This research reports on a three-month project designed to examine subjective driver well-being matched with objective driver behavior. Driving behavior was assessed using SmarTrack (from driver GPS systems) and related to longitudinal (over three time points) self-report questionnaires from drivers (at the beginning of the month for three months). This data provides important information on actual driver behavior, mindfulness and work related factors that may have an implication on driver safety and well-being issues at work. Ultimately this project allows for a data driven decision making and trend analysis of driver actual behavior and psychological (self-report) variable that includes matching of driver behavior with driver psychological and work factors (including mindfulness) over a period of time. This allows for the tracking of changes in order to view trends in driver mindsets, and work related issues, to assess the implication of these on mindfulness and driving outcomes.