Plantar fasciitis (PF) is a common cause of foot pain, affecting millions annually and costing the healthcare system millions of dollars. Identifying the relationship between workplace activities and PF remains challenging due to inaccuracies in self-reported activity data. This pilot study evaluates the feasibility of using a Posture Differentiating Insole (PDI), a smart insole that tracks sitting, standing, and walking, to measure activity durations and assess their correlation with foot pain. Thirty-four participants wore the PDI during their workday for up to five days, with data collected on foot pain and self-reported activity durations. The PDI correctly identified activities 99.3% of the time, revealing an average 24% error in self-reported data. Preliminary analysis suggests that increased standing and walking time may correlate with higher foot pain. This study highlights the potential of the PDI to improve activity tracking accuracy and its application in investigating workplace factors contributing to foot pain, recommending its use in larger studies for more definitive conclusions.