The Great Simplification with Nate Hagens

The Forgotten Skills of Dying and Grieving Well: How Engaging with Loss Can Help Us Live More Fully with Stephen Jenkinson

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Aug 13, 2025

Join Stephen Jenkinson, a cultural activist and author specializing in grief, as he challenges Western taboos surrounding death. He shares profound insights from his work in palliative care, urging listeners to view grief as a skill rather than an affliction. The conversation explores how engaging with loss can lead to a fuller life, the disconnect between societal attitudes toward death, and the often ignored wisdom found in grief. Jenkinson's thoughts on faith, mortality, and embracing ordinary moments bring a fresh perspective on living deeply.

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INSIGHT

Grief As Companion

Grief is a lasting companion, not an obstacle to overcome.
Stephen Jenkinson reframes grieving as ongoing skillfulness rather than an endpoint.

ANECDOTE

Dying Mirrors Living

Stephen Jenkinson recounts palliative care: dying people acted as they had lived, not as some elevated cue.
He observed death rarely produced the moral rise he had hoped for in patients and families.

INSIGHT

Hope As Cultural Obligation

Modern deathphobic culture generates hope as moral obligation and avoids facing dying.
That enforced hope compromises people’s capacity to inhabit their dying fully.

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In Western culture, topics surrounding death and dying are often considered taboo and are generally avoided in everyday conversations. But this reluctance to fully acknowledge and integrate death as a natural part of the human experience has rendered us less able to cope with the end of life and less prepared to show up for ourselves and the people around us as we inevitably navigate loss. But what if a more skillful engagement with death and grief could actually offer us a more mindful approach to living?

In this conversation, Nate is joined by Stephen Jenkinson, a cultural activist and author on the topic of grief, loss, and dying, to discuss his extensive work on grief literacy and the shortcomings of the dominant cultural attitudes towards death. Stephen reflects on his experiences as a palliative care counselor, offering insights on how to navigate the complexities of life and death, advocating for a more profound participation with grief.

What if we viewed grief as a skill rather than an affliction? What opportunities and insights become available to us as we more deeply understand and accept death as a part of life? In what ways does modern culture's reliance on hope act as a distraction from facing reality – and how does this harm us towards the end of life?

(Conversation recorded on June 12th, 2025)

About Stephen Jenkinson:

Stephen Jenkinson is a cultural activist and author on the topic of grief, loss, and dying. Along with his wife Nathalie Roy, Stephen co-founded the Orphan Wisdom School, where he writes and teaches about the skills of deep living, making human culture, and how to die and grieve well – skills he believes we have forgotten in our culture today.

Stephen holds a master’s degree in theological studies from Harvard and an additional master’s degree in social work from the University of Toronto. Additionally, he served for years as the program director of a palliative-care center in a major Toronto teaching hospital, where he provided counseling at hundreds of deathbeds. He is the author of many books, including the award-winning Die Wise: A Manifesto for Sanity and Soul, as well as his upcoming book titled Matrimony: Ritual, Culture, and the Heart's Work.

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