A system and method for learning and predicting personalized risk associated with a journey for a user are presented. Contextual data may be gathered and analyzed from a plurality of data sources relating to a journey of a user. A risk associated with the journey may be learned for the user according to the contextual data. One or more risk models may be generated according to the learned risks. One or more potential risks associated with a subsequent journey may be predicted using the one or more risk models.