We tested a social-cognitive model of career self-management (CSM; Lent & Brown, 2013) in the context of the multiple role management among a sample of 693 working men. The findings of the current study indicated that (a) conformity to masculine norms is linked to work-family positive spillover both directly and indirectly through multiple role self-efficacy; (b) the hypothesized relations were all significant for the full sample; (c) CSM predictors accounted for a significant amount of variance in working men's work-family positive spillover and job, family, and life satisfaction; and (d) the direct and indirect effects among the variables did not vary across participants' relationship status and ethnic minority status. Taken together, these findings provide strong support for the validity of CSM in explaining the multiple role management and well-being of working men. Implications for research and practice are discussed in relation to working men's work-family enrichment and masculine norms.