Choosing a career is an integral factor in life fulfillment. It is a complex process that requires an individual’s intention, knowledge, and readiness with the help of proper guidance and counseling. Despite its significance, some individuals feel pressure and difficulty as they face their independence in their career choices. Although one’s interest, perception, and judgment may be influenced by career knowledge, perceived benefits, and culture, this may result in hesitation and uncertainty in their chosen career. These variables are integrated into the Generational Cohort Theory (GCT) and Theory of Planned Behavior (TPB) to discover the significant variables that affect the career decision-making of Filipinos. Self-administered questionnaires were used to collect data and analyzed it by structural equation modeling using IBM SPSS AMOS. It was discovered that perceived benefits (PB) and career knowledge (CK) have a relationship with attitude toward the behavior (ATB), while Culture (C) is directly related to Social Norms (SN). Furthermore, ATB and SN have a significant relationship with behavioral intention (BI), as BI refers to the perception of correct decision (PCD). Through analysis of variance, results show that generational cohorts (GC) have a direct significance with PB and CK.