I facilitated and visually captured three conversations centered on humanitarian and environmental challenges through the lens of philosopher Roman Krznaric’s longtermism. The conversations were with improvisational theater teacher and professor Barb Tint, meteorologist Eric Holthaus, public health expert Michael Adekunle Charles, youth leader Dainalyn Swaby, social-ecological systems scholar Rhoda Malgas, and Roman Krznaric himself. Held in the early months of the pandemic, these dialogues aimed to foster connection and collective imagination at a time of deep uncertainty by inviting participants to envision futures rooted in care, justice, and long-term thinking.