Although study abroad is viewed in the United States as sine qua non, the study abroad experience is not a panacea to achieve distinguished foreign language speaking proficiency. This study attempts to uncover how persistence, study abroad, motivation, and learner autonomy play into the pursuit of distinguished speaking proficiency. Using the theoretical framework of complexity theory and phenomenological design, the study utilizes interviews of four educators at an institute in the western United States as the primary instrument of data collection. This study investigates the roadmaps which successful foreign language educators have utilized to achieve distinguished speaking proficiency through interviews and documentary research. Data analysis of interviews with the participants reveals distinguished speaking proficiency was a highly personal pursuit, characterized by different motivations based on the choice of a foreign language, engagement in the target culture, grit, and time. Overall, the participants were highly self-efficacious learners, many married to foreign-speaking spouses, who spent extended periods in the foreign culture and community. The study provides possible roadmaps for students and for educators who wish to achieve near-native speaking proficiency in a foreign language.