The issue of multiple jobs holding not a new phenomenon as it has arisen since many years ago. It becomes a trend especially among Generation Y in Malaysia to do more than one job in order to have better life. This becomes a trend as the statistics showed that Malaysia’s millennial or Gen Y experiencing financial stress at early life. A study was conducted showed that most of millennial not satisfied with their income and job situation. With the new initiatives of TN50, most of the feedback also mention that they want more flexible working conditions for example permanent job that allow them to work from home in which could enable them to have second or freelance career. Hence, this study aims to identify the determinants of multiple jobs holding either on monetary or non-monetary reasons among generation Y that living and working in Kuala Lumpur and Selangor by using online questionnaire. The difference of multiple jobs holding in term of gender also is examined. The method that being used in this study is Pearson’s Correlation, multiple regression and Independent sample t-Test. The result shows that there is weak positive relationship between monetary and non-monetary reasons with multiple jobs holding and there is no significant different of multiple jobs holding by gender. This is important as the increasing of complexity and diversity in financial product along with the issue of economic stability, the millennial are the group that more likely need to face financial risk than previous generation, and hence government should play active role in these matters.