What I Know Now is an interview series in conversation with leaders about the failures and successes of their careers.
It’s easy to define a person by what we see on the outside: their achievements, relationships, and hobbies. When we take the time to look closer, we might be surprised by what we learn about the people we admire in life and business.
Author Rupi Kaur is one of these people. More than three million Instagram followers know her through poetry and performances. Women and girls admire her beauty and ball gowns. Kaur grew up as a young immigrant in Toronto with the bare necessities. She wore boys' clothes. She was shy. In the last few years, she’s learned to become a business person. She’s had to get used to being financially secure. She feels empowered wearing a ball gown on stage.
Kaur, 26, grew in popularity on Instagram when she self-published her first book, Milk and Honey in 2015, while writing and studying at the University of Waterloo. Kaur was doing what she enjoys - creating - and calls her success “accidental.” She believed that she’d never reach success again. That’s when Andrews McMeel Publishing (AMP) came knocking. The ask of Kaur, while she was still in the throes of her unexpected success: write another book in three months. She said “no.”
Her decisiveness might seem premature for a young poet, but because Kaur has been designing and writing her whole life, she wanted to ensure the book was created on her own terms. Before she would write another book, she put AMP to the test: sell two million copies of Milk and Honey, and then she would consider the offer. They made it happen, and her second book, The Sun and Her Flowers, was published in 2017.
Today, Kaur runs Rupi Kaur Inc., with a team of six people in Toronto and recently launched an ecommerce shop. She’s writing her third book.
When we spoke over the phone on a Thursday evening in February, Kaur was at home in Toronto preparing for an upcoming performance in London. While we’ve never met, having a conversation with Kaur is like having a life chat with a friend: exploring the emotions of our work and lives. She’s humble, self-assured, and relaxed; while her life has changed dramatically in the last few years, Kaur has stayed grounded. She’s growing a business on her own terms:
YouInc: How are you preparing for your performance?
Rupi Kaur: The team handles all the technical stuff and getting the right players in terms of the tour manager and technology.
For me personally, I don’t have something I do every year. This time I looked up my script from my last year’s show, and I’ve been finessing it. I developed something in the summer, I toured across the US and Canada with the script and it changed and morphed. So, I updated it and I’ve been practicing memorization and sitting with a voice coach and really asking myself, “okay, but what’s the intention behind this line and who exactly am I saying it to?”
Writing is a personal process, where you’re writing for yourself, and it’s selfish, which isn’t a bad thing. As a performer, you have to step outward. Even if you did write it for yourself, you have to get into this habit of imagining this other person that you’re saying it to and being aware of the intention you want them to feel. Working with that coach has definitely been new. I think it’s going to elevate the performance that much more.
YI: How do you prepare yourself to perform in front of people of different cultures, whether you’re in Canada or you’re in India?
RK: It’s funny because I used to be like, “oh, I’m going to all these countries - that’s so many different things and they’re going to think different things, and I need a brand new thing for every place I’m in.”
No matter where I go, there’s so much similarity between readers regardless of language or the borders that separate them. The energy that they bring to the show is exactly the same. It’s like performing for the same crowd—that’s why we’re connected.
There's an honesty that I’m sharing and my light is connected to their light, and that’s what they bring to the show. So, it always feels comfortable and at home. I’m aware of asking, “what’s the political atmosphere of this country?” I don’t want to offend anyone, so there are pieces I might not recite. When I was in the Middle East, I was told by organizers not to include a lot of the poems about sexual abuse.
When I wrote my first book, it was like “oh, yeah, that was one, it was accidental.” I had imposter syndrome.
You have to dance around about what’s appropriate. You as a performer pick up what the crowd is ready for. I give myself 10 minutes at the start of the show to learn what they’re all about. Even touring America, there was similarity between the [different] audiences, and at a macro level - there’s deep respect.
Everyone comes to the show with life experiences that aren’t so pleasant. On a micro level and city-to-city, energy levels change. Miami was loud, fun, and crazy, but then DC was reserved and introspective.
There’s constant preparation that happens mentally and that sort of prepares you. I’m already reflecting subconsciously about what my last few London shows have been like, “okay, what are the changes I can expect this time? They’re going to know the book better than they knew it last time I was there.”
