If you haven't yet stumbled across it on BBC News, Engadget or the discussion boards here on Core77, there's a great little article making the rounds today, in which 13-year-old Scott Campbell is asked to give his opinions on the very Walkman his dad once toted (or hauled, if you want to be honest about the size of those early ones).
Besides the obvious entertainment value of hearing a (surprisingly eloquent) youngster discover how to flip a tape over, and "shuffle" tracks by randomly releasing the rewind button, there's some useful insight too, into the unavoidable coupling of intended and unintended consequences when technologies advance. Like the frog in the slowly warming pot, it's sometimes difficult to see the downsides of an improvement while it's being implemented, and even years into a shift as fundamental as the one from linear playback to random-access music devices, we have to put the two side-by-side and see them anew to appreciate how they've influenced our behavior.
The most obvious "loss" of the iPod generation, as mentioned in that Core77 discussion thread, and elsewhere, is the steady demise of the album as a coherent document: when the technology's limitations prevent us from going straight to the song we want, we're forced to listen to the whole thing, and maybe grow to love certain songs whose beauty reveals itself slowly. Without that linearity -- which would be seen as a failure today -- we'd probably have missed out on some beautiful but elusive tracks that our enormous, warbly tape players demanded we endure.
On the other hand, there's plenty we're gaining, and it's more than simply convenience. One danger of looking back on a nostalgiac medium is filtering for the good things and stating them explicitly, while leaving the old drawbacks, and new advantages, unspoken. We're fond of the warm crackle and rich timbre of a soul track on vinyl too, but do we spend as much time rhapsodizing about the sheer joy of being reminded of a song during a conversation, then cuing it up just a few seconds later? Of making music part of the discussion, rather than a distracting 15 minute dig through stacks of albums, often to find the sleeve is empty?
The potential for joy, exploration, emotional connection and (future) nostalgia in new technologies is often overlooked, and that's a pity, because objectively there's just as much to mourn in a new joy unappreciated as an old one lost. Smart 13-year-olds, with a democratic lack of allegiance to either, may turn out to be the best technology critics we've got.