At one point a humorous columnist on The Chicago Daily News, he had columns syndicated in newspapers from Britain to Borneo.
Drogin became interested in the scripts of the Middle Ages in the 1970s, researched palaeography independently at the Bodleian Library in Oxford, England, and wrote Medieval Calligraphy: Its History and Technique, which was published in 1980 by Allanheld, Osmun & Co. Publishers, Inc. and Abner Schram, Ltd.
During this period, he taught calligraphic workshops and lectured across the United States, Canada, England, and Iceland.
He is described on the back cover of the Dover edition of his calligraphy book as "a professional calligrapher of medieval styles, as well as illuminator, writer, and teacher."
His work for Maggs Brothers as an appraiser and medieval calligraphy expert were often employed in pricing pieces for sale both in Europe and the United States.