There is a stellar upsurge in the number of persons pursuing a master’s level of education as well as the institutions offering it in the current generation. Nevertheless, an explicit theoretical and empirical implication of how the tutelages, at this level, shape the well-being of learners—such that it could help individuals overcome career decision-making difficulties remains to be elucidated. The present study addressed two major objectives. Firstly, we investigated the well-being of master’s degree students along with career decision-making difficulties in India. Secondly, apart from exploring the possible influence of nationality of the respondents on career decision difficulty, the study expanded the literature on career decision-making difficulties to under-researched populations in developing countries. Through a cross-sectional research design, we recruited a sample of 136 master’s degree respondents. The result reveals that while the composite well-being resources significantly influenced Career Decision Difficulties, the nationality of respondents appeared not as a germane factor in this context. Following the evaluation of the direct effect of individual well-being resources; Self-acceptance and Personal growth proved to have a statistically significant effect on career decision-making difficulties. Also, among the constituents of career decision-making difficulties studied, lack of readiness appears to be the major concern among the respondents. The findings expand the literature on cognitive, vocational, and organization science vis-a-vis career decision-making difficulties and provide useful insights for educational institutions and practitioners. © 2021 The Author(s). This open access article is distributed under a Creative Commons Attribution (CC-BY) 4.0 license.