Career researchers have focused on the mechanisms related to career progression. Although less studied, situations in which traumatic life events necessitate a discontinuous career transition are becoming increasingly prevalent. Employing a multiple case study method, we offer a deeper understanding of such transitions by studying an extreme case: soldiers and Marines disabled by wartime combat. Our study highlights obstacles to future employment that are counterintuitive and stem from the discontinuous and traumatic nature of job loss. Effective management of this type of transitioning appears to stem from efforts positioned to formulate a coherent narrative of the traumatic experience and thus to reconstruct foundational assumptions about the world, humanity, and self. These foundational assumptions form the basis for enacting future-orientated career strategies, such that progress toward establishing a new career path is greatest for those who can orientate themselves away from the past (trauma), away from the present (obstacles to a new career), and toward an envisioned future career positioned to confer meaning and purpose through work.