This article focuses on the construct of linguistic risk-taking and outlines a new pedagogical initiative implemented at a Canadian bilingual postsecondary institution. The Linguistic Risk-Taking Initiative aims at encouraging language learners to target specific challenges and seek opportunities to practice their second official language (French or English) in authentic contexts beyond the language learning classroom. Using the lens of participatory action research, the article reports on how a Linguistic Risk-Taking Passport is used to support language learners' autonomous language practice in combination with metacognitive awareness activities and goal setting. A teacher's reflections and surveys with 296 student participants over five semesters indicate that linguistic risk-taking offers promise both in terms of innovative and engaging pedagogical practices and in terms of language teaching research.