Rupi Kaur on Finding Success as an Industry Outsider
Toronto author Rupi Kaur self-published her first book Milk & Honey in 2014 when she was just 21—and she never imagined it would become a number one New York Times bestseller and that she’d become a global literary sensation. With new pressure to support her family and to match the success of her first book, she built out a company of nine women, all while coping with anxiety and depression. In this episode, Daniella talks to Rupi about the imposter syndrome she felt as an outsider in an industry that sometimes wasn’t welcoming to her, what she’s learned from running a business as someone who feels from the heart, and what happened when she finally acknowledged her depression. She also explains why she’s so excited about her latest book and connecting with her audience in a more present way.
Daniella Pierson: Rupi, thank you so much for being on The Business of Feelings. I would love it if you could just share who you are, what you’ve built and why you are a business person. People oftentimes don’t think about authors or directors or anything like that as business people, but it truly is an entrepreneurial venture.
Rupi Kaur: Thank you for such a warm introduction. My name is Rupi Kaur. I am a poet, a performer, an author, and I am currently on a world tour doing what I love most in the world, which is performing and connecting with audiences. I’ve had the privilege since I started my company, in my early 20s, of managing a team of about nine incredible women. We’ve grown so much. There’s been so many stages of Rupi Kaur Inc. (RKI), and you’re absolutely right—I mean, “businesswoman” is a word that I never use in public but it’s a word I definitely often use in private because that is what I’m building, because I could not have gotten where I am by myself. It takes a whole team.
DP: In the beginning you launched Milk and Honey, which was such a success. Did you ever think that it would be received the way that it was? How old were you when that happened?
RK: I self-published it when I was 21, and that was 2014. Because it was self-published either people were purchasing from my website or anytime I’d perform locally, in Toronto or anywhere, I would bring all my siblings (I have three younger siblings, they were in middle school and high school at the time) and I’d bring two boxes of books and then we’d hand sell copies at the events. Absolutely had no clue. I couldn’t even dream of this for myself because this was not something that was in my reality. I grew up in a working class community where everyone I knew was a truck driver, a cab driver, a factory worker, and that was it. So when the book got published by a publisher in fall of 2015 and it really really took off early January 2016, the success of it did even put me in a state of shock almost. Because it is a book that is so raw and so personal and I’m so vulnerable in it. I self-published it thinking that a couple of people were gonna buy it and then I was gonna do my LSATs and go become a lawyer or something, and suddenly it took over and became bigger than me.
DP: That’s an incredible story and just to hear it directly from you… and how humble you still feel about that initial success! If you had to describe in five words what feeling you had the moment that the book took off and you became a global sensation, what would those five words be?
RK: I would say confusing, weird, scary, mind-blowing and wild.
DP: Those are great words and I would expect nothing less from someone like you! Would you mind telling our listeners what has happened in the years after Milk and Honey has debuted? How have the last seven years been for you?
RK: They have been full of so many blessings and extremely tumultuous. I think that when Milk and Honey became a success, I was sort of forced to become a businesswoman. It was like suddenly I was getting my MBA because I had to build a company. There was so much coming in that I couldn’t do it myself. A dear friend of mine, Rakhi Mutta, became my manager. I loved her. I trusted her. We just had a vibe and so she’s still my business partner and we venture into so many things together. We started building the company—hiring one person, two people, three people, four people, and it was so incredible to have a partner there because what happened after Milk and Honey was that I fell into an extremely bad episode of depression. For about three years I had suicidal ideations every single day, which is something that most people probably wouldn’t imagine at a point where I’m having so much success. When it comes to depression you can’t really point at any one thing and say, “That’s why it happened.”
But I think there was just so much pressure as well. Like I have no idea how I wrote Milk and Honey. I don’t know how I did it. I was doing what my heart was guiding me to do and writing is something that I loved and suddenly this book becomes a global sensation selling well over 5 million copies and over 43 languages, it has been on the New York Times list for over 100 and something ridiculous weeks. Then you sign a contract and you’re asked to do it all over again. And I’m someone who’s so ambitious that creating anything less than, I thought, That’s failing. There’s no way. The next thing has to do exactly what the first one did. There was that pressure and I think that really put me in a place where I just felt like buried by it honestly. I did feel like I had to prove something because a lot of people were critical of the fact that my work is so accessible.
