Career counseling, from the outside, appears to be little more than an established network of people who maintain binders of job postings and help people with tips about interviews. At the high school level, they are seen as the people who carry binders of college materials and help students fill out applications and write essays. These misconceptions do a significant injustice to the field of career guidance, for they miss the entire point of what it is that the career counselor does. Helping a person discover what it is that they want to define their life with and helping them achieve that goal requires the analytical skills of a psychologist, the patience of a priest and the business eye of a CEO. At the core of career guidance are schools of philosophy and thought which center upon the work of scholars the like of John Holland and Donald and Ann Roe. It is the purpose of this paper to explore these two theories of career guidance and to find their common and uncommon ground.