Background: Happiness and life satisfaction are well-known indicators. However, there has been little contribution by the scientific community on the positive career attitudes of master students and graduates. In an effort to provide deeper empirical understanding, the relationships between positive career attitudes, health satisfaction, financial situation and happiness and life satisfaction among master students and graduates were analyzed. Method: A link of online questionnaire was sent by mail to all students which independently of their social economic status obtained a financial aid from the government of Luxembourg, and to all master graduates (ex-students) who have been finished with their courses for one year. The data was analyzed using bivariate tests, correlation and multiple linear regression models. Result: 455 voluntary postgraduate/master students vs. 144 graduates participated. Students were younger than the graduates (mean age 26 vs. 29 years). Majority was female and had Luxembourgish nationality. Most graduates had a job and lived with their parents. Luxembourg natives were happier, and those who were living with their parents showed higher life satisfaction. For both samples, self-rated health satisfaction was positively associated with happiness and life satisfaction. For the students, the higher career adaptability and career optimism are, the better the happiness and life satisfaction will be. The higher the perception of the household financial situation is, the better the happiness will be. For graduates, the higher career optimism contributed to the better happiness. Conclusion: Happiness and life satisfaction of master students and graduates were affected, related to socioeconomic and perceived health difficulties, and career attitudes. Those indicators could be used routinely to monitor the situation of young people over time and their needs in terms of adaptability and optimism capabilities, which should be appropriately treated. These findings may help with the development of university and post university interventions aimed at improving happiness and life satisfaction among postgraduate students and ex-students.