You know, in the literary world being accessible is a bad thing. The literary world can be quite classist. So the fact that millions and millions of people were reading my work wasn’t necessarily seen as a good thing by my industry. I was at the same time as a 22-year-old, 23-year-old dealing with that and wondering, Oh my god, but I never asked for this success. But now, like, I’m being criticized for it. But, like, who even am I? I don’t know! I felt like I was just a kid and I think I spent most of my 20s overcoming that. Thankfully I was able to write book two, write book three and I even completed book four, which I have right here with me. And honestly I don’t even know how I did it. I think I was so scared. Each of those books I was like, There’s no way, I cannot, I can’t do it. Every cell in my body was like, You’re not gonna be able to do it. And I think I did it because I was so scared of losing everything that I built.
DP: That’s so interesting. I was speaking at a conference a couple of weeks ago and they said, “Do you identify as an entrepreneur?” and I said, “Of course, yes. But I mostly identify as a survivalist.” That almost mimics the exact feelings that I had when I was starting my company at 19. You just have to keep going—send the newsletter, send more emails, just push forward because there’s no other path. It just feels like you have to go forward and then oftentimes it does feel like, How did I do this?
RK: Yeah. You said the word “survivalist” and that is a feeling I’ve had since the age of 9, 10 years old not coming from a place where we were financially secure all the time. My dad, when we were younger, was extremely unwell, sick for a decade. I remember as a kid seeing him lie almost lifeless for like weeks at a time was horrifying. I would cry in the middle of the night because I’d be like, Oh my God, is dad gonna die? And then I’m thinking, What am I gonna do? If my dad dies… My mom is a stay at home mom, she can’t work. I have to work. I have to figure out how to feed everyone. That is a thought I’ve had since I was a kid and I think that the success of Milk and Honey came at a moment where we needed financial resources to keep our home. It was such a blessing when it all happened. But it’s funny because when I fell into it it brought even more anxiety. Suddenly it was like, Oh, it’s gonna be taken away from me. It’s gonna be taken away from me. How do I hold onto it? How do I hold onto it? And I struggled with that for years, the weight of that, even my family, seeing them stress over that. So failure wasn’t an option. I had signed a two book deal to write—contractually obligated to write book two and three, so many people were waiting for me to fail and that wasn’t an option. Then so many people were waiting for the next book and the next book. You just keep going and going and going.
It feels like the last seven years have been a sort of whirlwind that’s almost just settling because now I have my feet on the ground. For seven years I’ve prioritized RKI, the business; Rupi Kaur, the public persona or the author; the performer. Now hitting 30 I’m like, “OK, I need this to be something sustainable that I do for the rest of my life.” I wanna be on stage performing at 80 years old, but that can only happen if RKI and the businesswoman perhaps chill out a little bit. And my health and my emotional wellbeing also gets some stage time.
DP: First of all, I’m so sorry that you had to feel those pressures when you were so young. At 21 or 22 having a lot of success, coming from a very humble upbringing, how did it feel being younger than most of the world that has that kind of success and navigating that with friends, relationships…? How did you feel?
RK: When the first sort of big check came in I was like, “Oh my god!” Excited, running home, showing my parents, which was so exciting. But this one particular memory comes to mind. I would always show my mom first because my dad was always working. Then my mom would be like, “OK, you have to show your dad. Go show your dad.” Then dad would come home. My dad’s a truck driver and you know, he’s tired. He goes to bed. I remember showing him the check and he was just like, “Oh my goodness, I’m so proud of you.” And my mom was so emotional and later the next day, she was like, “Wow. You made in one month what your dad made in one year driving on the road.” It just was such a bittersweet moment. Sweet, because I was like, “Oh my goodness. I’m so happy and so blessed that I can finally take care of you now.” But it was so bittersweet because I was like, “Whoa. This world is so… the inequality is ridiculous.” My father, and so many folks, the hours that they put in, the physical efforts that they put in, it’s absolutely endless and what they get in return doesn’t match up.
But I’m really grateful that I do have the blessings that I have and it didn’t really change anything with any of my friends or any family. The money didn’t really affect any of our relationships. I don’t know why that is because so many people will tell you otherwise. Maybe because I’m not a showy, flashy person or I’m not gonna buy a Lambo and drive around my hometown. I love treating everyone and doing all the things but the money has not really affected any of my relationships, or the success has not. But I’ve always been the type of person to keep around people who I genuinely think are pure.
