Lilly Singh On Carving Her Path To Being The Ultimate Global Entertainer | Verve Magazine
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August 11, 2017

Lilly Singh On Carving Her Path To Being The Ultimate Global Entertainer

Text by Simone Louis

Behind the goofy, larger-than-life facade is a self-aware entrepreneur with the power to impact lives

It’s been three years since I last spoke to Superwoman, as she’s most popularly known…an exceptionally long time in the world of digital stardom. Since then, the Canadian YouTube whizz has had a mega world tour, a make-up deal, spots on Forbes lists, acting roles and music ventures, all while writing her book. Taking a cue from Bawse, the signature red lipstick that she launched with cosmetics giant Smashbox, her book — How to be a Bawse: A Guide to Conquering Life — quickly claimed the number one position on The New York Times’ business bestseller list. And, over and above being appointed as a Global Goodwill Ambassador by UNICEF, her first major acting role has just been confirmed. She’ll appear in an HBO adaptation of Ray Bradbury’s classic dystopian novel, Fahrenheit 451. While prepping for my tête-à-tête with her in Mumbai, during her second world tour, I wonder how much all this, along with her more-than 11 million subscribers, has changed her from the zany girl who once answered my question about her future by quipping, “Hopefully I won’t be homeless.” But the moment she walks in, unpretentious as ever, greeting every single person in sight and making self-deprecating jokes, I recognise the same woman — with a stronger aura. This here then is Superwoman 2.0….

“Let’s do this, I’m pumped!” she claps, ready for the first dialogue of the day, which is with Verve. Bantering with the photographer and stylists, having already learnt everyone’s names, she curses her waist-length hair in true Lilly Singh fashion and recalls our last chat. “Damn, it’s been a while, huh? This is now my fifth time here.” She gets visibly emotive while relaying her arrival at the airport; exiting to a swarm of fans with signs that read ‘Welcome home’. “That has never happened before…. I wasn’t born here, but people are still accepting me as one of them.” Support is something she values a great deal, mainly because she had to work hard for it. Her family understandably took a while to embrace her decision not to pursue her masters in counselling psychology and instead make funny videos for a living. Add that to backlash from the South Asian community who felt that she “should be quiet and not speak so much and be very obedient” and you have a delicate path to navigate. Because of this, the entrepreneur considers one of her greatest moments to be the time she visited her grandfather in Punjab after her first world tour. He announced that out of every single person in the family, male or female, she had brought the most pride to their name. “For him to say that to a girl, despite having an old-school mindset, that was a great accomplishment for me,” she reminisces.

Still, in the face of this progress, other hurdles have materialised. Gaining acceptance from her family and community is one thing, but trying to avoid being pigeonholed is a whole other task. Singh considers the colour of her skin to be both her biggest advantage and greatest disadvantage. When she started out, the fact that there was a South Asian woman speaking up online was intriguing, but the novelty of it wore off for her when people began referring to her only as ‘that Indian girl on YouTube’. “I have a name, you know?” she laughs. “There are other things to me besides just being brown.” She vents about the stereotypical questions that await her at almost every interview in America, like whether she knows whichever Indian person they’re familiar with, whether she and Priyanka Chopra are friends and whether she speaks ‘Indian’ at home. Having heard this often enough, she now just shrugs, rolls her eyes and responds with: “Yes, yes, yes; of course we all speak Indian!”

It’s this kind of goofy disdain and sarcasm that not only sets the 28-year-old mogul apart from other unattainable celebrity personas but also helps her to deal with the drawbacks of being all over the internet. You need to have thick skin and a great sense of humour to do it because, behind the presumed safety of a screen, “anyone in the world can leave a comment, and sometimes they are really harsh, mean, racist and sexist”. Despite it all, she’s adamant about always showing her unedited self. “Some people are offended, while others turn me into a role model — which is flattering. But I’ve never tried to intentionally be one,” she admits. Extremely active on social media, Singh is approachable to the point where her followers know exactly what she looks like when she has just woken up jetlagged, with puffy eyes and the previous night’s make-up smeared all over her face. The Kardashians would cringe, but this is one of the most important things about Singh and her peers. “Social media is a bit dangerous because people compare their blooper reel to other peoples’ highlight reels,” she articulates. “It’s very easy to go through Instagram and see everyone who is fit and in the gym or enjoying with their puppies on the beach and you think, ‘Oh, my life is not like that’. So I try to find a balance. Of course I want pictures in nice outfits that someone is clearly clicking for me, but I also want to put up the ones without make-up, in which I’m not looking the thinnest or the fittest…because I’m truly not!”

