Show him that you can fail and mess up also, lead by example, with my dyslexic 9 yo DS I get words and sentances wrong on purpose to show him there is nothing wrong with getting it wrong, even at my age. We also read stuff he likes, like Sky Sports news, the sports section of the newspaper, endless Dorling Kindersly books in Star Wars.
Are the school books any good? Our school recently got some proper boys books, instead of all that Kipper and Biff stuff. DS is reading one now about a spy and a time machine. Also sometimes just a sentance or two will do, not 30 mins of banging away forcing him to do it, which helps no one.
Also sometimes they like to do stuff on their own without us Mother's hovering over them! Drop him off a Cubs, a climbing wall, swimming party, mates house, just leave him to it, they feel less self concious sometimes when we are not there. DS went to a skate park with his scooter for the first time without me (with some other Mums), I was worried and nervous! He came back knackered, filthy, a couple of bruises and had loved it! You should make a mess, burn tea, fall off your bike to show him there is no problem to not doing it pefectly all the time! Sometimes I think you just need to back off, even the good praise and not be overly 'oh deary me' when things go wrong. My DS gets so frustrated sometimes, he freaks, but he's nearly 10 and has learned that it sometimes goes pear shaped, Rooney misses penalities sometimes!