Having aspirations and goals to strive for provides a sense of purpose and motivation, which can greatly contribute to one’s overall happiness and satisfaction. However, there is a lack of in-depth understanding of how individual aspirations interact with societal expectations and constructs, potentially resulting in feelings of anxiety and frustration. This collaborative cross-cultural autoethnographic study examines the interplay between the individual and the sociocultural, with a special interest in Eastern and Western lenses of well-being. Based on data from autoethnographic narratives, fieldnotes, and reflection with critical friends, this study aims to provide an insider’s account of an international doctoral candidate’s experiential journey of aspiration/s, and transformation/s, to meet societal expectation/s. Through analysis of these experiences, we propose that societal constructs should be given more attention in discussions of well-being, to envision a more equitable educational environment in which aspiration/s and transformation/s can be better recognized and appreciated.