Lilly Singh: Stop Trying to Prove Yourself to Everyone Else! (#1 Mindset Shift to Build REAL Confidence & Self-Worth)
In this episode of On Purpose with Jay Shetty, Lilly Singh shares her approach to personal growth and self-acceptance. She explains how she manages different aspects of her personality by naming her inner voices, uses tools like ChatGPT to process her thoughts, and practices self-compassion through nightly journaling. Singh also describes her transition from seeking external validation to focusing on proving herself right.
The conversation explores Singh's experience as a woman of color in entertainment, including her role as a late-night show host and her work addressing cultural taboos. She discusses managing pressure as a representative of multiple communities while maintaining her mental health, and shares insights about her film "Doing It," which aims to normalize conversations about women's sexuality and autonomy, particularly for women of color.
This is a preview of the Shortform summary of the Sep 17, 2025 episode of the On Purpose with Jay Shetty
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1-Page Summary
Personal Growth, Self-Acceptance, and Authenticity
Lilly Singh discusses her journey of personal growth, explaining how she manages different aspects of her personality by naming her inner voices. She uses tools like Chat GPT to differentiate between critical and positive thoughts, treating these voices as aspects of herself rather than defining traits. Through this practice, Singh demonstrates how she's learned to embrace all parts of her identity.
Singh describes her shift from believing she needed to commit to a specific life path to embracing continuous learning and exploration. With help from her therapist, she's learned to separate her identity from her accomplishments. She emphasizes the importance of self-compassion, sharing how she uses nightly journaling to recognize acts of self-kindness.
Navigating Cultural Expectations and Pressures
Singh reflects on her early career motivations, which were driven by a desire to prove doubters wrong and achieve conventional success markers. She describes moving away from seeking external validation to focusing on proving herself right. Growing up with cultural gender norms that discouraged outspoken women, Singh learned to challenge these limitations and create her own path, particularly through her YouTube career.
Overcoming Challenges in High-Profile Creative/Entertainment Roles
As a trailblazer in various fields, Singh shares with Jay Shetty the complexity of being "first" - particularly as one of the first women of color and bisexual women to host a late-night show. She describes the anxiety of working without a roadmap while managing intense pressure from various communities she represents. Despite these challenges, Singh continues to pursue creative ambitions while maintaining focus on personal growth and mental health.
Addressing Cultural Taboos and Empowering Women's Narratives
Singh discusses her film "Doing It," which challenges cultural silence around women's sexuality. The movie tackles taboo subjects and aims to normalize conversations about sexual autonomy, particularly for women of color. Through her work, Singh advocates for better education about women's health and wellness, while empowering women to reject limiting cultural expectations and embrace their authentic selves.
1-Page Summary
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Counterarguments
- While naming inner voices can be helpful, some might argue that over-reliance on tools like Chat GPT for managing thoughts could potentially reduce a person's ability to self-reflect without technological assistance.
- Embracing all parts of one's identity is commendable, but some may point out that certain negative traits or behaviors should not be embraced but rather worked on and improved.
- The idea of separating identity from accomplishments is powerful, yet some might suggest that accomplishments can be a healthy part of one's identity if they are aligned with personal values and not solely based on external validation.
- Nightly journaling is a beneficial practice for many, but others might find that it doesn't suit their lifestyle or that other methods of reflection are more effective for them.
- While moving away from external validation is generally seen as positive, some could argue that external feedback can still play a crucial role in personal and professional development when taken in a constructive manner.
- Challenging cultural gender norms is important, but there might be a counterargument that suggests working within cultural frameworks to effect change can sometimes be more effective than outright rejection of those norms.
- Being a trailblazer is inspiring, yet it's also worth considering that not everyone aspires to be "first" or to take on the pressures that come with it; some may prefer to contribute in less conspicuous ways.
- Addressing cultural taboos is necessary, but there could be a perspective that emphasizes the need for sensitivity and respect for different cultural contexts and values when discussing such topics.
- Advocating for women's health and wellness is crucial, but some might highlight the importance of including diverse voices and experiences within that advocacy to avoid a one-size-fits-all approach.
Actionables
- Create a personal avatar to embody your aspirations and use it as a motivational tool by drawing or designing a character that represents the person you want to become, focusing on traits like resilience, creativity, or compassion. Place this avatar in a visible spot in your home or workspace to remind you of your goals and the qualities you're striving to embody.
- Start a "bravery log" to document instances where you challenge your comfort zone or societal expectations, such as speaking up in a meeting, trying a new hobby, or expressing an unpopular opinion. Review this log monthly to see your progress and to reinforce the value of personal growth over external validation.
