Contemporary careers (CCs), characterized as being person-centered rather than organization-centered, have garnered significant theoretical attention in recent decades. However, research on CCs often lacks an exploration of the mechanisms that underlie the dynamic process of career development over time. Drawing from sensemaking theory, we integrate the literature to examine how individuals with a CC orientation make sense of their evolving careers. We suggest attitudinal and behavioral mediators as the core elements of the career sensemaking process and outline a process model that captures these dynamic career processes. Our findings offer insights for individual career actors as well as organizations seeking to accommodate their employees’ CC orientations throughout their tenure. We also guide future scholarly work surrounding CCs by outlining research questions that can advance our understanding of CCs within organizational contexts.