Don't you think you're contradicting yourself a bit you encourage him to be persistent in fixing problems and never giving up but on the other hand you tell him

Don't you think you're contradicting yourself a bit you encourage him to be persistent in fixing problems and never giving up but on the other hand you tell him to give up and let the school have its way. The hacker mentality doesn't just abruptly stop once we're not dealing with programming issues. Being relentless and constantly pushing to get what you want is a way of life.