Students transitioning from high school to college are met with many challenges beyond academics including social acclimation, campus culture integration, and holistic wellness. Researchers agree that a successful and purposeful transition for incoming college students requires involvement and engagement with peers to help students adapt and increase their likelihood to graduate (Astin, 1999; Kuh, 2009; Tinto, 1998). This autobiographical narrative inquiry reflects on past experiences in assessing the needs of transitioning students at the University of South Florida and developing a purposeful programming model to support students. I aim to help the reader understand my personal commitment to these programs through a reflection of self and guide the reader through critical decision points in the growth of the Academic and Cultural Engagement program (ACE), a summer transition program that originated for out-of-state and international freshmen. Concluding thoughts focus on variables that impact program development, defining strategic priorities and relationships, balancing inconsistencies in authority and accountability, and the power of pivoting. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]