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

Release Date: September 17, 2025
Host: Jay Shetty
Guest: Lilly Singh
Location: Live at the Le Calkins Opera House in Denver

Overview

In this heartfelt and deeply honest episode, Jay Shetty welcomes his close friend, trailblazing creator and comedian Lilly Singh, for a live conversation in Denver. Together, they delve into the roots of true confidence and self-worth, breaking down the unhealthy compulsion to prove yourself to others, and the mindset shift necessary to build a life anchored in genuine self-love. With equal parts vulnerability and humor, Lilly shares her journey—from her early life facing cultural expectations, to pioneering firsts in her career, struggling with internal critics, and, ultimately, learning to celebrate the wholeness of her real self.

Key Discussion Points & Insights

1. The Burden and Reality of Being "First"

[05:30–10:41]

• Lilly’s Trailblazer Status: Jay highlights Lilly's string of firsts—from early YouTube creator to the first bisexual woman of color with a late-night show—emphasizing how being celebrated as "the first" comes with deep loneliness and anxiety.
• Lilly’s Motivation: Lilly reveals how her drive was originally rooted in a desire to prove her worth to skeptical family members and a culture that valued sons over daughters.
  • “From a very young age it was abundantly clear to me that my extended family was not thrilled at the idea of a second daughter being born... for most of my life, I’ve had this chip on my shoulder.” – Lilly ([07:34])
• Breaking from Expectations: She describes the sense of emptiness after achieving fame for others, not for herself—“I got those things... but I still felt really empty because I was trying to prove other people right. Now... I try to prove myself right.” ([10:50])

2. Navigating Cultural & Familial Expectations

[11:31–19:56]

• Gendered Cultural Pressures: Lilly narrates experiences of being boxed in by expectations—“girls shouldn’t be so outspoken... should be generally timid”—and the implicit lesson that other people’s definitions often get imprinted as personal burdens.
• Late Night Struggles: Lilly opens up about her internal struggles hosting a late night show, bearing the weight of representation, and feeling responsible for making a billion people proud.
  • “People would literally come up to me and say verbatim, a billion people are counting on you. Like, all the Indians are counting on you. All the gays, all the women... that’s a lot of people that are counting on me. There’s no way I could make all of them proud.” – Lilly ([16:38])
• The Freedom to Say No: Only in recent years has she developed the self-love to say, “Actually, it’s not my job to make a billion people proud.” ([17:37])

3. Growth Through Adversity & Reframing Self-Talk

[19:56–21:49]

• Self-Growth From Challenge: Lilly credits difficult periods—her late-night stint, career setbacks—for propelling her self-understanding: “There's no way I would... be where I was if it wasn’t for the moments that kicked my butt.” ([18:48])
• Universal Survival Rate: She offers a practical reflection technique—writing and journaling about past hardships survived—to build confidence:
  • “Thus far in life, you have a 100% success rate of getting through things... You feel like a failure and you have 100% success rate.” – Lilly ([20:42])
• Jay expands on this, urging listeners to record their accomplishments and resilience as a reminder—especially when our minds fixate on failure ([21:49]).

4. Rewiring Expectations & Practicing Self-Compassion

[27:51–35:58]

• Impossibly High Standards: Lilly discusses how her expectations for herself and others can be unrealistic, often mapping her own self-criticism onto relationships.
  • “If they don’t do it to 100, they don’t love me, they don’t care about me…” – Lilly ([29:17])
• Nightly Self-Compassion Ritual: She shares a powerful practice of writing three ways she showed compassion or grace to herself before bed.
• Breakthrough Moment: Over months, she finds herself naturally extending grace to others, showing growth—“Suddenly... my brain didn’t go automatically to ‘they don’t love me’... I was starting to give people grace solely because I monitored the grace I gave myself.” ([31:42])
• Jay’s Federer Analogy: High performers balance standards with grace: “You never had to be perfect for it to be good enough.” ([34:26])

5. Living With, Not Against, Your Inner Voices

[35:58–42:31]

• Parts Theory: Lilly introduces “parts theory”—the idea that we contain multiple inner voices, each with its own role (her critic is “Todd,” her manager is “Susan,” her fun side is “Jellybean,” her grace is “Hope,” and her loneliness is “River”).
  • “You’re not a lonely person... You have a part of you that is that... What you want to do is say, ‘Hey, today Susan, I don’t need you.’” – Lilly ([40:36])
• Embracing the Whole Self: Both agree the inner critic never fully goes away. The goal is to coordinate these voices like instruments in a band, giving center stage only when useful.

