Calhoun left This American Life from 2014 to 2017 to serve as Vice President of Content and Programming at WBEZ, the NPR affiliate in Chicago.

Calhoun began his journalism career when he joined Chicago Public Radio as an unpaid intern during the summer of 2000.

He appeared on episodes of the Week in Review on WTTW-TV's Chicago Tonight program, where he provided commentary on current political news.

In 2005, Calhoun was awarded a grant by the Illinois Humanities Council that allowed him to pursue his interests in documentary work.

Additional support was provided by Chicago Public Radio, where he used the grant to direct, edit, and curate an exhibition of audio and photo documentary work entitled The Daily Meaning: Life Inside America's Service Industries that went on display at the Peace Museum on September 2, 2005.