Stephen Jenkinson is a culture worker, author, and founder of the Orphan Wisdom School. He holds master’s degrees from Harvard Divinity School and the University of Toronto and is the author of numerous books, including Die Wise and his most recent work, Trembling, Still.

This conversation began as an attempt to discuss Stephen’s earlier work on death and grief, but quickly moved elsewhere. Instead, we found ourselves talking about culture itself: what it owes, who it serves, and what happens when people inherit a world that no longer provides reliable ways of belonging, remembering, or understanding their obligations to one another.

We discuss Canada as a country shaped by immigration, displacement, and reinvention, the role of ritual and elderhood in modern life, the tension between freedom and obligation, and the challenge of building wisdom in an age increasingly detached from inherited forms of meaning.

Finally we turn to his new book, Trembling, Still, written in the wake of a serious neurodegenerative diagnosis, and Stephen’s reflections on illness, identity, and the possibility of becoming a stranger to oneself.

Stephen’s Links

Orphan Wisdom School:

https://orphanwisdom.com/

Trembling, Still and Other Books by Stephen Jenkinson:

https://orphanwisdom.com/books/

The Canadians Links

Website:

https://www.thecanadianspodcast.ca/

Support Page:

https://buymeacoffee.com/thecanadians

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Conversation recorded on April 22, 2026

Opening Song: Aria 51 by MicroBongo Soundsystem, used with permission.