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Over-optimizing the creative process and designing your way out of the Valley of Sh*t

November 9, 2026 · 57 min

Show notes

Everyone creative person has been in the Valley, the miserable stretch in a project where nothing works. In this episode, we talk about some of the tricks we use to get to the other side: sleep, sneak attacks, talking it out, word-association games. But we also ask: are we optimizing creativity out of the design process? We weigh efficiency against good work, the value of the Valley, and whether it's a phase that you can skip or just have to work through. Plus handwritten type experiments, ballot design across counties, and why voting needs a big red button.

David McGillivray is a designer and creative director in upstate New York, designing for early stage tech companies through his own practice. He also co-founded Offhours and runs Corners, an art and design store in the Catskills.

Jacob Heftmann is a Los Angeles-based surfer and graphic designer. He is currently the Design Director at Grilli Type. Previously he was on the faculty at Parsons and founded XXIX and Index in New York City.

Artwork by Pablo Delcan
Music by Mondo Boys
Artwork typeface; GT Standard Mono by Grilli Type

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