This chapter explores the intricacies of attending to people and processes over products and deliverables. Authors detail how intentional care is as much about what to disrupt and exclude—through a description of each of our core programs and initiatives—as it is about what to include and uplift. In this chapter, we draw heavily from our colleague Dr. Jovonne Bickerstaff’s 2017 essay, “We who would build: Re-visioning resistance & theorizing beyond the gaze,” to explore the considerations, missteps, and revelations that guided the African American History, Culture, and Digital Humanities Initiative’s (AADHum) early development and programming. We work to unveil the intensive emotional labor, all too often performed by Black women, required to cultivate dynamic initiatives and generative programming. We detail the multiple program initiatives of AADHum: Reading Groups, Conversation Series, Digital Humanities Incubators, AADHum Scholars, digitization efforts, and our national conference, Intentionally Digital, Intentionally Black. Just as our experiences offer lessons on how to serve as better stewards of Black wholeness—cultivating space for joy, weariness, hope, despair, abundance, mistakes, dreams, and more—it also suggests novel approaches institutions can take to support those charged with shepherding such initiatives into being.