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Duncan Dobbelmann has a long and varied work experience, beginning in 1994 as an Adjunct Lecturer and Graduate Teaching Fellow at Baruch College. In 1999 they were a Writing Fellow at CUNY Hostos Community College and an Acting Faculty Coordinator for Literature, Media Studies, and Critical Thinking and Adjunct Assistant Professor / Adjunct Lecturer of Humanities at New York University. From 2002 to 2009, they worked at Brooklyn College, serving as Director of the Learning Center, Assistant Director of Macaulay Honors College, Substitute Assistant Professor of English, and Postdoctoral Fellow of Macaulay Honors College. From 2009 to 2017, they worked at Bennington College as Associate Provost & Dean of Studies, Associate Dean of the College, and Associate Dean for Academic Services. In 2021, they took on the role of Ski Instructor at Stratton Mountain Resort, and in 2022 they became a Content Contributor at Boardroom Labs.

Duncan Dobbelmann holds a Doctor of Philosophy - PhD in English from The Graduate Center, City University of New York, which they obtained from 1993 to 2000. Duncan also holds a Bachelor's degree in English from Vassar College, which they obtained from 1989 to 1993. Additionally, they hold a High School Diploma from Brunswick School. Duncan also holds several certifications, including a Certified Level II Ski Instructor from PSIA - AASI Professional Ski Instructors of America - American Association of Snowboard Instructors obtained in March 2022, a Children's Specialist 1 certification from PSIA - AASI Professional Ski Instructors of America - American Association of Snowboard Instructors obtained in January 2022, and a The Secret to Better Decisions: Stop Hoarding Chips certification from LinkedIn obtained in September 2021.