McEnany enrolled at
Second City in Chicago in the 1990s, where she had
Stephen Colbert as a teacher. McEnany worked for
Morningstar, Inc. in Chicago for 10 years, first in customer service and then as a technical writer. She eventually joined Second City's touring company when she was 40, and led the ensemble "Judo Intellectuals" at the Chicago's
Playground Theater. ==Personal life==