I never looked at this as a professional career. I was doing something that came to me: something that I loved and I morphed into this. For the first time I’m treating this experience like a career, “okay, what does an athlete do before they run a marathon? Warm ups. Why am I not doing that? What are the warm ups I can do before a performance and for my voice?” Those things will elevate the show and what I’m practicing.
YI: When did this whole experience start feeling like a career? Sounds like you’re saying now.
RK: Once I wrote my second book, I was like, “oh, I could do this forever now.” I mean, we hear that a job like this isn’t sustainable. What? Poetry? I could have never imagined that it would allow me to hire a team of people to work and invest in the things I’m doing and that I could be touring globally.
Those are things you don’t think about. Not that I didn’t want them; they weren’t in my periphery. When I wrote my first book, it was like “oh, yeah, that was one, it was accidental.” I had imposter syndrome. “This book accidentally came to me and it’s never going to happen again.” Then once I published the second one I was like, “okay, maybe it can happen.”
Then I was touring other parts of the world. I ended up touring again last year with the same book. Now I’m like, “okay, this can be a 40 or 50-year career.” It will morph and evolve, but I’m accepting the power in that and letting it guide and empower me.
YI: Yeah, wow, sounds like you’re in for the long run and you’ve found your purpose.
RK: For sure. Creatively I’ve been in it from the time I was born. From my earliest memory, I’ve been making things with my hands. This is going to be my 10th year performing, and I’ve been drawing and painting even longer than that. Creativity is my life-long partner. I’ve accepted that, “okay, it can also feed me lifelong, so how am I going to pair these two together in a way that’s sustainable for my craft and my art and my heart?” There’s also a fine balance [sighs] between how you remain honest in your creativity and honour that creativity.
I’m glad I wrote my second book when I did, because if I didn’t push and force myself to write the book, I might never have been able to write a book again.
The universe chooses you and delivers through you, so how do you sustain that relationship and give to that relationship without completely selling yourself out? That’s also something I consider when I’m writing and creating: what’s the intention behind this [work]? Why am I putting it out?
YI: You said after self-publishing Milk and Honey, the publishers were pushing you to write faster. You said no. Do you still feel like you can say no?
RK: Definitely. I had less clout to do it the first time. When it comes to poetry, people were figuring it out, because nobody was reading poetry. Then, all of a sudden, it was becoming this thing. I self-published Milk and Honey, and I had sold 18,000 copies on my own. I didn’t know that was a good number. In my mind, it was too small because I was like, “c’mon, we can do better.”
For the industry it was great, and that’s why I got the publishing deal. Then when they gave me that deal, they didn’t think it would become what it did. I didn’t do a single interview. I did no media. Nobody wanted to talk to me. I didn’t think about anyone, because I thought, “okay, nothing’s really going to happen.” Then I left the country for three months and when I came back everything had changed.
So, there was pressure, everybody was feeling pressure and I was at the center of feeling it all. Because they were like, “we don’t know what’s happening: is this fad going to go away?” It crushed me.
I’m glad I wrote my second book when I did, because if I didn’t push and force myself to write the book, I might never have been able to write a book again. I don’t know how I wrote the first one. The second time there was a lot of discipline involved. My relationship with creativity is so spiritual. I never sit there and say, “okay, I’m going to write a book and this is the plot and one poem a day, and then in a year, this is going to happen.”
I remember at one point they gave me three months to start and deliver. I was like, “what do you mean? I had 20 years for the first one and you want something in three months?” I pushed and pushed and pushed, and now I’m at a point where I can say, “no, I’m actually not going to do that and I feel empowered in what I've accomplished. No, I deserve what I deserve.” I worked a lot for my freedom; I didn’t come from a lot. We didn’t have much growing up and I worked hard to get to this place, so I should feel free in this place. But, why is it suddenly that I feel more tied down and more constricted?
My publisher, agent, and team have been kind and supportive in pushing back deadlines. I want to put the best work out there and if that’s going to take four years, then it’s going to take four years—I’m sorry. I try to use an adult approach and say to myself, “she’s sort of doing what she wants, when she wants to do it, but when she delivers, it feels right and it feels pure and it feels honest.”
YI: Why didn’t you self-publish the second book?
