Benjamin dropped out of college at the age of 19, spending the next 25 years as a professional musician and jazz educator.

Having emigrated to the United States after receiving his PhD, Benjamin has since become professor of history in the Frederik J. Meijer Honors College at Grand Valley State University (GVSU) in Allendale, Michigan.

Benjamin served as Treasurer and Vice President of the International Big History Association from its inception in January 2011 until July 2018.

He is a consultant for the College Board and former co-Chair of the Test Development Committees of the Advanced Placement World History exam, and current Chair of SAT World History exam.

He continues to play jazz, and served as President of the West Michigan Jazz Society, and also as Chair of the Easton Special Events committee which organizes the Eastown Street Fair in Grand Rapids, which draws around 10,000 people each September.