An oft-quoted African proverb says that it takes a village to raise a child. Winchester Thurston—driven by its commitment to progressive education—embodies a parallel belief: that it takes a whole school community to nurture learners into active, engaged citizens who challenge inequities, address real problems, and make an impact on their school and their city. Two new members of the WT community—Director of Equity, Inclusion, and Wellness Jessica Walton (R), and Amy McTighe, Ph.D., Director of Student Support Services (L)—are experts in areas essential to creating the change that progressive education allows. As the 2021–2022 academic year unfurled, Thistletalk invited Walton and McTighe to a conversation about those areas; how their work helps students feel healthy, safe, and supported; and how their respective domains overlap and impact the entire WT community.