Many individuals wish to change, but struggle to act. The field of positive psychology has advanced the study of well-being, identifying interventions and measurements to enhance the experience of positive emotion and human flourishing. However, identifying pathways to initiate and sustain engagement with these resources remains a critical need for individuals and communities to implement the science of well-being effectively. The following exploratory study examines the user experience of Peloton, an at-home exercise bike that live streams class content, as an opportunity to identify the pathways that initiate and sustain engagement in positive behavior change. A self-report survey of 104 Peloton users is analyzed using Grounded Theory along with a literature review of positive psychology, and performance psychology. Through the analysis, the PERMA well-being framework (Seligman, 2011) and hope (Snyder, 1994) emerge as key theories to facilitate pathways to initiate and sustain users in activity that enhances well-being. A framework and discussion for future directions is proposed emphasizing convenience and pathways of synchronous and asynchronous agency and connection.