Craig received his Master's Degree in Cultural Studies from Holy Names University in Oakland, California, and his Teaching Certificate from the University of Iowa. He has been an educator for the past 35 years, the first ten of which were spent in America. He then came to Uganda as a Peace Corps Volunteer in the Education Sector in 1997, teaching in the country's Eastern Region. After finishing his service, he remained in Uganda and founded the for-profit branch of Mango Tree in Kampala, focused on the sale of local language educational materials. He became an East Africa Ashoka Fellow in 2002, and founded Mango Tree Literacy Lab in Lira in 2008. His favorite game is Settlers of Catan, and his favorite book is The Diary of a Young Girl (Anne Frank).