For myself, riding is a calculated risk. By that I mean I wear as much gear as possible, and try to adapt my riding style depending on time, road conditions, traffic, location, etc, etc. Even after only 1 season, most of my 'fear' of riding itself is gone, in that I'm not afraid of the bike itself -- moreso just the idiot drivers out there which also worry me (albeit less) when I'm in my car. I also told my family about my intent to start riding right from the start. I can't say they were overly happy (my dad was in a motorcycle accident years ago, but with no idea how to ride and with zero gear), but they were accepting of it, and knew I'd approach it as 'safely' as one possibly could.
Reading the posted article though, I'm surprised he didn't know better regarding riding 'aggressively' in downtown Toronto -- I actually try to stay away from there on both the bike or in the car (and commute down instead) as there are too many things out there to kill you or be killed (aka lemming pedestrians). Also regarding riding in the twisties, I always try to late apex and go into a corner in such a manner that I can see out of it if at all possible. If I can't, then I'll play it cautious just in case there is gravel, debris, etc on the road ahead, or in case there is a cage coming the other way.
Also as others have said, as cliche as it has become you do 'only live once' -- and riding is one of those things I'd rather take a calculated risk and do, vs always be wishing I had when I'm laying on my deathbed in old age.