The last year has been one of firsts for Lilly Singh. For one, her debut feature film Doin’ It premiered at South by Southwest [SXSW]. For another, she and her mom finally had the sex talk.
In Doin’ It, which she co-wrote with Neel Patel and Sara Zandieh, Singh stars as Maya, a 30-something, Indian-American virgin who gets a job teaching high school sex ed. Great premise! But not the most comfortable one to discuss with, for example, your Indian immigrant mother, someone who never gave you “the talk” and who you realize you might need to hop on a call with after you submit a script that’ll have you in a, um, compromising position on screen.
So when she asked her mom if she was going to be OK with it, she was surprised by the response she got.
“She said the sweetest words to me, she said—I’ve never heard my mom be so evolved—she said, ‘Are you OK with it?’ And I went, ‘I am.’ She goes, ‘Then I think it’s fine,’” Singh laughs. “And my mom actually helped me with some of the movie on set. She’s making sex jokes, and I’m like, ‘What’s happening? We’ve opened up the matrix!’”
If you’re not among the 14.4 million subscribers who followed Singh’s early career on YouTube (where her parents’ strictness was a fairly common theme), maybe you know her from her NBC late-night show, A Little Late with Lilly Singh, or from The Muppets Mayhem on Disney+ (she was the human).
Or maybe you don’t know her yet—though we’d wager you’re about to.
Meet Lilly Singh
Singh was born and raised in Toronto’s Scarborough district and is a self-described tomboy with a creative flair and an unflagging spirit. Her career began on YouTube in the early 2010s, when, then using the name Superwoman, she started filming short skits and first-person videos that shared her experiences as a first-generation Indian-Canadian.
The silly sketches landed with an audience of young brown girls who saw themselves reflected in Singh’s humor, and she became one of the emerging video platform’s earliest stars. But she hasn’t posted new skits to that channel in years; she’s been busy writing and filming and producing. There’s Doin’ It; there are her two bestselling books; and there’s Unicorn Island, her combination production company and charitable fund.
Singh is a true multi-hyphenate… which is why being called a “YouTuber” today can sometimes be a source of frustration. “Sometimes, when I read a headline or read anything about myself, it’ll say ‘YouTuber,’ and I was trying to figure out why that unsettles me,” Singh says. It’s a perception she’s been battling since she stepped away from the platform to pursue new passions.
In December, for example, she was the subject of a Washington Post profile that asked, “Where does Lilly Singh go from here?” The piece was an in-depth and personal look at her career highs and lows following the cancellation of her NBC late-night show. Then, you get to the correction at the bottom of the piece: “A previous version of this story incorrectly stated that Singh still regularly produces content for her YouTube channel.”
“I think it unsettles me just because I think, naturally, everyone wants to grow. Everyone wants to evolve,” she continues. “And everyone wants to be described in a way that’s accurate to what they’re doing right now.”
YouTuber? It’s not that Singh resents or regrets that career—it was empowering to run and grow her own media company, and she was an inspiration to a legion of young women who followed her, including actress Iman Vellani, aka Ms. Marvel, who told Singh she grew up watching her videos.
It’s just that it feels reductive. No one these days, she quips, is calling Justin Bieber a YouTuber.
Doin’ It, for example, is the first feature film from Singh’s Unicorn Island Productions, which also produces an animated children’s series (The Mindful Adventures of Unicorn Island) and has a drama (Arzu, starring Bridgerton’s Charithra Chandran) in the works. On the charitable side, the Unicorn Island Fund is empowering girls and women in India to overcome shame and unleash their full potential.
Lilly Singh: A storyteller
“Really, what I do is, I’m a storyteller,” Singh says, noting that it took her some time to figure that out. “I’ve used various mediums to tell stories, whether it’s a quick video on Instagram or a feature like Doin’ It, but I believe in the power of telling stories.”
That’s why the production company and the charitable fund exist under the same Unicorn Island umbrella; both are trying to change the world by telling stories.
“And I’m trying to tell stories that look like the real world,” she says.
You can see the evolution in Singh’s life and career in the differences between her two books, 2017’s How to Be a Bawse: A Guide to Conquering Life and 2022’s Be a Triangle: How I Went From Being Lost to Getting My Life Into Shape.
In How to Be a Bawse, Singh uses stories from her career as a how-to guide for becoming a strong and confident person who’s taking control of their own life. The chapter titles alone tell a story of inner turmoil—how did the titular “bawse” get so lost?
When I mention that Singh doesn’t strike me as a person who’d need to get her life in shape, she smiles and shakes her head. “I’m not shocked to hear you feel that way, because a lot of people were like, ‘You get your life in shape? You’re all about the hustle and the goal setting and the vision boards!’” But something happened in the years after her first book hit shelves: “Years later, I was like, ‘Oh, I think I’m sad.’”
Singh’s first book explained how to work really hard and get all the things—the accolades, the career, the respect—she’d been working toward in her own life. It didn’t explain what acquiring all that success and acclaim was supposed to mean. And that’s because, Singh says now, she frankly didn’t know.
When people would ask her about herself, she found she had a habit of rattling off career highlights: I was a YouTuber; now I act; I’ve been on late night; I’m starring in these shows. She realized she’d started to feel disconnected from her sense of self, from who she really was.
