Technologies increasingly afford new possibilities as people use readily-accessible digital devices to access vast information repositories on the web, create calendar reminders synced with others' schedules, or store and seamlessly refer to personal reference materials in the form of photos, notes, videos, or recordings. Each decision about how and when to use these digital devices stands to influence people's goals, including enhancing life satisfaction, obtaining knowledge, or a host of other outcomes. Yet, given the constant evolution of new media, people tend to know little about the ways in which collaboration with new digital technologies reshapes basic cognitive and communicative processes. Building on frameworks of metacognition, this conversation centers around the cognitive skills a person must obtain to take control of their media use while pursuing their goals. This working group will discuss research in the media effects tradition that is relevant to understanding consequences of technology mediation linked to peoples' decisions about media use. This group will then contemplate future research directions in understanding and predicting the skilled use of media.