I find myself floundering with this statement from saying "go then'' to letting him know how I don't approve, to saying nothing.
Well what you should say is actually a combination of those. "I care deeply about you and don't want you to go, but I want you to be happy and if you feel that leaving will make you happy then I support your decision." You're telling him you don't approve, but you accept his decision. And it does have to be his decision, you shouldn't tell him to go (unless you're ready to drop the rope).