DP: I can also identify with the story of your father. My mother is an immigrant from Colombia, where she had to work so hard. Anybody coming from a third world country who is trying to become a professional… She became an oral surgeon. It is brutal—not that it’s not here! But it truly is. She was poverty level poor and literally grew up 20 feet away from a mass grave. Her house was the size of a normal American’s garage. I’m oftentimes reminded that I know I work very hard and there’s sleepless nights but there are so many people that work so much harder than me and have so little to show for it. I feel as though a lot of people, especially minorities, count themselves out of ever being successful. I never saw a Latina woman in her 20s worth 100s of millions of dollars. I’m sure you didn’t see anybody who looked like you being a world renowned name and this incredible business person.
How do you feel now, almost a decade later, about the haters out there who were not welcoming to you and your success? Do you think that it was anything to do with not coming from a prestigious background or maybe your culture? Do you think that the publishing world has changed? If not, how would you like it to change?
RK: I think that there has been change. I see more women being published, more diverse authors, more people of color for sure. I can’t speak for numbers. I’m not an expert in this. Sometimes I think begrudgingly they publish us because they’re like, “We have to do this now. Diversity, you know?” I am somebody who I don’t think I could have gotten success from within the industry—I got it from the outside and then I got into the industry. I think that so many people can go the traditional way and they can find success but if that doesn’t feel right for you and that’s not working for you then you can’t stop. You have to find another way to build your road if this is what you wanna do. I have often thought, Oh my goodness if I went to Stanford and Harvard, would I be more legit? And I thought about that a lot, you know? After publishing Milk and Honey, millions of copies later, I was looking at MFA programs, prestigious MFA programs that famous writers have been to that make them legit so that I could become legit and my friends were like, “We’ll let her do this for a hot minute,” but they were like, “Girl, you have a world tour that you have to go on. Like, how many poets are on world tours? You’re trying to do your MFA? Stop it!”
DP: Oh my goodness. That’s so real and vulnerable and honest because I know a lot of very successful people who have literally built billion dollar companies and they’re like, “Should I go to business school?” And it’s like, really? Like you need that? Like you’ve sold millions of copies of your first book and still felt like you needed to check a certain box. When did that feeling go away where you were like, “You know what? I may not have done this the conventional or prestigious way but I kicked ass and I’m one of the biggest writers in the world, I’m gonna accept the fact that I don’t need that validation?”
RK: I think that probably came maybe in the last year or two because, you know, I talk about my feelings. (I love that it’s called The Business of Feelings!) I obviously have built a career on talking about emotion and feelings. But when you’re told that, “Oh, this is not real writing. This is not real literature, it’s just confessions. It’s for girls. It’s for young women. It’s just this and it’s just that,” it can make you feel, as a young woman, that you are not intelligent and you are not smart because all you do is talk about your feelings. I think it took me a couple of years to realize, “Wait a minute. No, I don’t need to go to Harvard and learn big big words to be intelligent. I don’t need that because I can sit and talk about my emotions, find words for them and then sit with other people and have discussions for them. That is my intelligence and that is very powerful.” That’s something that I’ve learned probably within the last year or two. I hit the road again in May when my world tour started and it feels different than any other tour because I feel more confident and feel more powerful than ever. It’s the first time I’m touring where I’m not depressed and so I can actually feel things. I feel the presence. When my audience tells me things, I listen and I hear it. It is life changing every single night.
DP: I am someone who has also struggled with depression. I have OCD, I wasn’t officially diagnosed until I was about 21. So I’d love to know, when you were in your most depressed state, how did you navigate it? I know you said that after quite a bit of time you felt, OK, this isn’t normal. I need to get help. But while you were in the thick of it before you realized you needed to get help, how were you feeling?
RK: I just kept telling everyone “I feel weird.” I was like, “I feel weird.” Everyone’s like, “Oh my god.” I’d go to events and people I grew up with, people who saw me rise slowly year after year, they’re so excited. So they run up to you at an event and they’re just like, “Congratulations, how does it feel?” And I’d just be like, “Fine, it feels… weird?” Because I couldn’t feel anything else. Because when you’re depressed, it’s not the same experience for everyone, but I became extremely numb. It’s the most confusing feeling but at the same time that you feel numb you feel like something is dying on the inside. I just powered through it because I think it didn’t cross my mind that I could be depressed because I thought I was too smart to be depressed without knowing it. Depression wouldn’t make sense because on the outside everything was so amazing and great. At year two or three of being really really low is when I started to use the word “depression”. I think the folks around me who are so loving and so caring, they didn’t really know what to do. I mean they were there, they held me. Rakhi, my business partner, drove me to the office every single day. Everybody held me down but it really had to come from me like, “Well, I need to do something.”
