On Purpose with Jay Shetty Lilly Singh: Stop Trying to Prove Yourself to Everyone Else! (#1 Mindset Shift to Build REAL Confidence & Self-Worth)
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Sep 17, 2025 
Join Lilly Singh, a trailblazer in digital media and the first bisexual woman of color to host a late-night show, as she shares her journey from seeking external validation to embracing self-worth. In an honest conversation, she reflects on the loneliness of being a pioneer while discussing the importance of self-compassion and daily rituals like journaling. Lilly emphasizes the need to quiet our inner critic and recognize that our true value can't be defined by achievements, but by our growth and resilience as individuals.
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From Proving Others Wrong To Proving Yourself Right
- Lilly Singh explains many of her early choices were driven by proving her worth to others rather than passion.
- She later shifted to proving herself right, prioritizing internal validation over external approval.
First YouTube Video Sparked By Loneliness
- Lilly recounts making her first YouTube video in 2010 while feeling lonely and stuck in a linear life path.
- Seventy people watched that first video and she felt alive for the first time making content for herself.
Late-Night Show: A Painful ‘First’
- Lilly shares saying no initially to a late-night show and later accepting because of historic significance and pressure to represent.
- The show proved mentally and physically exhausting and taught her hard lessons about limits and expectations.