With the emergence of an entire generation of technologically infused learners comes a new challenge for educators to combat their desire for technologically enhanced isolation. The impact of social media on self-absorption and the ramifications of excessive screen time are already evident in our current generation of tech-native students. Meanwhile, the need for more empathetic employees who show compassion toward clients, exercise tolerance for co-workers and demonstrate cultural awareness in all aspects of their work is already being prioritised over discipline-specific skills and even STEM expertise by current business leaders. Similarly, the demand for more empathetic creatives is being catalysed by a design industry that now values human-centredness. Empathy brings the human component to user-experience and interface design and is now widely acknowledged as the first step in any design process. As a corollary, the development of empathy as a pedagogical deliverable will not only be necessary for the workplace of the future but for future generations to become fully-functioning members of society. This research explores how an inclusive art and design pedagogy can foster collaborative learner-centred approaches to develop empathy as a key component of emotional intelligence. Our methodology for triggering meaningful experiences and transformational growth harnesses collaborative play as a way to engage learners in stimulating, socially conscious teamwork. By becoming more intentional about designing the future of higher education in order to nurture more empathetic career creatives, we also lay the groundwork in preparation for educating the most technologically advanced, yet potentially socially isolated learners of any generation yet.