A method of supporting self-learning and a system for performing the method are disclosed. The method includes estimating an object of interest of a user in content based on user performance information inputted by the user in response to content situation information and the content being received from a learning module including the content, analyzing the content situation information, determining whether to generate support information for supporting the user to perform the content based on the estimated object of interest and the analyzed content situation information, and generating the support information that allows the user to self-learn the content according to whether to generate the support information, and outputting the support information to the learning module.