Meet the Digital Powerhouse that is Lilly Singh

She’s one of the world’s highest-paid female YouTube stars and has had tea with Michelle Obama. Here, new author Lilly Singh tells Alix O'Neill why she’s written the ultimate no-nonsense manual for millennials on how to make it to the top

It’s a bold move penning a guide to ‘conquering life’ when you’re barely a quarter of the way through it. But Lilly Singh has good reason to be self-assured. The world’s third highest-paid YouTube star, 28-year-old Canadian actress and comedian – better known by her alias, Superwoman – has over 11 million subscribers on the social-media channel (her videos have been viewed more than 1.5 billion times), 6 million followers on Instagram @iisuperwomanii) and a cool 2 million Twitter fans.

She’s collaborated with Selena Gomez, Seth Rogan and James Franco, embarked on a 27-city world tour, made a movie and squeezed in tea at the White House with former US first lady, Michelle Obama. Not content with dominating the digital sphere, she’s also a savvy entrepreneur who’s released a book How To Be A Bawse (that’s ‘boss’ in New York speak) and teamed up with Smashbox to create a signature ‘Bawse’ lipstick in deep red.

‘Am I saying it right… Bawse?’ I ask Singh, attempting an American drawl. ‘Yes, you said it so well. I’m very impressed,’ she laughs, apologising for her ‘groggy’ morning voice – it’s early in LA. ‘I sound like this for about three hours after getting up.’ Now that we’ve nailed the pronunciation, what exactly is a ‘bawse’? I ask. ‘It’s like a boss, but so epic I had to change the spelling. It’s someone who exudes confidence, turns heads, gets hurt efficiently, communicates effectively and hustles relentlessly.’

Relentless is a good word to describe Singh’s MO. She’s worked tirelessly to get to the top and expects the same unwavering commitment from those keen to emulate even a fraction of her success. The book is, unlike many of the softer self-help career guides out there, unapologetically frank – filled with tough-love advice on everything from relationships to FOMO. ‘I’ve been through some pretty unique experiences,’ says Singh. ‘So I’ve been able to come up with guidelines to help people be the best version of themselves – not in a fairytale way, it’s a very practical read.’

This no-BS approach strikes me as comfortingly old school, but then Singh doesn’t have much time for millennial sensitivities. ‘One of the reasons I wanted to write this was because I feel like my generation was raised in a society based on validation. Some people think taking a selfie in the gym is more important than working out. There’s this idea that everyone is special and you should reach for your dreams. There are many times in it where I say things like, “You think that’s unfair? Deal with it.” I wanted to be like that trainer who yells, “There are no shortcuts to success!’” Singh’s ‘no pain, no gain’ ethos isn’t for everyone, but you can’t say she doesn’t walk the talk. Her first YouTube video, posted in 2010, received just 70 views. ‘Every video and every tweet has counted. My climb was slow. I took the stairs, not an escalator.’

Growing up, Singh wanted to be a Power Ranger – ‘I really wanted to be a strong woman’ – or a rapper. Her mum and dad suggested she pursue a more traditional career path, so she ended up doing a degree in psychology. ‘I’m pretty sure that up until four seconds ago, my dad wanted me to be a lawyer. My parents believe in having back-up plans and that a degree will get you there. That’s not as true any more.’ When Singh told them she wanted to create digital content for a living, they agreed to give her a year to try it out. ‘I was on a countdown, which is why I worked so hard to succeed.’

Although fame has its perks, Singh says it’s the opportunity to highlight crucial social issues that motivates her. She’s openly discussed her struggles with crippling depression in the past and credits YouTube with pulling her out of a dark period. ‘The reason I posted my first video was because I was sad. I thought if I can make other people laugh, then I can make myself laugh.’ Last year, tapping into another global movement, she launched an online campaign encouraging women to compliment one another using the hashtag #GirlLove in an attempt to ‘break down girl-on-girl hate’. The initiative was backed by Michelle Obama and Singh donated the revenue from the promotional video to the Malala Fund, which supports educating girls around the world.

Does she worry that ‘tough love’ career manuals like hers, urging people to excel both professionally and personally, might be putting too many demands on them when they already feel overwhelmed by images of success on social media? ‘There’s definitely more pressure to get it right these days, because we see everyone’s highlights on Twitter or Instagram,’ she says. ‘But that’s not a real representation of our lives. Ultimately, the number-one person you should be competing with is who you were yesterday.’ And with these final words of wisdom, Singh dashes off to her next meeting – with a couple of wrestlers. Lilly Singh’s book, How To Be A Bawse: A Guide To Conquering Life (£14.99, Penguin), is out now

Bawse it up Lilly Singh outlines the skills you need to win at work

Get used to discomfort: Throw yourself into scary scenarios. Fear and unease are speed bumps on the road to success, not dead ends.

Let go of FOMO: Ask yourself, ‘What will your future self thank you for doing today?’ Miss the party and get an early night if you have an important work day tomorrow.

Have a dream: Create a vision board and be honest about what you want, even if it’s a big house. Can’t make a decision about something? Refer to your board and see which option aligns best with your goals.

Negotiate hard: Life is one big negotiation. You’ll never get exactly what you want, so ask for more than you need. There are three possible outcomes: ideal, workable and horrible. A bawse isn’t afraid to aim for ideal, because she knows that at worst she’ll end up with a workable scenario.

Lose the safety net: Instead of having a Plan B (graduate school) and C (an office job), I started treating my YouTube career as if it was a guarantee. The only things I was willing to alter were my strategy and technique.

Create a ‘bawse’ environment: In order to grow, it’s essential to be with people who are smarter than you. In LA, everyone around me knows more about YouTube than me and it’s made me better. I’m more productive in one day here than I am in a week back home in Toronto.