Two years ago, Microsoft attempted to transform Hotmail, its ancient webmail service, into a program fit for modern times. The company put a great deal of thought into redesigning the site from top to bottom, and I loved the result—I thought the then-new Hotmail was as easy and pleasant to use as Google’s Gmail, which I’ve long regarded as the best email system on the planet. Hotmail even had some features that Google’s venerable emailer lacked, like a preview pane to see your inbox and read messages on the same screen and a one-click filtering system called “Sweep.” Hotmail’s only problem was that it was chock full of animated graphical ads, which I found far more distracting than Gmail’s innocuous text-only ads. “If Hotmail switches to text ads, I’d seriously consider ditching Gmail,” I wrote.
I wish I could tell you that my rave review sparked renewed worldwide interest in Hotmail. It didn’t. By virtue of its age (it was launched in 1996), Hotmail still has hundreds of millions of users around the world, but it’s not growing nearly as fast as Gmail. This isn’t surprising. The problem with Hotmail isn’t how it works, it’s the service’s digital standing. A hotmail.com email address long ago became a mark of naiveté, an address for grandmas and other schemers. Telling people to contact you at Hotmail was an invitation for ridicule—the Internet equivalent of wearing a Kick Me sign.