Rupi Kaur on 10 Years of Milk & Honey, Overcoming Imposter Syndrome, and Empowering Others

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1:22Welcome to the Daily Stoic Podcast, where each weekday we bring you a meditation inspired by the ancient Stoics, a short passage of ancient wisdom designed to help you find strength and insight here in everyday life. And on Wednesdays, we talk to some of our fellow students of ancient philosophy, well-known and obscure, fascinating and powerful. With them, we discuss the strategies and habits that have helped them become who they are and also to find peace and wisdom in their lives.

2:07Hey, it's Ryan. Welcome to another episode of The Daily Stoic Podcast. As you know, this was the 10-year anniversary of Obstacle. I was just talking to my father-in-law that Daily Stoic is on its 10-year anniversary next year. and you don't think about it at the time, but you're always kind of part of a class, right? A bunch of people, this is what the selection bias is creating on us at all times, right? It starts out in a big group and it winnows and winnows and winnows. And then you realize, oh, these were my peers all along, even though maybe we didn't know each other or connect in any way.

2:43But I had a guest out to the podcast a month and a half ago. Then we've been waiting to run it for a little bit. And she had just put out the 10-year anniversary edition of her book. I don't know if you've seen Milk and Honey, which my guest today, Rupi Kaur, self-published in 2014. And it became one of the best-selling poetry books of all time. It was briefly outselling even The Odyssey. Her collections have sold something like 12 million copies and been translated into 40 languages. As I said, Milk and Honey is one of the highest selling poetry books of the 21st century. So as she was using social media and the internet to sort of help people rediscover poetry, I was doing the same thing with The Daily Stoic.

3:26And so last year, 2024, technically this year while I'm recording it, but we were both celebrating our 10-year anniversary edition. And she brought a copy of it. We sell a ton of Milk and Honey and Sun and Her Flowers and Homebody at the Painted Porch. because they're all beautiful and little and they make great gifts. But anyways, she brought her 10-year anniversary edition of the book. And I had just gotten copies of the 10-year anniversary edition of Obstacle. And I was like, oh man, you did it way better than I did. Because what she did, she took this poetry book and then it's annotated by her and by fans of it, including some people who've been on the show, like Camila Cabello.

4:04But it was just a beautiful idea seeing how people, like if you've ever seen The 40 Laws of Power, It's got the little sort of annotations, little things on the side and the marginalia. And she did that, though, with people reacting to the poetry. And literally, the first thing I did was take pictures of it and send it to Robert Greene and go, Robert Greene, I would kill for an annotated edition of The 48 Laws of Power. And you know what he told me? And I'd forgotten about this. He's like, about 10 years ago at auction, Michael Jackson's copy of The 48 Laws of Power went up for sale. And his annotations were in the margins.

4:35I was like, that's what I want. I want to see four-star generals and celebrities and academics and people who read it while they were in prison. I want to see those people's reactions to the things in the book. All of which is to say, I really thought that this new annotated edition of Milk and Honey was great. Rupi put out a book in 2022 called Healing Through Words that's worth checking out. So anyways, this is a great conversation. We talked about our experience. It's like, what is it like to revisit something you wrote? I don't even feel like I could have a 10-year-old book, let alone to have a book that is still selling 10 years old.

5:13It's just crazy. I don't feel old enough, but here we are. And so it was a great conversation. I really liked it. You can get signed copies of the 10th anniversary edition of Milk and Honey and the original Milk and Honey, Son of the Flowers and Homebody at The Painted Porch. I will link to that in today's show notes. You can follow her Instagram, where she is, of course, very popular, at RupiKaur. That's R-U-P-I-K-A-U-R. Rupi and my wife hit it off. She left with a big pile of recommendations, which I'm sure we will post on YouTube soon enough. By the way, every time we have a guest, we walk through the bookstore after and I pick out books that I think they'll like.

5:47We run those over on the Ryan Holiday YouTube channel. I'll link to that. Enjoy.

5:54It's weird being an author or writer and then you have to like talk to people. you're like this is why i i uh i became this thing because i don't like doing that thing right right right yeah yeah i like performing though yeah there is a element of performance to poetry that i don't yeah yes i do love that are you giving talks or yeah usually do you enjoy it well i feel like like music it's playing you know there's like i think if you're giving a talk or performing there it's not as it's not fun like i don't know that many people that are like yeah i really became a writer because i like to talk in front of large no we don't like to talk is why we write yes exactly come on yeah no no it's for me writing is the engine that drives it all and then there are these other things that you have to do in this day and age i'm sure for you that's like what social media is yes but like it's actually the doing the thing that you that's what i love the most but it's wild i mean all of the other things now take up more time yes than the thing i like to do and i'm really trying to figure out how to just do the thing i love to do but it's such a difficult no no no i've i've thought about that a lot like the reward for succeeding at your craft should not be that you don't have time to do the craft anymore exactly but that's how it goes yeah uh and i wonder if there's like a way i mean there is you just have to like i don't know spend less time doing other things, less panels, less paid gigs, I guess.

7:25There's a Frank Ocean line where he says you just have to be comfortable making less money. Yes. That's very hard. Yes, yes, exactly. It's like the opportunity costs of not doing the craft are not visible, right? So the day like you don't see the poem that you didn't write, you don't see the pages that you didn't do, or just like you don't see the reading that you didn't do. But there's a number attached to the gig that you turn down or the appearance that you don't do or the whatever. Right. So it requires this is obviously first world discipline, but it requires a lot of discipline to be like, no, I'm going to turn down X amount of money and I'm going to stay home and do what looks like nothing to most people.

8:12I love that line that you said about you don't see the poem you didn't write. Yeah. And you don't see it day to day, but I think you do see it piling up. Yeah. And I think it's complicated, too, because like, even though like me and you, we've had so much success. I don't know. I still struggle with the fact that there isn't security in being an artist. Yeah, for sure. So I'm like, OK, well, let me just do all the paid things while I'm still getting them. Yes. Yes. And maybe that's like a fear mindset that like, you know. No, there's like a scarcity. you know, at some point, they're not going to be offering it to you.

