Abstract: A system and method for helping a user optimize time use during transition times between scheduled activities, includes the steps of maintaining a schedule database including at least first and second consecutive scheduled activities for a first system user with a transition period between the first and second consecutive scheduled activities, during the transition period subsequent to the first activity and prior to commencement of the second activity, detecting at least a first trigger set of circumstances, upon occurrence of the trigger set of circumstances, automatically identifying a secondary activities set including at least first and second secondary activities that may be initiated during the transition period, presenting the secondary activities set to the first user via at least one affordance, receiving selection from the user of at least one of the secondary activities from the activities set and facilitating the selected secondary activity via at least one affordance.