This paper investigates how integrating speculative and friction-based approaches can transform the design of wellbeing-centered information systems from a focus on clarity and efficiency toward a more critical, imaginative, and reflective design practice. Convergent information design often prioritizes legibility, objectivity, and behavioral optimization, reducing wellbeing to static, quantifiable indicators. In contrast, speculative information design invites ambiguity, plural perspectives, and embodied experiences, provoking users to question, reinterpret, and co-construct meanings around personal and collective wellbeing. Drawing on a comprehensive review of literature and case studies, we identify a set of thematic tendencies, including provocation, participatory speculation, and ethical interrogation, that disrupt normative data narratives. We then propose a conceptual framework for speculative information design, articulated through six guiding principles: friction and disruption, openness and ambiguity, plurality and inclusion, embodied engagement, temporal layering, and ethical transparency. These principles serve as a practical rubric for designers seeking to engage users in reflective, situated, and relational explorations of wellbeing. We argue that embracing friction and speculation allows information systems to move beyond informing and persuading toward awakening and co-creation, ultimately reshaping how wellbeing is understood and experienced. Our work aims to offer both theoretical insight and actionable guidance, contributing to more inclusive, empathetic, and future-oriented design practices.