What I mean is he has traits that are similar to people in our family who are less than successful. The prefaced Uncle, my mother's eldest brother, is in his fifties and is still relying heavily upon his mother for financial and emotional support. He has had many life struggles and his solution has never been to learn from them. He falls back to his mother, or has to be bailed out by other family members.
Our father has never held a job longer than five years, save his service to the marine corp. He is very rpoud of his service, and has every right to be, but I have never really seen much of a 'marine' in him growing up. Our father let our mother support the family, he did what he wanted, and when he was holding a job would complain that we didn't appreciate his 'sacrifice' enough. (The sacrifice being that he was working.) He now lives in a small apartment and draws government help and complains about it.
The traits my brother shares with these two men are not related to work ethic. My brother is a hard worker. He has strong principles. He desires to be more. He shares similar opinions as they do, which have little bearing on anything I think. The main thing is my father is very big into sports, especially NASCAR, and knows everything there is to know about it. My uncle knows everything about Star Wars and Godzilla. My uncle did not go to college or vocational school; my Dad attended but did not complete (he went to Vietnam.) The mistakes these men have made they do not seem to have learned much from them. There is always someone else to blame.
My brother knows a whole lot about seemingly useless things (Star Wars, Star Trek, Halo) and has no desire to attend any sort of higher education beyond highschool. Which, to me, is fine. He'll go to school when, and if, he's ready. My mother has always encouraged education, though. School has always been stressed; learning (book learning) has always been stressed. My brother also spends a lot of time playing video games. He takes his XBox almost everywhere with expectation that he will be able to use it.
That, I think, is what may be triggering my mother to fear he may not get very far. I can see the similarities between my brother and these people, but I can see how he isn't going in their direction. He's just, as you've said, trying and erring. Just not the way she wants him to. I suppose while my brother may be living for the struggle, she wants him to not have to?