The present invention provides a method and system for supporting serendipity and pseudo-serendipity. A collection of profiles are generated to model the user's worldview. A collection of shadow profiles are generated to model divergent knowledge based on the user's profiles and external information or knowledge sources. A collection of items are retrieved from the profiles and used to perform a deliberate search for laterality. The initial and lateral items are merged into a search string. The search string is used to perform a search or wandering process that is aware of potential serendipitous stimuli in an information space. The discovered, unexpected, unsought, unforeseen stimuli are intended to be subsequently presented to the user.