Critical events in Leonard Matlovich’s life depict a reluctant activist for lesbian, gay, bisexual, transgender/gender diverse, and queer+ (LGBTQ+) equality. He served in the US military and subsequently came to personify the broad social challenges to the military’s homophobic culture and recruitment practices. Matlovich’s experience of a series of life metamorphoses made a difference beyond the individual. His example inspired multitudes of other concerned citizens in how to undertake their metamorphoses to challenge institutionalized homophobia. Breakthrough learning experiences in Matlovich’s life are presented to explore and refine aspects of transformative learning theory by applying Jane Martin’s metamorphosis model. The learning nexus between individuals and society is shown to be a dynamic interaction where both aspects of Matlovich’s story and his influence are explored in the context of today’s LGBTQ+ equality struggles. The article shows the conducive personal and societal conditions that enabled his various metamorphoses as whole-of-individual identity and sociocultural crossings toward transformational change. Additionally, the implications of Martin’s educational metamorphosis are discussed. Adult educators are encouraged to emphasize learning located in the learner’s life circumstances, exemplary case studies to inspire cultural crossings against injustice, and transformations as being about grasping in situ learning opportunities in the cross-influence between the whole person and their socio-historical context. Matlovich’s experiences show how relevant dimensions of Martin’s theoretical approach, coupled with support from allies, can contribute to personal agency and can build a groundswell of learning needed to support activism for social justice movements.