The Diary of a CEOLilly Singh: My Deepest Insecurities Led To My Greatest Achievements | E136
CHAPTERS
- 1:00 – 3:30
Early Life: Born a ‘Disappointment’ and Learning Gendered Rules
Lilly describes her childhood in a traditional Indian family where her birth as a second daughter was seen as a letdown. She internalized strict expectations of how girls should behave while simultaneously feeling rebellious and craving something different.
- •Grandparents weren’t told of her birth for weeks because she wasn’t a boy.
- •Childhood lessons: there were rigid rules and expectations for women (e.g., don’t talk too much, don’t whistle).
- •She felt accepted, but sensed she had to fit a mold to make disappointed relatives proud.
- •Early tension between conforming to expectations and her rebellious, expressive nature.
- 3:30 – 9:00
Chip on the Shoulder and the Drive for Power and Influence
She connects the devaluation of girls in her upbringing to a lifelong chip on her shoulder and need to prove her worth. Power, money, and influence became her chosen language to gain respect from the men who controlled decisions in her family and culture.
- •Realizes as an adult that a deep-seated chip on her shoulder has driven nearly all her pursuits.
- •Wanted to prove that being a girl was worthy of celebration.
- •Men around her understood power, money, and influence more than intangible impact or purpose.
- •Achievements like Forbes lists or having her own show finally made male relatives ‘go wide-eyed.’
- 9:00 – 25:00
Discovering YouTube: Obsession, Spreadsheets, and Creative Freedom
While in university and applying to grad school, Lilly discovered YouTube as a way to be creative without gatekeepers. Her obsessive personality and data-driven mindset kicked in, turning a small channel into a global platform—at a psychological cost.
- •Stopped writing a grad school essay she didn’t care about and told her parents she wanted to make videos.
- •Parents gave her one year to try YouTube before going back to grad school—a motivating ‘ticking clock.’
- •Early views were in the low thousands; hitting 1,000 subscribers felt huge.
- •She manually tracked views and subs in wall spreadsheets, becoming hyper-obsessed with growth.
- •Recognizes now that obsession + metrics is a “bad recipe” for mental health, even if it bred success.
- 25:00 – 34:00
Disruptor Identity: Firsts, Tomboy Roots, and the Need to Break Systems
Looking back, Lilly sees a consistent pattern of disruption in her life—from being a tomboy to entering Hollywood via YouTube to being the first queer woman of color to host a late-night show. She now embraces ‘disruptor’ as her core purpose, despite its exhaustion and ego traps.
- •Self-identifies her life’s throughline in one word: disruptor.
- •Examples: tomboy kid, outspoken in rooms of uncles, entering entertainment via YouTube instead of traditional routes, then late-night firsts.
- •Initially hated always being ‘the first’ and the pressure it brought.
- •A visit to her grandfather, who once didn’t want to know about her birth, ends with him saying he was wrong—validating disruption’s power.
- •Acknowledges disruption is fueled both by injustice and by ego; success is addictive and can drive endless ‘more’.
- 34:00 – 1:00:00
Reframing Pain, Purpose, and Being ‘Enough’
The conversation shifts to how people reframe past trauma as necessary in hindsight, but still perceive current pain as intolerable. Lilly shares how she uses logic, her 100% success rate of surviving hardships, and a sense of purpose to push through, while rethinking what it means to be enough without losing ambition.
- •She’d change nothing about her past, acknowledging that painful moments led to growth.
- •Humans repeatedly believe current pain is the worst, forgetting future perspective will soften it.
- •She asks: is the struggle worth it? For her, purpose makes the answer yes.
- •Initially believed that thinking ‘I’m enough’ would kill her drive; realized it actually kills fake ambition.
- •Knowing she’s enough allows her to care less about trolls and ratings, and more about telling meaningful stories.
- 1:00:00 – 1:16:00
Growth vs. Relevancy: Letting Go of Old Identities
As YouTube began feeling like a cage rather than freedom, Lilly grappled with stepping away from a massive audience and the fear of losing ‘relevancy.’ She explains that growth requires reallocating finite energy and letting go of outdated versions of herself.
