Abstract: Career coaching comprising defining a number of employment positions, wherein each employment position comprises a number of required skills. Relationships between the employment positions are modeled, wherein the model maps potential transitions between employment positions according to similarities of required skills. A number of persons who have occupied the employment positions are modeled according to skills, employment history, and job performance. A user provides user data that comprises skills, employment history, and job performance. The user data is compared to the modeled persons, and a number of potential employment opportunities from among the number of employment positions are matched to the user based on similarities between the user and the modeled persons. The potential employment opportunities are then displayed to the user on a graphical user interface.