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Jay Shetty Podcast

How To Destroy Your NEGATIVE THOUGHTS & Achieve Anything You Want | Lilly Singh

Jay Shetty sits down with Lilly Singh to talk about breaking free from the norm and knowing how to become the person you want to be. Our society often has rules, standards, and systems that are seen as absolute, unbending, and necessary.

Lilly SinghguestJay Shettyhost

Apr 4, 20221h 12mWatch on YouTube

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CHAPTERS

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Chapter summaries

Lilly’s parents, protection, and the lens of generational context
Lilly reflects on how her parents’ worries come from a desire to protect her, not from a lack of love. She frames their mindset as shaped by the realities they grew up with and the world they were trying to navigate.
- •Lilly says her parents’ concerns were rooted in wanting to protect her from the world
- •She emphasizes that protective reactions can be misunderstood as lack of support
- •She hints at how perspective changes over time as you understand family context
Jay welcomes Lilly back and frames the conversation around her new book
Jay introduces Lilly Singh and highlights her creative career and upcoming projects. He sets up the episode as a deep dive into her book and the personal work behind it.
- •Jay describes Lilly’s work across entertainment and digital platforms
- •He introduces the book and encourages listeners to engage with it
- •Their friendship and shared history becomes part of the interview tone
Why “Be a Triangle” — building a foundation when work stops defining you
Lilly explains why she fought to keep the title “Be a Triangle,” tying it to a realization she had when her usual work structures disappeared. She describes feeling unmoored when she couldn’t measure her value through events and productivity, and how the triangle represents a strong foundation for life.
- •Lilly says she had to fight her team/publisher to keep the title
- •She describes COVID as a moment where work disappeared and her sense of value collapsed
- •She realized she lacked a clear belief/value foundation beyond achievements
- •She uses the triangle as a metaphor for building a strong base to hold life experiences
Where our value systems come from: culture, school metrics, and survival mindset
Jay asks where people learn to tie self-worth to external markers, and Lilly traces it through cultural expectations and schooling. She contrasts being measured by grades and promotions with rarely being validated for qualities like patience and mental growth.
- •Lilly connects values like degrees, marriage, and kids to cultural expectations
- •She attributes her parents’ worldview to survival and limited resources in their upbringing
- •She notes school and work reward measurable outcomes more than inner growth
- •She describes rethinking a past “chip on her shoulder” about her culture after therapy
Dismantling the value system: honesty about money, validation, and the fear of losing it
Jay and Lilly explore how hard it is to examine what you truly value, especially when it’s socially uncomfortable. Lilly shares that she caught herself “performing” honesty even while writing alone, and reframed achievements as consequences of values rather than the source of worth.
- •Lilly describes how scary it feels to question what drives your happiness
- •She admits she cares about things like money and status, and stresses being honest about it
- •She reframes awards and metrics as consequences of values, not personal value itself
- •She describes the difficulty of doing this work because there’s no clear roadmap
“Home” as a mental place: safety, no judgment, and changing the mirror dialogue
Lilly explains why “home” isn’t a building but a feeling of safety and reset, especially after COVID isolation. She describes how self-criticism can make “coming home” difficult, and why she’s learning to give herself permission to be human.
- •Lilly defines home as safety, security, no judgment, and a mental reset
- •She says being physically at home during COVID didn’t always feel like being ‘at home’
- •Jay notes how people often criticize themselves in the mirror; Lilly agrees
- •Lilly describes creating an internal space where she stops self-judgment and allows humanity
All-or-nothing thinking, control, guilt, and learning to let imperfect moments be good
Lilly links her harsh inner critic to an all-or-nothing mindset and a desire for control. She gives a personal example of perfectionism around hosting, and explains how guilt and rigidity can ruin experiences instead of supporting growth.
- •Lilly describes herself as ‘all or nothing’ and connects it to control
- •She gives an example of feeling an evening is “ruined” when something goes off-plan
- •She talks about replacing perfection demands with celebrating “really good” outcomes
- •Jay shares how guilt blocked his growth; Lilly relates it back to the ‘home’ concept
Allowing yourself to evolve: redefining success beyond achievements
Jay and Lilly discuss the fear of changing your beliefs and the tendency to label past selves as “wrong.” Lilly explains how her definition of success expanded to include happiness and fun, without rejecting ambition or hard work.
- •Lilly rejects rigid “right vs wrong” labeling when people evolve
- •She describes how her definition of success changed from possessions and accolades to include happiness and fun
