Asking the plans after college can be stressful for undergraduates, especially for firstborns who are expected to fulfill significant roles in a family. Priorities play a significant role in their decision-making, but it is still unclear how firstborns from millennials and generation z prioritize their plans and dreams after graduating from college. A descriptive quantitative and survey questionnaire were executed, and a comparative analysis of post-graduation priorities among the selected sixty Filipino firstborns, thirty each from millennials and generation z cohorts was conducted. It reveals the perceived expectations and responsibilities of firstborns are embedded in the traditional Filipino family such as household work, sibling duties, and family obligation, however, it shows that they were still able to have their personal autonomy. The fulfillment of their plans and dreams varied as the majority of the millennials fulfilled them already, while generation z are still in the process of fulfilling them. Generational gaps are manifested too, as the firstborn millennials immediately prioritized employment to provide for their family, while there are generation z took a rest, and pursued postgraduate studies. Still, they are similar by prioritizing their personal development encompassing self-growth, work-life balance, career growth and financial stability.