8:49And you're you would kill to do it for half that amount, a quarter of that amount, or for free, you know, but your books 10 years old now. Like you've been telling yourself that for 10 years. Yeah. And it's like, I've been telling myself that for 10 years. And the clearly the solution I've been applying for 10 years isn't working or leading me to be happier. And at this 10 year mark, I'm really like, okay, the solution I'm applying needs to change now for the outcome to be different. Yes. So what am I going to do at the end of this tour that is different? And I think I know what I'm going to do.

9:26What is it? But it's scary. Like, I've been talking about taking a real break for how many years now? I feel like for five years now. That means stepping away from social media. It means not feeding that engine. It means not rushing to write the next thing. It means really just I have not prioritized my personal life at all, really. And relationships suffer because of it. Friendships suffer. And so I think it's like time for me to live. And that's scary. I love my work. I'm such an ambitious person. But clearly, work success doesn't feed that human need to feel love and connected. Well, I'm always interested in the distinction between confidence and ego.

10:13And so there's obviously ego in like that. Oh, the audience will still be here when I come back. Right. There's like, I don't know. Will they? No, no. But like there's an ego in just saying like, oh, of course, everyone will wait on me. I'll put the thing out when I'm done. Like there's an ego version. And then there's a confidence version where you're like, it would be OK if I took a year off. Yeah. Some audience will still be there when I come back. I believe in my ability to earn an audience back, to get the momentum back, you know? And then there's like, there's also the insecurity of if I stop, it will never come back together.

10:49Yes. Or whatever, you know? And that, yeah, that's so hard. The last, I'm really, yeah, I relate to the last two with the confidence and yeah, that it might not come back. But then I'm, I think that and I sit with that fear and then I'm like, it might not, But what's the alternative? Me just continuing to live and work the way that I have been. And then what's going to change if I've been saying that it isn't working? Well, then do you have the success or does the success have you? If you can't stop, then like, do you own anything or does the thing own you? Like, there's something sad about that.

11:24If it is true that you couldn't stop and take a year off or slow down or do it differently because it would all fall apart. and that may be true as I think about it but that's like not so impressive then is it that like you're a change to it for the rest of your life exactly that's not true success to me then no yeah it's like a form of slavery exactly you're like locked in the golden cage yeah like running on that hamster wheel it's not always fun what is it like to come back to your work your first book 10 years after you put it out? It's really cool. I mean, it's so, I tried to like put the feelings of what it's like to come back to it in the introduction.

12:11I started writing the introduction earlier this year and it's not, I've read Milk and Honey since it came out 10 years ago. I've read it cover to cover maybe three times. Twice when I had to record an audio book and a third time this year when I had to write, you know, put together the 10 year anniversary edition. And, you know, I feel like sometimes my work, like I cringe at myself. You know, we all do, I think, when we read our work and it's been around for many years. But when I read it earlier this year, I was like impressed with my younger self. Oh, I was like, wow, that teenager, she kind of was like cooler than she gave herself credit for.

12:52And she kind of was like never she never celebrated herself. yet how brilliant was she to lead me to the doorstep of the woman I am today yeah she delivered me to this moment and that is phenomenal and so it's very bittersweet as well because I get to like I feel like she created so fearlessly yeah and she had very little self-doubt but that's like she wasn't she had nothing to lose really she had no audience this wasn't her dream she It wasn't even in her reality. So she was just totally driven by passion. There's like an unencumberedness to doing your first thing because you don't know what you don't know.

13:33Exactly. And you're just doing it. Exactly. And then the fear came after. And the self-doubt came after. And all the other things that aren't fun. And I was like, oh, I don't think I can do it again. And yet I wrote many books. I remember I wrote book two and I still was like, I'll never do it again. And I wrote book three. I think now I'm like, okay, it will be hard. It'll never get easy, but I will do it again. But it's funny because like, I'm often referring back to my 21 year old self for inspiration and for, I'm like, let me tap into her strength and let me tap into her fearlessness. So that's kind of been.

14:11No, I can relate to that. Cause I'm just, I just did a 10 year anniversary of my first book. I think my first feeling was, I can't have a 10 year old book. Like I don't feel like I could do that. Because it also just feels so fresh. Weird. Yeah, it feels like it just happened. And then the other part that struck me was like, during the pandemic, I was trying to put my son to sleep one day. And so I was like, I'd read all his stuff. He wasn't going to bed. I was like, okay, I'm going to read you one of my books like as a punishment. And I was reading it. And what struck me about it was like, I was like, where did this person get off?

14:44I meant that in like a nice way. Like, I was like, how did this 24 year old possibly think they knew any of this? And then in some cases, like I didn't know and it was wrong. Right. Like, and I went back and fix that. But then the other part of me was like, how did I know something that I really had no business knowing? Like there's where you see the audacity. Yeah. The flashes of like, how could you, how could you have gotten something right that maybe you hadn't even fully experienced yet? It's so cool. Cause I feel like I totally relate to you and it's like, I do feel like ideas sometimes they work through us.

15:19Yes. So you don't know, but the universe chose you to deliver that message. And that's pretty cool. But I feel you. I mean, when I was reading Milk and Honey again earlier this year, I was like, what? And the audacity to put it out? It's absolutely wild. Yeah, the not going, how would this look for a insert age person to be saying this and to just say it as that person? To me, the enemy of good art is self-consciousness. Like, how is this going to come off? What are people going to think? You have to be in the moment and just do it. And I imagine with poetry, it's even harder because poetry is more of a, I don't want to say antiquated, but it's not, it's a thing so many people do badly and so few people get to be able to do.

16:08And so there's probably something about poetry too, where you're just like, like an imposter syndrome feeling that would creep into doing poetry, I imagine. I don't know. I think when I'm writing, I mean, it hasn't been like this all the time. When I was writing Milk and Honey, I was so present with each piece. And so in those moments, I felt truly free. And I was writing without a focus on outcome or result and writing without judgment. And so that was very freeing. And in a way, because I'm writing about my own experiences, that's freeing. Because I'm like, yeah, you might not like it, but it's my experience.

16:47You can't take my story away from me. So, you know, and I struggled with book two and three because then I was thinking about the outcome and I was thinking about the results. And when I'm thinking about that, then as I'm writing, the judgment is right there. And that's when the writer's block comes out for me. But I'm finally, I mean, 10 years later, back in a place where I am writing without judgment. Were you able to do, I don't know the timeline exactly. Like, Bilk and Honey, the book, or most of the poems come before social media, right? A lot of them do. Like, I started writing them in maybe 2010, 2011.

