Wren -
I'm coming to this post a bit late but think it is a very good question about how to teach and role model the balance risk taking with learning to use prudence and caution.
When my kids were fairly young, they got into rock climbing and joined a local team with an amazing coach who taught them all of the horrific risks associated with irresponsible behavior. The kids became very good at assessing danger and risks while also learning to push themselves past their own fears to take calculated risks. It has served them well, and it helped teach them things that I don't think I could have. Once they knew how to drive, my two older kids would join up with other kids on the team and travel to remote parts of our state to climb in their favorite spots. When storms approached, they cleaned their equipment off the routes and moved to safety. They religiously checked the safety of their equipment and refused to climb with some who they considered reckless. That balance between risk and freedom flowed over to most other areas of their lives.
My preference would have been to bubble-wrap them and duct tape them to the wall until they metamorphosed into responsible adults, but it doesn't seem to work that way.
