Novel media experiences are currently witnessing a shift towards personal data leverage which is helping produce highly customised content that is relevant and relatable to the audiences. But while personal data affords many capabilities for media service enhancement, it simultaneously introduces a number of socio-technical challenges into the scheme. Concepts such as data legibility, negotiability and agency could be useful in addressing some of these challenges. Nevertheless, the contextualisation of these principles within the scope of media and exploration of design measures within this space remains an active challenge. This workshop aims to explore this space by bringing together media enthusiasts, designers and researchers in order to help clarify these contextualised definitions and apply them by looking into practical design responses to these challenges.