In higher education, the field of student affairs, as demonstrated in previous research, suffers from high turnover, and often, the choice to leave the student affairs field seems to coincide with starting a family and simultaneously taking care of elder family members. Previous research has demonstrated that care-giving commitments hinder women in the advancement of their career and given the changing culture of shared care-giving responsibilities, the previous findings may now be true for men as well. This study focused on Caucasian male middle managers’ perceptions of the student affairs work environment in relation to their families and workplace supportiveness and advancement. I interviewed eight Caucasian, male student affairs middle managers about their perceptions about workplace supportiveness of family obligations in the student affairs field. The participants placed high importance on family and were no longer willing to risk family life for career success. All eight men talked fondly of their family obligations and were willing to change career paths to demonstrate how much they valued their families. In addition, these men frequently commented on the desire to represent cultural change. Therefore, student affairs divisions should implement supportive informal benefits across the board to all professional full time employees for increasing long term stability in the field of student affairs.