Well, to start, I'm hardly wealthy - mostly (and finally) financially stable, which is my goal, but still facing mountains of debt between students loans and our mortgage. And the company where I currently work, and plan to stay for quite a while, doesn't require a college degree for any of its positions. I understand this is unusual for a so-called "white collar" job, but there are tons of jobs I could have access to without having gotten straight As in high school or attending an Ivy League college. The early success I experienced hasn't brought me any sustained meaning or joy. But your question does bring to light a frustrating tension -- how do I set my daughter up for success while also challenging traditional notions of success?