Was the work supposed to define her? Was she supposed to keep hustling more and harder? Having achieved so much of what she wanted to accomplish in life, what was she supposed to feel? What number or achievement would finally make her feel as if she’d made it?
“So, Be a Triangle was really a way for me to make sense of it all: make sense of the hustle, make sense of the success, make sense of the goals,” she explains.
“Even to this day, sometimes I stress—I have 14 million Instagram followers right now, and I’m like, ‘What if it goes to 13.9?’ And what if it goes to 13.9?” she laughs. “Then what? What’s gonna happen? Someone’s gonna come revoke my success card?”
YouTube as a career
Singh is quick to tell quips like this at her own expense; she’s affable and likable, a fast talker with an easy smile who makes you feel like you’ve known each other forever. The gregarious performer you see onstage or on camera—that’s Lilly to her core.
But Singh also has a quieter side. She plays Catan online every day, and she recently started making ice cream for her friends. She bakes; she keeps a journal. And if it’s not already obvious, she puts an intense amount of pressure on herself. Her drive to succeed is immense.
In the past, that’s been out of necessity. In 2010, she was proving to her parents that she could turn YouTube into a meaningful career as a way to avoid being forced into grad school. In 2015, she moved to Los Angeles, the first person in her family to move out of the house (let alone to a different country) for a reason that wasn’t marriage. She had no choice but to make it work, to make it worth it.
At 35, Singh says she’s driven by something less concrete but perhaps more meaningful: legacy. “Maybe that’s me getting older, maybe this is me seeing younger people coming up in the industry and being like, ‘Oh my goodness, I have such a soft spot for them,’” she says. These days, Singh finds herself wanting to do whatever she can to make it so that the young brown women who come after her might have a slightly easier time than she did.
“The truth is, all the headlines about me will disappear one day… I don’t know if people will watch my YouTube videos in 30 years,” she says, smiling in a wry way that suggests, in some ways, that might almost be a relief.
Singh is tremendously proud of the work Unicorn Island has done and continues to do, and that work—both on the production and charitable sides—will continue to occupy much of her time and energy over the coming years.
But legacy is only a part of it. There’s also a renewed search for joy.
Staring in a Disney+ series
In November, The Muppets Mayhem, the Disney+ series in which Singh played the human lead, was canceled after just one season, despite the fact that the show would go on to win an Emmy for Outstanding Children’s or Family Viewing Series one month later.
The show’s cancellation felt like a huge blow. But the more Singh thought about it, the more she realized why its cancellation hit her so hard.
“I was sad about it because it was so much fun,” she reflects. “I don’t get to talk to Muppets anymore! Do you know how awesome it is to not talk to humans and talk to Muppets?”
It wasn’t about the critical acclaim, and it wasn’t about the numbers. For the first time in her life, Singh realized that she was sad about the loss of a professional role because it brought her such a tremendous amount of joy.
“It won the Emmy, and I was like, ‘I would rather not have this, and I would rather just be able to have another fun season,’” Singh says. “That was a thing I never thought I would think in a billion years! If you told me 10 years ago, ‘You could win an Emmy,’ I’d say, ‘Give me the Emmy!’”
She admits that she’s still not sure exactly what compelled her next action—was it mania or a stroke of brilliance?
She called Brad Slater. The Rock’s agent.
“I said, ‘I want to do all of the things that little Lilly would just lose her mind over, all the things that bring me joy,’” she recounts. “So, I’m just letting you know that I’m going to have to work with Dwayne Johnson.”
Creativity as a goal
Moving forward, the indefatigable Singh says her goal is to spend as much time as humanly possible being creative. This year, she says, pulling out a handwritten list of her latest goals, she’s arranged her life so that she isn’t stuck doing any task that someone else on her team can do—a big step for someone who’s been personally approving every single social media post Unicorn Island has shared for as long as she can remember.
She’s already started writing her second feature, and on a personal level, she’s working to practice the kind of self-love that involves separating your worth from the success of your professional projects. (Stars: They really are just like us!)
And, you know, maybe soon she’ll be working with The Rock.
Singh knows that having a career in the industry necessitates grit and determination—but those are things she has in spades. She’s Type A; she’s focused; she’s driven. She’s a maker of vision boards, a setter of goals, a keeper of lists.
Now, she’s putting all that drive and effort into telling her own story.
A few months ago, Singh was driving around LA when she saw a billboard for a Mindy Kaling show she’s still thinking about. It read, “From the mind of Mindy Kaling.”
That phrasing has stuck with Singh, who, since making the move to more traditional media, has sometimes found herself second-guessing her own instincts or deferring to someone else in the room, assuming they must have more experience.
She’s come to realize that Hollywood has more than enough insiders—and Singh didn’t get into this business to do things someone else’s way.
“So, I actually have on here, ‘From the mind of Lilly Singh,’” she says grinning, holding up her handwritten list.
“That’s the mantra for 2024.”
SMAG credits should be: This article originally appeared in the July/August 2024 issue of SUCCESS magazine. Photo courtesy of Nick Onken.
