With political polarization, geopolitical conflicts, and shifting regulatory landscapes upending the status quo, philanthropy is clearly at a fork in the road. How can foundations, individual donors, and impact-driven organizations remain effective when policies, funding environments, and democratic norms are in a state of flux, and even chaos? Double down or scale back—or somewhere in between? In this candid conversation, we will explore how funders can adapt to a rapidly changing situation, support democratic institutions and civic engagement, and navigate new restrictions on funding and advocacy, grappling with both the risks and opportunities presented in this unique moment.