Sorry for my late reply! I've been on the road.
So glad you're enjoying my writing here!
Yep, I'm from Canada. I started writing in the late 80s, as a student journalist at the University of Toronto, and then kept doing it for pay after graduating. (Bad pay for a long time, lol; I've always been a freelance writer.)
As for what and how I write here -- very good question. I tend to read a ton (as per my recent post on using RSS to follow 400+ blogs and web sites) and a lot of my ideas for essays flow out of the thinking and sparks that come from my reading. Though I also integrate a lot of my personal experiences -- ranging from this stuff here about phone calls to my cycling.
I keep a huge list of essay ideas; the instant I get one I jot it down, and sometimes try to write a few sentences speccing out what the argument could be. Then every few days I look at the huge list ... and see if any of them feel "right" to write at the moment.
Things change once I start writing. I've learned over the years that sometimes an idea seems slight -- i.e. there's not much to say about it -- but it evolves once I dig in. So it's a leap of faith often ...