There are many social, cultural, and biological factors that contribute to the construction of masculine identity. These factors are investigated in this article from the personal perspective of a male practitioner and educator with 25 years of experience in a field that is predominantly composed of women. An amalgamation of attributes necessary for success as a male art therapist is discussed from a new paradigm, defined and explained as a middle man perspective. A middle man is one who skillfully negotiates stereotypic androcentric notions of masculinity by incorporating into his self-structure a stance that confronts patriarchal oppression and cultural blind spots surrounding power and privilege so easily ignored by many western Caucasian men.