This College of the Atlantic (COA) story provides some answers to the questions about how democratic systems of governance in a small, experimental college have shaped the students and institutional decision making. Born during the turmoil of the 1960s, COA went on to survive 50 years with its progressive roots intact. Part memoir (I was a faculty member at COA in the 1990s), part study involving COA alums, and part a footprint in the sands of the history of progressive higher education, this story provides inspiration and analysis of the "perpetual dream" in education that drives experimentation (Grant and Riesman 1978). Higher education emerged as a culprit in the 2024 election, which divided along education lines (Brooks 2024). Was there ever a time that demanded a rethinking of higher education more than now?