Purpose: This study was a pilot of a brief psychological capital (PsyCap) intervention with a sample of transition age youth with disabilities (N = 24) in a school setting. Substantial evidence supports the relationship between PsyCap and employment outcomes. Transition age youth with disabilities are an important target for pre-employment counseling interventions due to a lack of parity in postsecondary outcomes. Researchers have successfully boosted PsyCap in adult samples using brief interventions. Methods: PsyCap and vocational outcome expectancy (VOE) were compared in a repeated measures design. Results: PsyCap and VOE, and PsyCap and school performance were significantly correlated in our sample, but no differences were observed in PsyCap or VOE postintervention. Conclusion: As the first known effort to develop a PsyCap driven pre-employment intervention for transition age youth with disabilities, our experience and findings provide several implications for practice and future research. Aspects of the intervention to be modified for future efforts are presented.