17:25I was performing first. Yeah. So I was on stage in front of a microphone. That's where, that's how I fell in love with the craft. And then I would write to perform. And all of my pieces were much longer performative pieces, anywhere from two to six minutes. and then my friends were like you know there's social media now you can reach more people and I was like okay I guess I'll experiment with it and I found Tumblr yeah and I had many different blogs and at first I was just sharing my visual art I was painter I drew and I wasn't sharing my poetry and when I began sharing my poetry I mean there were so many iterations of my different blogs and I was publishing a lot of my work first anonymously, but the sort of shorter, more concentrated poem that I want to hit like sort of like shots came when I found Tumblr because I realized the difference between performance poetry and paper poetry at that point, because when I'm standing in front of an audience performing a six minute poem, I can see the way that poem comes to life and the way that it moves them.

18:30they're laughing, they're crying. We're sort of like building up to a high frequency together. I take that same poem, I post it on Tumblr and it's not felt in the same way at all. And then I started to experiment with poems that I felt like were coming alive on paper. And so those are the poems that most people know me for, the shorter, more concise pieces. And then, yeah, then a few years later, I found Instagram when nobody was publishing anything with words on it on Instagram. And I feel like I grew with the platform, you know? I was just wondering if there's probably a before and after, like before your mind is aware of the algorithm and how before your mind has the ability to do that twisted thing of like, how's this going to do, you know?

19:16And because I can only imagine like what it would be like for me if every one of my pages was independently judged by the up or down of the social media algorithm. And how hard it would be to tune that out. Like to make something great that is a cohesive whole, you have to be removed from that. Yes. But it's hard to turn off the like, how's this going to do? People like this. Is this the kind of thing that does well? I've thought about, I remember when I went to write my second book, The Sun and Her Flowers, I sat at my desk and I was like, at that point, Milk and Honey had sold like millions of copies.

19:53It was on the bestsellers list every week for God knows how long. And the pressure was definitely there to repeat that type of success. And I went to write and I couldn't write a single word because I was like, wait a minute. I don't even know how I did it the first time. I wasn't even aware of it. So what do I do? And I don't know what the answer is, but the answer for me, it's always been writing poetry is such a spiritual and personal experience. the magic I think comes from me being honest about where I am and I wrote to find answers to the questions that I was having and so that's kind of what I tried to do I mean for a long time I didn't publish my poems about depression and anxiety until the third book because I was like well my audience really likes the pieces of healing and heartbreak so like maybe this is going to be weird and then they're going to be like you have all this success why are you depressed And then, you know, I ended up just going for it during the pandemic and it landed and it was like, OK.

20:56And I think these little small wins, these little reps that I'm doing and then they're received by people. It does help. And I think over time, and I'm sure you feel the same and I want to hear about that. Eventually, you just stop caring, too. You're just like, all I can do is what I can do and write what I know. And I am so grateful to have been received for this long. And I hope that continues. But I have to honor myself first.

21:29We just took our kids to an outdoor performance at The Nutcracker. They had a snow cone. And then they went insane in the car ride home. And one of the things I try to remind myself when that's happening is that I don't control my kids' behavior, especially when they're too far gone like that. But I do control how I respond. right? That's stoicism, but it's also what Dr. Becky talks about. Dr. Becky is a clinical psychologist and a bestselling author, and she founded Good Inside, which is there to give parents practical, actionable tools for handling those everyday challenges with confidence. My wife introduced me to Dr.

22:05Becky's books. I love them. I've recommended them a million times. I've had her on the podcast. And as it happens, Dr. Becky is hosting two live Q &A events for Good Inside members. I am one of them. She signed me up for it about a year and a half ago. I've loved it ever since. On December 1st, you can join Dr. Becky for her How Not to Raise Assholes event, which is about avoiding entitlement and raising kind, empathetic kids. And on December 15th, she's hosting her How Not to Lose It Over the Holidays event, which I'm sure we could all use. As I said, I'm a big fan of Dr. Becky. She's been a great influence for me as a parent And just as a human being and daily Stoic listeners can join for 15 % off with code STOIC15, you just got to head over to goodinside.com to catch the events.

22:57Thanks to Toyota Trucks for sponsoring this episode. When I bought my ranch in 2015 out here in Bastro County, I drove my car about halfway down the dirt road that we live on, thought this isn't going to work, stopped, parked it, walked the rest of the way home, borrowed my wife's car, drove in Austin and bought a truck. What I bought was a Toyota Tacoma. And this truck wasn't just transportation getting me to and from my house. It unlocked a whole different style of living for us, not just on the ranch, but in our little Texas towns. There were places I could go now that I couldn't go before, especially out here in the piney forests, through the fields, and on the unpaved roads like the one that I lived in.

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24:34It's also, there's something about like, you've done it. And so, you know, you've done it. And then you can kind of weirdly be a little bit more indifferent to results. You know, like I imagine it's like, if you haven't won a championship, it's hard to be like, I just love playing. You know, it's easier to say that once you've done the, like, once you've scaled whatever the objective heights of your given profession are, like you're a scientist, you win a Nobel prize. They didn't be like, I just like seeing where the science takes me. That's harder to do if you don't have, like confidence is easier when you've like objectively earned it.

25:13Yeah. You know, like we've done the thing and you can point to that thing. That's true. Yeah. For you, was writing the following books, like after the first, how was that experience for you? Did it get harder? Has it gotten easier? How are you reflecting on that 10 years? Well, I got lucky. So my first book was about marketing, so it was sort of totally different. And then I wrote this book about Stoke philosophy that I didn't think would do big things and my publisher didn't think would do big things. And when it came out, really didn't do big things. I think it sold like a few thousand copies its first week, but I'd already sold the second book.

25:46So I was just busy doing that. And so the fact that it wasn't disappointing, but it just, it wasn't, it didn't exceed or it didn't like register really at all, but I was busy writing this second book and it was sort of kicking my ass as, as all projects do. And then by the time the obstacles away really did start to take off, I was like towards the end of that second book and still getting my ass kicked. So I feel like it shielded me from the downside and the upside. And then what it did was I was really established like in my writing process, in my writing style, independent of the success. Whereas I know a lot of people like James Clear, Mark Manson, who like their first book sold like what my first three or four books sold combined, you know?

