A combined calendar/diary application leverages several input mechanisms to enrich the historical record kept by a user. First, the application classifies events sensed by sensors and software monitors to capture and classify data indicative of events of significance to the user. It then requests additional information from the user to create a diary entry. Second, on the basis of the same event data, it may add the classification data to the diary as indicia of financial, emotional, or other states of the user or environment. Third, the system augments appointment using other data, including user input. Fourth, data is extracted from other sources for direct inclusion in the diary database. For example, contemporaneous news data from an Internet news feed may be added. Fifth, the application may periodically prompt the user for diary entries. Sixth the application may support deliberate diary-entry procedure as is done with current diary applications.