The winter of 2018 I was living in New York but I came back to Toronto to visit my family. And I couldn’t leave my bed for days and was just a mess. Oh my God. I just want to sleep and never wake up again—that was a thought I had every day. Then I was taking inventory of the fact that that’s been the thought that I used to calm myself down. It provided me comfort that I could end it. And I was like, That’s really dangerous. But I didn’t notice it because it had slowly become normalized and when it becomes a normal thought over such a long period it’s a red flag. And I sat, I remember, on the steps of my parents’ house and I was like, “How many more years can I continue to live like this?” Then I said, “Maybe I might survive three years, but I don’t think I’ll be able to make it to year four.” And that was the moment where something cracked open. I was like, “I need help.”
DP: What was your first step after that?
RK: This was a year before COVID and it was a year of me trying everything. I signed up for a meditation course, then two weeks after that I found a therapist and I was kind of on this wild journey to try different things to find what worked. So many things did and so many things didn’t. It was never one thing. It was a combination of many many things. Getting better wasn’t a straight line. In January, when the journey of getting better started, it was going really well and then it’s just like “meh” and then it goes well and then it’s like all over the place until you realize, Oh, that’s how life is. It took probably two years to get to a place of actually putting in effort every single day until I could say, “Oh, I’m not depressed anymore.”
DP: Well, congratulations. That is a very big feat to get across and I don’t know if I would’ve been able to get across my depression and my debilitating OCD and anxiety without medicine. What is something that you do, still now to this day, that really helps you feel OK?
RK: Yeah, medicine was also something that I started that I was very resistant about. There was this idea that if I took medicine I’d become a zombie or I couldn’t be creative.
DP: That’s so common and something I often talk to my co-founders about. How did you get through that roadblock?
RK: I had a friend who said that she was on medication and she gave me such a positive review on it that I was like, “What do I have to lose?” And it was so helpful. It made me feel back to myself again. Some of us just need that extra chemical thing to get back on the same pace as everybody else, so it was really helpful.
DP: Thank you for being transparent about that because when I saw a therapist at my lowest low and a psychiatrist and I started taking medicine, I didn’t tell my parents. It’s so expensive and there’s so many inequities. But there was a point where my father looked at me and he was like, “Medication is for failures.” So about a year ago after my entire life had changed and I’ve proved that I could have mental illness and still be a business person I asked my dad, I said, “Dad, if you went to the doctor and they said you have high blood pressure and they told you to take this medicine, would you take it?” And he said, “Yeah.” And I said, “Then if someone said you have OCD and here’s a medication, what is the difference?” And he looked at me and he goes, “I know what you’re saying and I can’t give you an answer, but for some reason it feels different.” Truly, I think the way that we get over that stigma is having people like yourself, like Selena, like Mandy, being open and saying “Actually, I do take medicine,” to take out the shame or the stigma that can oftentimes be surrounded by it.
RK: Selena was actually one of the people in the midst of my darkest moments. I remember hearing her talk about it so openly for the first time and my friends who I was sharing with, “Oh my God, I feel this way,” sending me videos of her. That’s why I eventually did write an entire chapter about it in my third book. I wouldn’t have ever talked about it if maybe she hadn’t. Seeing somebody in her position saying that she was also going through this and these are also her challenges helped me step out of that denial.
DP: I hope you know that you’re doing the same exact thing to many people right now. Talking about the business side and the creative side, did you often feel like you had to be emotionless in business? Or because your business was being very emotional and open did you feel like they could coexist?
RK: I’ve always felt like they can coexist. I don’t really know how to be anything other than me. I just have never been able to spend energy pretending. I think what made my journey in business really helpful was having Rakhi by my side as my sort of anchor. I feel like I handle the creative, I have these visions, and then she sort of makes those visions come to life. I can be really emotional. She balances me out in so many ways. I feel like we’re sort of like a yin and yang. It’s always been strong partnerships and friendships with women that have been able to help me grow as a businesswoman and as an artist. I’m not someone who could have done it without the support of women in my life.
DP: That’s amazing and it often touches on a co-founder’s sort of relationship or delegating things that seem like only you can do and allowing somebody into that world. Did you ever get burned in business in some way that made you really think that the business world needs to change?
