Over the past century, Western societies have developed various theoretical frameworks, training models, and institutional practices for helping professions like social services, healthcare, and psychotherapy. As these helping professions and the Bodhisattva path share the similar aspiration and spirit, many Western Buddhist practitioners have entered these helping professions to become “Professional Bodhisattvas”. However, Buddhist organizations have yet to develop comprehensive institutional support for those individuals, so these pioneer Professional Bodhisattvas have been bridging their Buddhist practices and their vocational pursuits mostly at an individual level. In this paper, I combine the method of semi-structured interviews with Buddhist teachings and relevant social science theories to explore the structural challenges faced by Professional Bodhisattvas among North American Chan Buddhists with a particular focus on Dharma Drum practitioners. Specifically, I discuss from the perspectives of “techniques of the self” and “self-care” to explore how to transform these challenges into future opportunities. A deeper understanding between Buddhist institutions and helping professions could on the one hand, encourage the Sangha to learn limitless approaches to Dharma, and on the other hand, help Western Chan Buddhists use compassion and wisdom to alleviate suffering in appropriate and effective ways.