One embodiment of the present invention provides a system for automatically reporting progress in completing objectives and goals of a plan. During operation, the system receives data indicating user selection and/or configuration of a plan with one or more goals, objectives, and/or milestones. The system obtains data generated by sensors in a sensing device and/or a mobile device. The sensors generate physiological data or data from detecting activity or environment associated with the user. Next, the system analyzes the data to determine whether the user has completed an objective, milestone, or goal of the plan. If the system determines that the user has completed an objective, milestone, or goal of the plan, the system pushes an alert to the mobile device indicating that the user has completed the objective, milestone, or goal.