A system and method for assisting with the maintenance of healthy lifestyle habits by generating tailored strategy messages within an expert system and then pushing those messages to the corresponding individual users of the cellular phones or other portable devices. The system and method allows diet and exercise plans to be tailored to individual users based on their preferences and provides consistent and appropriate strategy messages designed to encourage and motivate users toward successfully maintaining healthy lifestyle habits. Users complete initial assessments which detail individual food and physical activity preferences. The system uses the assessments to generate individualized messages that are pushed to user devices through a system incorporating cellular technologies. Tailored messages are pushed from the computer based expert system to user devices at predetermined times each day.