I'm glad to know we're not the only ones with an ultra cautious child. My ds6 is so reluctant to try new things, and he always assumes the worst is going to happen. He's afraid of trying new things, even ones that are not dangerous, because he can't stand failure and knows how frustrated he gets. He still doesn't know how to tie his shoes, button his shirts, or ride a bike. I feel like a terrible parent sometimes knowing my child can't do these things yet, but it's tough to always have to push him. He definitely needs the nudge, and he often does just fine once you force him to try something. If we waited for him to ask to try something new, he'd never get there. It's truly awesome and totally worth it though to witness his feeling of confidence and pride when he tries and succeeds.