26:39And that would be really destabilizing and disorienting. And I imagine for you, like - Very similar. Your first book comes out, it's self-published, and then it does more than anyone could have imagined, even had it been like a huge expected hit. Like it was a monster, your book. And so, yeah, following that up would create a whole bunch of pressure and expectations. I had like 23. Yeah. I didn't thankfully really have to deal with any of that. I dealt with it in different ways in different parts of my life. But as far as the books go, I had the luxury of like a slow, steady build, which it's funny when you put something out, whether it's on social media or a book, everyone wants it to be a monster success out of the gate.

27:19But it's funny when you talk to people who that happened to, they tend to see it as kind of a bird. Like they talk about how hard it was. Obviously, they're grateful for it. But you think you want things to go a certain way, but you actually don't. You have no idea the difficulties and the challenges it will bring. Yeah. I was so naive and so clueless. Because, I mean, I thought a few hundred people were going to buy the book. Right. And I had already brought my, I was still in college. I had already bought my LSAT prep books. And I was like, hey, now I need to make real money when I get out of the school.

27:48I need to pay my student debt off. Obviously, you can't be a poet. That's not a job. No. Yeah. And I was performing for years, always for free, because I was like, I just love doing this. I'll do it for like nothing. Yeah. But yeah, it's taken, it's really interesting what you said about being able to develop your process through book two as well. I feel like only now am I less destabilized and developing a process that I'm like, okay, I can lean into this and it's working. Yeah. Yeah. Like you didn't get to be a regular person or a regular developing writer. You went from no one to unrealistic expectations.

28:25You just didn't get any kind of safety net or safe space to develop as in obscurity. I mean, again, like if you had to choose between that and it not happening, you'd of course choose your thing. But it's a lot. Yeah, it's a lot. It is a lot. And I'm just so grateful that I got through it because there were lots of years where I was like, this is the biggest mistake I've ever made. Really? Like, I, how do I put this into words? It just sort of knocked me off my center, pulled the ground beneath my feet. And it felt like I got on a train with self-publishing and I was excited to get off a few stops later.

29:05Yeah. The train not only did it not stop, it kept going faster and faster and faster. And it, you know, brings with it its own sort of challenges. And I was very tough on myself through it. I was like, oh, my God, I've dealt with this horribly. I'm failing. I'm doing this. I'm doing all the things wrong, even though from the outside it's looking great and fantastic. But now I'm like, OK, it's fine. Like I had to go through the hard bits of it. And now I'm the confidence is finally here. the stillness and the calm is finally here. And I know that it might not remain forever, but what I know now that I didn't know then is I can get through the hard moments and they won't like win.

29:46Yeah. Tennessee Williams calls it the catastrophe of success, which I think is a beautiful phrase. And again, for people who are listening and this sounds like, well, you should be so lucky. Of course, at the same time, a lot of people don't survive it. You know, this is why we have things like the 27 Club and why so few people have a second follow-up success. A lot of people, first off, it's just hard to do it once. It's hard to do it twice. It's really hard to do it twice after you've done it once because, yeah, you have all these expectations. You have all these distractions. You can get complacent.

30:27You can feel like you're not worthy of it. There's just all this stuff that can kind of creep in that makes it hard for you to just sit down and do the thing from like a pure, authentic, like loving place. Absolutely. Exactly. I relate to that. And what I try to remember, what keeps me grounded during the hardest moment, ironically has been my readers and even going, I'm on the 10 year anniversary tour right now. And I feel really grateful because I'm meeting them each night and there's so much love and they're like, don't worry, you don't need to rush the next one. Go off, like take a year off, do this.

31:11And I'm like, okay. Cause here, you know, I've also told myself the narrative that people are just taking and taking and taking and taking. And now they have all these expectations and actually they're like, they want you to take better care of yourself. Yeah, exactly. So that's been a nice reminder. Yeah. Yeah. Also, yeah, you meet someone and you go like, it's a surreal thing. I'm sure you've had this where someone tells you this like story about the completely outsized impact your work has had on them in a way that like, obviously has very little to do with you and everything to do with them.

31:44But you're just like, if that's the only positive thing that my work has. So if my work had sold one copy, but it's all this one person who was going through cancer or like I've heard from people, they're like, I use your book. I was in this cult and now I'm not in the cult. And you're just like, well, like that, if you had said at the outset to me, or as I was conceiving the idea, like, Hey, you're going to write this book and it's going to help this person, you know, like it's going to save their life or it's going to save their marriage or it's going to pull them out of this horrendous situation.

32:12You'd be like, Oh, that, that, I guess that's success. That would be worth all these hours. And, and you, you obviously have that times a lot of things, but then it's easy to kind of abstract all that into the numbers of like total copies or the size of an advance or followers or whatever. Really like just any of those things would be, make it plenty worthwhile. That's exactly what I try to remember. I was in Brazil in 2023 when I was on my world tour and I was about to recite my final piece. But before that I was sort of sharing some sort of like details about the challenges I've had, kind of like what we're talking about.

32:50And this woman shouts out, she's like, can I tell you a story? And my audience is always like talking back at me, which I love. There's so much fun banter. But then when somebody says, can I tell you a story? I get a little nervous because I'm like, where is this going to go if I hand you the mic? Yeah, there's all these people in the audience. This could be a disaster. And I hand the mic 99 % of the time. So I was like, sure. and then she goes on to tell me the story about how um so my brazilian publisher ended up knocking at her door after my book became a bestseller in brazil because they were they were knocking on her door because they were looking for women of color writers writing about the themes i was writing about and they wanted to bring that to like a wider audience in brazil And so they ended up finding her.

33:36They published her work. And then she became a national bestselling author and poet. And she was like, I couldn't have done that if it wasn't for Milk and Honey. And then all of these women in the audience started lifting their books and going, me too, me too, me too, me too. and in that moment as I am sharing about these challenges and difficulties I was like okay fine yeah you know what all the challenges and the pain that I've like felt privately they're worth it if this is the outcome if it's like allowed people to write and share and express I'm trying to find the actual milk and honey uh poem in here obviously I I knew the book and I've I've read I'd read a bunch of the poems, but like sometimes, you know, there's things where you're like, oh, that's where the title comes from.