But even as I observe Singh animatedly talking about her fans — who she lovingly refers to as ‘unicorns’ or ‘team super’ — and being no different in person than what she is in videos, I remind myself again that her life has changed drastically. So what happens when someone, whose brand relies so heavily on her being relatable, begins to walk red carpets with a crew that could be mistaken for a Hollywood star’s entourage? She nods, “Yes, it has been brought to my attention that the more places I travel, the more boats I take pictures on, the more my life becomes unrelatable. That’s why I proactively make it my job to experience as much as possible and extract lessons from it all. If I’m travelling, I’m going to talk about the experience at the airport, on the plane, of eating junk food in my hotel. I make it a point to not change too much about my life. I know that there are some things that are out of my control, but I still eat 99-cent mac ‘n’ cheese every day; I still use Uber X! I want to be basic at least for the parts that I can control.”

Clearly, this pop culture superhero has her head firmly on her shoulders. Her reputation for having a strong vision and focus precedes her in the industry, and her work ethic garners a lot of respect from collaborators. It’s been a long journey to get here, but it’s safe to say that she now calls the shots when working with any brand — a refreshing occurrence in an age when so many celebs, given enough money, will endorse anything. “There won’t be a situation where they tell me to say something even though I don’t want to and I’m like, ‘Okay’. That never happens,” she confirms. “But I did have to work to get to that point. Early on in my career, there were a lot of companies that I told, ‘Hey, I’m not going to work with you anymore because you’re not letting me be my authentic self’. You can’t start from the top…you start from the bottom and work your way up.” From this vantage point, it makes sense to me that she is often irked by the feeling of entitlement that digital fame has given rise to. While Singh is grateful for the ways in which the internet is helping people, she would love to change the blind faith in fluffy posts and the mindset that you don’t really have to work that hard to be rewarded. It’s certainly not an unwarranted sentiment, considering she began building her empire in 2010, when YouTube wasn’t what it was today. “It was the biggest gamble I’ve ever made,” she confesses. Since then, a major part of her life has been about making rules as she goes, because there never was a set path for this job. “It’s a challenge — making it up and hoping that I’m doing it right.”

The more we talk, the more I understand why so often her loyalists send her messages to rest and take care of her health. Not even sleep stops Lilly Singh, something that applies to many YouTubers. “I used to say that I don’t want a nine-to-five job but now I have a 24-hour job,” she chuckles. “One of the biggest misconceptions is that we’re doing this because we failed at everything else, or because we’re taking the ‘easy route’. The job is everything but easy!” She makes a strong point. Social media is a non-stop entity. Making a five-minute video does not take five minutes; it takes a lot of people and a lot of time. Most importantly, you’re expected to always be ‘on’ — whether you’re having a bad day or not. “It’s about being mentally, physically, spiritually and socially durable at all times.”

But don’t for a second think that Singh is being ungrateful. One of the most appreciative public personalities around, she stretches herself thin to make everyone happy and, at the same time, make a difference. One of my favourite things that she’s spearheaded is Girl Love — a social media campaign aimed at ending the cycle of girl-on-girl hate. In addition to awareness videos, collaborations with other empowering women and motivating Singh’s younger audience to support each other, Girl Love sells a bracelet which helps girls in Kenya to go to school. “There are a lot of issues that negatively impact women. It has just been way too long and I want to do my part,” she explains.

It’s quite lovely to see her growth from a fangirl to an example of grace and authenticity. Even while being her silly self, Superwoman is an emotional guide of sorts to many people. Having spoken a lot about depression and coming out of it, she has let herself be vulnerable in her videos and on social media in a way that takes great courage…but not as exposed as she is in her book. “I’ve written the ‘Out Of The Blue’ sections in a very raw manner and I don’t think I’ve spoken like that or sounded like that before. I actually, for once, felt more comfortable being off-camera. I could only write it because I knew they wouldn’t be able to see my face,” she muses. Quickly and characteristically lightening the mood, she tells me the funniest chapter she wrote — the one called Be Active. “Because me? I cannot make it to a gym! I was writing the chapter thinking, ‘No one is going to take this seriously’. It was hard to learn that my brain can be going really fast and I can be hustling really, really hard but as I get older, my body can’t keep up.”

Does she still clearly remember her younger self, though, I wonder aloud. What would she say to the girl who was uncertainly yet buoyantly just making her very first video? Singh’s eyes sparkle. “I would say two things. One would be, ‘You should be yourself a little more. Stop trying so hard to be cool; be weird because that will get you far’.” While relaying her second piece of advice, however, she seems to resemble Paramjeet — the beloved parody version of her mother which she plays in some of her most popular videos. “I would also say, ‘Do NOT call yourself Superwoman, because you will have to pay a lot of money for it…you idiot!’”

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