- Organize a "self-compassion swap" with friends or family where you share stories of self-kindness and support each other's journey towards self-acceptance. This could be a monthly gathering where you discuss personal achievements unrelated to work or societal standards, focusing on acts of self-care and emotional milestones.
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Personal Growth, Self-Acceptance, and Authenticity
Lilly Singh reflects on personal evolution, self-acceptance, and the continuous journey of committing to lifelong learning and self-compassion.
Embracing all Aspects of one's Identity and Personality
Lilly Singh delves into the concept of self-acceptance by discussing the various internal "voices" she has named and identified as part of her identity. With names like Susan (her inner manager), Todd (her critic), and Badamjeet (her dictator), Singh personalizes these inner voices and acknowledges their roles in her life. She also celebrates Jellybean and River, symbols of her curiosity and loneliness respectively, and emphasizes the importance of recognizing these parts of herself as aspects rather than defining traits.
Singh explores how she manages these voices by using tools like Chat GPT, which help her differentiate between critical and positive thoughts. She personifies her self-critical and positive voices to understand when each should take prominence, illustrating self-acceptance and illustrating her path theory, where the distinct parts of one’s personality can alternately rise to the forefront or take a backseat as needed.
This practice also aids in recognizing which thoughts are not truths but simply facets of her internal dialogue. Jellybean, embodying curiosity and fun, and River, her latest voice, embodying inner loneliness, are recognized for their positive influence, and by naming these diverse parts, Singh demonstrates her journey of self-discovery. She commits to embracing all these voices within herself, valuing each as crucial to her complete identity.
Committing To Lifelong Learning and Growth
Singh recalls a time when she believed she had to commit to a specific path, thus missing out on exploration and risk-taking. Now, she aspires to rediscover and live more freely, emulating the curiosity of a child. She discusses the transformative process of learning to separate her identity from her accomplishments, crediting her therapist and AI technology like Chat GPT with guiding her toward an understanding that embraces her personal qualities independent of professional achievements.
Singh considers herself a perpetual student, embracing challenges and growth opportunities as essential building blocks for fulfillment and personal evolution. She encourages moving from the mindset of needing to 'arrive' at a destination to an 'act of being,' signifying growth and learning as an ongoing journey.
Lilly Singh advises her younger self to relish her childhood and avoid rushing into adulthood, advocating for self-compassion and the appreciation of life's stages. She accepts the changing aspects of her identity, insisting on the importance of granting oneself grace during life's transitions.
Prioritizing Self-Compassion and Giving Oneself Grace
Singh emphasizes the importance of self-compassion, celebrating personal resilience and accomplishments, and advising the practice of chronicling past successes to bolster self-esteem. Singh uses a nightly journalin ...
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Personal Growth, Self-Acceptance, and Authenticity
Additional Materials
Counterarguments
- While personifying internal voices can be helpful for some, others may find it confusing or less effective than other therapeutic techniques.
- Tools like Chat GPT can be beneficial, but they may not replace the nuanced understanding and personalized guidance of a human therapist.
- Embracing all aspects of one's identity is important, but it's also crucial to work on changing or improving aspects that may be harmful or unproductive.
- Lifelong learning is valuable, but it's also important to recognize and accept that there may be times when it's okay to feel content with one's current level of knowledge or skill.
- Advising growth as an ongoing journey is a positive mindset, but some individuals may find fulfillment in setting and reaching specific goals or destinations.
- Self-compassion is essential, but it should be balanced with accountability to ensure personal growth and responsibility for one's actions.
- Celebrating personal resilience and accomplishments is good for self-esteem, but it's also important to remain humble and grounded.
- Reducing self-criticism is beneficial, but a certain level of self-critique is necessary for self-improvement and avoiding comp ...
Actionables
- You can create a "Voice Gallery" in a journal where you draw or describe different internal voices as characters, assigning them names and roles based on their nature, such as "The Optimist," "The Realist," or "The Critic." This visual and narrative approach helps you acknowledge and understand the diversity of your thoughts, making it easier to engage with them constructively.
- Start a "Growth Tracker" where you log daily or weekly challenges you've faced and the lessons learned from them. Use a simple notebook or digital app to record these experiences, focusing on the growth aspect rather than the outcome. This habit reinforces the concept of growth as a journey, encouraging you to appreciate progress over perfection.
- Implement a "Self-Kindness Alarm" by setting ...
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Navigating Cultural Expectations and Pressures
Lilly Singh provides insight into how she navigated societal conditioning, gender norms, and the burden of representation in her career and personal life.