RK: I didn’t self-publish the second book because of distribution. When I accepted that deal, I didn’t want to give up a lot of my creative control. That’s why I self-published in the first place because I was like, “no, I want to pick the paper size. I want to pick the colour. I want to design the cover. I want to do this and I want to do that.” I had those skills and I wanted my book to look the way I wanted it to look, because I felt my poetry wasn’t just this universe that I created inside me.
Self-publishing was the perfect route, so when Andrews McMeel Publishing (AMP) reached out to me and said they wanted to bring it worldwide, I was hesitant because I was like, “well, what does that mean? Does that mean you’re going to take these pages out, because you don’t know how to market them? Are you going to change the cover, because you think this doesn’t fit in the market?”
They said, “no, no, no, we're not going to change anything.” Also, you get way less royalties when you go with a publisher, versus self-publishing. In the end I went with the publisher only because of distribution. It turned out to be the greatest decision for me personally only because the book could be in more places and in front of more people.
You have yourself and that’s what you come into the world with and that’s what you leave with. You have to believe. I believe that if you believe in yourself, you can be your own superhero.
That was a no-brainer for the second time around. I used to do events and my entire family would come with me; my siblings would sit with me at the table. It was all hand selling and going store-to-store in Toronto and then Waterloo, where I studied, and being like, “hey, do you want to keep this book in your store and see if someone wants to buy it?” It was a lot of work, so having a publisher is a machine that gets the books where they need to be, when they need to be there. It helped me grow.
YI: When did you realize you needed to build a team? Who was your first hire?
RK: I hired someone part-time after AMP published Milk and Honey in 2015. It was when I went to India for three months. I thought, “I’m not going to have an internet connection, and I need someone to check email and respond to book shows.” At that point I was taking bookings from universities and organizations and I was flying across Canada and the US. She was my first hire, and she no longer works with me, but she was with me for some time.
Then that March a friend and I were in India together and we were like, “okay, maybe we can work on this together.” She began to manage me. She was a bit older than me, and she naturally fell into that caring role and watching over me. She’d come support me at my book events and she ended up protecting me. People would come and ask silly questions, and she’d be like, “uh, okay, we're going to move it along.”
She naturally fell into a management role. I hired her in 2016 and quickly the both of us began to negotiate with my publisher and said, “hey, you need to put more resources behind the book.” There really hadn’t been much happening, and we really believed in the book and asked, “why is this book not being sold in different languages. What’s the hold up? And, no we’re not even going to consider book number two, until we sell a million copies and until you can prove to us that a million copies can be sold. We’ll sign the book deal then.”
AMP is one of the most agile publishers out there right now and they made it happen. Every goal we’ve given them, they’ve made happen. Then in 2017 we hired a third person and he was a videographer and a documentary photographer. In 2018, after we came back from our India tour, we hired about four new people, all different roles in the office whether financial, executive assistant, or project lead.
YI: What part of the business do you feel you struggle with most?
RK: I would say that there’s so much to do all of the time. For years I was doing it alone and that burns you out. Then for a year Rakhi [business manager] and I were doing it alone. We were doing the jobs of three people. I mean you can only do that for so long, right? It gets to a place where I can't focus full-time on the creative. That is my role and Rakhi manages the business and operations full-time. We have other businesses as well. We started an e-commerce company last year before Christmas, because my readers were like, “we want canvases, we want poster prints.”
I started at a three-minute performance and now we're at a 90-minute show.
What takes the most time is really tedious things. My brain is not good at switching between the business back to the creative. When I’m in the business, I’m in the business. When I’m in the creative, I’m in the creative. The goal this year is to get me to a place where I don’t have to focus on the business, because the team is strong and can do that. I’ll be writing the new book and doing whatever I decide to focus on.
YI: Beyond your poetry, you’re a brand. You’re marketing Rupi Kaur. How does it feel to wear the ball gowns and being the face, versus being behind the words?
RK: I don’t think about being the face of it, because I feel like I’ve always been.
It wasn’t an intentional choice. Ten years ago, I performed for the first time because I felt like I had something to say. It went against everything I was: super shy, introverted, and a fly-on-the-wall, because that’s how I grew up. I decided in 2009 - there was a local event happening - that I was going to write a poem and recite it. Like, why would I do that?
