Hi Beatrix,

It sounded like you were describing my eldest DS who is 5 in July. I too worry about him as he is such a sensitive and highly anxious child, and he too worries about things that a child of his age shouldn't be. I don't know whether it is because he is the eldest he feels more responsibility for his brothers, or if it is just his personality. My DH is was diagnosed with panic attacks and suffers anxiety so I worry greatly.
To give you an examply the other day he started crying because his baby brother (who is 1) was looking at Lewis (DS2) but didn't look at him. That made him burst into tears. At swimming lessons if the teacher tells him he is doing something wrong in a firm manner he starts crying gets out of the pool and refuses to do rest of the lesson. He also gets distracted easily and always needs to know what is going on, listens in on adult conversations, has to be around adults most of the time incase he misses out on something.

Now to answer your questions I too am not sure if I'm parenting correctly, we try to give him a lot of praise, and acknowledge even the smallest of achievements as he seems to need the reassurance that he is doing well. Lots and lots of encouragement, and like you are doing lots of talking about how he feels, especially if something has been good or made him happy I really try and focus on that rather than any of his perceived negative things. e.g the other morning he was worried that one of his new kinder buddies mightn't want to play firefighters with him, I said to him well you can ask him to play with you, his answer, what if he says no? I honestly don't think he is ever going to be that confident kid that is the extovert of the group but I too just want him to believe in himself.
I think when he starts school I will talk with his teachers and get their assistance on how best to encourage him.

Good luck, and I wiill watch this thread in the hope that some other wise women may have some good advice.