One one level everything is new and unprecedented. But after enough years I also see patterns repeating themselves, patterns that I think have to do with our fundamental relationship with technology.
It's true that the occupation of WebMaster is new and couldn't have existed before the Internet. But three decades ago I was a broadcast engineer, tending a radio transmitter--an information transmission device not fundamentally dissimilar to a Web site--and the rhythms of being a radio engineer are much like the rhythms of being a WebMaster today. The similarity is most noticeable in the fact that we routinely do maintenance on both devices in the wee hours of the morning, when the audience is smallest/the traffic is lowest. Thirty years ago I routinely pulled allnighters at radio stations; at eBay last year I routinely pulled not just allnighters but a couple of 48 hour shifts, upgrading the Web site during its quietest time. On the surface everything is different comparing a radio transmitter to a Web site, yet the life of the techies who work with both are very much the same.
My perspective on the Web designer side of the equation is more classically evolutionary than a matter of history repeating itself. Before the Web came along, I worked as a programmer, technical writer, and sometime technical illustrator (nowhere near Tom's fulltime focus), book designer, magazine publisher, general desktop publisher. All of those skills, in new and novel combinations, form the basis of Web design. It's as if the first couple of decades of my professional life were spent in training for the Web.
So the Web, I guess, is an example of something both new and unprecedented, yet simultaneouly old (or better to say, a continuation of tradition) and entirely precedented. Maybe the Zen of the Geek is that, on the one hand, absolutely nothing that people might come up with in the way of technology should be surprising, since that's what homo sapiens sapiens does; at the same time each and every new thing is a marvel and a delight.
Just gotta keep learning! If you stagnate in the computer industry, you'll not only find yourself unemployed but unemployable.
One of the pleasant ironies of computers in combination with networks is that they're a tool-of-tools and very much a tool for continued learning. At the same time that the pace of computer development keeps on the pressure to keep up, the computer also provides the means to keep up. Life is good when you're riding the wave and the forces are in harmony.