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 inner voices we all carry, from the critic to the voice of compassion, emphasizing the importance of practicing daily self-care to balance high standards with grace. Lilly shares her personal rituals such as journaling, naming her inner voices, and reframing failure as growth, while Jay emphasizes the transformative power of reflecting on the past as proof of resilience. Together, they remind us that even in moments of pressure and imperfection, we are not defined by our accomplishments but by the person we are becoming.

In this interview, you'll learn:

How to Turn Failure Into Growth

How to Quiet Your Inner Critic

How to Practice Daily Self-Compassion

How to Live with Your Inner Voices

How to Stop Chasing Outside Validation

Every challenge you’ve faced so far has proven that you are stronger than you think, and every step forward is a reminder that you are capable of creating a life that feels true to you.

With Love and Gratitude,

Jay Shetty

What We Discuss:

00:00 Intro

03:20 Growing Up Without Options

09:28 Realizing You Always Have a Choice

17:37 Committing to a Life of Growth

19:01 Learning to Stop Self-Blame

21:56 Breaking Free from Unrealistic Standards

27:55 Why Good Enough Is Enough

31:26 Living Alongside Self-Criticism

36:47 You Are More Than What You Do

41:32 Finding Strength in Past Resilience

44:42 Proving to Yourself You Can

48:25 Why Women Aren’t Taught About Their Bodies

52:40 Past, Present, and Future Reflections

59:39 Friendship That Stands the Test of Time

Episode Resources:

Lilly Singh | YouTube

Lilly Singh | Instagram

Lilly Singh | Facebook

Lilly Singh | TikTok

Lilly Singh | Books

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