How Questions Shape Your Life | Stephen Jenkinson

It's not often I feel nervous. I worked for many years as a photographer and met people from every stratum of society, from the wealthy and famous to the outcast and downtrodden. One thing I learnt early on is that nerves resulted in bad imagery. So when it came time for this podcast with Stephen Jenkinson, a man whose work I've followed for nearly a decade, I was nervous. It's not that Stephen is difficult to talk to or combative; it's because Stephen is a master of the English language, and each word he uses is carefully chosen based on its etymology. He also doesn't let you get away with anything if he believes you've incorrectly identified something. My nerves quickly abaited once I felt Stephen's generosity of spirit.

 

This is one of the most meaningful conversations I've had. Stephen traverses:

- What we have lost in our modern societies, if there is a way back, and if there were, to what we think we are to return to.

- Death and our lack of education around the ultimate which every life faces.

- What it truly means to cultivate a mindset that sees us creating genuine connections to one another to create communities that will benefit future generations.

Most of all, Stephen reminded me that our lives are shaped by the questions we ask rather than the answers we seek—in his own words, "I'm far more in favour of the wonder of the question than the certainty of the answer." As the great poet E.E. Cummings phrased it, "Always the most beautiful answer to he who asks the most beautiful question."

It was an honor to speak with Stephen, and I know you'll get something significant from his life-long pursuit of asking the most beautiful questions. 

It was an honor to speak with Stephen, and I know you'll get something significant from his life-long pursuit of asking the most beautiful questions. 

 

About

Stephen Jenkinson, MTS, MSW ~ Culture activist/ farmer/author ~

Stephen teaches internationally and has authored seven books of cultural critique. He is the creator and principal instructor of the Orphan Wisdom School, co-founded with his wife Nathalie Roy in 2010. The School’s new project, The Scriptorium (2025), is creating an archive and library of his life’s work.

Apprenticed to a master storyteller as a young man, he worked extensively with dying people and their families. He is former programme director in a major Canadian hospital and former assistant professor in a prominent Canadian medical school. Stephen has Masters’ degrees from Harvard University (Theology) and the University of Toronto (Social Work).

In 2023 Stephen received a Distinguished Alumni Honours Award from Harvard University for “helping people navigate grief, exploring the liminal space between life and death, and connecting humanity through ceremony and storytelling.”

In August 2025, Sounds True will release Stephen’s newest book: Matrimony: Ritual, Culture, and the Heart’s Work. 

He is also the author of Reckoning (co-written with Kimberly Ann Johnson in 2022), A Generation’s Worth: Spirit Work While the Crisis Reigns (2021), Come of Age: The Case for Elderhood in a Time of Trouble (2018), the award-winning Die Wise: A Manifesto for Sanity and Soul (2015), Homecoming: The Haiku Sessions (a live teaching from 2013), How it All Could Be: A workbook for dying people and those who love them (2009), Angel and Executioner: Grief and the Love of Life (a live teaching