About seven years after she posted her first video on YouTube, Lilly Singh has become an Internet sensation.

Last year, the 28-year-old ranked third on Forbes’ list of the world’s highest paid YouTube stars.

The Canadian writes, directs, shoots, edits and stars in comedy videos that are released every Monday and Thursday.

Over 11 million subscribers to the Superwoman channel gobble up every post.

Among Lilly’s most popular videos are How Girls Get Ready and Shit Punjabi Mothers Say.

Lilly also posts a vlog daily talking about her day and her emotional status for her mega-fans who call themselves Team Super.

Apart from this, Lilly is a motivational speaker, a rapper who has made cameos in a few films, has a signature lipstick shade called Bawse with Smashbox and, now is also an author.

The 50 chapters of How To Be A Bawse: A Guide to Conquering Life reflect Lilly’s beliefs regarding work ethics, empowering women, self love and saying it like it is.

First things first – who is a bawse?

“A boss is someone you have in your workplace who you take orders from. To be a bawse means that you have conquered your whole life both professionally and personally. A bawse strives to be the best version of themselves,” Lilly explains.

Lilly didn’t want to write a book for the sake of writing one.

“Before I wrote this book, I was approached by many publishers to write a book. I guess they knew my audience would buy it. I decided to only write when I was at a point where I was content; I had met a lot of cool people who I had learnt from and, I had something to say.”

Writing the book gave Lilly a chance to reflect on her life and people she had met and extract lessons from them.

While she’s been writing since her first YouTube video, the experience of writing the book was nothing like what she had expected.

“I had this whole image in my head of what the writing process would be like. It was all very romantic. I take three months off, sit by the fire and the book would pretty write itself,” she told tabla! during a visit to Mumbai.

Instead she found herself writing in bits and pieces between gigs and other commitments.

After years of writing sharply observed comedy skits for channel, long form prose came with its own set of challenges.

“I normally don’t shy away from talking about things in my video. But what I did notice when I was writing was that I did get more vulnerable. It felt more raw, honest and hence more difficult to write. I guess it was because I wasn’t saying to anyone but writing it.

“I didn’t have to think about things like how long a video would be or where a punchline needs to be. Also, I was used to people seeing what I have written twice a week while a book took a longer. There were days when I didn’t know if the book was going where I wanted it to go. Thankfully it all worked out,” she says, flashing a smile.

At the Beginning

The daughter of Indian immigrants, Lilly was working towards a bachelor’s degree in psychology in 2010.

She wanted to get a master’s and become a counsellor.

Unexcited at the prospect, Lilly fell into deep depression.

It was a chance discovering of YouTube that turned her life around.

She began producing videos on her Macbook to present her online avatar Superwoman’s humorous take on life.

“Lily and Superwoman are kind of the same in the sense that they are both weird; they believe in the same thing. In terms of values and qualities they are the same people. But, Superwoman is a performer. When I am on stage, I am Superwoman. She is not shy or nervous; she just floats. Lilly runs the business. She is human and she gets tired sometimes.”

Lily’s online success helped her bolster her own mental health.

“When it comes to mental health, there is no universal right or wrong way to find a solution. I channelled my feelings through these videos on YouTube and self love, distraction and working towards a goal helped me overcome depression. That doesn’t mean that it would work for everyone. When it comes to mental health, I always say ‘if you need help, seek help’. There is no shame in that. Find what works for you.”

Her Extraordinary Life

Over the years, Lilly collaborated with the likes of Michelle Obama, Bill Gates, Selena Gomez and Malala Yousafzai.

“My life feels like a series of surreal moments.”

There’s that time at an after-party for an award show when Leonardo DiCaprio grazed her back.

Or, when in a meeting she was told that Pharrel Williams is a fan of hers. In the book, Lily writes about shooting for How My Mother Stole Christmas that features Seth Rogen and James Franco playing Santa and an Elf.

“When I reflect back on that story, I think ‘wow! I was dressed as my mom and kissing Seth Rogen’… yeah that’s a weird sentence.”

There’s juicy detail of this story involving mood-enhancers that Lilly seems to have conveniently skipped.

When asked to pick one “surreal” moment from her career, Lilly immediately talks about the first time she met Shah Rukh Khan.

“It was my first trip to Mumbai and I was performing on stage. I had just shot a video with Madhuri Dixit and Shah Rukh Khan called me on my phone to invite me to his house! Before that he came to my show and on stage he did the Superwoman S sign before leaving.

“I vividly remember wanting to throw up because I was so overwhelmed. I remember telling my friends that I was feeling something so intense that I don’t understand it.”

The Rock And Lilly

Shah Rukh might have left Lilly overawed but there is only one man she is obsessed with – Dwayne The Rock Johnson.

“Recently a friend from Grade 5 reached out to me. In his message, he wrote about this one day that I remember vividly. We were sitting in my bedroom and talking what we wanted to do when we grew up.

“The only thing, I said was, ‘I don’t care if you don’t believe me but one day, I am going to know The Rock’. And, they were all like ‘ya, right!’ That friend’s message ended with ‘holy crap! You are actually friends with The Rock!'”

Since she first met Dwayne about two years ago, Lilly calls him a big influence in her life.

“Before I got to know him, I believed that people like Dwayne could be nice but I didn’t know for sure. I wasn’t friends with anyone of the calibre of Dwayne.

“After meeting him, I saw the effort he puts into being humble and grounded and giving back. To be honest, it gave me a lot of faith in humanity. It made me think that someone as rich, famous and busy as him could still be a kind human being, that’s exactly what I want to be.

“When I started in this industry, everyone would tell me that when you become big you’ll become a diva. Dwayne has proved that you don’t have to take that path,” she gushes.

In the book, Lilly writes about the time she shot with Dwayne for her documentary film A Trip to Unicorn Island.

“I was there with my crew. He walked around the entire room and introduced himself to everyone. It might seem like a small thing but it made a big difference. I do that now. There are some character traits of his that I replicate because I know the impact it has when he does it. Whether it’s shaking someone’s hand, appreciating people or the meaningful captions that he writes. I want to follow in his footsteps.”

Future Perfect

Lilly moved to Los Angeles recently to “hustle and conquer”. Acting is on her mind.

“I don’t know if acting is the next step for me. It is an additional step. But acting doesn’t mean that I would want to leave behind what I am doing now. But I would love to act. I want to do both traditional and digital media.”

There’s a lot going on in her life and Lilly won’t have it any other way.

“I am a workaholic. I think about Superwoman and what to do next all the time.”

But that doesn’t mean she doesn’t reflect on the journey that’s been.

“I think, little Lilly Singh would be proud of where the adult Lilly Singh has reached. I think, Lilly would also be surprised because she didn’t know YouYube. Little Lilly would be intrigued and amused.”

tabla@sph.com.sg