34:25I guess I'd never actually seen the Milk and Honey poem, but it's just for people who haven't heard it. Of course, I want to be successful, but I don't crave success for me. I need to be successful to gain enough milk and honey to help those around me succeed. So that woman was basically telling you the back made real the whole underlying idea of the thing you had done that must have been kind of a magical it was very magical it's very magical and it just is like goes to show how connected we can be and how putting yourself out there it could change the life of a person and like it's like you said it's not me i didn't change that life it took them sort of stepping into their own light the way that we're connected.

35:14It's like really cool. It's very powerful. Yeah. I try to tell people, I think that's helpful for people to hear when they tell you all the things that your book did for them. I try to remind them, it was like, you did it. Yes. Like it was just sitting there. First, have you read it? But second, like the words don't mean anything unless you do something with them. Like you did the work. Exactly. Absolutely. I try to remind them of the same thing because I'm like, I'm not out here trying to save anybody's life. So if you saved your own, you should know that you did that. Yeah, you can't save someone's life with a poem.

35:46Do you know what I mean? They have to take it and believe it or use it. I had a super weird experience in Brazil a month ago, the same thing. So what happens when I was 20 years old, I bought Mark's Realist's Meditations. This specific translation came to me on Amazon and I read it. I remember just like, this is the most amazing thing I've ever read. I was like, everyone should know about this. That was what I thought. And so I was just in Brazil. I was doing a talk and I'm walking through the airport and I see out of the corner of my eye a copy of Mark Sturlus' Meditations in an airport bookstore in Belo Horizonte, I think.

36:19And so first off, that's 20 years ago when I read Mark Sturlus. And even today, it's not a book you see in airports very often. Obscure schools of ancient philosophy do not get a lot of airport bookstore real estate, let alone in Brazil, right? And so I walk over and I look at it because it's the translation that I loved. And I think I have it. I don't have it here. I guess I have it in my office, but it's this translation, but it's in Portuguese. But then at the top is a quote from me. It's my endorsement of the book, which I did not know anyone had taken and put. And so I'm just like, oh, wow, this is incredible.

36:59And I was like, oh, I did it. I read this book and it meant something to me and I wanted people to see it. And then you flash forward almost two decades and I'm, I'm bumping into that thing that got unleashed in the world. And you're just like, oh, what a magical moment. It was crazy. Wow. That is a magical moment. Yeah. Did you buy the copy? I did. So it was actually funny. So I bought, but they were like, it was like 10 of them wrapped together. And so I was like, I went to the woman, I was like, can I buy one of these? And she's like, what? You know, she goes, I don't speak Portuguese. And she tries to ring me up for like eight, like 10 of them.

37:36And I'm like trying to explain. And then finally someone who spoke English in Longit got out and explained it. And I was like, no, I'm buying it because I'm, that's me. Yeah, yeah, yeah. Like I just wanted to tell this random stranger, like that's me. But yeah, it's crazy when you, like you have this idea to do this thing and there's something insane about it. Yeah. And then you do it. Yeah. Like I got to imagine yourself publishing a book about poetry in 2014. What does success to you look like? A hundred copies? 500 copies? I wasn't even thinking about a number because it was so, I mean, my professor who had initially asked her for advice and I was like, I'm trying to get published.

38:17What should I do? And I mean, she just told me what she knew. She was just like, well, you're not going to get published. Nobody publishes poetry. Like find another genre. Yeah. Or, you know, you could submit to poetry journals and anthologies, which I tried to do, but I felt like I was like cheating on my work. Yeah. Because I thought that it's meant to be experienced as a body of work. And I just did it because the feeling for me feeling, I think it comes from performing is when I'm performing, I'm so connected to my audience. And it's such a magical feeling that that's why I wanted to put the book out.

38:51It was like being connected in a different way. we were having conversations about these topics, whether it was violence, sexual abuse, healing, trauma, love. We're having these conversations online. And I'm such a lover of books. Like, it's a totally romantic idea. Just it existing was success. And so I was like, okay, great. I'll put it out. You know, I had like less than 10 ,000 followers on Instagram at the time. And then, yeah, I put it out and everything that happened after that was a surprise. And even when my publisher came knocking in 2015 about like eight months later. I also what I think what helped is I had no clue what the standard was.

39:31I had sold about 18 ,000 copies of the self-published edition, which to me was nothing because the only concept I've had of like numbers was music sales. Yeah. So I'm like, oh, so-and-so is like triple platinum silver. That's like a million trillion copies. Like I'm so far away from that. Yeah. And so when they came knocking, I eventually signed over with them. And then when that edition came out exactly like a year later, I was still in school. That book came out. I graduated that month. Like so much happened that month. And then I went off social media. I went off to India. There was like no press, no marketing.

40:10That's how much I didn't expect anything to happen. Yeah. And then I come back and it was insane because it was just word of mouth, people passing the book on to each other. Yeah, I try to tell people that it's like a gold album is 500 ,000 copies in music. I would say like a gold book is like 50. It's like 10 times lower. Yeah. I think books punch above their weight culturally, but it's a relatively small. So anytime you hear about something selling a million copies, it's enormous. miss it's you know what i mean like it just doesn't happen it's hard to sell books yes a lot of my friends like i'm not going to name names but they you know they're like one of them is like an incredible accessories and shoe designer she sells shoes that are like 800 a pop and she wrote a book and she comes to me and anytime my friends publish books i really have to like bring their expectations from here to here and then she comes to me and she's like girl selling books.

41:09I don't know how you do it. She's like, it's the hardest thing I've ever done. It's easier for me to sell$800 shoes. Of course. Yeah. It's, it's. Well, you can just put on an$800 pair of shoes. Like a book is worth, like not only is, is it first time music is free to download or to stream. So like, that's a huge part of why they do these huge numbers. But also it's like, it's not asking anything of you. A book, even a book of poetry is asking someone to sit down and not do anything else and spend hours with this thing. And that's like a lot. And it's expensive. Yeah. So it's kind of a crazy set.

