A career management system facilitates career management an online environment. The career management system introduces gaming elements to career management in order to make career-related tasks more enjoyable to participants. In one embodiment, a computer-based career management system generates a virtual career path customized based on a particular player's current career position and career goals. The virtual career path includes one or more challenges for the player to complete. The career management system tracks completion of the one or more challenges in the online environment and provides rewards and incentives as the player progresses.