<p>The last decades have seen the emergence of a new academic conversation on entrepreneurial well-being amongst business ethicists and organisational scholars. In most cases, studies engaging in this line of discourse have linked entrepreneurship to global psychological measures of well-being in order to draw out the difference with other categories of work, typically with an emphasis on the non-financial values that can be gained from the pursuit of entrepreneurial activities. However, the intimate links that exist between entrepreneurship and the good life have only been narrowly drawn. In fact, most previous studies have used and borrowed the theoretical and empirical language of mainstream and quantitatively oriented scholarship to explain the relations between the two—rather than developing the “thicker” language and conceptualisation that can be achieved through hermeneutics and reflexive analysis. In an attempt to address this, we explore and reflect on accounts from 66 transnational entrepreneurs, who share their experiences of entrepreneurial life and well-being whilst living and starting up their companies abroad, in China. Adopting a reflective narrative approach, inspired by the work of Charles Taylor, the paper draws on rich qualitative data from in-depth interviews (totalling 117 h of recordings) to illustrate the moral depth and the historical complexity of transnational entrepreneurs’ motivations and experiences of well-being and to further conceptualise entrepreneurial well-being as a hermeneutic process of self-expression. Our findings and interpretations open an ontological-moral window to new understandings and crucial new directions for advancing scholarship on entrepreneurship, business ethics, and well-being.</p>