41:45Like of all the artistic mediums, it might be like the hardest sell. Maybe other than like physical sculpture, because it's like, what am I supposed to do with this? You know what I mean? Thank you for putting that into perspective, actually. Yeah. You pay for it upfront and it takes hours of the person's time. Yes. And in some cases, it's challenging them. Like music is like, let me make you feel good. Or let me, music's not like, let me confuse you. Or let me challenge your deepest held assumption. Or let me trigger you. Yeah, exactly. So it's a tough sell, I think. Absolutely. But I mean, I think you and I would, I mean, I'd keep doing it again and again and again.

42:24But you don't have a choice. You don't get to choose the medium that you're called to. Exactly. Although it's funny, though, because I think you're so big at this point. I think there are some people, and this is a sign, I think, that someone's done something well, where it looks easy. So I imagine some people think that, first off, it's poems. It's not that many words. It's not that many words. And yeah, like, it's sort of like anyone can do it. Yeah. But if anyone could do it, a lot more people would do it. And the average poetry book wouldn't sell, you know, 16 copies. Yeah, it's funny because I use very simple diction.

43:00Yeah. And that's very purposeful because I don't I mean, there's so many different types of poetry and they're all great. But for me, I started writing poetry. I mean, I wasn't even aware that it was poetry. I was just trying to do the emotional work. And for me, that required the simplest sort of diction because I wanted I didn't want to have to decipher what the poem was saying. I wanted to read it and it hit me quick and fast so that I could sit there with it and do the emotional labor and do the emotional work of figuring out, OK, what does this experience mean and how do I process it? So those smaller pieces that are even like four lines are so much harder to write than the ones that are four pages.

43:43Like what I'm working on a book of prose and it's like I'm so excited about that because I'm like, oh, my God, thank God. It's easier. It's so much easier. Interesting. Because there's more space for me to like dive into many different directions. But the books with the shorter pieces, it's that. So much of it I have to leave up to the universe to sort of like work through and deliver through me. I find that much more challenging.

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45:20There was this early Stoic named Cleanthes, and he was saying that poetry like life, the constricting nature of it is what creates the opportunities. So he says the fetters of the poetry pushing air through a flute, that's what creates the music. If you could do whatever you wanted, and your poetry is not super rule-based, I would say, But if you had unlimited space, it wouldn't have the same effect. It's the constraining nature, the obstacles like we experience in life that create the music of the poetry. Like a haiku is the ultimate example. Yes. You can only do this, this and this. And it makes you get weird with it.

46:03Like it makes you get creative in ways that you wouldn't, if you had a choice, do. That's like writing a poem is like putting together a puzzle. Yeah. And so, yeah, like we all have our own sort of rules. Even I have them. And that's what makes creating the puzzle really fun. Yes. Yeah. And meaningful. Yes. Because if it was just blah. Yeah, exactly. Exactly. So, I mean, and there's a freedom in the prose I'm writing. Yeah. Because I'm like, okay, I could just relax and just go whatever direction I want to go in. But then bouncing back and forth between the two is also nice. But then, yeah, when you go back and edit it, though, the constraints come back in.

46:40You're like, this is boring. This is taking too long. I got to tighten this. I've said this before. I think people think writing is the stream of consciousness. That's like the, you know, you hear about Jack Kerouac writing on the road in some like 36 hour, you know, bender or something. I don't think any great literature has ever actually been done stream of consciousness. That might be how you get some of it down. But it's in the rewriting and the edit. I imagine even a four line poem for you. Oh my God. It didn't take 30 seconds. No, I'm like writing hundreds of drafts. I save each edit and each version I save.

47:18I love editing like that because I'll like write the piece and then usually I write it in my journal. And if I feel like and then after days of writing, I'll like look through and I'm like, oh, this one works. This one's cool. I'll circle the ones that I like, whatever I get for my free writing session. I translate that over to like a document. And then when I begin the editing process, it's like I edit it. And then I copy paste below, edit that, copy paste below. Cause then I can see the different versions and the evolutions of it. Cause sometimes you do over edit. And then you're like, oh my God, that the version four versions ago was so much better.

47:52Let me go back. And so it's, you know, each book is thousands of pages long. Like when you look at all the versions of the pieces, but it's so, it's really beautiful. That's the funnest part for me, right? Like, have you heard that Mark Twain thing about the difference between the right word and the almost right word? No. He says it's the difference between lightning and lightning bug. Oh, no, I haven't heard that one. There is some, it's like, you'd think it's like, okay, I got the sentence down. But it's actually like 14 versions of the sentence later that you get it exactly in the right order.

48:23And you're just like, fuck, that's it. And then it hits you and makes your stomach turn and it's such a good feeling. Yes. I think that's what keeps a writer going is that. Exactly. The couple times that happens. What are the rules? like some of my rules when I'm writing, I explore those in my fourth book, Healing Through Words, like with the shorter pieces specifically. Each poem, I try to have one thesis statement and every word in every line has to do the heavy lifting of trying to prove that thesis of the poem correct. That's my sort of like rules. Do you have rules when you're writing or constraints?

48:58I don't, I think most of my constraints are more like you have only a certain amount of space to do this. like this is what the format the style of the book like of the like right now i'm on this four book series so it's you know this is the style so it has to fit in here and you only have so much space i i heard this thing about raymond chandler once where he would write on these in his typewriter because that's when he was writing he would write on these small pieces of paper and his rule was that like something had to happen on each page so you know if you're just writing like a word doc is not a page in a book.

49:32It might be three pages in a book. So you can kind of be, you feel like you have more time and space than you actually do. So I break each of my books up into, let's say it's 30 chapters. It's 30 documents. It's not until the very end that it all comes together and then I edit it as a whole. So by breaking up in these smaller pieces, that thing has to really sing. Like not exactly the same as a poem, but it's like I'm doing these individual individual little arguments. And then that argument contributes to the overall thesis. And then, you know, later when you're editing it, you have sort of tags or, you know, it comes together as this cohesive piece.

50:11But I think the big rule for me is that it has to work as this independent chunk. And if it doesn't, then it's not what it can be. I think that's a big one. Yeah. I love that idea. And I love that what you said about each page has to do something. that same with each poem. That's how I feel. I'm like, if you're going to take up space in my book, you better work hard. Yeah. I think another rule, like I got, so my, I was a research assistant for this writer named Robert Green, who wrote The 40 Laws of Power. And he was talking to me early on about like diversity in this stuff. And he wasn't arguing it from a political correctness standpoint, or even like a social justice standpoint.

