This research study aimed to bring out the various perspectives of student affairs practitioners whose contemporary student affairs administration evolved from a simplistic outlook as surrogate parents or disciplinarians to more complex and dynamic student affairs administration to truly meet the evolving needs of students. Responses were derived from 17 informants selected through purposive sampling and who composed either the focus group or in-depth interviewees. Research questions revolved around the past and present experiences of student affairs practitioners, their coping mechanisms with the challenges of the practice, and their insights from their experiences. Past and present experiences came out with the following themes: job assignment, training and exposure, administrative support, records and documentation and academic personnel support as their very dilemma. Specifically, problems of the informants included lack of preparation and formal training for the job; no documents for them to start with; no administrative support in terms of decision making, appropriate recognition and no budget for operations. Remarkably, student affairs practitioners coped with the challenges by their proper attitude like considering their job as a mission and being creative and dynamic in addressing the needs of Millennial or Generation Z. Insights of the participants included the need for empowerment for both students and student affairs, anchoring student affairs practices with the VisionMission-Goals of the institution and that student affairs leadership must take to heart that practices evolve as students evolve too.