Background:
DS2 is one of youngest in class. Socially and emotionally a bit immature. Academically average (but good considering age relative to classmates).
He really has very poor self-esteem. Hates trying new things. Says 'I am rubbish'. Gives up easily.
Not good at sport. His strengths are probably more artistic - drama, possibly music (but hates practising) and isn't really that good relative to peers again.
The whole situation isn't helped by the fact that he has a very talented, academically gifted older brother who has loads of friends and just breezes through life easily 
I need a plan for DH & I to work on to really build DS2's self esteem. I am really worried he is going to become 'typecast' and stuck in his current mindset.
He certainly has talents, but he is never the 'very best' IYSWIM so he always just says 'X is better than me... why bother?'
What can we do differently? I really need some strategies and a plan !