Lilly Singh: Stop Trying to Prove Yourself to Everyone Else! (#1 Mindset Shift to Build REAL Confidence & Self-Worth)
On Purpose with Jay Shetty
iHeartPodcasts
4.8 • 28.5K Ratings
🗓️ 17 September 2025
⏱️ 62 minutes
🧾️ Download transcript
Summary
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
See omnystudio.com/listener for privacy information.
Transcript
Click on a timestamp to play from that location
| 0:00.0 | This is an IHeart podcast. |
| 0:04.4 | Thus far in life, you have a 100% success rate of getting through things. |
| 0:09.5 | There's not a single thing in your life, if you're sitting here right now, that you have not gotten through. |
| 0:14.0 | So anytime you felt like this in the past, you got through it. |
| 0:17.2 | And I think we need to remind ourselves that a little bit, that we can beat ourselves up. |
| 0:20.5 | But just because your brain is saying it, it doesn't mean it's true. We lie to ourselves all the time. |
| 0:25.5 | The number one health and wellness podcast. Jay Shetty. Jay Shetty. He won, the only. |
| 0:31.2 | Jay Shetty. |
| 0:31.8 | I am so excited to be here tonight at the Ellie Colkins Opera House House in Denver with the one and only my dear friend, Lily Singh! |
| 0:41.3 | Let's go! |
| 0:43.3 | First of all, you know I'm going to uproot this whole thing. You know this, I don't follow rules. |
| 0:47.3 | How awesome is Jay Shetty though? Come on! |
| 0:51.3 | This is your show now. |
| 0:53.3 | No, it's not my show. It's your show. |
| 0:55.0 | I'm so honored. First of all, Jay has way more famous friends than me. So the fact that I get to close out this tour, all of you, this is the last tour stop. Isn't that amazing? We get to be here? I mean, I'm not going to uproot too much, but I just have to, like, I know we're all thinking it. Jay's brain, he's so kind. |
| 1:10.8 | I'm going to give you all the tea of what Jay's actually like off the podcast |
| 1:14.1 | because we're all thinking it. Jay's brain. He's so kind. I'm going to give you all the tea of what Jay's actually like off the podcast |
| 1:14.1 | because we're actually real friends. Oh, I will, baby girl. Don't you worry. What's your name? |
| 1:20.3 | Pamela? Pamela? Okay. Her name is Jay Shetty. There's an open bar here and I like it. |
| 1:28.3 | No, but Jay is an incredible human being. |
| 1:31.3 | I'm so honored to be here on this last tour stop. |
| 1:34.3 | Everything you know about Jay from the podcast, I don't know how to even explain to you that he's even better off the mic and behind the scenes and behind the camera. |
... |
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