Deconstructing the Societal Conditioning to Seek External Validation
Lilly Singh reflects on her early career aspirations, motivated largely by a desire to prove doubters wrong and pursue conventional markers of success like fame and money. Initially, she sought external validation, striving for influence to show she could achieve what others thought she couldn't. However, she admits that once she reached these goals and received external approval, it left her feeling hollow.
Focus On Proving Oneself Right, Not Others Wrong
Singh acknowledges the conditional validation that came with accomplishments, such as good grades or career success, which was deeply ingrained in her from a young age. She admits that her focus used to be on proving people wrong but now has shifted to proving herself right, seeking internal rather than external validation. This change reflects a move towards personal growth and fulfillment, rather than responding to what others expect of her.
Resisting Gender Norms
Defining One's Path Despite Expectations
From a cultural standpoint, Singh grew up with gender norms that suggested girls shouldn't be outspoken or the center of attention. Observations on her characteristics were often seen as a burden to be either embraced or altered. Over time, Singh learned to challenge these impositions, saying "Nah, I'm good," and refused to accept limiting beliefs placed on her. She hints at the struggle of balancing personal desires with societal expectations but ultimately pushes for the acceptance of her evolving self.
Singh recounts adhering to her parents' expectations by attending university and feeling the initial disappointment in her family for not being a son due to cultural gender preferences. This cultural pressure co ...
Here’s what you’ll find in our full summary
Navigating Cultural Expectations and Pressures
Additional Materials
Counterarguments
- While seeking internal validation is important, external validation can also play a significant role in personal and professional development, offering feedback and benchmarks for success.
- The shift from external to internal validation might not be a linear process and can coexist; external achievements can still be a source of personal pride and motivation.
- Challenging gender norms is crucial, but it's also important to acknowledge that societal change is gradual and individuals often have to navigate existing structures while advocating for change.
- Pursuing a non-traditional career path like YouTube can be empowering, but it's also worth noting that not everyone has the means or opportunity to do so, and traditional careers can be equally fulfilling for some.
- While it's important for public figures to stay true to themselves, their representati ...
Actionables
- You can start a personal growth journal to track your internal validation journey, noting down moments when you feel proud of your actions or decisions, regardless of external praise. This practice helps you become more aware of your intrinsic motivations and celebrate your personal achievements. For example, if you completed a project at work that you're proud of, write down how it made you feel and why it's important to you, not just the recognition it might receive from others.
- Create a "Challenge the Norm" jar where you write down one societal expectation you want to defy each week and then take a small step towards that goal. This could be as simple as speaking up in a meeting when you usually stay quiet or choosing an outfit that makes you feel confident even if it's not the current trend. Each slip of paper represents a commitment to personal authenticity over societal conformity.
- Develop a personal mission statement that encapsulates your values and ...
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Overcoming Challenges in High-Profile Creative/Entertainment Roles
Lilly Singh and Jay Shetty delve into the complexities of navigating high-profile creative careers, discussing the intersection of personal and professional growth, mental health, and embracing vulnerability.
Navigating Loneliness and Anxiety as a Trailblazer
Challenges Of Being the "First"
Jay Shetty acknowledges Lilly Singh's achievements as a trailblazer in various respects: being one of the earliest creators on YouTube and one of the first women of color and bisexual women to have a late-night show. Singh reveals the loneliness and scariness of not having a roadmap or previous examples to follow in her career, despite the prestige of being a pioneer. She describes the anxiety of being in uncharted territory, emphasizing how being first is both incredible and daunting. In response to Shetty's questions, Singh discusses being approached to host a late-night talk show due to the historic nature of the decision, given that no other late-night hosts looked like her at the time. Her desire to pave the way for others added complexity to the decision.
Balancing Career Ambitions With Personal Growth and Self-Care
Prioritizing Mental Health and Well-Being Despite Intense Pressure
Singh talks about the intense pressure she felt as the first bisexual woman of color to host a late-night show. She acknowledges the expectations that communities placed upon her and the personal impact of living up to those high standards. She recounts the challenging experience of hosting her late-night show, which took a toll on her mentally, emotionally, spiritually, and physically. Despite these challenges, Singh continues to engage in deep work, healing, and reflection processes. She is actively building her career, preparing for the release of her first feature film, where she presents her abilities in directing and acting. At the same time, she emphasizes the harmony of pursuing creative ambitions with maintaining personal development and mental health.
Embracing Vulnerability and Authenticity in High-Stakes Creative Endeavors
Taking Risks and Being Seen, Even When Uncomfortable
Singh evolved from her persona of being super confident and extroverted to acc ...
