Rabbi Anna Wolfe believes Jewish life should feel creative, welcoming, and deeply alive. She loves gathering people, asking thoughtful questions, and building experiences that bring people closer to one another and to something larger than themselves.

Before rabbinical school, Rabbi Anna built her life in the Chicago theater world. She studied improvisation, is a graduate of The Second City, and wrote and performed her own solo work on Chicago stages. Over time, she felt drawn to work rooted in deeper connection and shared ritual, which led her to Mishkan Chicago, where she first experienced intentional Jewish community and joined their professional team. As Family Program Coordinator and a founding educator of the Mensch Academy, Rabbi Anna designed programming and curriculum that brought inspired, grounded Judaism to children and their families. She is especially attentive to how learning environments shape belonging and strives to create spaces with multiple entry points into Jewish life.

Throughout rabbinical school, Rabbi Anna spent three summers at the Brandeis Collegiate Institute as a Program Fellow and Performing Arts Educator, working with young adults to bring Jewish ritual and the arts into conversation in joyful and transformative ways. She has worked across Hillel settings, congregations, and pluralistic communities, engaging Jews across denominations, generations, and life stages.

Rabbi Anna’s passion for pastoral care deepened through Clinical Pastoral Education at Massachusetts General Hospital, where she provided spiritual care in medical, oncology, psychiatric, and hospice units. Most recently, Rabbi Anna served as the founding Rabbinic Fellow of Base Jamaica Plain through Mem Global, building the program from the ground up, shaping its vision, hosting Shabbat dinners and holiday gatherings, cultivating partnerships, and developing the infrastructure to sustain a thriving young adult community.

Rabbi Anna lives in Washington, DC, with her husband Sam, their two year old Heschel, and their small scrappy dog Evie. She loves a crowded Shabbat table, thinking outside the box, and ending the night with a scoop of ice cream - preferably mint chocolate chip.