You can beat out the brattiness out of someone but it's much harder to cure self-hatred. The only way for you to finally manage to be able to get past self hatred is to work hard for something and achieve it.
This is really true.. and to work hard at the same time with self-hatred is the most exhausting and difficult too, especially when you work hard you would find failure before success and every failure lead to another self-hate... Sigh
I mean, you did say you won't let him do anything that he won't regret so....