A computer-implemented system and method for flexibly taking actions upon activation of rule-based triggers are provided. A collection of documents is stored in a storage device within a computing environment. An activity of a user performed on a document from the collection is observed. At least one of an application, operation, key word, time, place, project, topic, different document from the collection, and different user is identified. A connection associated with the user is determined to at least one of the application, operation, key word, time, place, project, topic, different document from the collection, and different user based on the observed activity. A rule based on the connection and the observed activity is defined. The rule and a corresponding action are stored as a trigger. Rule satisfaction by at least one of a further activity, event, and stimuli activates the trigger, which causes performance of the corresponding action.