Before that he was employed by Keene State College as an instructional designer, and by MIT as director of community outreach for the OpenCourseWare Consortium.
He has worked in educational technology since 1997. Among projects from the late paleolithic were the Persona Project, an attempt to integrate English Composition classes with the creation and maintenance of a student-produced online encyclopedia (1997); Transcript Media, a site which made public domain educational material available to P-12 educators (1997-2000); GameGoo, some of the first commercially produced Flash-based educational games on the internet (1999); Columbia Online, a simulation-based online curriculum for Columbia University (2000-2003, as part of Cognitive Arts), and various e-learning projects for Fortune 500 companies.
Since 2005 he has focused his energy on understanding how online communities and open resources can make students and citizens more effective and informed, most prominently at MIT as the first director of community outreach for the OpenCourseWare Consortium, but also as a founder of a number of local and hyperlocal online communities, and in numerous instructional design projects at Keene State College and WSU. He has been recognized for his thinking on these issues, both at national conferences and through Hapgood, his long running blog on educational technology issues (hapgood.us). He was the 2017 editor of the EDUCAUSE New Horizons feature on the future of educational technology.
He has been described by George Siemens as one of “a few genuinely original people doing important and critically consequential work” in the field of educational technology. He has worked extensively with wiki inventor Ward Cunningham on applications of wiki to education. His work has been covered by The Chronicle, Times Higher Education, The Wall Street Journal, TechCrunch, Bloomberg, Newsweek, and Vox. He has appeared on the Today Show to talk about issues with modern social media.
Outside of education, he is possibly best known as a co-founder of the 5,000 member online political community Blue Hampshire in 2006, a site described by Daily Kos founder Markos Moulitsas as “one of the most influential blogs in the nation”, and one of eight blog communities chosen in 2007-2008 for syndication by Newsweek’s Ruckus Project.Blue Hampshire ran from 2006-2014.
In May 2011, Mike Caulfield’s lo-fi electro song “Miss McGinty’s Ghost” reached #26 on the Latvian Radio airplay charts. He still has no idea why.