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Humble the Poet
01/30/2026
Humble the Poet
I’ve known Humble the Poet for years, but this conversation reminded me why he’s one of the most thoughtful, grounded, and quietly intense people I’ve ever met. We started light — Punjabi pronunciations, growing up with big families, why Canadians seem to understand America better than Americans — and then jumped headfirst into the big stuff: identity, privilege, race, class, capitalism, and why resentment might be the most corrosive emotion in the world. What I love about talking to Humble is that he never drifts into hollow inspiration. Everything he says comes from lived experience: teaching school in Toronto, grinding in the arts for over a decade, navigating fame, navigating community, and learning how to build a life that doesn’t fall apart the second the algorithm looks away. We dig into his book How to Be Loved, the privilege we ignore, the trauma we glamorize, and the weird, beautiful freedom of creating before anyone knows your name. This is one of the most honest conversations I’ve had on this show. Pick up his most recent book, Pre-order his upcoming book, Follow Humble The Poet:
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