During the past ten years, succession planning and managing executive transitions have emerged as important issues in the nonprofit sector. Demographers and economists have speculated for years about the potential effects of the retirement of baby boomers. The time has finally arrived: the oldest of the baby boomers are now eligible for retirement. The question that remains is how this trend will affect the nonprofit sector and the communities they serve. This study examines the issues of turnover and succession planning at the executive level, along with career development among young nonprofit professionals in Charlotte, North Carolina. Not only do the findings suggest that the community may very well see a crisis in leadership, but they also illustrate a growing disconnect between executive leaders and young professionals in nonprofit organizations. In addition to struggling with the realities of working in the nonprofit sector (limited benefits, challenging workloads), most young professionals reported that they felt undervalued by older managers and staff, and very few aspire to the position of executive director. Taken together, these findings have important implications for the local community and the broader nonprofit sector.