I have written at some length, including in the book We’ve Got Blog [short for “Web log”], that during the 1998–2001 Web “gold rush” I couldn’t fucking get arrested. One reason was I knew more than they did. Another was that knowing more than they did intimidated typically mediocre Toronto “recruiters.” Plus my personality is viewed as quite forward by many Canadians, whom I would simply describe as backward. The result was that everyone and his dog (who also got space in the office) had a job and I didn’t.
After I signed the book contract, the doors closed and I gave up pining for an actual day job. It simply never occurs to me. (Except once recently, but I discount that case.) I am nonetheless reminded frequently that the majority of my confreres simply never have to worry about money. They all actually have jobs. The minority that do not nonetheless have many more freelance contracts than I do.
That era looks like it is set to repeat less than a decade later, as “Web 2.0” businesses start up and are bought out. I am not opposed to either of those phenomena (and I think Yahoo’s $36 million for Flickr was criminal underpayment), but I am also pretty sure that I won’t benefit in the slightest from this next bubble. You’ll all continue to have jobs and contracts, some of you will become Butterfield/Fake–level rich, and I won’t.