50:50He was just like, you want to have a lot of readers and every reader should be able to see something of themselves in the book. Right. And so it's like, if all your things are from 20th century American history, that's only going to be relevant to some people. And so he was like, no, you've got to get something from everywhere. So Chinese history and then business history and sports and music and white and black and East and West. And so one of the, I think another rule that really helps me is, is the sort of forced, it's not quotas, because I don't think about it that way. I'll just get a sense of like, I'm talking too much about the same people or the same kinds of people.

51:29So now I want to go find someone or something that's like out of left field here. And that forces me to take on new characters that I work. And I ended up going down these whole rabbit holes and finding this whole other perspective. And I get really excited. I'm like, I didn't know anything about, you know, this person or that person. And now emerging from the book, they're like one of my heroes. Yeah, you get to like learn yourself and it stays exciting for you and continues to feed you. Because the worst thing is when you're doing the work and it's no longer feeding you. Yeah, you're just doing like you said earlier, where you're just doing if you're just doing the same thing over and over again, it's like very boring.

52:07And then ultimately boring for the audience. Like you want you want to be on fresh territory as often as possible. Exactly. Exactly. I think it was like in my mid-20s, I was really struggling with this idea of staying relevant. And I could not figure out how to move past that. And my therapist was like, you're relevant right now because you're interested in what you're writing about. The moment you stop and the moment you're just thinking about the audience, you're going to stop being relevant. So like focus on that. And that was really freeing because I was like, okay, that means I can, it gave me the permission to just serve myself.

52:45Because that is what she was saying was keeping the work alive and relevant and all of these things. Yeah. You know who Rick Rubin is? Yes. Yeah. He's talked about, he's like, as soon as a band is trying to like do what's relevant or like what's popular now, they're dating themselves. He's like, you should go to a museum and find yourself inspired by something that's a thousand years old. You want to find those more eternal, timeless sources of inspiration. You want to serve something that's fundamentally human as opposed to whatever people are talking about right now. By the time you write about it and by the time it comes out, you've probably already missed the wave.

53:26Exactly. Times change. Yeah. Was it weird? Because what's cool about this book, which I didn't think to do, I love that, is your book, a book isn't just what it is. It's the people that read it and are influenced and connected to it. The idea of hearing what other people thought about the poems and what they meant to them, that must've been really cool. Yes. Are you speaking about the other annotators? Yeah. All the annotators. Yeah. That's such a cool idea. Yeah. I remember reaching the end of my own annotations and realizing as I was writing the introduction, like Milk and Honey is not just my book anymore.

54:03I wrote it. Cool. And it was mine when I wrote it. And then I like shared it with the world. But the way the world has received it, it belongs. It's not fully mine anymore. And so the 10 year anniversary edition, it wouldn't make sense to just have my voice in it. And so then I started reaching out to friends. And I remember the first time I met Malala. I didn't know that she'd read my work. And she comes to me and she's like, I read all your works right before I got married. Your books were the ones that I was reading. And I was so moved by that. So then I invited her to annotate and then also Camila Cabello.

54:39And she shared one of my things on Instagram once. It was very cool. I listened to the episode with you and her, which is so great. She's so well-spoken and lovely. But it was really cool to just sort of give these women the book. These are like women who've arrived at my table after publication. Then I also went to women who helped me build that table and who were there before that table was even built. Women who've been in my life forever and watched me do this. And it was interesting to see the pieces that they picked and how they reflected on it and how they included other women. I love Malala's annotation referencing the girls in Afghanistan who don't, you know, are losing so many human rights.

55:19um isn't it crazy we were talking about like someone coming up to you and their your work's meant something to you i i don't know about you but i i sometimes get very self-conscious because i'm like i wrote this thing from my experience which was a fraction of your that person's experience the idea that they were going through cancer or some you know horrendous thing where they're winning the super bowl they're doing so i'm like you really took like a chance like putting weight i'm not sure that this was a weight-bearing book you know what i mean like for someone like her who's had this incredible life and is so incredibly brave to be like oh no this is true like this is good that must have been you're like what it's crazy it's crazy it's like nice sometimes too because i'm like all i do is sit in my head and beat myself up so like that's really nice thank you yeah i'm just like oh you're making real life decisions based on what's in here like uh yeah okay you never know how something's gonna land like i don't have a single poem and i think any of my books i think i'm pretty sure about battling cancer any type of sickness but the amount of people who've said to me on this book tour uh this is like i was reading all your books again and again while i was like fighting this disease and i was hospitalized for so long and i'm like which part like but it's like amazing because i mean human emotions are clearly so universal that they land with people in unexpected ways.

56:45It's like, I was writing this because I was frustrated in traffic. And then you're taking it to, you know, it's like a world-changing cause that you're fighting for. And, and like, I'm honored that it spoke to you, but like, I'm also just like, yeesh, like that would, like, like, I'm glad it held up because like it was built under flimsier circumstances than the stress test that you are subjecting it to absolutely so you know yeah like a mountain climbing equipment it's like set up for different weights and it's like i only tested this a little bit and then you are taking your life in your hands yes like there's something surreal about it is it's really surreal it's wild and i mean yeah the stories i mean you've heard the stories people tell you their stories and i mean and that's why i always tell like so many people come up to me at book signings and they're like, I write, I'm scared.

57:39Should I put my work out? Am I supposed to feel nervous? And I tell them, I'm like, as long as you feel safe, put it out. You've absolutely no idea who the hell is going to find your work and how it's going to transform them. So do it for you. If it makes you feel alive, it's a wonderful feeling to feel connected with people, but you have no idea like the audiences that are going to find it and find comfort in it. Yeah. It's like, sometimes it's helpful. Like no one I knew went to like Ivy league schools. No one growing up was like really successful. Then you meet some like really well-educated idiots, you know, or some like incredibly successful people that you're just like, oh, they did it.

