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Jay Shetty PodcastJay Shetty Podcast

#1 Mindset Shift You NEED to Build REAL Confidence!

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: https://www.youtube.com/channel/UCfm4y4rHF5HGrSr-qbvOwOg https://www.instagram.com/lilly https://www.facebook.com/LillySingh/ https://www.tiktok.com/@lilly https://lillysinghbook.com/ https://www.instagram.com/jayshetty https://www.facebook.com/jayshetty/ https://x.com/jayshetty https://www.linkedin.com/in/shettyjay/ https://www.youtube.com/@JayShettyPodcast http://jayshetty.me

Lilly SinghguestJay Shettyhost
Sep 16, 20251h 2mWatch on YouTube ↗

At a glance

WHAT IT’S REALLY ABOUT

Lilly Singh reveals confidence built by grace, choices, and self-compassion

  1. Lilly Singh explains that chasing “firsts” (YouTube, late-night) was fueled by loneliness, cultural gender expectations, and a need to prove worth to people who valued fame and status.
  2. She reframes confidence as remembering you’ve survived 100% of your hardest moments and recommends journaling specific past breakthroughs as a practical resilience-building tool.
  3. Singh describes how unrealistic standards and conditional approval created high self-criticism that spilled into relationships, and how daily self-compassion tracking helped her extend grace to others.
  4. They discuss “parts” (inner manager/critic/loneliness, etc.) as voices to acknowledge and strategically sideline rather than eradicate, building choice and self-leadership.
  5. Singh shares her upcoming film “Doin’ It,” a raunchy sex comedy addressing how women—especially women of color—aren’t taught about their bodies, pleasure, or sexual health without shame.

IDEAS WORTH REMEMBERING

5 ideas

Confidence grows faster when you stop proving others wrong.

Singh notes external validation (status, money, headlines) can motivate but often leaves you empty; shifting to “prove myself right” creates a healthier, more sustainable drive.

You already have evidence you can survive hard seasons.

Her “100% success rate” framing turns past endurance into current confidence; writing down specific moments you overcame combats the brain’s bias toward failure memories.

Journaling is the practical bridge between inspiration and change.

Both emphasize that insight alone fades—documenting past wins and rereading them is the repeatable practice that builds resilience when you’re spiraling.

High standards need to be paired with high grace.

Singh’s perfectionism improved only when she intentionally practiced self-compassion (three bullets nightly), which unexpectedly reduced how harshly she judged friends too.

Don’t try to delete your inner critic—learn when it’s useful.

Their shared view: self-criticism may help in performance contexts, but it’s harmful after loss or disappointment; maturity is choosing when it has the mic.

WORDS WORTH SAVING

5 quotes

Thus far in life you have a 100% success rate of getting through things. There's not a single thing in your life, if you're sitting here right now, that you have not gotten through.

— Lilly Singh

I was like, I now have the confidence and self-love to say that I actually could've said, "Actually, it's not my job to make a billion people proud."

— Lilly Singh

I started because I was like, "Oh, you don't think I can do this? You'll understand a million people watching my video. You will understand the size of my house. You will understand those things." Then I got those things, and don't do me wrong, it felt really good, but then I still felt really empty because I was trying to prove other people right when really what I try to do now is I try to prove myself right.

— Lilly Singh

So many times you don't do things 'cause you don't wanna look like an idiot even though the thing is worth looking like an idiot for.

— Lilly Singh

You never had to be perfect for it to be good enough.

— Jay Shetty

Being “first” and the loneliness of no roadmapCultural gender expectations and conditional approvalChoice vs automatic acceptance of others’ burdensConfidence from past resilience (100% success rate)Unrealistic standards, perfectionism, and self-graceParts work/inner voices as tools, not enemiesSex education taboos and women’s bodily autonomy (film: “Doin’ It”)

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