This article represents a journey into education undertaken by two Latino educators from diverse generations. Through the content of the narratives, we emphasize that success was achieved within the presence of oppression. The narratives reveal significant constructs that shaped our journey. For the first author, Pablo, role models, pivotal moments, and resistance had a powerful influence in his journey. Family lessons and self-sacrifice were key to the success of the second author, Yolanda. These constructs contributed to both of our resilience and success. We suggest that the aforementioned constructs have significant implications for Latino youth in the educational system.