6. Innovative Use of AI for Self-Growth

[42:31–45:48]

• ChatGPT as Therapeutic Mirror: Lilly describes how she uses ChatGPT to process therapy sessions and track the voices inside—sometimes asking it to describe her without referencing her accomplishments, resulting in an unexpectedly emotional and humanizing experience.
  • “If you’re so smart, ChatGPT, you tell me who I am and don’t use a single one of my accomplishments. And then she did... Didn’t name Late Night, didn’t name followers, didn’t name a single TV show.” ([44:56])

7. The Weight of Negative Memories vs. Positive Ones

[48:24–48:53]

• Jay and Lilly reflect on how we internalize setbacks more deeply than successes. Jay urges listeners to create their own positive record to balance the emotional scale:
  • “When we go through something good, we celebrate for a night... When we go through something bad, we cry for a month.” – Jay ([48:43])

8. Ongoing Growth & Acting from a Place of Self-Validation

[53:58–56:08]

• Lilly explains the important mindset shift from hustling to “arrive” to simply being and growing.
• Making "Little Lilly" Proud: Her core driver now is not to prove others wrong but prove herself right; she wants to honor the younger version of herself by working through fear and trying new things:
  • “I want to make little Lilly proud. I’ve tried so hard to make everyone else proud, I’m just trying to make little Lilly proud now.” – Lilly ([56:08])

9. Breaking Sexual Taboos With Her New Movie

[56:31–60:51]

• Lilly introduces her upcoming feature film Doing (in theaters Sept. 19), which humorously but powerfully addresses sex education, shame, and expectations for women—especially women of color.
• Families and taboos: She shares the lighthearted but real conversation with her mom about accepting the project:
  • “As far as I’m concerned, my mom has never had sex... And now I’m telling her... There’s like a masturbation scene... [She said] ‘If you think it’s okay, then you should do it.’” – Lilly ([57:30])
• Empowerment Message: The film aims to make women feel comfortable in their bodies and voices, addressing the lack of positive sex education.

10. "Past, Present, Future" Lightning Round

[61:16–65:05]

• Past: First celebrity crush – “It’s the Rock.” ([61:25])
• Present: Imaginary reality TV show: “Creative ways to torment yourself.” ([61:55])
• Future: What she’ll embrace as she ages – “Always being a student.” ([62:47])
• On looking back at a childhood photo: The advice she would give her young self? “Be a kid. Live your life. You have your whole adult life to be an adult, be a kid.” ([64:21])

11. Closing Reflections on Friendship & Authenticity

[66:31–69:35]

• Jay pays tribute to Lilly’s generosity—she was one of his first podcast guests before On Purpose was famous.
• Lilly highlights Jay’s genuine kindness, sharing how he always supports friends, donates to charities, and is “even better off the mic and behind the camera” than on the show:
  • “This is not a facade. This is who he is… Any resource or time you spend supporting Jay is not wasted because he is such a good person and he deserves it.” – Lilly ([68:00])

Notable Quotes & Memorable Moments

• “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 ([20:42])
• “You never had to be perfect for it to be good enough.” – Jay ([34:26])
• “You’re not a critical person. You’re not a lonely person. You have a part of you that is that... and you just need to navigate that voice because that voice is there for a reason.” – Lilly ([40:36])
• “I want to make little Lilly proud. I’ve tried so hard to make everyone else proud. I’m just trying to make little Lilly proud now.” – Lilly ([56:08])
• “Be a kid. Live your life. You have your whole adult life to be an adult. Be a kid.” – Lilly ([64:21])

Practical Takeaways

• Practice self-compassion: Each night, jot down three ways you treated yourself kindly or with grace.
• Reframe setbacks: Remind yourself of your 100% record in making it through tough times—journal these moments for proof.
• Name your inner voices: Understand your motivations and critical voices; don’t try to eradicate them, but manage their role.
• Separate worth from achievement: Challenge the habit of defining yourself by what you do or what you’ve accomplished.
• Find growth in setbacks: Embrace life’s difficult “kicks” as crucial to self-growth.

Timestamps for Key Segments

• 05:30 – Navigating the responsibility of being “first”
• 10:41 – Moving from proving others wrong to proving yourself right
• 16:38 – The pressure of representing a community in the spotlight
• 20:42 – Lilly’s advice: Remember your 100% survival rate
• 27:51 – Tackling self-expectation and extending grace
• 35:58 – Coexisting with your inner critic and parts theory
• 42:31 – Using ChatGPT for mental health and self-understanding
• 53:58 – Shifting mindset: From hustle for arrival to growth in being
• 56:31 – Speaking up for sexual empowerment in her new film
• 61:16 – “Past, Present, Future” game and advice to her younger self
• 66:31 – Closing remarks on real friendship and authenticity

Tone & Vibe:
Candid, humorous, vulnerable, and highly relatable—this episode combines real talk on mental health and self-worth with moments of levity, wisdom, and deep friendship between Jay and Lilly.

For listeners:
If you find yourself struggling with the need for external approval, feeling like you’re not enough, or simply want practical ways to build inner confidence, Lilly Singh’s journey and Jay’s insights will leave you feeling seen, empowered, and ready to embrace all parts of yourself.

Next Episode Recommendation:
Jay recommends his conversation with Tom Holland on overcoming social anxiety, especially while sober—an exploration of authenticity in uncomfortable settings.