Director of Public Relations at the District of Columbia Housing Finance Agency, Yolanda McCutchen, discusses her family’s roots in rural South Carolina and the aspirations that lead her to eventually work in Washington D.C. Beginning, first, by explaining her enjoyment of daily walks on the Wilson Bridge Trail and gardening at her home, Yolanda details the ways Covid19 has necessitated her making adjustments to her daily routine. Regaling memories from her childhood, as the youngest of many siblings, Yolanda describes the trusted relationship she formed with her grandmother as well as her family’s work ethic and unflappable interpersonal skills. Having extended family in both D.C. and New York City, Yolanda often left her rural hometown to visit the city. In her young adulthood, though describing her family’s connection to South Carolina State University, Yolanda describes the initial emotional strain of leaving home and her family to pursue a college education at Hampton University. After persevering through a difficult first year, Yolanda is serendipitously introduced to the son of a family friend. Acting as her “parents away from home,” this relationship enabled Yolanda to visit and receive support from her family while she pursued further education and expanded her professional experience. This oral history interview was conducted under a grant from the Humanities Council of Washington, DC to the Ward 8 Woods Conservancy.