The present disclosure generally relates to systems and methods for generating data representative of an individual's insurance risk based on actual driving behaviors and driving environment. The systems and methods may include collecting data from personal electronic device sensors, vehicle sensors, driver inputs, environment sensors and interactions of the vehicle, the driver and the environment. The systems and methods may further include analyzing the data to generate data representative of an individual insurance risk. The systems and methods may further include presenting the data representative of the individual insurance risk to an individual.