- •Felt obligated to keep making the same style of videos, serving fans and the algorithm.
- •Feared losing relevancy, which modern culture treats like currency.
- •Uses a 100%-energy-per-day metaphor: energy spent maintaining old habits limits what’s left for growth.
- •Decides she can’t expect to grow and stay the same; must make space for new creative directions.
- 1:16:00 – 1:34:00
Late Night Show: Promise, Constraints, and Creative Misalignment
Lilly details the realities behind her historic NBC late-night show: rigid format rules, under-resourcing, and lack of control made it nearly impossible to ‘break the mold’ as advertised. She’s candid that she doesn’t think the show was good and that she was more proud of the headline than the work.
- •Initially turned the show down; later accepted due to historic responsibility and ego.
- •Show structurally locked into 22:23 runtime, monologue-first format, strict ad breaks, and audience expectations inherited from other hosts.
- •Tiny writers’ room, no proper showrunner, and 96 episodes in three months turned it into a quantity game.
- •Best, most authentic moments (warm-ups, mistakes) often couldn’t air due to lack of cameras or format rigidity.
- •She felt endless heartbreak knowing she couldn’t deliver a show that matched the historic promise.
- 1:34:00 – 1:51:00
Backlash, Anxiety, and Learning Whose Opinions Matter
The emotional toll of season one peaked when a single unreviewed episode triggered severe backlash from the Sikh community after an offhand joke about turbans. Lilly describes spiraling guilt, renewed perfectionism, and developing anxiety and panic during the show’s run.
- •Skipped reviewing exactly one episode (out of 96); it contained a joke conflating towels and turbans, offending Sikhs.
- •She apologized but felt she’d betrayed the very community she wanted to uplift.
- •Experience reinforced her unhealthy belief that she must do 300% of every job to avoid disaster.
- •Reported crying heavily, dissociative moments, and panic-like symptoms in her green room.
- •Developed anxiety and panic attacks—feeling her body and thoughts out of control.
- •Began differentiating between constructive critique (from experienced peers) and invalid criticism from uninformed spectators.
- 1:51:00 – 2:06:00
Show Cancellation, Ego, and the Gift of Clarity
When the show ended after two seasons, Lilly felt both bruised ego and profound relief. She realized the universe had removed something she never truly wanted but would have forced herself to continue out of duty and pride.
- •Secretly hoped both that the show would continue (for the community) and that it wouldn’t (for her health).
- •Immediate gut reaction to cancellation was relief, signaling misalignment.
- •Recognized late night had been a distraction from her true passions: acting, producing, storytelling.
- •Ego still struggled with public rejection and optics of ‘failure.’
- •Learned to stop defining herself entirely by job labels like ‘late-night host.’
- 2:06:00 – 2:18:00
Pandemic, Identity Void, and Building the ‘Triangle’ Foundation
The pandemic wiped Lilly’s schedule, confronting her with how little value she felt without work. This catalyzed deep introspection and the creation of her ‘triangle’ framework—an internal foundation independent of external achievements, detailed in her book.
- •With gigs and projects canceled, she felt like she ‘ceased to exist’ without work.
- •Realized she had no original thoughts about what she truly valued; she’d mostly lived by others’ scripts (parents, school, society).
- •Committed to treat her life as her greatest project and build a durable inner safe place.
- •Discovered the triangle as the strongest structural shape and a metaphor: adding to it expands it without changing its essence.
- •Defined four unchanging pillars: relationship with self, relationship with the universe, understanding distraction, and implementing design.
- •Wrote “Be a Triangle” as a concise blueprint for this inner foundation.
- 2:18:00 – 2:28:00
Breathwork, Panic Attacks, and Partnering With Yourself
Lilly shares her recent experiences with panic attacks—distinct from generalized anxiety—and how breathwork and meditation became crucial tools. She reframes meditation not as stopping thoughts, but as devoting time to a relationship with herself.