It was a day that changed my life, because I wrote this piece and I went to perform, and I had no idea what spoken word was. I had no idea that people even recite poetry, like that’s a normal thing. We do it in my culture: we sing poetry, we recite it in groups, and we go to the temple. I hadn’t seen it in the English-speaking world.
I loved the experience so much: being in front of the microphone, having my voice heard and having people receive it—that’s why I kept doing it. Then over the past 10 years, my poetry evolved and elevated. I started at a three-minute performance and now we're at a 90-minute show. What are we going to do next? I’m always interested in growth and making things more interesting than they were last year. Even now, I’m like, “okay, cool, we did some great things last year, now how are we going to elevate it, so it can be fun for me?”
YI: You wear ball gowns at your performances around the world. Where did the idea come from?
RK: Let me think about why. I had a poet look before. I’d always wear high-waisted jeans with a head scarf. Then I began to perform in bigger venues and they were more elegant. I’d walk on for sound check in these beautiful theatres. It felt natural to elevate my look to fit into the space. I started to buy and collect pieces that I thought fit in. I’d look at photos to see what the venue looks like: what colour is it, “omg, red would look so great with this.” I’m a visual person, and I feel the visual experience has always been a part of creating. That’s how I watch movies. It’s how, when I shop, it’s a visual experience and I’m stimulated by colour and texture. And then over the years as everything else was elevating, the clothes [weren't].
I cried so much in the bathroom, because I felt like a girl for the first time. I had never thought about how I didn’t feel like one before.
In 2017, I hired a stylist for the first time and he dressed me in gowns. Now it has become a part of the process, because it does something to your spirit and your energy. It feels amazing and powerful to walk into a beautiful theatre with 3,000 seats and walk on stage with a dress. That person, who gives off a giant energy, is different than the person who was performing a couple years ago in a cafe wearing a shirt and jeans. I’m becoming more aware of how things elevate my energy and how they don’t. That’s why my look is the way it is.
YI: Do you also feel that’s a way people relate to you?
RK: I have an interesting relationship with fashion. I’ve always loved fashion, but because we’re immigrants and we didn’t have a lot of money, I wore boys’ clothing for most of my life. It was boys' clothing made in India with terrible material.
I never really felt pretty or beautiful until one day when one my aunts came over. She worked at a Sears outlet and she brought me a pair of red corduroy jeans. I had never wore girls’ jeans before. My parents were like, “no, no, no, we don’t want them. Thank you so much, but don’t worry about it, that’s doing too much.” My aunt was like, “no, let her try them on.”
I still remember - I think I was in elementary school - when I went to try these jeans on. They were red corduroy bell bottoms, and I had never worn bell bottoms before. They had these beautiful flowers embroidered into them. I cried so much in the bathroom, because I felt like a girl for the first time. I had never thought about how I didn’t feel like one before, but I knew at that moment, “wow, this is how I can feel. I can feel confident? Oh, I actually look nice.” In that moment, it was important to me.
In grade eight we had a dance. I went to the dollar store and with all the money I could muster, I bought this little pink tank top. I took it home and I stitched it a bit, made it cute, and I felt so feminine and pretty. Then, I started to shop at thrift stores, while I was in university. I remember the first dress that made me feel sexy. It was from H&M. It was $50. It was the most amount of money I spent.
I even thought of going into fashion design. I was told that I’d never make it in fashion, and that it was a shallow thing. I think it’s amazing to get to incorporate those things again and feel beautiful and confident. I always laugh because it’s like I get to do prom night, like every other night I’m on tour. I never thought I’d be able to, because I’m Indian—if I get married, I’m not going to get to wear a dress.
I was hating myself, but then I’d have to go on stage and talk about self-love to all of these people. Inside I was like, “can they tell I don’t look myself right now?”
YI: Even if someone isn’t at your show, and they see a photo of you on Instagram, there’s strength and power in your presence.
RK: I get criticized for wearing what I wear as well, right? Like, “why are you focusing on that? It isn’t Vogue, calm down.” I gave myself permission to be like, “I want to feel like this today.” In turn, I had no idea that it gave other women and girls permission to do the same. Last year, I started to see women come to the shows in beautiful gowns. Dressing up became a process of coming to these shows, which I thought was nice.
YI: You have what seems like an immense amount of self-assurance. How have you learned to love yourself, especially after the trauma you’ve experienced?
