The walkman delivered value I couldn't get otherwise. I wanted to carry an extra device because I wanted music, and I couldn't play music otherwise. (Unless I carried a boombox on my shoulder, which some people did in awesome rap videos).
Google glass doesn't add tremendous value over what I can currently do with my phone. It takes pictures...faster...but I can already take pictures with my phone.
Right now.
And yet, isn't one of your points that it's not a micro improvement? You're saying here it's a micro improvement on your phone... but that's a bad thing in your blog.
It's not hard to imagine Glass having a phone built in (in fact I'd welcome it, the apps I really need on my phone could easily be in Glass, and I could do without the distraction of the others), so I really am having trouble following your arguments based on a very very beta product that has plenty of years of runway to develop.
Transistor radio? Panasonic portable cassette[1]?
The Walkman had three things: size, stereo and marketing. Maybe you had a need for portable stereo playback in 1981, but for me and my friends it was the size and the marketing. Then again I never had a transistor radio, so I had no opportunity to be pre-jaded.
[1] http://3.bp.blogspot.com/_TjQbHKV2Vuc/S59ezmCHH7I/AAAAAAAAA3...
FWIW, when I was an intern at Google, Sergey wore them 24/7. He looked a bit weird the first couple of times, but after that he just looks like Sergey. It's like people wearing glasses when they previously didn't. Weird for a bit, then perfectly normal afterwards.
sunglasses = cool
google glasses = dorky
99% of what Google glass can do I can do on my smartphone WITHOUT THE HASSLE and WITHOUT making me look like a dork.
The Walkman, while creating detached non-social behavior, still only distracts the user, or a nearby busybody.
Glass turns you into that busybody, potentially prying into everyone else's business.
A potentially always-on camera recording into the cloud is unfriendly and unwelcome in a lot of ways.