the marketplace for all of their present and future competitors. All of their product features and characteristics were designed purely to counter the features and characteristics of their competition. They burned all of the players in the email market, and they pounced on any new entries, scorching the entire segment, whereupon, Microsoft ceased all forward motion on their product.

Other email client companies were just as culpable in their own demise. Eudora was an excellent client in the late 1980s. It was invented by a solo engineer, so it was quite powerful but had the characteristic engineer-designed interface that was usable only once you scaled its learning cliff and then used it for at least a couple hours every day to stay current with its idiosyncrasies. It was standard issue at my company until we came to need an email client that interacted with appointment calendars.

Microsoft handed it a loaded Luger and Eudora obliged by shooting itself.

Nobody wanted to change to Outlook, but we really needed our email to integrate with our calendar. I remember sending email to Qualcomm pleading with them to upgrade Eudora. Qualcomm, who purchased Eudora from its inventor in 1991, was a telecom hardware company. Hardware companies never understand the unique economics of software and never give it the respect it deserves. Hardware companies owning software products is a relationship that never works, and Eudora became the ugly step-sister in Qualcomm’s lineup. Microsoft handed it a loaded Luger and Eudora obliged by shooting itself.

There was a golden moment in the early aughts when the time was ripe for a new entry in the email client marketplace. Sure, Outlook owned the market, but it had been revealed as a bad piece of software sold by a company that was not your friend. It was expensive, hard to support, and frustrating to use. But instead of seeing the enormous market potential, all the investment community saw was the enormous bully, Microsoft.

The characteristic behavior of the software community has always been driven by two forces: (1) The crazy innovation of solo inventors, and (2) the damping force of people with money. The inventors move us forward and the money people consolidate the marketing and operations functions. But there is no intrinsic force in the technology world to create better products aside from the conscience of a few entrepreneurial leaders — I’m looking at you, Steve Jobs. Entrepreneurial leaders are typically overpowered in the end by the money people. Even Jobs was tossed out by the money people until the money people realized they were pissing in their own soup.

It is not a coincidence that Instant Messaging Services, chat, and text messaging exploded just as Outlook solidified its hold on the market.

It is not a coincidence that Instant Messaging Services, chat, and text messaging exploded just as Outlook solidified its hold on the market. Since then, we’ve seen the emergence of many different platforms for email-like communication, including Slack, Twitter, Dropbox, and dozens of proprietary messaging services. You might argue that these go beyond email, but all of their functions could have been built on the email platform of 1990. Sufficient functionality to do so was well-established by the late-80s in the X.400 standards.

Once Microsoft’s Outlook was the last man standing around the turn of the millenium, they saw no need for any further improvements. Yes, there were a lot of changes made to the interface of Outlook in those years, but that was just young Microsoft employees trying to get their fingerprints on a known winner. None of their changes were improvements.

Each subsequent layer of cruft made Outlook more a lumbering, bloated beast.

The needs of users never played a significant role for Microsoft, although they danced to the tune of IT managers. So Outlook was encrufted with lots of functionality and adaptability that IT managers wanted. Each subsequent layer of cruft made Outlook more a lumbering, bloated beast. The venture capital community refused to see the potential, and the inventor community was distracted by this shiny new Internet toy that was just starting to blow up. Email innovation was kicked to the curb in favor of newer, weaker platforms. Weaker, but more user-centered. Instead of building messaging on the email platform, it was built on an entirely new one, forever condemning us all to opening at least two apps to know what is going on.

Sorting and searching mail on a railroad car circa 1940.

Today, the email standard is Google’s nameless client. They took the market away from Microsoft by using Microsoft’s time-tested formula. Google added search to the inbox, and gave the product away for free. It will take years for the installed base of Outlook users to dwindle away, but it will. Google Mail, meanwhile, is still built on the 50-year old paradigm of an endless inbox filled with identical entries in chronological order, with no information age tools for organization, visualization, and management. Google Mail’s mental model, like them all, still sustains the ancient physical model of snail mail, a box filled with envelopes, stacked in chronological order.

“Meet the new boss, same as the old boss.” — The Who

You may see the pattern emerging here: that when companies find a winning product strategy in the software business, they cease further innovation until someone with a bigger stick knocks them out of the winner circle. They don’t see that user expectations grow. The economics of business mitigate against innovation. Making things better for users simply doesn’t motivate companies that are making vast quantities of money right now doin’ bidness. It requires too much long term thinking.

What’s more, the economics of sticky software products make it expensive to compete with incumbents. You need innovation to beat the current winner, but you need cash to even play the game. The history of innovative products disrupting incumbents is clear and bold, but enticing only to inventors and universe-denters. It is scary to money people, and seemingly unnecessary to business people. Eudora thought they were unassailable until a company came along with more money and one new feature. Outlook was unassailable until a company came along with more money and one new feature. Now Google has a market leading product that remains steadfastly non-innovative. Who has enough money to want to take their market away?

If history is any judge, some of you are rarin’ back on your hind legs and angrily saying, “Well, what would you do to improve email?” It’s hard to think outside the inbox. That said, thinking up new and better approaches to doing things is what Cooper, my company, and I do for a living. Email me at if you’d like to explore how we might work together.

You can read about my 7 Rules of Email Etiquette here.

My esteemed colleague, Jonathan Korman, tweeted a storm of interesting comments about this post and collected them here.

Ancestry Thinker, Software Alchemist, Regenerative Rancher

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