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

ℹ️ EPISODE INFO

Released

April 21, 2022

Duration

1h 29m

Channel

The Diary of a CEO

Watch on YouTube

▶ Open ↗

📝 EPISODE DESCRIPTION

This is also the first instalment of The Diary of a CEO: USA. Over the coming weeks, you will get to see some incredible conversations with guests the likes of which we’ve never seen before. Bringing more value, more incredible stories, and more world-beating expertise. Lilly Singh is one of the biggest influencers on the planet who was the first woman of colour to have a syndicated talk show on network television, but after it was abruptly cancelled she’s had to start from scratch on what she wants to do and where she’s going. 0:00 Intro 01:27 Early Years - Having to prove I was worthy 07:00 The reason for starting on Youtube 13:14 What helps you when you’re going through pain 16:38 The skill that made you different 19:58 Why are you wired to be disrupted? 26:03 Do you think you are enough? 31:15 Advice when stuck at a crossroads 35:50 Your late-night talk show 42:50 The impact criticism had on you 53:36 What happened after the show got cancelled? 01:01:52 What makes up the foundation of your life? 01:04:25 Panic attacks, meditation, and breath works 01:08:41 Struggling to form friendships 01:15:11 What does success mean to you? 01:16:31 Relationships and expectations 01:20:41 What's the hardest question you could be asked? 01:27:10 Our last guest's question Lilly: https://www.instagram.com/lilly/ https://www.youtube.com/channel/UCfm4y4rHF5HGrSr-qbvOwOg Lilly’s book: https://www.amazon.com/Be-Triangle-Being-Getting-Shape/ Listen on: Apple podcast - https://podcasts.apple.com/gb/podcast/the-diary-of-a-ceo-by-steven-bartlett/id1291423644 Spotify - https://open.spotify.com/show/7iQXmUT7XGuZSzAMjoNWlX FOLLOW ► Instagram: https://www.instagram.com/steven/ Twitter: https://twitter.com/SteveBartlettSC Linkedin: https://www.linkedin.com/in/steven-bartlett-56986834/ Sponsors: Huel - https://my.huel.com/Steven Craftd - https://bit.ly/3JKOPFx Location courtesy of The Nightfall Group: www.nightfallgroup.com

🎤 SPEAKERS

• Steven Bartlett

  host

• Lilly Singh

  guest

• Narrator

  other

🧾 EPISODE SUMMARY

In this episode of The Diary of a CEO, featuring Steven Bartlett and Lilly Singh, Lilly Singh: My Deepest Insecurities Led To My Greatest Achievements | E136 explores lilly Singh Turns Insecurity, Disruption, And Failure Into Fierce Self-Belief Lilly Singh traces how being born a “disappointment” in a traditional Indian family created a lifelong chip on her shoulder that fueled her obsession with power, influence, and achievement. She explains how YouTube success, late-night TV, and constant ‘firsts’ were driven by insecurity, disruptive instincts, and ego as much as by purpose. The late-night show became a painful lesson in misalignment, burnout, public criticism, and anxiety, ultimately forcing her to question her identity, labels, and definition of success. Through the pandemic and deep inner work, she rebuilt her foundation around self-worth, spirituality, breathwork, and a new philosophy captured in her book “Be a Triangle,” aiming now for aligned creativity rather than external validation.

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