- •Describes panic attacks as episodes of irrational, intrusive impulses (e.g., imagining slamming her head into a table or driving off a cliff) that feel uncontrollable.
- •Therapist explained her nervous system was in overdrive from constantly operating at “10.”
- •Breathwork helps bring the nervous system back down from 11 to a calmer state.
- •Meditation is framed as showing up for yourself, not about emptying the mind.
- •Counters common excuse ‘I can’t meditate because I have too many thoughts’ by suggesting maybe those thoughts need to be heard.
- 2:28:00 – 2:35:00
All-or-Nothing Thinking, Friendships, and Unlearning Perfection in People
Lilly examines how her all-or-nothing mentality, which drove career success, sabotated friendships and joy. She recounts rigid expectations for parties and friends, and how she’s learning to accept imperfection, prioritize depth, and maintain adult friendships intentionally.
- •Used to write off events or people when they didn’t match her exact expectations (e.g., one no-show makes the whole party ‘nothing’).
- •Admits this mindset eliminates celebration, progress, and nuance.
- •Struggled to form adult friendships in LA, initially valuing only friends who knew her before fame.
- •Jay Shetty modeled healthy, low-agenda friendship maintenance (check‑ins, calls without a reason).
- •Now sees that not every belief needs to be scrapped; instead she toggles which patterns serve a situation and which don’t.
- •Has about four or five real friends she can call without agenda and is satisfied with depth over volume.
- 2:35:00 – 2:41:00
Coming Out, Context, and Rejecting Simplistic Cancel Culture
Lilly revisits her coming-out story and challenges the expectation that parents must instantly respond perfectly. She emphasizes contextual empathy, especially across generations and cultures, and criticizes online cultures that deny people space to learn, evolve, or make mistakes.
- •Initially resented her parents for not immediately celebrating her coming out, despite their support.
- •Later realized it was unfair to expect people without her lived experience to respond with perfect, instant understanding.
- •Highlights that her mother didn’t grow up with queer culture, Western media, or LGBTQ+ discourse.
- •Critiques cancel culture for expecting others to operate from our experience and knowledge base.
- •Argues we must allow for learning curves and meet in the middle, rather than permanently condemning imperfect first responses.
- 2:41:00 – 2:54:00
Romantic Relationships, Forgiveness, and Being in Love With Herself
Turning to romantic relationships, Lilly is candid about being difficult to date due to high expectations and prior inability to forgive. She connects her rigid standards for partners to her own lack of self-forgiveness, and explains how working on self-love has softened her relational patterns.
- •Says exes would call out her inability to forgive and her “absurdly high expectations.”
- •Realizes she struggled to forgive others because she had never learned to forgive herself.
- •Since doing inner work and writing the book, she now finds she can actually forgive people and allow human imperfection.
- •Used to want a partner just like her—hyper-ambitious, obsessive—but now understands that would be disastrous.
- •Embraces the need for complementary partners who bring balance rather than mirrors.
- •Defines ‘properly in love’ as situations where both people become better versions of themselves; counts three such loves (self, mother, one romantic partner).
- 2:54:00
Future Vision: Storytelling, Representation, and Success Without More Labels
In closing, Lilly outlines ambitions centered on elevating underrepresented stories through acting and producing, while insisting she doesn’t want her identity to hinge on new titles. Her real goal is to maintain the inner foundation she’s built—so complete that she never needs to write another ‘blueprint’ book.
- •Current goals: act in and produce film/TV that center underrepresented voices, especially South Asian stories.
- •Believes stories are how we understand ourselves and others, so there should be stories for everyone, not just about everyone.
- •Runs a book club, Lilly’s Library, focusing on South Asian narratives.
- •Says her goal is to never need to write another book like “Be a Triangle” because the foundation will hold for life.
- •Defines success at 60 as still knowing she’s a complete human being, regardless of what did or didn’t happen career-wise.
