It's rough when a son feels he's a disappointment even to his own Mom. As boys we somehow expect our mothers to be there for us and always protect us and help us. When that doesn't happen it really hurts, no doubt about it - and that hurt stays even when we're older.
But the reality is that it was never up to us to "earn" approval. We deserved that from the start, regardless of what we did or didn't do or achieve. A mother who doesn't or can't act on that basis is just being manipulative and cruel.
Nobody living can ever stop me
As I go walking my freedom highway.
Nobody living can make me turn back:
This land was made for you and me. (Woody Guthrie)