Here’s what you’ll find in our full summary
Overcoming Challenges in High-Profile Creative/Entertainment Roles
Additional Materials
Actionables
- Create a personal growth journal to track your journey through challenges and successes. Start by dedicating a notebook or digital document to reflect on your daily experiences, focusing on moments where you felt like a trailblazer or encountered a new challenge. Write down how you felt, what you learned, and how you can apply this to future situations. This practice will help you recognize patterns in your growth and areas where you can improve.
- Schedule regular "mental health check-ins" with yourself to maintain balance. Set aside time each week, perhaps 30 minutes, to assess your mental well-being. During this time, engage in activities that promote reflection and relaxation, such as meditation, a walk in nature, or free writing. Use this as an opportunity to consider if your current ambitions align with your personal well-being and make adjustments as necessary.
- Embrace a "vulnerability challenge" where you share something auth ...
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Addressing Cultural Taboos and Empowering Women's Narratives
Lilly Singh’s work in film and media challenges traditional norms around women’s sexuality and autonomy, aiming to empower women, especially women of color, to reclaim their stories and embrace their identities.
Challenging Shame and Silence Around Women's Sexuality and Autonomy
Lilly Singh written and stars in a sex comedy "Doing It," which tackles the taboos associated with sex. The film plays a significant role in challenging the cultural silence and shame surrounding topics of sex, exemplified by a personal conversation Singh had with her mother discussing the movie's content. In an attempt to normalize the conversation on sexual autonomy, "Doing It" includes scenes that openly address the use of a vibrator and masturbation.
Art and Media Exploring Female Sexual Empowerment and Pleasure
The themes within "Doing It" dive deep into sexual education and empowerment, focusing on the perspectives of Indian culture and the unique experiences of women of color. Singh's commitment to these themes is further illustrated when she gave out vibrators after a South by Southwest screening, signaling her support for female sexual empowerment and her stance against taboos surrounding women's sexuality.
Addressing the Education Gap in Women's Health and Wellness
Singh emphasizes the lack of education about the body and the concept of pleasure for women, especially women of color. This insufficient knowledge often leads to discomfort and shame, which the film, "Doing It," seeks to challenge. It strives to destigmatize women's experiences and normalize the healthy exploration of their sexuality.
Normalizing and Destigmatizing Women's Experiences, Especially for Women of Color
The movie’s narrative focuses on a 30-something-year-old virgin, confronting and subverting traditional expectations imposed on women concerning sexual knowledge and experience. By not making the virgin the butt of the joke, the film positions her as a character reclaiming her narrative and redefining societal standards.
Empowering Women to Reclaim Their Stories and Self-Definition
Singh reflects on the path laid out for her, acknowledging the limited options available to the women who came before her. She recounts her first YouTube video as a moment of authenticity and rebellion, contributing to her journey of self-e ...
Here’s what you’ll find in our full summary
Addressing Cultural Taboos and Empowering Women's Narratives
Additional Materials
Counterarguments
- While Singh's work is empowering for many, some may argue that her approach to challenging taboos might not resonate with or be appropriate for all audiences within the diverse spectrum of Indian culture and women of color.
- The act of giving out vibrators at a screening, though symbolic of sexual empowerment, could be seen as a controversial or provocative gesture that might not align with everyone's personal or cultural values.
- The focus on sexual empowerment and education, while important, might overshadow other critical aspects of women's health and wellness that also require attention and education.
- The narrative of a 30-something-year-old virgin reclaiming her story could be criticized for perpetuating the idea that virginity is a significant aspect of a woman's identity or value.
- Some may argue that the film's portrayal of sexual autonomy and empowerment does not fully account for the complexities of consent and the diverse experiences of women with different sexual orientations and identities.
- Singh's personal journey of rejecting gendered expectations and prioritizing her narrative might not be a feasible path for all women, especially those in more restrictive or conservative environments.
- The emphasis on individual narrative and self-def ...
Actionables
- You can start a personal journal to explore and document your thoughts on sexuality and autonomy, focusing on how societal norms have influenced your perspective. Writing down your experiences and feelings can help you understand your own narrative better and identify areas where you might want to challenge existing taboos or expectations. For example, if you've felt uncomfortable discussing sexual health, journaling could be a safe space to express and work through those feelings.
- Create a private book club with friends to read and discuss literature that addresses women's sexuality and empowerment. Choose books that tackle these themes from various cultural perspectives, including those of women of color. This can be a supportive environment to learn from each other's experiences and broaden your understanding of sexual autonomy. For instance, you could start with a book like "The Vagina Monologues" by Eve Ensler and discuss how it resonates with your personal experiences.
- Engage in self-education by curating a list o ...
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