I've always been cautious and at times, fearful. I come from a family of fearful, neurotic Jewish women, and I've broken through most of that... that said, my mom was adventurous, but born at the wrong time. She was very athletic, and she really only put it to use in high school, in the 1940s. I just wish I had started outdoor stuff earlier, because I think I would have had less fear in my 20s or 30s. I don't have particularly great bike handling skills on downhills, and at this point, I am not sure what else to do. It scares the crap out of me. The other parts, well, I *am* a bike trip leader, so I try to mitigate danger by planning routes that don't have awful intersections, uphill stops, etc. You probably wouldn't notice anything bad about my riding unless you saw me descending! I also no longer do big group rides, and I even don't like riding with "my" group sometimes because of the incredibly poor skills. This is why I volunteer to be the sweep a lot of times! I don't like the unknown and I do get anxious if I am on a group ride and try to anticipate what I will have to be doing. I am better than I used to be, though. I have no issues taking the lane, signaling, etc, but within the confines of my familiar area or in other suburban/rural roads.
I will ride just about anywhere around where I live and I like climbing. However, I couldn't ride in Boston. I don't even drive in Boston. Too many azzholes and things I can't control.
I am less scared when I am nordic skiing. I descend pretty big hills on those skinny skis. Maybe because it's closer to the ground and snow is softer than pavement. However, today, there was a lot of ice at the beginning of our ski, on a small descent and my legs started shaking uncontrollably, I guess because I was scared. It made it very hard to descend with my knees together, but I got down without falling.
I have osteoporosis that is being treated and I am back into the osteopeinia range now. But, it makes me more cautious. Really, though, my fear is mental and somehow, I have been able to work through in skiing, not so much in cycling. At the end of the day, though, I feel like Shooting Star. I am out there doing what 99% of other 60year olds don't do.