RK: Ugh, it’s such a personal process. After I wrote Milk and Honey, and it was out in the world, I felt good. I was like, “shit, I really worked through this crap that I’ve been through.” I was so proud. I remember the day it came out, I felt this pressure lift off my head, like in the cartoons when steam comes out your ears. I felt that; it was the greatest gift. But it didn’t last, and then I was confused again and I felt like a fraud, because I was going through a bout of some of the worst self-esteem I’ve experienced. I was hating myself, but then I’d have to go on stage and talk about self-love to all of these people. Inside I was like, “can they tell I don’t look myself right now?”
I have to be honest: that’s a cycle and that’s how life is. I don’t know if it comes from being the oldest. I was determined. There was so much security that I was responsible for providing to myself, so I had no other choice, but to believe and keep going.
Being the oldest of four siblings and from an immigrant family, I had to rely on myself for mostly everything. I couldn't have my parents’ support in a lot of things. They couldn’t guess what was going on in Canada and being a kid and what that meant.
It wasn’t like I was coming home and sharing with them. I was rolling around and figuring it out. Now as I’ve been going through my own dark period of denying myself happiness and joy, and then coming back to the fact, “hold on, you brought yourself here—you got this.” I think because I spend so much time alone and look inward that I trust the universe. I don’t even feel like I’m sure of myself. You have yourself and that’s what you come into the world with and that’s what you leave with. You have to believe. I believe that if you believe in yourself, you can be your own superhero.
YI: In moments of self-doubt, how do you build yourself up?
RK: I don’t think I was realizing when I was breaking down in the last couple of years. It wasn’t apparent to me, “hey, I’m not being so great to myself, or I’m feeling a bit stressed or feeling a bit anxious.” Only when I hit rock bottom did I realize, “whoa, I need to work on this.”
But I was lucky that I was surrounded by such a great support system of people and friends, who were like, “hold on, we need to take a break, we need to fly back home, we need to take care of this.”
Now there are things I do. I was not feeling present and that came with the last three years being so tumultuous, and my life changed so much. It’s confusing, because I’m still living the same life at home, when I come home. When I come back to Toronto, I’m going home, and I’m taking care of my parents; they’re still struggling and having some problems we’ve been having. Then, I have to fly out to the Golden Globes or something. It’s a different mind state.
My relationship with money and my relationship with time has had to change. My relationship with everything has had to change.
I went from having financially nothing to being financially secure, but my brain was confused about it, because my brain was like, “omg, how do I protect this [money], because one day I’m going to wake up and it’s going to go away." I’m used to having nothing. So having to teach myself how to come into this new life, has been difficult. My relationship with money and my relationship with time has had to change. My relationship with everything has had to change, and I had to do things I thought I’d never have to do like meditation classes. I try everything. Even when I came back last December, my dad got me a Himalayan salt lamp. I have a yoga mat next to my bed, where I meditate every morning. I have an oil diffuser. I tried everything I could, because I was determined to pull myself out of that dark period. I’m still figuring it out. I think now when I hit the road again, I’m going to be a lot healthier.
YI: Who do you go to for support? If you’re at the Golden Globes, and you need to talk to someone, who do you call?
RK: I call a couple of friends here. I’ll call Rakhi, my business partner. She’s the one who grew this with me. I’ll call one of my good friends Kiran; before I was on the road, she was my creative partner. It does feel weird being at these events and you have to be confident and smile. Like, what is a red carpet? I didn’t grow up in that world. I feel like I’m going to say something weird. I also see a therapist, so she’s someone I’ll check in with and get support from.
YI: What are your days like when you’re not writing? What brings you joy?
RK: It’s interesting because it’s hard. What I struggled with the most is that writing brought so much of my joy; it made me the happiest person in the world. Then it got tainted when it became a career: I had to perform and use this thing that I love to put food on the table and make sure we’re making enough money, so that all of the employees get to eat, and blah, blah, blah.
That was really difficult because I lost the thing that brought me joy. I have to find it again and I have to create two separate relationships with it, where I’m like, “this writing is for me. I’m going to write today for me, and my heart needs it for me, and if it never sees the light of day, that’s completely fine.”
If I’m doing something that’s purposeful, brings me joy, and brings good to the world, then I’m successful.
