What's the worst that can happen?

In my previous life BC (before child), one of my roles was as network manager for our company's computer networks. As part of that role, I had to create Risk Assessment documents - think of anything that could go wrong with the network, decide what impact it would have, and come up with a plan to put in place in the event it happened. (And yes, it was as boring as it sounds lol).

I'm finding myself using the same skills trying to parent a child like Billy. He is constantly coming up with grandiose schemes, and while my first instinct is always to say "no", I'm trying to do what I can do to turn that into a "yes". So I'm trying to train myself to go through a "risk assessment" in my mind - what's the worst thing that can happen if I say yes? Or can I come up with a scaled down version that we're both comfortable with?

Take his current scheme. In the car on the way home from the library the other day, he decided he could set up a library himself so anyone could borrow our books. Hmmmm... We talked through some of the problems (if its open to anyone, we don't know whether the people will return the books or take care of them, what if the people who came to the house were robbers etc) and that was the end of the conversation. So I thought...

Today he grabbed the label maker & some cardboard so he could start setting up his library. He'd narrowed the idea down to just people we knew in the neighbourhood. Ok, I'm more comfortable but I'm still not that much of a fan of lending out my books.. In the end we compromised on a few of his friends and they could borrow his books. Part of me is still screaming Noooooo though.

So what's the worst that can happen?
* the books will get ruined and / or not returned - I know all of the families he's going to tell about it. I'm pretty sure they'd take care of the books. Most of his books are second hand anyway so it's not really a big deal. I'll try to persuade him to not to lend out his good or special books.
* no-one will borrow any - not a problem for me, but he'd be disappointed. Well, that's one of life's lessons learnt in a gentle way.
* people will think we're weird - hmmm, we're already the weird, homeschooling family. I think we've got that one covered..

So nothing really that would warrant me saying no. Just that it's not what you'd expect someone to do. It's amazing how many times it seems to come down to this for me. All my life (well, as much as I can remember of it), I've tried to fit in, not stand out, be one of the crowd. Its a complete shock to me that I'm doing something as out of the norm as homeschooling. And to have a "weird" child - one who doesn't seem to even notice, let alone care, that they're standing out and doing something "odd" - is way outside my comfort level.

I'm betting I'd better get used to it though. Something tells me its just the beginning!