Encouraging the Cautious Daredevil

It all started with peek-a-boo around the ladder.

As I kid, I never felt fearful of trying new things and pushing myself physically.  I swam in waters deep at a very young age, loved climbing trees, and took on new challenges without hesitation.  To be honest, I never even thought much about it until I was faced with a wave runner.  I was in college when a friend invited me to try one out.  Getting on the machine wasn't hard, but I found myself quite afraid of trying the flip-arounds some riders do so well.  At the time, I was extremely frustrated with myself for not having the confidence to keep trying it, for being afraid.  Later, I realized that it was often the encouraging voice of my dad that allowed me to feel it was safe to try new things as a kid.  I guess I had a trust that if he thought I could do it, I could.

Luckily, Beansprout is no daredevil - not by any stretch of the imagination, really.  For this I am truly grateful.  That being said, he is a cautious explorer, meaning he does indeed push himself to do the usual things kids need to do to help them develop.  This has left me in the conundrum all parents must I'm sure face - allowing him to do things that make me cringe because of my fear he'll get hurt.  Naturally, I know it's necessary and par for the course, but still, I cringe.

"So tall!"

Before I continue, I have to admit that in the spring I feared he wasn't challenging himself physically -- you know, developing those gross motor skills he needs.  I needn't have worried it seems.  We have a ladder in our home, leading to a cozy little loft space above our bedroom which with a little work could be the perfect kid's hide-away for our Beansprout.  Though I'm not quite ready for him to have his own secret loft space yet, I am trying to be that encouraging voice telling him he can do it.  I am accepting the gray hairs I can see growing right before my eyes as he heads (quite safely, I must say) up the ladder "two times".

How many gray hairs did you give your parents as a kid?  How would you handle encouraging cautious exploration of somewhat dangerous endeavors?