The college transition is a multifaceted experience. Navigating the unfamiliar terrain of college allows for tremendous growth and self‐discovery while simultaneously evoking fear and uncertainty as students encounter new struggles. How students come to make sense of their transition experiences, especially moments of struggle, informs how they come to define who they are, who they can become, and where they belong. Robust psychological investigation has advanced three motivations for making sense of struggle: the need to understand, the need for self‐integrity, and the need to belong. Scholars target these motivations to design educational interventions and improve outcomes for students from marginalized backgrounds. What is missing is an exploration of how the uncertainty and marginalization arising from negotiating multiple social worlds can incite paradoxical expectations, messages, and cues that shape these three motivations for meaning‐making. In this paper, we aim to nuance these three motivations by attending to paradoxes. Unearthing the paradoxes lurking within each motivation advances a better understanding of what it means to make meaning from the margins and, consequently, offers new directions and possibilities for psychological research.