The purpose of this research was to inform best practices for creating institutional self-assessments for measuring financial sustainability. The project took place at a small tuition-dependent college that will be referred to as ABC College. Participants and data collected in Cycle 1 of this action research project consisted of a series of seven interviews with administrators at ABC. The purpose of the interviews was to learn more about the Pals Program, an initiative aimed at increasing student retention from freshman to sophomore year where staff volunteered to mentor (as "Pals") to groups of students. All interviewees were either administrators of the program or volunteer mentors in the program. The findings from the first cycle of research informed the action step: to create a meaningful and recurring financial sustainability assessment for the Pals Program for the VP for Enrollment and Dean of Students, the two key collaborators who were charged with overseeing the program. The action steps consisted of examining existing data needed for the assessment, creating a volunteer workbook to track and collect more data, drafting an assessment including institutional data with publicly available data sets, and finally evaluating the assessment with ABC collaborators and external stakeholders. These action steps were designed, implemented, and evaluated in Cycle 2 in order to have a dashboard of information that displayed overall programmatic progress towards the goal of retaining students as well as framing the program into the broader financial context of the organization. Findings suggested that colleges can create financial sustainability assessments by examining the context of the assessment to define its scope, by allocating resources to the assessment, and by fostering an organizational culture supportive of change and tolerant of risk. Recommendations to ABC include a call to reestablish their pre-COVID culture of experimentation and enthusiasm for growth, as well as to consider data infrastructure enhancements and investments to be able to better measure the full student experience. The findings of this research might be of use to college or university finance and enrollment leaders. [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://www.proquest.com.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]