Alain de Botton's Philosophy of Success
Alain de Botton is a Brit who founded The School of Life to promote learning about the things that we actually care about in life (work, family, travel, etc.) rather than the abstract concepts we tend to study in school. He is also the author of the new book The Pleasures and Sorrows of Life, an insightful and humane exploration of the joys and perils of working life. He has a great knack for articulating the fears and anxieties that we all feel as we start to think about our "careers" and society's definition of "success."
Catch a glimpse of what he's all about in this interesting TED talk: