Academics generally present the acquisition of academic proficiency as a learning process dedicated to specializing in an area of expertise. During their careers, scholars are expected to develop their academic profile by progressively building on their knowledge and their professional networks in their chosen specialty. However, prompted by reflections on their own experiences and by exploratory conversations with colleagues, the authors find that this portrayal of streamlined professionalization in academia hides playful deviations from the primary path into new intellectual and social spaces. They introduce the notion of a Spielwiese [literally: playing meadow] to describe these spaces, how they emerge, and how academics engage with them. The authors conclude by laying the groundwork for a typology and outline a research agenda for Spielwiesen in academia, whose utilizers should consider national career systems, disciplinary contexts, and different cohorts and career stages.