This guy has a real insight into why we are where we are in the computing world today, having been part of its development from the start. Some of the problems stem from lock-in, smaller programmes which get bigger and relied upon by many other programmes, until everything gets too complicated to change. It's their way or the highway - Facebook anyone? And these programmes then force us to use them a certain way - for instance, you have to chose your profile's Relationship status from one of few possibilities. So our human individuality and subtlety is coralled for the convenience of an insensitive programme.
Or take MIDI, the computer's representation of a musical note. Not a bad effort for the 1980's technology of the time, but it's not perfect and falls far short of conveying the nuances of individual notes. But too bad - a whole industry and their computers now rely on the 1980's imperfect representations and that's that. We're locked in.
As Lanier says, if you could go back in time and report to the founders of the world wide web that the pinnnacle of twenty year's human endeavour is a mediocre encyclopedia, wouldn't you be depressed?