A system and method for analyzing wearable sensor data in reconciliation with calendar entry data. A computer processor is coupled to a user configurable calendar system and a user wearable device. The processor detects one or more user activity events from one or more electronic wearable devices associated with the user and detects one or more user calendar events from a user configurable calendar system. The processor is configured to determine a course of action to be taken by the user based upon the one or more calendar events and the detected one or more user events.