Art Department Trainee (with Sam O’Leary — Season 8 Premiere)

Did I Do That? is back again, even though every time someone says that, it presages a disaster. Globetrotting art director, father, and genuine jack-of-all-trades Sam O’Leary sits down with Sean for our season 8 premiere to talk about his creative missteps… as well as the “good” stuff “kids” go for, woofing, and North America: where everybody knows your name.

Sam O’Leary is a maker, storyteller, and professional tinkerer who has been making a glorious mess since 1986 — in art, life, work, and in all the places they overlap. Whether it’s a large-scale identity system or a one-off handmade object, Sam values the same things: resonance over reach, clarity over cleverness, and good questions above all. Over the years, he's worked on brand strategy, narrative frameworks, illustration, animation, sculpture, motion design, set design and build, woodworking, hand-painted signage, murals. public installations, props, books, toys, posters, whimsy, good times — and probably many things he's forgotten. Originally from Wellington, Aotearoa, Sam is now based in Portland, Oregon, where he lives with his partner and their three wonderful, wild children.

You can find Sam’s work and more at his website, conduction.co.nz! You can also find him on Instagram at @samolearypresents; there, you can check out the “Artisan Designer for Hire” box he made for OMFGCO that we talk about in the episode, as well as lots of his other work!

Special thanks to the great Sarah Hollowood for connecting Sam and I for this episode—you rock!

This episode was recorded 10 January 2026 in the Rat’s Nest.

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