Lilly Singh — Indian-Canadian YouTube pioneer turned actress and author; first woman of color and first openly queer person to host a major US late-night show (A Little Late with Lilly Singh).
The gist
Lilly Singh traces how being born a second daughter in an Indian family, treated as a disappointment, instilled a lifelong 'chip on her shoulder' and a drive to disrupt and prove herself worthy. She explains why she became obsessed with YouTube metrics, why she eventually left a 14-million-subscriber channel to grow, and how her late-night show became a heartbreaking experience of compromise, criticism, and anxiety. She describes developing panic attacks, finding relief in breath work and meditation, and the self-work she did during the pandemic that became her book Be a Triangle. She closes on relationships, her inability to forgive rooted in not forgiving herself, and learning that knowing you're enough is the foundation of real ambition.
Big reveals
- Her great-grandparents in India weren't told of her birth for two weeks because 'if it's not a son it's not worth calling home about.'
- She announced her first world tour in India and visited her grandfather, who greeted her with a flower garland saying 'I was wrong, you have made this family more proud than anyone else.'
- She admits she's not proud of her late-night show and that she rode the historic headline while the work couldn't back it up, breaking her heart every day.
- The single episode of 96 she didn't pre-watch (the Jessica Alba interview) contained a turban joke that got her dragged online the next day, her lowest point.
- She developed anxiety and panic attacks during season one of the late-night show, having never been an anxious person before.
- When the network cancelled her show, her gut reaction was relief, signaling the universe did her a favor she'd never do for herself.
- She says her goal is to never write another book, meaning Be a Triangle would be a permanent blueprint for her life.
Things worth remembering
- She kept physical spreadsheets on her wall tracking daily views and subscribers in 2010 before YouTube had complex analytics.
- Her parents gave her one year to make YouTube work or she'd go to grad school.
- She shot 96 episodes in three months, two to three a day, while traditional late-night hosts do one a day.
- Her rule: don't take advice from people criticizing you 'from inside their comfort zone' who've never done the thing.
- The triangle is her metaphor because adding to a triangle keeps it a triangle, while adding to a square or circle changes the shape.
- Her four foundation pillars: relationship to yourself, relationship to the universe, understanding distraction, and implementing design.
- Her therapist explained her panic attacks come from an obsessive, all-or-nothing personality that pushes her nervous system into overdrive.
- She calls her parents by their first names, not 'mum and dad,' reflecting an emotionally distant upbringing.
- She tells new partners upfront that if they betray her trust she will struggle to forgive them, rooted in not forgiving herself.
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Be a Triangle
Lilly Singh
“the biggest silver lining was the work i was forced to do on myself and is when i wrote this second book be a triangle” — Lilly Singh 00:59:23Find it on Amazon
How to Be a Bawse
Lilly Singh
“i built an entire brand out of hustling anyone that knows anything about me it's a hustle harder hustle she wrote how to be a boss or first book” — Lilly Singh 00:25:21Find it on Amazon
A Little Late with Lilly Singh
Lilly Singh
“welcome to the first episode of a little late with lilly singh you got given a late night show” — Diary of a CEO 00:00:18Find it on Amazon