Key Moments

Lilly Singh: My Deepest Insecurities Led To My Greatest Achievements | E136

The Diary Of A CEOThe Diary Of A CEO
People & Blogs6 min read90 min video
Apr 21, 2022|249,017 views|6,161|564
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TL;DR

Lilly Singh discusses how insecurities fueled her success, the challenges of late-night TV, and embracing her disruptive nature and personal growth.

Key Insights

1

Childhood feelings of disappointment, particularly as a second daughter in an Indian family, instilled a deep-seated need to prove herself, acting as a significant motivator throughout her career.

2

The desire for power and influence stemmed from observing men as decision-makers in her upbringing, driving her to achieve visibility through money and influence to gain their understanding of value.

3

YouTube provided a creative outlet and a sense of community, fueling an obsessive drive for success measured by metrics, which, while difficult, led to significant achievements.

4

Singh identifies as a 'disruptor,' a core part of her identity that drives her to challenge norms and break systems, leading to numerous 'firsts' for women of color and the LGBTQ+ community in media.

5

Her experience on a late-night show, despite its historic nature, was challenging due to system constraints, leading to a realization about the importance of passion, fun, and creative control over superficial achievements and external validation.

6

The pandemic forced introspection, leading to the concept of building a strong internal foundation, symbolized by a triangle, to maintain stability independent of external validation and work.

7

Breathwork and meditation have been crucial for managing anxiety and panic attacks, helping to regulate her nervous system and cultivate a healthier relationship with herself.

8

Challenging the all-or-nothing mindset, particularly in friendships and romantic relationships, is an ongoing process of learning to embrace imperfection and compromise for genuine connection.

9

Redefining success beyond accolades and external validation to a state of inner completeness and the ability to forgive oneself and others is a key tenet of her personal growth.

10

Navigating the conflict between personal creative vision and industry compromises, especially as a minority storyteller, requires strategic negotiation to achieve progress.

THE ROOTS OF AMBITION: CHILDHOOD INSECURITIES AND THE QUEST FOR PROOF

Lilly Singh shares how her upbringing as a second daughter in an Indian family, where she felt like a disappointment, profoundly shaped her drive. The societal expectations for girls instilled a deep-seated need to constantly prove her worth, a 'chip on her shoulder' that fueled her pursuit of power and influence. This motivation was amplified by observing men as the primary decision-makers in her culture, leading her to believe that money, power, and influence were the only metrics that would garner respect and recognition.

YOUTUBE AS A CATALYST: CREATIVITY, OBSESSION, AND THE METRIC GAME

Discovering YouTube offered a crucial outlet for creativity, something she felt societal norms discouraged in adulthood. This led to an obsessive dedication to mastering the platform, tracking every metric with spreadsheets, a behavior that, while detrimental in some ways, was instrumental in her early career success. This phase highlights the dual nature of obsessive ambition, especially when tied to quantifiable results, and the significant hustle required to gain traction in the early days of online content creation.

THE DISRUPTOR IDENTITY: CHALLENGING NORMS AND FORGING PATHS

Singh identifies her core purpose as a 'disruptor,' constantly questioning established norms and finding new ways to approach challenges. This identity, evident from her tomboy childhood to her groundbreaking media career, led her to break barriers as the first woman of color with a network talk show. Initially resistant to the pressure of being a 'first,' she has come to embrace this disruptive nature as integral to her being, driven by a need to challenge existing systems and molds.

THE LATE-NIGHT TRIAL: NAVIGATING SYSTEMS AND THE QUEST FOR FUN

Her experience hosting a late-night show, while historically significant, was fraught with systemic limitations that hindered her ability to truly innovate. Despite initial intentions to break the mold, she found herself constrained by the show's structure, resources, and predetermined formats. This led to a profound lesson: the importance of pursuing projects that are fun and passionate, rather than those driven by obligation, ego, or external validation, principles she now prioritizes.

BUILDING A FOUNDATION: THE PANDEMIC, INTROSPECTION, AND THE TRIANGLE

The pandemic forced Singh into a period of intense self-reflection, where she confronted a fear of lacking intrinsic value outside of her work. This led her to develop a concept of building an unshakeable internal 'foundation,' symbolized by a triangle—the strongest geometric shape. This foundation, built on pillars like relationship to self and understanding disruption, aims to provide stability independent of external achievements or life's fluctuations.

THE JOURNEY TO SELF-ACCEPTANCE: FORGIVENESS, AMBITION, AND RELATIONSHIPS

A significant part of Singh's growth involves learning to forgive herself and others, stemming from her initial high expectations and difficulty in extending grace. She has worked to redefine success not by external measures but by internal completeness and the ability to love herself unconditionally. This journey has also reshaped her approach to relationships, emphasizing authenticity, compromise, and finding partners who offer balance rather than mere reflection.

REDEFINING SUCCESS AND NAVIGATING CRITICISM

Singh articulates a shift in her definition of success from external validation and accolades to a state of inner peace and completeness. She emphasizes the importance of self-awareness and personal growth, acknowledging that external achievements are supplementary rather than defining. Both her own internal struggles and external criticism, particularly regarding projects she poured her heart into, have taught her resilience and the necessity of grounding her self-worth internally.

THE STRENGTH OF BREATH AND MINDFULNESS

Experiencing panic attacks led Singh to explore breathwork and meditation, which she describes as life-saving tools for managing anxiety and grounding herself. These practices are not just spiritual pursuits but scientific methods for regulating the nervous system. Meditation, in particular, is viewed as a crucial act of self-love and a commitment to understanding oneself, even when facing uncomfortable thoughts or emotions, fostering a healthier relationship with herself.

LESSONS IN FRIENDSHIP AND ROMANTIC COMMITMENT

Singh candidly discusses her struggles with an 'all-or-nothing' approach to friendships, where rigid definitions and high expectations initially hindered deep connections. She has learned to embrace a more organic and less perfectionistic view of relationships. Similarly, she initially resisted romantic commitment, perceiving it as restrictive, but now applies the concept of designing relationships that work for both individuals, emphasizing mutual understanding and shared values over preconceived notions.

EMBRACING IMPERFECTION AND UNLEARNING LABELS

A crucial aspect of Singh's evolution is unlearning the tendency to label herself and others, recognizing how these labels can become prisons. She advocates for embracing imperfection, extending grace, and understanding that personal growth involves a continuous process of unlearning and adapting. This perspective extends to how we view societal expectations, encouraging empathy for differing contexts and experiences rather than immediate judgment.

THE FUTURE OF STORYTELLING AND AUTHENTIC VALUE

Looking ahead, Singh's goals are centered on elevating underrepresented voices through storytelling, whether acting, producing, or writing. She is passionate about creating stories for everyone, believing in their power to foster self-understanding and connection. This focus on authentic creative expression, devoid of the pressure of external validation, represents the culmination of her journey towards embodying her true self and values.

Common Questions

As a second daughter in an Indian family, Lilly learned early on that there were specific rules and expectations for women, and that fitting a certain mold was necessary to make people proud. She perceived being a girl as 'lesser' in her culture, which influenced her drive to prove herself.

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