What is a Good Life? #135 - Longing, Belonging, and Matrimony with Stephen Jenkinson

Aug 12, 2025

Stephen Jenkinson, a cultural worker and author, dives deep into the complexities of life, love, and matrimony. He discusses the significance of ceremonies, emphasizing the importance of community in weddings and the bittersweet transitions they embody. Jenkinson contrasts longing with belonging, suggesting true connection comes from appreciating one’s ancestry and responsibilities to future generations. The conversation also highlights the need for meaningful endings in rituals, advocating for a collective memory that honors our shared human experiences.

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INSIGHT

Condition Of Pondering

Stephen Jenkinson describes life as a 'condition of pondering', not a single burning question.
He asks what to do now that the gods have spoken.

INSIGHT

Dream Another World Has Of You

Stephen Jenkinson suggests lives may be 'the dream that another world has of you'.
He argues memories can come from ancestry and the dead, not just personal experience.

ADVICE

Act For Seven Generations

Consider consequences for seven generations when making important decisions.
Stephen Jenkinson frames this as a citizen and spirit obligation to future people.

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On the 135th episode of the What is a Good Life? podcast, I’m delighted to welcome our guest, Stephen Jenkinson. Stephen is a cultural worker, teacher, author, and ceremonialist. He is the creator and principal instructor of the Orphan Wisdom School, founded in 2010. He has master’s degrees from Harvard University (theology) and the University of Toronto (social work). He’s the author of Come of Age, the award-winning Die Wise, Money and the Soul’s Desires, and Reckoning (with Kimberly Ann Johnson). His latest book, Matrimony: Ritual, Culture and the Heart’s Work, invites readers to contemplate the significance of matrimony, ceremony, and cultural articulation—and how to redeem them for future generations.

In this rich conversation, Stephen explores profound questions about life, love, and the nature of existence. The discussion delves into the essence of ceremonies, particularly in matrimony, emphasising the need for meaningful endings and the responsibilities we hold towards future generations.

The discussion weaves fate, ancestry, humility, and the call to “proceed as if you’re needed” into a meditation on how we might live fully inhabited lives.

For Stephen's latest book, Matrimony:
To buy your copy: https://orphanwisdom.com/store/matrimony/
About the book: https://orphanwisdom.com/books/matrimony/

For more of Stephen's work:
Website: https://orphanwisdom.com/

Contact me at mark@whatisagood.life if you'd like to explore your own lines of self-inquiry through 1-on-1 coaching, my 5-week group courses, or to discuss experiences I create to stimulate greater trust, communication, and connection, amongst your leadership teams.

- For the What is a Good Life? podcast's YouTube page: https://www.youtube.com/@whatisagoodlife/videos
- My newsletter: https://www.whatisagood.life/
- My LinkedIn: https://www.linkedin.com/in/mark-mccartney-14b0161b4/

00:01 – Introduction

01:37 – The Condition of Pondering

06:28 – Roots of Pondering

10:16 – The Dream Another World Has of You

19:36 – Needed vs Important

21:46 – Matrimony and the Presence of the Absence

26:00 – Longing and Belonging

31:00 – Modern wedding and the privatisation of love

35:47 – The Art of the Ending

41:40 – Pompe and the Necessity of Closure

43:47 – Ritual as a Gift to the Village

45:45 – The White Heat of Possibility

51:25 – The Active Witness

53:43 – What Is a Good Life for Stephen?