Abstract: Disclosed embodiments include systems, computer-implemented methods, and computer-readable media for scheduling work sessions for an entity during a period when the entity has previously performed work. In an illustrative embodiment, a system includes a scheduler configured to access a computer-based calendar system for an entity. The scheduler is also configured to access at least one additional computer-based resource configured to identify times during past calendar intervals at which the entity has interacted with the resource. The scheduler is further configured to identify at least one time period during the past calendar intervals when the entity is in a first state for which interaction with the resource indicates performance of work. The scheduler is also configured to prospectively schedule at least one work session during at least one future calendar interval at a time corresponding with the time period when the entity was in the first state.