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Lifestyle modification is a key facet of the prevention and management of chronic diseases. Mobile devices that people already carry provide a promising platform for facilitating these lifestyle changes. This paper describes key lessons learned from the development and evaluation of two mobile systems for encouraging physical activity. We argue that by supporting persistent cognitive activation of health goals, encouraging an extensive range of relevant healthy behaviors, focusing on long-term patterns of activity, and facilitating social support as an optional but not primary motivator, systems can be developed that effectively motivate behavior change and provide support when and where people make decisions that affect their health.