This article describes a summer bridge writing course that engages students who are actively transitioning from high school to college. The summer bridge course curriculum supports students’ meaning-making efforts through a variety of text-based writing activities which helps students begin the process of critical inquiry: extending arguments, poking holes in theories, and putting these theories in conversation with multiple voices from the real world. The writing activities in the program create a common ground for students where they can encounter texts and discover their own voices. Fostering open-endedness in students is a gradual process, and students acquire critical inquiry skills in increments over multiple semesters. The article showcases foundational writing activities that create opportunities for open-ended thinking that will lead to self-discovery.