Mercury in a tight conjunction with saturn can indicate this 'giving up' trying, too soon. But the thing is that he will probably keep trying, but he just needs a break first. He may quit and walk away in defeat. But after a little while he will come back with a stronger resolve.
I would try and not make a big deal about it when he fails and runs off. just let it go and wait a bit. He will probably come back even more determined. ALSO, POSITIVE REENFORCEMENT is VITAL with Mercury/Saturn conjunctions. When he does succeed he will be thrilled if you give him some positive recognition.
The Moon square Asc may give him a fluctuating 'sense of self' and it is important for him to learn to stabilize that. if the family 'meme' is that he is a defeatist or gives up quickly, then it might stick to him like glue. As a loving Auntie, you might help him create a new meme. He preservers, never gives up, against all odds, etc etc...