The author's career path can best be described as "unconventional" or "non-traditional" for a senior student affairs administrator. Being a first-generation college graduate, the author's focus was on what he characterizes as a "clear cut career path" for a Myers Briggs Extraverted Sensing Thinking Judging (ESTJ): management and banking. In this article, the author shares his experience and his effort at achieving a greater degree of work/life balance for his family.