A system to assist users with the completion of tasks in a wellness program itinerary. The system assists users in completing tasks by recommending a controlled number of tasks for a user to perform in a next task period. The system determines the number of tasks to recommend by computing a pace that would enable the user to complete all wellness programs in the itinerary within a recommended time period. The system determines which tasks to recommend to the user based on several factors, such as a user state and user environment. The user environment is based on the location of the user, and may include the weather and surrounding landmarks at the location.