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The Roundup: Living a double life

Lessons we learned from Mason Currey, author of Making Art While Making a Living

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Eli Woolery
May 08, 2026
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As designers, many of us got into the profession because we had other creative passions. Perhaps we grew up drawing, or painting, or were into music or performing arts. Then the daunting reality of making a living set in, and we started asking: what careers let you actually get paid for being creative?

In high school, I loved illustration, and thought I might end up going to art school. But I ended up at a liberal arts school that wasn't known for its art program. I also loved making and building things. So the product design major seemed like a blend between art and engineering that I could embrace. I struggled through many of the engineering requirements, and despite surviving four years of advanced math, I still need to lean on ChatGPT to assist me when my daughter asks for help with her homework.

Detail from an illustrated alphabet I drew in high school

I’m sure many of you wrestled with similar challenges (though it’s not unlikely that you’re better at math than me!). Like me, you might be curious how some of the best known artists out there made their art while supporting themselves.

This week we published our interview with Mason Currey, author of Making Art While Making A Living, a book that uses the lives of artists, writers, and composers to ask the same question many of us been challenged with: how do you maintain a creative life while still paying the bills?


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Mason Currey: Spotify, Apple Podcasts, Substack

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Meet Crafted, the evolution of UserTesting’s Human Insight Summit — designed for teams who intentionally build with customer insight at the center. In Seattle, Eli Woolery will host AI & Design Thinking, a hands-on workshop exploring how generative AI can sharpen (not replace) your creative process.

Secure your spot at events.usertesting.com/crafted with code DesignBetter100 for $100 off workshops.

May 28th: Seattle, September 17th: London

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The double life

One of the most surprising findings in Mason’s research is how many canonical artists had parallel professional lives that had nothing to do with their art. Wallace Stevens was an insurance executive. William Carlos Williams was a family physician. Franz Kafka spent his days at an insurance office, writing letters and diary entries that dramatically overstated his misery — even as he was, by most measures, actually getting writing done.

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