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Mickey Boylan's work experience begins in 2008, when they worked as a Little League Umpire for the Northville Baseball Softball Association. In 2010, they became a Contractor for Continental Canteen, a position they held until 2012. Mickey then worked as a Marketing/Sales Intern for HYDRIVE Energy LLC. from June 2011 to August 2012. In 2012, they volunteered as a Men's and Women's Basketball Tournament Volunteer for the Big Ten Conference. In 2013, Mickey served as a Communications Intern for the Pittsburgh Penguins. From 2011 to 2014, they worked at Penn State University in various roles, including Women's Tennis Media Contact and Sports Information Student Assistant. In 2014, Mickey joined the Florida Citrus Sports as a Communications Assistant, responsible for various duties related to public relations and media efforts. Mickey then worked their way up within the same organization, becoming the Manager, Senior Manager, and eventually the Assistant Director of Marketing & Communications.

Mickey Boylan attended Father Gabriel Richard High School from 2006 to 2010. Following this, they went on to attend Penn State University from 2010 to 2014, where they earned a Bachelor's degree in Public Relations.