Many community-based organizations use digital storytelling as a strategy for community development, aiming to cultivate increased social agency and community leadership in participants through practices of storytelling and media production. Reporting on a three-year study of digital storytelling with newcomer women in Toronto, and drawing on Winnicott’s theories of creative living, this paper suggests that the successes of such social justice projects might be better understood if we consider the ways in which the capacity for social engagement is cultivated through experiences of emotional risk-taking and psychological creativity, and made possible by the holding environment offered to participants.