Arianna Huffington, CEO of Thrive Global, asked the 2013 graduating class of Smith College to redefine success as a means of surviving in a workplace that is ever-changing and challenging. Members of the Millennial generation, re-entering campuses as faculty members with the mindset of ‘changing the world’, are met with a culture where innovation, dedication and loyalty is rewarded with excessive workloads, unattainable expectations and toxic leadership that has little time for mentorship; all ingredients guaranteed to exacerbate burnout. In this chapter, we propose an approach to academic success and wellbeing based on Huffington’s Third Metric and advocate the element of wonder to cultivate a working environment based on social connection and creativity. Two self-reflective case studies covering cross-disciplinary Communities of Practice and students-as-partners teaching initiatives exemplify how the enactment of the ‘four pillars of success’ has served to prevent ‘millennial burnout’ in an academic context.