Lorel - I was just like you as a child and wish I would have been pushed more outside my comfort zone. I think it a great idea to strongly encourage him to do it. Especially if it's an issue of trying something new and scary. Would anything make it more appealing to him to try?

And don't feel guilty either! It's one of those things that if he does it, he will never regret it. He may well regret NOT doing it though!