In 1918, the author's great great aunt, Sophie Judd Cooke founded a small progressive school in Honolulu. Her brother Henry named it Hanahau'oli School, which means joyful work school. In this essay the author's mother, Linda Summers Strong and the author reflect on the impact of Hanahau'oli School's Deweyan approach to education on the development of the family's culture. The author and her mother start with memories of the author's grandmother, Catherine "Cappy" Cooke Summers, who attended Hanahau'oli School in the 1920s. Then they recount their own experiences at the school, which were remembered over a series of dialogues and inquiries that they engaged in with one another over the past couple of months. Finally, they share observations of the author's daughter, Catherine "Cappy" Kala'iopua Makaiau, who is currently attending Hanahau'oli School as a junior kindergartner. At the end of the essay, the author and her mom comment on the special role that women played in progressive era education reforms, including the ways in which the women in their family have integrated a Deweyan approach to teaching and learning into their family culture. [This essay was written with Linda Summers Strong.]