I've always been more concerned with experimenting than maintaining archives of my blogging, which I don't regret (a permanent public record has its drawbacks), but, for the sake of vanity, I do wish it were a little more apparent how long I've been doing this. I registered tuttlesvc.org on September 9, 2002, and started blogging using some simple code I wrote myself some time thereafter. Before that, I had Radio Userland blog, which had some kind of identifying number in the URL. I wrote a lot on that over a relatively short period of time and then accidentally erased it. That would have been some time after ETech 2002 in May, which first focused my attention on blogging.
I first heard of "web logging" while driving around listening to The Connection on NPR in May of 2000. My first impression was that it was the dumbest thing I'd ever heard of, although at the time I must have already been reading Slashdot, which, arguably, is a weblog.
It would be, by the way, really interesting to listen to some of these archived radio shows on technology circa 2000. The Connection was way ahead of its time.