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On Purpose with Jay Shetty

On Purpose with Jay Shetty

Lilly Singh: Stop Trying to Prove Yourself to Everyone Else! (#1 Mindset Shift to Build REAL Confidence & Self-Worth)

Sep 17, 2025 · 1h 6m

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About this episode

Do you feel like you need to prove yourself? Who do you think you’re trying to impress? Today, Jay sits down with his close friend Lilly Singh for a transformative and deeply honest in-person conversation at the Ellie Caulkins Opera House in Denver. Known for being a trailblazer in digital media and late-night television, Lilly reflects on the hidden challenges behind being “the first”, from navigating cultural expectations to battling loneliness and self-doubt. Lilly shares how much of her early success was driven by the need to prove her worth to others, and how she is now shifting toward proving herself right instead of chasing outside validation. Together, Jay and Lilly explore the…