When Arthur Cohen launched "New Directions for Community Colleges" ("NDCC") in 1973, the focus was on sharing updates and practical advice for those leading and working in community colleges. At the time, scant attention was given to these institutions as most research centered on 4-year colleges and universities. The context of community colleges matters in how finance and governance occur and in how leaders help their institutions navigate a constantly changing external environment that requires flexibility in meeting workforce needs. Fifty years have passed since the initial issue of "NDCC" was published, and this retrospective draws connections on three topics over time. First, this article reviews how finance and governance evolved, taking note of how the expansion of the sector and the complexity of operations altered operations. Second, a look at career and technical education (CTE) and workforce development occurs. The historical roots of vocational education in community colleges translate to new approaches to developing a skilled workforce to address employer demand. Finally, a review of leadership since the first issue was published shows how ideas of leadership have expanded and help identify new challenges leaders face.