- •She emphasizes evolution without calling the past version of herself ‘wrong’
- •They critique the internet’s tendency to force either/or identities instead of complexity
Coming out to family: expectations, compassion in both directions, and repairing closeness
Jay reads a vulnerable passage from the book, and Lilly describes coming out as bisexual to her family and the emotional aftermath. She explains how she planned for extremes, struggled with the in-between response, and later recognized she needed to offer compassion to her parents’ context too.
- •Lilly shares she came out to herself shortly before coming out to her family
- •She describes preparing for extreme outcomes and being thrown by a nuanced reality
- •She admits she was dismissive because her parents didn’t respond with the exact script she expected
- •She reflects on distancing herself due to insecurity and fear of disappointing others
- •She frames her parents’ concerns as protection shaped by their upbringing and circumstances
Meditation that works for her: music, checking in, universe-connection, and redefining distraction
Jay asks about Lilly’s current meditation practice, and she explains how she made it flexible and personal. She uses music rather than guided tracks, checks in with herself, connects to the universe to reduce vanity and control, and reframes distraction as anything that pulls her away from her intended inner “home.”
- •Lilly says rigid daily routines didn’t work for her; she meditates a few times per week
- •She meditates to music (including Janavi’s), saying guided meditations don’t work for her
- •She starts by focusing on four themes: self-relationship, universe-relationship, distraction, and design
- •She defines distractions as states like pettiness, comparison, and ingratitude that pull her from where she wants to be spiritually
- •She describes sending compassion and ‘love and light’ outward, including to contestants she judged
Implementing design and unsubscribing from unhelpful ideas
Lilly explains “implementing design” as blending practicality with spirituality—stopping the mental loop of why something can’t happen and designing life to make it possible. She and Jay discuss how both once believed certain callings couldn’t be “real jobs,” and how unsubscribing from those ideas changed their paths.
- •Lilly describes designing life intentionally rather than rehearsing limitations
- •She gives an example of rejecting the belief that creativity can’t be a career
- •She calls many social expectations ‘invisible contracts’ people sign without realizing
- •Jay shares his own experience of unsubscribing from treating teaching wisdom as only a hobby
- •They agree these are ideas—not facts—and question who wrote the rulebook
The “missed calls from the universe”: loss, exchange, and quarantine as a catalyst
Jay asks about Lilly’s concept of missing signals from the universe, and she ties it to how people interpret failure and loss. She explains that painful moments often contain an exchange—something lost and something gained—and describes quarantine as the most recent period where she felt derailed but gained the space to do deep inner work.
- •Lilly says people often assume the universe is against them during sadness and setbacks
- •She reframes experiences as an exchange: loss paired with some form of gain or learning
- •She encourages reflecting on what difficult past moments gave you, not just what they took
- •She describes quarantine as a time she felt lost physically and professionally, but it forced reflection
- •She calls the book a gift that came from that pause and inner work
Making fun non-negotiable: breaking the climb habit and being present
Lilly explains how she now makes joy a core requirement for commitments, placing “Make sure you have fun” at the center of her vision board. She describes how the ‘climb’ can become a habit that persists even after you’ve earned the ability to choose, and reflects on missing presence during a major tour due to perfectionism.
- •Lilly says her vision board is placed where she’ll see it daily, and the center is ‘Make sure you have fun’
- •She describes saying no to opportunities that won’t include fun, even if they seem impressive
- •She reflects on doing gigs she didn’t care about to ‘earn stripes,’ then keeping the grind habit afterward
- •She shares regret about not remembering moments from a major tour because she focused on perfection
- •Jay echoes that earning stripes isn’t the issue—the habit of postponing joy is
Final Five: defining purpose as disruption, redefining friendship, and making context mandatory
In the closing rapid-fire segment, Lilly shares advice she lives by, rejects “this is how it’s always done,” and defines her purpose as being a disruptor. She also explains how she changed her view of friendships formed only “before fame” and argues the world needs a stronger commitment to context in judgment, debate, and decision-making.
- •Lilly shares a guiding quote about not letting the past define you, but letting it shape who you become
- •She calls ‘this is how it’s usually done’ some of the worst advice across life domains
- •She defines her current purpose as being a disruptor of systems, ideas, and storytelling norms
- •She explains she no longer values friendship only based on knowing someone before fame; she values building new history
- •She proposes making ‘context’ a required habit/law to reduce conflict and rushed judgment

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