Wolfe spent twenty-one and a half years as a college professor. During that time he worked largely with undergraduate students, although he did supervise some master's degree students in education after 1895 and some master's degree students in philosophy and psychology in 1906. Among Wolfe's students were many who went on to be successful as attorneys, business owners and particularly as school teachers and administrators. Twenty-two of his students went on to become successful in the discipline of psychology. Three of Wolfe's students later served as presidents of the American Psychological Association.