Girl Scouts aims to foster leadership by encouraging girls to discover themselves, make connections, and take action to make the world better. This paper chronicles the five-year journey of eight professional mothers of color who sought to provide their daughters with a space to 'think and live differently' as Girl Scouts and young women of color in (post)colonial Hawai'i. Through questionnaires and a semi-structured focus group interview, mothers reflect on their original intentions to create a 'safe space' for their daughters to engage with the politics of gender, race, and class and to rethink, review, and rework their identities. Mothers' reflections reveal success in creating safe spaces for the critical analysis of gender, but comparatively less success in critical analyses of race and class--a phenomenon that the mothers suggest may have been complicated by (1) the enduring myth of Hawai'i as a multicultural paradise, (2) Girl Scouts' assimilationist history, and (3) the mothers' own relatively privileged positions.