The study used qualitative case-study methodology and involved six participant superintendents in semi-structured interviews, two from each of western, Atlantic and northern Canada. The findings revealed work lives significantly impacted personal and family life. Regardless of location or size of school district, all described an all-consuming work life: rampant with political agendas, conflict, public scrutiny, unreasonable expectations, and one where technology has left superintendents more exposed to the whims of the disenfranchised. They were clearly hindered across all selected jurisdictions by troublesome and disruptive elements present in their work role. The evidence is so compelling it calls into question the current system of elected school board governance and forces consideration of how the system can better support school superintendents.