I had long forgotten this Carl Steadman response to Michael Sippy's "Just One Question - What do you want for Christmas", but the response from 1997 is fantastic and frames the 1990s as the broken decade. (I'll wait for you to go read it)
I'm not so sure that Carl's broken decade got better in the first half of the 2000 decade, but it really started to. We are much farther along now. Our consumer world started to improve quite a bit and slowly business systems and services are slowly improving. The initial part of Carl's rant focusses on the number of steps to get something going. Once it is working the steps are still clunky.
Carl gets in a great rant about time and how broken it was in the 90s within technology (calendaring and syncing is still a beast and likely to for a bit longer - you understand the problem sets and pain points if you have ever tried to build syncing). With calendaring and its related activities we now have Tempo, which is freakishly close to the next step scenario I used in many of the Come to Me Web presentations and Personal InfoCloud presentations from 2003 through 2007 (I've been getting requests to represent them as this is what more and more developers and designers are dealing with today and need to have a better foundation to think through them). There was an internal Yahoo presentation (and follow on day of deep discussions and conversations) with a version of the Personal InfoCloud and Come to me Web flow that is nearly identical to the Tempo app video scenario and ones spelled out in Robert Scoble's interview with Tempo CEO, which is utterly awesome that it is getting built out some 10 years later (we had the technology and tools to do this in 2004 and beyond).
Carl's rant gets worn away over time though consumer devices, services, and applications. The refocus on ease of use and particularly the use through mobile, which requires a very different way of thinking and considering things. It thinking through design, the dependancies, and real user needs (all while keeping in mind the attention issues, screen size, networking, and device limitations). The past couple years mobile finally caught on with mainstream users and people doing real work on the mobile and tablets - Box 40% mobile access of files stored there over the last couple years. Many other business vendors have had mobile use rates of their services from mobile over the past two years. When talking to users they opt for mobile solutions over their full enterprise tools as they are much easier to use, which quickly translates into getting more work done. As Bernd Christiansen of Citrix stated in an onstage interview the employee's most productive part of the day is often the walk from their car to the front door of the office working on their mobile devices.
This world is not fully better and fully easy to use from the days of Carl's rant, but it is getting better. We still have quite a ways to go.