We normally think that once we become successful, we "have made it," and that success in itself takes care of the problems of life: we feel secure in who we are, people admire us for our accomplishments, we make an impact on the world. Rodriguez reminds us that success is, in itself, not successful--it is how we use our accomplishments to understand our world and our lives that constitutes our real success. A bi-cultural identity always necessitates negotiation between both cultures that compose the individual; one needs to give meaning to the other to forge an integrated self. Rodriguez's difficulty is accomplishing that: enabling his success in the Anglo world to give meaning to rather than alienate him from the other parts of his identity and what might constitute success there, that Hispanic part of his identity that connects him to his family and history.
I think this refers to when Rodriguez reminisces about the deep impact education had on his life. He always made good grades, but he denied his past. It was only through education that he was able to understand his past. Education brought him to this understanding, but it also caused a wider gulf to grow between him and his parents because he saw his teachers as role models rather than his parents.