I actually started keeping an electronic journal while I was still in Jr. high since we had a computer and well my dad was always at me to keep up my typing skills and speed, so I use to use that as a way to get faster in typing and what not, it worked I now have over a GB of electronic journal entries that I’ve been keeping since the late 80s.
However, when it comes to online entries of a blog nature I started doing that back in 97 when I started going to University, though it wasn’t called blogging back then and when I started doing it it was more along the lines of journaling transferring my digital journal into online format and posting it to my web site.
It would go like that write an entry post it to my site and so on and so forth, it wouldn’t be till April 02 that I started actually blogging on a site built for it, I started my first actual blog on DeadJournal (the site is still active as is my log there) would actually be the first one that I’d use till I was able to get onto LiveJournal (which I still update from time to time).
As to why I started posting my journal entries online, I started doing so because I found it was a good way to interact with those who where on my site and gain feed back at the same time. It was also a way of expressing myself and not lousing my paper based diary which I was forever doing the old fashioned way, doing a log digitally for me was much easer and being able to print it out and add it to a book was much easer then the other way that I had started out doing it all. That and digital wise it was easer for me to read my own entries since my hand writing years ago wasn’t great and even now its not always readable even by myself.