After graduating with Architectural Degrees from Wentworth Institute of Technology, The Boston Architectural Center and Harvard University, Michael moved to San Francisco to work as a senior urban designer at Bechtel. In 1985 he began working as a design consultant to architecture, construction and development firms where he became involved in a wide variety of projects including hotels, casinos, restaurants, shopping malls, housing developments and resorts internationally. In 1993 Michael relocated his business to Marblehead and founded his custom residential design firm, Michael McCloskey Design Group. Since 1993 MDG has completed over 300 buildings with a construction value of $80,000,000.

Michael has been a thought leader in business development and management for small design firms at Build Boston for over 3 years and has lectured on leadership and managing change at Harvard University. In 2003 Michael received a certificate of graduation from the Advanced Management Development Program in Real Estate at Harvard University. He is an instructor at the GSD and is a member of the Executive Education Advisory Board.