58:19It's like, it's very helpful. Cause then you just, oh, it's like, nobody really knows what they're doing. You think there are these like adults out there that are just, you know, perfect. And then you're like, oh yeah, there's something silly about imposter syndrome as if one everyone's not feeling it and there aren't some like actual imposters out there getting away with it who have ivy league yes i agree oh totally i mean i'd sold millions of copies of milk and honey it was like you know doing all of these wild things and my number one obsession was trying to find a master's like program to go into so that i could be an official more feel more official doing it because all of these other poets they went to like they did their MFA over here and that.

59:00And I was like, I need that to like call myself a writer. Yeah. There's a lot of interest in kind of mystifying things and making it seem more significant than it is and dramatic and glamorous than it is. And that because I don't know, but it, but it has the effect of being very intimidating to people who are on the outside and it's really not, you know, and people perpetuate it too. Like they go like, what kind of pen do you use? And it's like, this is the least important question. Like none of this shit matters. Like none of us know what we're doing. Yeah, just do it. Yeah, exactly. And then when people are like behaving too much, like they know what they're doing, I'm now a little suspect.

59:43I'm like, just chill. Yeah. It's, it's not, I try to remind myself of like the silliness and the absurdity of it too. It's not that, it's not that important. It really doesn't matter that much in the big scheme of things anyone can do it and it just to kind of because if you build it up too much in your head and intimidate you it also i think can make it make you self-important right you're like like this isn't that special yeah you know there's no one right way to do it yeah so you could find your own way to do it like my when my book hit number one on the new york times list for the first time i was like oh this is incredible you know i was on a book tour so i was mostly just busy i was like oh shit i gotta go to the airport now but then like the next week or a couple weeks after like Donald Trump Jr.

1:00:25hit number one and he hit number one. And then the story came out that like one of their PACs had just bought all the copies. And you're just like, oh, the accomplishment that I was just like, I want for a second was going to take as like the, you know, the culmination of all my work or, you know, it's like the Nobel prize was invented by this guy who felt guilty for having invented dynamite. You're just like, none of these things are that impressive. In fact, most of them are like corrupt. I mean, I have a bookstore. We just sent an email to the New York Times list every week and we're like, we sold this many copies.

1:01:00It's not like, it's first off, there are companies that will help you deceive that system. Yes. And many of the books that you think were super successful, it's just because the deep pocketed person bought it or the company turning it into a movie paid for it or whatever. And then also it's like, yeah, Even if it did matter, like the Olympics, where it was like, this is objectively the fastest person in the world. It's not who gives a shit. You know, it doesn't matter. You can't give it that much importance. Exactly. Otherwise, it traps you. Yes. And it's not fun. And I mean, to me, the real test is like, is it still here in 10 years or 20 years or 100 years?

1:01:39Not that, you know, creating something that outlives you is that meaningful, too. But it's just like, why was success to you being the best for a very brief moment? You should make something that has staying power. But then what is success? If it's not that, it's not being on the list. And then is it staying power? Is it not that? Like, I often wonder then. And it's a question I'm answering. I don't know yet. I mean, at this point in my life, and maybe the definition changes every few years. I'm like if I can do that that should give me freedom to find joy in my life and so if it hasn't done that yet I'm doing something wrong and so I'm on that journey of like running towards the joy rather than running towards the numbers yeah I mean if you're not happy how successful are you exactly for sure but I mean I think your definition in the milk and honey poem like I need to be successful to gain enough milk and honey to help those around me succeed.

1:02:35Like, did your thing facilitate success for other people? Did it open doors for other people? Were you a good steward of what you had? And did you use it to help other people realize their potential? I mean, that to me is a much more meaningful. I have a chapter in the, in my justice book about coaching trees, like Greg Popovich, you know, that is he's the head coach of the San Antonio Spurs. He's one of the most winning coaches in the history of not just the NBA, but all sports. But I think it's much he also has the greatest what they would call the greatest coaching tree. Wow. So like his assistants have gone on.

1:03:12Wow. To win the most games. Incredible. And to like he was one of the first basketball coaches to hire a female assistant coach. He was the first one because he stepped out in the game. He let her coach. She was the first woman to coach an NBA game. Right. So like for all of his success, what actually would you sort of step away from it? Because their last championship, I think they won in like 2015 or 16, something like that. So already it's already drift receding into the background. But what endures is like what the doors that you've opened for other people. Absolutely. And that continues to be the most rewarding thing is to see how you can use your platforms or your power to bring other people on the ride with you because it's not fun to be on the ride alone.

1:04:00It's only fun when you're there with other people. I'm sure many people have gotten poetry book deals that you were not offered when you were writing your first book. But as a result of the success of that, like there's something about not creating a genre because obviously poetry is very, but there's something about creating a resurgence of a genre or being popular in a genre that floats all the boats. Absolutely. It's been amazing to watch how this genre went from being at the back of bookstores to closer to the front. And sometimes like right at the front when I walk in, that's been really cool, really interesting.

1:04:37And I just did on this book tour, we've been doing a lot of community events as well to give access to lots of different people. And one of my favorites was an open mic night we did in the Lower East Side with my friends at Cotton. They're like a sustainable ethical clothing brand out of Toronto. And I wanted to do that open mic because the moment that changed my life was the first open mic I did in 2009. There were 20 people in the audience. I had a really bad, cringy poem. Didn't matter. I went up, I performed it, and the people in the audience didn't laugh. They surrounded me afterwards and they were like just in awe.

1:05:17I mean, they were eight to ten years older than me and they see me as like, you know, I'm like this little teenager. I'm like shaking, my knees are trembling and I'm like, you know, reciting and they surrounded me afterwards. And they're like, you did such a great job. Like, wow, we need you to come back. And that's what the poetry community is and does. It just uplifts you. And on my world tour, I had opening acts from different cities come and perform. and then two weeks ago at this open mic that we held in Lower East Side, I had people sort of submit poems. I picked a few and these nine poets, watching them on stage and just sitting in the audience and cheering them on filled my heart more than a list ever could.

1:05:58It was so beautiful. You can't pay those people back, but you can pay it forward. Exactly. Exactly. Yeah. Well, congrats. Thank you. You want to go look at some books in the Yes, let's do it. Thanks so much for listening. If you could rate this podcast and leave a review on iTunes, that would mean so much to us and it would really help the show. We appreciate it. And I'll see you next episode.

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