You have to be in tune with yourself. I only write now when my heart is calling for it. Because if in the moment that it’s not, I’m like, “nuh-uh, I’m pushing it too far and I’m going to go into that self-hate pattern again.” If I’m not doing that, I’m painting and I’m drawing, and I’m spending time with my siblings and my family and friends. That’s also where my inspiration comes from—conversation and connecting with other people. With touring and never being home, stuff gets ripped away from you, so whenever I’m back, it’s top of my mind to incorporate those things into my life every day.
YI: What does success mean to you?
RK: What is success in the external world? I used to think, if my book sells so many copies than I feel successful. If I’m on the New York Times Best Seller list, then I’ll be successful. You know what? None of those things made me happy. None of those things fulfilled me in any long-term way. It would be exciting in the moment and then that sort of thing would fade and I’d be on to the next thing.
I learned quickly, and I’m glad, that I was never going to find the success I needed by collecting external things. If I wanted to feel successful and I wanted to feel proud of myself and feel that I had attained enough, then I needed to step inside again and recalibrate.
Now success is asking, “am I doing the things I want to do?” If I am, then I’m successful. Many of us spend so much of our time doing things we don’t want to do. Sometimes we do things we don’t want to, but I don’t want to be doing that all of the time. If I’m doing something that’s purposeful, brings me joy, and brings good to the world, then I’m successful.
YI: What do you know for sure?
RK: Oh my God, that’s hard [laughs]. That it’s going to be okay. That’s the only thing I know. That’s what it’s been so far. You get swept up by micro things. These things drive you insane. They weigh on you so heavy. But it’s going to be okay. That’s what I tell myself when going through difficult times: this will work out.
YI: You are not your work: your poems, your books, your Instagram. You’re Rupi. Who are you, for those of us who don’t you?
RK: I’m fun. I’m silly. People think that I’m this person that’s probably serious all the time, and so deep, and I don’t even walk, I sort of float. Then people meet me and they’re like, “oh, but you’re relaxed. What the hell?"
I don’t think I show my goofy; my siblings get to see that the most. I’m my silly self around them. The Internet gets one per cent of me, which is this made up curated human being and it’s serious all of the time—it’s hard to live up to that image in real life.
YI: Have you considered posting a silly face or capturing something funny before you go on stage?
RK: I do on my Instagram stories. Especially when I’m on tour. If you watch my stories, you can hear my voice. You can see how I interact. When we’re on tour, we have a competition to see who can scare each other more.
I have considered posting photos, it’s just a matter of time. It would surprise you and most people that I actually hate taking photos. That’s why when I started my Instagram in the early days, I never posted photos of myself. People came to my first book launch and asked other people, “Which one is she?” They didn’t know what I looked like.
I’ve empowered myself financially...so that other commercial companies and institutions and systems can’t ask me to change my art or messaging to suit them.
I was like, “okay then, I’ll take photos.” If you scroll way down, you’re going see me taking photos of half of my eyeball and my eyebrows and I look moody and serious.
I hated having my photo taken, but then I had to start getting my photos taken because, “oh, this person wants to do an interview with you and they’re bringing their photographer.” I actually didn’t document my travels in 2016. Then we started to document and we realized, “oh shit, this is important," and I want my business to grow.
That’s when I started to take photos. I wish I had more silly photos. It’s just not top of mind. I want to show people moving forward, like, “hey, I don’t look like this all the time.” People are like, “oh my God, you're so pretty.” I’ll show them, “but it took five people to make me look like this; I woke up looking different.” So, that’s more top of mind for the future in terms of what I share.
YI: What do you want other entrepreneurs to learn from your journey?
RK: I’m lucky to be an artist in this time. One of the things I’m proud of is that I’ve started to do everything in-house. Even when I started to launch natural canvas prints, it’s easy to think, “first, we have to find a merchandise company and then we have to do this and do that." No, we’re going to do it. Or, if I release a spoken word album, I don’t have to go and sign a deal with a record label, I can go and do it on my own.
When people find out I have a team of seven or eight full-time people, they’re so confused by it. They’re like, what do you need them for? I’m proud of being able to do that for myself, because I’ve empowered myself financially and also remained independent so that other commercial companies and institutions and systems can’t ask me to change my art or messaging to suit them. It’s about maintaining what you want to do and what’s important for you.