Dear A.,
Well, you have a shy child. So now you have to accept him as he is. You and Dad stay very close and communicative with him,
do not pester him to act any different, just carry him, or guide him along when you are where he feels scared. He will gradually gain confidence. Ask the teacher how he is in school. There is a very good book about raising boys, it has a lot of very good ideas. Remember boys are not girls and they never will be. He will have a very responsible roll when he is an adult, (as would his sister, if he had one), but men have different types of pressure on them, so give him a chance to build a base of good feelings and confidence. Find what he. himself is interested in and guide him toward activities in that area. He is a unique person, noone on earth is exactly like him, so do not listen to what other boys are doing. He is your boy and not THEIR boy.
I just happened to think, maybe he is not in Kindergarten yet, and that is good. I wish that I had held my son back one year from entering K. at the age of 5. His whole life would have been better, I believe.
I feel like I have been very straightforward and a bit surley to you, maybe it is because I want to zero into your brain that what I am telling you is good, not bad. Try to find that book about boys, I am sorry that I cannot remember the name and author right now, but it can be found on EBAY for maybe $5 or so .
You two together can do this thing right. C. N.