This exploratory study aims to understand the antecedent factors (sustainable/entrepreneurial orientations, self-determination motivation, and contextualities) that may influence a future young entrepreneur’s intentions in developing sustainable enterprise practices (SEP). Adopting humanistic values from a service-dominant logic framework, we evaluate how a future young entrepreneur’s mindset can be shaped in adopting sustainable enterprise best practices on ethical and moral altruistic decision-making. Based on the self-determination theory (SDT), we looked at the autonomous and self-regulatory motivation factors as key influencers on the individual decision-making process, and on how he/she weights contextual complexities in deciding to pursue doing good for the wellbeing of the organization and the community or preferring opportunistic self-interested rewarding goals. Combining online surveys and in-depth interviews in Canada and in China, it was found that intrinsic motivation factors influence the development of sustainable entrepreneurial orientations (SO) and sustainable enterprise practices (SEP). Although contextual and cultural factors moderate the effects of intrinsic motivations, one should capitalize on learned behaviors. As suggested through the in-depth interviews with experienced entrepreneurs, future young decision-makers should be expressly taught about ethical, social, and environmental issues to develop SEP intentions and potential future sustainable entrepreneurial behaviors.