RK: For sure, I would say maybe the first time was 2016. When you sign contracts and they all look great and then two, three years into it you’re like, “Yeah, I don’t wanna do that anymore.” And then not doing it means you have to pay these giant giant fees. Paying those fees for the first time was gut wrenching. It fed into that fear of like… this financial security that I had, I knew it was gonna go. It hurt so so so much. But then you get smarter and smarter each time and surround yourself with better people.
DP: Did you ever feel like you lost control of your own career and then you had to take it back because people saw you as the creative or the talent?
RK: I functioned so much from the outside when I started this partnership with Rakhi. Her career before me was working on the front lines in Brazil, in Kenya, in India, helping those on the ground, working with child soldiers, survivors of rape and sexual assault. Then she started venturing into more creative, directing, writing shows. So she also had no experience in managing a company but she’s always had that rigor in her. We both started to build this company from the outside. I had no agents. We didn’t even know that an author could have a team of nine people. Because we were in Toronto and we were building from the outside, I insulated myself with such strong people. We realized that the way that I’ve done it, it could only be done if I did it myself. For example, I design all my book covers still to this day. That’s only possible because I have a team who helps me and supports me. Because we do so much in house, I think it really really protects me and it keeps a lot of power on my end.
But now as I dive more into the establishment, working with the agents and this and that, I’m like, “Oh, I see you.” I see them now trying to take the wheel and they’re confused. They’re like, “But why doesn’t she get an agent?” And we’re like, “But we don’t need it because we’ve sold ten million books.” But they’re just so confused. And so I think fortunately we’ve seen how we can do it without them. Now as we’re diving into new ventures within the establishment there is that sort of fine balance. I am very wary of “I’ve built this but I can’t let this become something that traps me.”
DP: For sure. I love that and how much of a business person you are that you brought everything in house immediately. I don’t know if you knew it at the time but (you probably know from other authors) everything is outsourced. How did you and your business partner decide who to hire and how to build this internal team?
RK: I think we figured out pretty quickly that the thing that we looked for most was the lack of ego. Rakhi and I have never had ego. We will be on the floor sorting out receipts and doing the bookkeeping and doing all of the things. So every person who’s joined the team (some of them have been with us for four or five years now) they have to be willing to get their hands dirty there. There’s no ego in any part of the job and the agility is so important with such a small team. We could be working on a project for six months and at the seventh month something could go terribly wrong in the world and it just doesn’t make sense now to put this project out. But no one should be able to take that personally.
DP: That’s so great and so wise. What is the biggest evolution or transformation or lesson in business that you feel like you have grown into in the last seven years?
RP: One is very practical. Somebody told me, “Spend the money (and it’s gonna be more money than you wanna spend) on lawyers and accountants. Don’t mess with that.” That’s one thing.
And second—something that I’m learning in the long run is that businesses have their ups and downs and there’s so many successful businesses that you think probably have no chaos. There’s so much chaos happening inside almost every single business and that’s OK. That’s the way of it. When COVID hit, we had to cancel world tour and so many places where we expected revenue to come from. It was scary because I was like, “That’s it. Should I just shut it all down, save what I got and go?” And the lesson was “No, this is business. You’re gonna have rough years, maybe rough periods. You keep going and you keep going. You build for the long run, not the short.”
DP: What would you tell somebody who wants to be a freelancer, a writer, any sort of position where you really are going out on your own and maybe doing it the unconventional way? What advice would you give them?
RK: I would say that if you’re thinking about doing it and you think that you don’t have what it takes, you do. It’s something that just takes time and practice. You know what? You might try and decide it’s not something that you actually wanna pursue, which is totally fine. But I would say don’t quit your day job. Start slow. Get your feet wet. It takes time. If you’re trying to be a freelancer, writer, journalist… It takes time to get your first story. It takes time to build a reputation and you have to step back and look at the bigger picture and just take it one day at a time.
DP: I love that. I asked you earlier in the episode for five words that you felt when you had just released the first book Milk and Honey. If you had to say five words for when you get up on those stages across the world, how do you feel now?
RK: Blessed, privileged, powerful, confident and excited.
DP: I love that. Well what an evolution, Rupi. Thank you so much for being so vulnerable. Where can our audience find you and your incredible work?
DP: Thank you so so much for your time Rupi. It was such a pleasure.
RK: Thank you. Appreciate you so much.
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