Team Simon here! As we take a short hiatus, A Bit of Optimism will return with brand-new episodes on March 24, 2026. Until then, we’re revisiting some of the conversations you loved and we still think about long after the microphones turned off.

This week, we’re rewinding to Simon’s conversation with the wildly creative and endlessly curious Jacob Collier.

To create something truly original, do we build something new or break what came before? Perhaps the answer is both—simultaneously.

Jacob Collier does exactly that. A songwriter, multi-instrumentalist, and Grammy Award winner, Jacob has built a career on blending structure with spontaneity. He’s known for turning entire concert halls into three-part choirs, transforming audiences from spectators into collaborators. His album "Djesse Volume 4" was nominated for Album of the Year at the 2025 Grammy Awards, alongside icons like Beyoncé, Billie Eilish, and Taylor Swift. Although Beyoncé's "Cowboy Carter" won, Jacob snagged his seventh Grammy for his rendition of "Bridge Over Troubled Water."

Simon sat down with Jacob in a music studio just days before the 2025 Grammys, surrounded by pianos and possibility. What unfolded was more than a conversation about music. It was a masterclass in creativity, about holding opposites at once, embracing imperfection, and having the courage to follow curiosity wherever it leads.

If you’ve ever wondered how creativity really works or how to find your own voice without losing what came before—this one’s worth another listen.

This… is A Bit of Optimism.

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For more on Jacob, check out:

http://jacobcollier.com

‪@jacobcollier‬

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Revisited: How to Turn Stress Into Creativity With Grammy-Winner Jacob Collier

A Bit of Optimism

Revisited: How to Turn Stress Into Creativity With Grammy-Winner Jacob Collier