This study extends existing research on psychology of working theory by assessing components of the model among two community samples (N = 364) of high school youth. We examined structural models linking student perceptions of external barriers to higher education to three indices of adaptive career progress, work volition, career adaptability, and school motivation. We also assessed the roles of student perceptions of proactive personality, critical motivation, and teacher social support as moderators of perceived external barriers for the three career progress indices. The findings reveal main effects, rather than moderating contributions for critical motivation and proactive personality, with only teacher support being a significant moderator for career adaptability and work volition. The moderating effect was inconsistent with theoretical expectations, however. The results are discussed with attention to further research and applicability for vocational intervention.