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Holding Paradox Through Play: Can serious play be a portal to wisdom?

This is an episode about puzzles and care. Andrea has a conversation with puzzle maker Jason Robillard (StumpCraft) about how puzzles cultivate new ways of being and seeing, holding paradox by repeatedly joining opposites only to realize they were never quite opposites but mirror-like pieces of a coherent whole. Robillard describes his wooden, laser-cut puzzles built from Canadian fine art, with uniquely drawn organic pieces, symbolic elements, sensory “shock,” and sometimes multiple valid placements that challenge assumptions of a single solution. He connects puzzling to embodied experience, attention, OODA loops, cognitive biases, and navigating complexity through “alternating base camps” and Goldilocks destabilization, relating this to career upheavals and identity change. The conversation emphasizes care as community glue and highlights values embedded in his work—curiosity, creativity, integrity, and generosity—plus a resonance with David Whyte’s poem “Start Close In.”

00:00 Paradox Through Play
02:36 Podcast Intro Puzzles Theme
07:54 Meet Jason And His Work
09:20 Puzzles Holding Paradox
11:38 Designing Artful Wooden Puzzles
14:47 Embodied Senses And Touch
16:58 Career Shift Into Puzzles
23:24 Serious Play And Homo Ludens
25:50 Moving Childhood And Safety
31:57 Base Camps And Destabilization
34:30 Polarity Recipes Beyond Flatland
38:47 Designing Paradox Puzzles
39:48 Many Solutions Mindset
42:54 Puzzles as Conversation
47:53 Liminal Times Need Puzzles
56:00 Sensemaking and OODA Loops
01:00:22 Home Gifts and Community
01:03:17 Four Values in Design
01:11:29 Start Closer In Practice
01:13:39 Care Belonging and Vulnerability
01:18:52 Where to Find Jason
01:19:57 Closing Poem Reading

StumpCraft Amazing Instagram Photos and Videos of Games

Jasen’s writings: Releasing the Muse

Jasen on LinkedIn

OODA loop (observe, orient, decide, act)

Homo Ludens

Jasen Robillard was always a closet creative who long denied the creative muses, focusing instead on a “secure” engineering career until it dried up in 2017. As is often the case, necessity proved to be the mother of invention… In 2016, Jasen started designing and prototyping his whimsical puzzles which were inspired by other wooden laser-cut puzzles he had enjoyed years earlier. He noted a lack of wooden puzzle availability in Canada, as well as a severe lack of deliberate focus on Canadian fine art. After a year of playful prototyping and a clear end to his engineering-focused career, Jasen decided to launch StumpCraft formally in 2017.

Since the formal launch, StumpCraft has experienced growth and praise as more and more fans share their love of puzzles with friends and family members. StumpCraft was also the recipient of the 2021 Made in Alberta Award in Games & Leisure, exposing us to an ever more rapidly expanding fanbase.

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#83 Wisdom Gates: Paradox, Care and Discovery with Puzzle-Maker Jasen Robillard

Love & Philosophy

#83 Wisdom Gates: Paradox, Care and Discovery with Puzzle-Maker Jasen Robillard