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Michael Stailey has a diverse work experience spanning multiple fields. Michael began their career in 2002 as a Freelance Writer and later worked as a Marketing Director and Media Analyst at DVD Verdict. In 2013, they took on various roles as a Professional Actor, Director, and Instructor at Patrick Dorow Productions, The Players' Ring, and Get-A-Clue Productions. Michael also worked as a Patient Educator at UMass Medical School, Tufts University School of Medicine, and Harvard Medical School during the same period. From 2014 to 2016, Michael served as a Social Media Manager and Professional Actor at Hackmatack Playhouse. More recently, they worked at Ogunquit Playhouse, fulfilling roles such as Ticketing Services Manager, Marketing Strategist, and Associate Marketing Director.

Michael Stailey earned their Bachelor of Science in Electrical Engineering (BSEE) from the University of Iowa, which they attended from 1986 to 1993. Following this, they pursued further education and completed their Master of Business Administration (MBA) with a focus on Business Strategy at DePaul Driehaus College of Business, where they studied from 1997 to 1999. In addition to their formal education, Michael obtained additional certifications, including the title of Reiki Master Teacher from Anne Donnell in May 2021 and a Level I Yoga Instructor Certification from Bending Bodhi Yoga in February 2021.