In developmental processes and outcomes, the individual and the context are inextricably connected throughout the lifespan. As an individual from an unorthodox background, my academic career is full of continuities and discontinuities, as one of the most influential books from my advisor, Jerome Kagan, asserted. In retrospect, my upbringing gave me the cultural, ethnic, minority worldview. From the start my education gave me the opportunity to have essential intellectual tools and eventually become bicultural and critical of our academic field. Consistently and strategically, my scholarly, administrative, and volunteer work led to questioning and pushing boundaries of the dominant academic canon; this was achieved by making critical connections with like-minded scholars and institutions, and working directly at the top of mainstream scholarship, educational institutions, and professional organizations. A contextual developmental analysis of my academic trajectory provides evidence of the constant, powerful dialectic relationship of the individual and the context. It all makes sense now.