Lilly Singh has had a chip on her shoulder.
The YouTube star was one of the earlier successes on the platform, amassing a following of 14 million subscribers who would tune in for her take on social mores and Indo-Canadian culture. Singh parlayed her online success into book deals, world tours, acting roles, and her short-lived late-night talk show on NBC, A Little Late with Lilly Singh.
Singh admits that the driving force of her ambition has been to prove her worth through numerical metrics and accolades because that’s what she felt translated to success. “Creativity was supposed to be a phase growing up. It wasn’t supposed to be a career,” Singh says in the latest episode of Fast Company’s podcast Creative Control. “And I wanted to challenge that. I wanted to prove that wrong.”
Deeper still, Singh wanted her success to supersede gender.
“The chip on my shoulder was to be in a position of influence. I was born into a reality that being born a girl was a disappointment, and I always wanted to be in a position of power and influence to combat that,” Singh says. “From a young age, I wanted to be a movie star. I wanted to be a musician. I wanted to be anything that would put me in the spotlight to prove that I was worthy. And so YouTube was this thing that connected those dots.”
However, Singh realized how flawed her value system had been during the pandemic when the work she so closely tied her worth to slowed down dramatically.
“I felt like I wasn’t even a real human being, and that made me sad because it made me think, ‘Is that all you are? You’re just a shell of a human being that goes to work?'” Singh says. “I realized it’s because I’ve never done the work as a kid or as an adult to really think about what I want out of life. Who do I want to be and what is important to me because those things were always told to me. They’re always told to me by parents or society or school, and I never gave it any original thought.”
She did give it some thought and turned it into her latest book, Be a Triangle: How I Went from Being Lost to Getting My Life into Shape.
In a way, Be a Triangle is a sequel to her 2017 bestselling book How to Be a Bawse: A Guide to Conquering that covers such topics as goal setting, making a great first impression, and how to achieve your dreams. “Be a Triangle is, okay you got all of those things—what do they mean?” Singh says. “It is deeper. It is more spiritual. It is me assigning and unassigned value to different things in my life and really building a strong foundation, mentally, that will not change no matter what comes in my life.”
“When I started Googling ‘strong foundation,’ Google said, you mean the triangle because structurally speaking, a triangle is the strongest shape,” she continues. “So I thought that’s how I want to build my life.”
Lessons learned in late-night
“When I got asked to do the late-night show, I initially said no, because I never grew up with a desire to be a late-night host. That was not my dream. The reason I said yes, to be really honest, was a mixture of pressure, a responsibility I felt, and a little bit of ego because I was told that it would be historic and this could make a really big change [in] representation. But I also thought, oh man, if I say no to this and it goes to someone else, there’s a chance this historic moment could not even happen and that would a great disservice.
I was naive to think that that feeling would help me get through multiple seasons of this show because that’s a hard thing to hold onto when you’re shooting for like 17 hours every single day, and it’s the most emotionally and physically and spiritually tough thing you’ve ever done. It’s actually really important for me, if I’m going to work this hard, for me to really care about [what I’m] working on. I recognize that’s a privileged thing to say, but I feel I’ve earned that position of privilege.”
Does Hollywood respect digital creators?
“Yes and no. I think now no one in Hollywood can deny people that have come up on social media, because they have such massive followings and they obviously are natural marketers and they’ve got what Hollywood wants. They’ve gotten eyeballs. They’ve gotten people invested in themselves and their stories. I think where the disconnect is, all of the reasons we are successful are the things Hollywood tries to change. Digital creators are successful because they are authentic, because they don’t have to have perfect talking points, because they aren’t perfect. They’re just real. As soon as you try to take that person and put them into a setting that has to be perfect and you have to sit behind a desk and this episode has to be exactly 22 minutes and 22 seconds, that’s when you start taking away all the magic of what makes this work. So until those systems are broken, I don’t know if that will ever translate.”
A new relationship with content creation
“My relationship to content creation now is one of pure expression where I want to create simply to express where I’m at in hopes other people may see themselves in that. I also create content now very honestly and bluntly knowing that if I post on social media, that is a tool for my job. I think part of the reason I had an unhealthy relationship with social media for so many years is that I assigned it more value than I think it should be given. It is a great tool that we should use. It should not use us. It used me for many years. I think knowing that there’s a level of performativeness to it is something we can embrace.
So I’ve acknowledged that while all my words are so true, it is still a tool for my job and to connect with an audience. It is not my value. It is not real life. It is not how I want to have all of my conversations with the people I love and care about. It is not where I believe meaningful conversations can solely take place.”