Before studying law, Jamie completed his graduate studies in economics, focusing on rural and community development, and was a visiting Fulbright Scholar at the Appalachian Center, University of Kentucky. After law school, he articled with a solo practice in Toronto specializing in cases of state and institutional misconduct, civil rights and Indigenous rights, and taught part-time in the Department of Food, Agriculture and Resource Economics at the University of Guelph. Jamie then clerked at the Federal Court of Canada before returning to graduate studies in law.

Jamie is interested mainly in food systems, agriculture, land, rural-urban connections, and local governance. Most of his work looks at what are sometimes called the "working rules" that shape human interaction and cooperation--those rules and norms that operate where formal laws and actual practices meet.